WO2023107966A1 - Formes salines et solides du diéthylamide de l'acide lysergique (lsd) et analogues - Google Patents

Formes salines et solides du diéthylamide de l'acide lysergique (lsd) et analogues Download PDF

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WO2023107966A1
WO2023107966A1 PCT/US2022/081041 US2022081041W WO2023107966A1 WO 2023107966 A1 WO2023107966 A1 WO 2023107966A1 US 2022081041 W US2022081041 W US 2022081041W WO 2023107966 A1 WO2023107966 A1 WO 2023107966A1
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lsd
solid form
acetyl
crystalline
radiation
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PCT/US2022/081041
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Matthew Duncton
Samuel CLARK
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Terran Biosciences, Inc.
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Publication of WO2023107966A1 publication Critical patent/WO2023107966A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/48—Ergoline derivatives, e.g. lysergic acid, ergotamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • A61K31/36—Compounds containing methylenedioxyphenyl groups, e.g. sesamin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
    • C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
    • C07C55/02—Dicarboxylic acids
    • C07C55/10—Succinic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/13—Dicarboxylic acids
    • C07C57/145—Maleic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/13—Dicarboxylic acids
    • C07C57/15—Fumaric acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
    • C07C59/06—Glycolic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • C07C59/255—Tartaric acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • C07C59/265—Citric acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • C07C59/285—Polyhydroxy dicarboxylic acids having five or more carbon atoms, e.g. saccharic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/105—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic
    • C07C65/11—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic with carboxyl groups on a condensed ring system containing two rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
    • C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 8
    • C07D457/06—Lysergic acid amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Definitions

  • LSD lysergic acid diethylamide
  • ALD-52 1-acetyl-LSD
  • 2-bromo-LSD 2-bromo-LSD
  • difficulties in formulating LSD, 1-acetyl-LSD, 1- propionyl-LSD, and 2-bromo-LSD e.g., salt and solid forms of LSD, 1-acetyl-LSD, 1-propionyl- LSD, and 2-bromo-LSD. Accordingly, the present disclosure addresses this unmet need.
  • LSD lysergic acid diethylamide
  • 1-acetyl lysergic acid diethylamide (1a-LSD or 1-acetyl-LSD or ALD-52)
  • 1-propionyl lysergic acid diethylamide (1P-LSD or 1-propionyl-LSD)
  • the solid form of LSD, 1-acetyl-LSD, 2-bromo-LSD, and/or 1- propionyl-LSD is a polymorph of the free base form of the compound.
  • the solid form of LSD, 1-acetyl-LSD, 2-bromo-LSD, and/or 1-propionyl-LSD is a salt, e.g., a polymorph of the salt.
  • the salt may be formed from an acid selected from hydrochloric acid, fumaric acid, galactaric (mucic) acid, naphthalene-1,5-disulfonic acid, citric acid, sulfuric acid, d-glucuronic acid, ethane-1,2-disulfonic acid, lactobionic acid, p-toluenesulfonic acid, D- glucoheptonic acid, thiocyanic acid, (-)-L-pyroglutamic acid, methanesulfonic acid, L-malic acid, dodecylsulfuric acid, hippuric acid, naphthalene-2-sulfonic acid, D-gluconic acid, benzenesulfonic acid, D,L-lactic acid, oxalic acid, oleic acid, glycerophosphoric acid, succinic acid, ethanesulfonic acid 2-hydroxy, glutaric acid, L-aspartic acid, cinn
  • a stoichiometric ratio of acid to LSD is from about 0.4 to about 2.2, such as from about 0.5 to about 2, or from about 0.5, 1 or 2.
  • the solid form may be a crystalline solid, a hydrate, or a combination thereof.
  • the crystalline solid may be substantially a single form, such as a polymorph form.
  • the polymorph may be selected to have one or more desired properties, particularly improved properties, such as physical properties, chemical properties, pharmacokinetic properties, or a combination thereof.
  • the one or more desired properties may comprise melting point, glass transition temperature, flowability, thermal stability, mechanical stability, shelf life, stability against polymorphic transition, hygroscopic properties, solubility in water and/or organic solvents, reactivity, compatibility with excipients and/or delivery vehicles, bioavailability, absorption, distribution, metabolism, excretion, toxicity including cytotoxicity, dissolution rate, half-life, or a combination thereof.
  • a pharmaceutical composition comprising a solid form of a disclosed compound, and a pharmaceutically acceptable excipient.
  • a method for administering the salts and solid forms, e.g., crystalline polymorphic forms, of LSD, 1-acetyl LSD, 1-propionyl LSD, and/or 2-bromo LSD also are disclosed herein.
  • the method comprises administering to a subject an effective amount of a solid form of LSD 1-acetyl-LSD, 1-propionyl-LSD, and/or 2-bromo-LSD, or a pharmaceutical composition thereof.
  • the subject is suffering from a neurological disease or a psychiatric disorder, or both, such as a neurodegenerative disorder.
  • the neurological disorder or psychiatric disorder, or both may comprise depression, addiction, anxiety, or a post- traumatic stress disorder, and/or the neurological disorder or psychiatric disorder, or both, may comprise treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, or substance use disorder.
  • the neurological disorder or psychiatric disorder, or both comprises stroke, traumatic brain injury, or a combination thereof.
  • the method may comprise further comprising administering an effective amount of an empathogenic agent and/or a 5-HT2A antagonist to the subject.
  • the 5-HT2A antagonist may be selected from MDL-11,939, eplivanserin (SR-46,349), ketanserin, ritanserin, altanserin, acepromazine, mianserin, mirtazapine, quetiapine, SB204741, SB206553, SB242084, LY272015, SB243213, blonanserin, SB200646, RS102221, nefazodone, MDL-100,907, pimavanserin, nelotanserin and lorcaserin.
  • administering the solid form of the compound comprises oral, parenteral, or topical administration.
  • FIG.1 provides an XRPD diffractogram of crystalline LSD (form A).
  • FIG.2 provides an XRPD diffractogram of crystalline LSD . fumarate (form 1).
  • FIG.3 provides an XRPD diffractogram of crystalline LSD . gentisate (form 1).
  • FIG.4 provides an XRPD diffractogram of crystalline LSD .
  • FIG.5 provides an XRPD diffractogram of crystalline LSD . phosphate (form 1).
  • FIG.6 provides an XRPD diffractogram of crystalline LSD . maleate (form 1).
  • FIG.7 provides an XRPD diffractogram of crystalline LSD . mesylate (form 1).
  • FIG.8 provides an XRPD diffractogram of crystalline LSD . mucate (form 1).
  • FIG.9 provides an XRPD diffractogram of crystalline LSD xinafoate (form 1).
  • FIG.10 provides an XRPD diffractogram of crystalline LSD glycolate.
  • FIG.11 provides an XRPD diffractogram of crystalline LSD xinafoate (form 2).
  • FIG.12 provides an XRPD diffractogram of crystalline LSD (form B).
  • FIG.13 provides an XRPD diffractogram of crystalline LSD (form C).
  • FIG.14 provides an XRPD diffractogram of crystalline LSD . fumarate (forms 1 and 2).
  • FIG.15 provides an XRPD diffractogram of crystalline LSD gentisate (form 3).
  • FIG.16 is a graph of intensity versus diffraction angle, illustrating the X-ray powder diffraction (XRPD) spectrum for a sample of 1-acetyl LSD crystalline Form A.
  • FIG.17 is a graph of intensity versus diffraction angle, illustrating the XRPD spectrum for a sample of a crystalline solid of 1-acetyl LSD . p-toluenesulfonic acid Form A salt.
  • FIG.18 is a graph of intensity versus diffraction angle, illustrating the XRPD spectrum for a sample of a crystalline solid of 1-acetyl LSD . hydrochloric acid Form A salt.
  • FIG.19 is a graph of intensity versus diffraction angle, illustrating the XRPD spectrum for a sample of a crystalline solid of 1-acetyl LSD . phosphoric acid Form A salt.
  • FIG.20 is a graph of intensity versus diffraction angle, illustrating the XRPD spectrum for a sample of a crystalline solid of 1-acetyl LSD gentisate Form A salt.
  • FIG.21 is an overlay plot of the XRPD pattern calculated from single-crystal data (top trace) with the pattern provided in FIG.16.
  • FIG.22 is an overlay plot of the XRPD pattern calculated from single-crystal data obtained from the gentisate salt (top trace) with the pattern provided in FIG.20.
  • FIG.23 is a graph of intensity versus diffraction angle, illustrating the XRPD spectrum for a sample of a crystalline solid of 1-acetyl LSD . p-toluenesulfonic acid salt.
  • FIG.24 is is a graph of intensity versus diffraction angle, illustrating the XRPD spectrum for a sample of a crystalline solid of 1-acetyl LSD . hydrochloric acid Form A salt.
  • FIG.25 is an overlay plot of the XRPD pattern calculated from single-crystal data obtained from the phosphoric acid Form A salt cocrystal (top trace) with the pattern provided in FIG.19.
  • FIG.26 provides an XRPD diffractogram of crystalline 2-bromo-LSD . HCl.
  • FIG.27 provides an expanded section of the diffractogram of FIG.26.
  • FIG.28 is an XRPD diffractogram of 1P-LSD free base.
  • FIG.29 is an XRPD diffractogram of a 1P-LSD free base sample following DVS showing no form change relative to that of FIG.28.
  • FIG.30 provides a 1H NMR spectrum of 1P-LSD free base.
  • FIG.31 provides an XRPD diffractogram of 1P-LSD . hydrochloride 1.
  • FIG.32 provides an XRPD diffractogram of 1P-LSD . maleate 1.
  • FIG.33 provides an XRPD diffractogram of 1P-LSD . L-malate 1.
  • FIG.34 provides an XRPD diffractogram of 1P-LSD . phosphate 1.
  • FIG.35 provides an XRPD diffractogram of 1P-LSD . phosphate 2.
  • FIG.36 provides an XRPD diffractogram of 1P-LSD . succinate 1.
  • FIG.37 provides an XRPD diffractogram of 1P-LSD . sulfate 1.
  • FIG.38 provides an XRPD diffractogram of 1P-LSD . sulfate 2.
  • FIG.39 provides an XRPD diffractogram of 1P-LSD . L-tartrate 1.
  • FIG.40 provides a 1 H NMR spectrum of 1P-LSD L-malate 1.
  • FIG.41 provides an XRPD diffractogram of 1P-LSD . mesylate 1.
  • FIG.42 provides an XRPD diffractogram of 1P-LSD . ethanesulfonate (esylate).
  • FIG.43 provides an XRPD diffractogram of 1P-LSD . mesylate 2.
  • FIG.44 provides an XRPD diffractogram of 1P-LSD . hydrochloride 2.
  • FIG.45 provides an XRPD diffractogram of 1P-LSD . maleate 2.
  • FIG.46 provides an XRPD diffractogram of LSD freebase Form A.
  • FIG.47 provides an XRPD diffractogram of LSD gentisate Form 3.
  • FIG.48 provides an XRPD diffractogram of LSD HCl.
  • FIG.49 provides an XRPD diffractogram of LSD L-tartrate.
  • FIG.50 provides an XRPD diffractogram of LSD maleate Form 1.
  • FIG.51 provides an XRPD diffractogram of LSD maleate Form 2.
  • FIG.53 provides an XRPD diffractogram of LSD maleate Form 3.
  • FIG.54 provides an XRPD diffractogram of LSD Xinafoate Form 2.
  • FIG.55 provides an XRPD diffractogram of 1A-LSD citrate.
  • FIG.56 provides an XRPD diffractogram of 1A-LSD Fumarate.
  • FIG.57 provides an XRPD diffractogram of 1A-LSD L-malate.
  • FIG.58 provides an XRPD diffractogram of 1A-LSD Succinate.
  • FIG.59 provides an XRPD diffractogram of 1A-LSD sulfate.
  • FIG.60 provides an XRPD diffractogram of 1A-LSD L-tartrate.
  • FIG.61 provides a calculated XRPD diffractogram of 1A-LSD Tosylate Form A.
  • FIG.62 provides an XRPD diffractogram of 1P-LSD citrate Form 1.
  • FIG.63 provides an XRPD diffractogram of 1P-LSD esylate Form 1.
  • FIG.64 provides an XRPD diffractogram of 1P-LSD fumarate Form 1.
  • FIG.65 provides an XRPD diffractogram of 1P-LSD maleate Form 1.
  • FIG.66 provides an XRPD diffractogram of 1P-LSD succinate Form 1.
  • FIG.67 provides an XRPD diffractogram of 1P-LSD sulfate Form 2.
  • FIG.68 provides a 1 H NMR spectrum of 1P-LSD sulfate Form 2.
  • FIG.69 provides TGA and DSC profiles for 1P-LSD sulfate Form 2.
  • FIG.70 provides a 1 H NMR spectrum of 1P-LSD succinate Form 1.
  • FIG.71 provides a 1 H NMR spectrum for 1P-LSD maleate Form 1.
  • FIG.72 provides TGA and DSC profiles for 1P-LSD maleate Form 1.
  • FIG.73 provides a 1 H NMR spectrum for 1P-LSD fumarate Form 1.
  • FIG.74 provides a 1 H NMR spectrum for 1P-LSD esylate Form 1.
  • FIG.75 provides TGA and DSC profiles for 1P-LSD esylate Form 1.
  • FIG.76 provides a 1 H NMR spectrum for 1P-LSD citrate Form 1.
  • FIG.77 provides a 1 H NMR spectrum for 1A-LSD tosylate Form A.
  • FIG.78 provides TGA and DSC profiles for 1A-LSD tosylate Form A.
  • FIG.79 provides a 1 H NMR spectrum for LSD xinafoate Form 2.
  • FIG.80 provides TGA and DSC profiles for LSD xinafoate Form 2.
  • FIG.81 provides a 1 H NMR spectrum for LSD phosphate Form 1.
  • FIG.82 provides TGA and DSC profiles for LSD phosphate Form 1.
  • FIG.83 provides a 1 H NMR spectrum for LSD maleate Form 1.
  • FIG.84 provides TGA and DSC profiles for LSD maleate Form 1.
  • FIG.85 provides a 1 H NMR spectrum for LSD gentisate Form 3.
  • FIG.86 provides TGA and DSC profiles for LSD gentisate Form 3.
  • FIG.87 provides a 1 H NMR spectrum for LSD freebase Form A.
  • FIG.88 provides TGA and DSC profiles for LSD freebase Form A.
  • FIG.89 provides a 1 H NMR spectrum for 1P-LSD HCl Form 2.
  • FIG.90 provides TGA and DSC profiles for 1P-LSD HCl Form 2.
  • FIG.91 provides a 1 H NMR profile for 1P-LSD mesylate Form 2.
  • FIG.92 provides TGA and DSC profiles for 1P-LSD mesylate Form 2.
  • FIG.93 provides a 1 H NMR profile for 1P-LSD mesylate Form 2.
  • FIG.94 provides TGA and DSC profiles for 1P-LSD mesylate Form 1.
  • FIG.95 provides TGA and DSC profiles for 1P-LSD L-malate 1.
  • FIG.96 provides a 1 H NMR profile for 1P-LSD L-tartrate 1.
  • FIG.97 provides a 1 H NMR profile for LSD maleate Form 1.
  • FIG.98 provides TGA and DSC profiles for LSD maleate Form 1.
  • FIG.99 provides a 1 H NMR profile for 1P-LSD sulfate Form 1.
  • FIG.100 provides TGA and DSC profiles for 1P-LSD sulfate Form 1.
  • FIG.101 provides a 1 H NMR spectrum for LSD mucate Form 1.
  • FIG.102 provides a 1 H NMR spectrum for 1P-LSD phosphate Form 2.
  • FIG.103 provides TGA and DSC profiles for 1P-LSD phosphate Form 2.
  • FIG.104 provides a 1 H NMR spectrum for 1P-LSD phosphate Form 1.
  • FIG.105 provides TGA and DSC profiles for 1P-LSD phosphate Form 1.
  • FIG.106 provides a 1 H NMR spectrum for LSD mesylate Form 1.
  • FIG.107 provides TGA sand DSC profiles for LSD mesylate Form 1.
  • FIG.108 provides a 1 H NMR spectrum for 1P-LSD HCl Form 1.
  • FIG.109 provides TGA and DSC profiles for 1P-LSD HCl Form 1.
  • FIG.110 provides TGA and DSC profiles for 1P-LSD Freebase Form A.
  • FIG.111 provides a 1 H NMR profile for 1A-LSD phosphate Form A.
  • FIG.112 provides TGA and DSC profiles for 1A-LSD phosphate Form A.
  • FIG.113 provides a 1 H NMR spectrum for 1A-LSD HCl Form A.
  • FIG.114 provides TGA and DSC profiles for 1A-LSD HCl Form A.
  • FIG.115 provides TGA and DSC profiles for 1A-LSD gentisate Form A.
  • FIG.116 provides a 1 H NMR profile for LSD gentisate Form 2.
  • FIG.117 provides TGA and DSC profiles for LSD gentisate Form 2.
  • FIG.118 provides TGA and DSC profiles for LSD freebase Form B.
  • FIG.119 provides a 1 H NMR spectrum for LSD phosphate Form 1.
  • FIG.120 provides TGA and DSC profiles for LSD phosphate Form 1.
  • FIG.121 provides a 1 H NMR spectrum for LSD xinafoate Form 1.
  • FIG.122 provides TGA and DSC profiles for LSD xinafoate Form 1.
  • FIG.123 provides XRPD overlay plots of recrystallization attempts of 1-acetyl LSD. The top plot is a 22 mg scale crystallization. The bottom plot is a 100 mg scale crystallization.
  • FIG.124 provides XPRD overlay plots of the XRPD diffractogram of the XRPD pattern calculated from single-crystal data of 1-acetyl LSD tosylate salt (Form A, top) and an experimental XRPD pattern of 1-acetyl LSD tosylate Form A (bottom).
  • FIG.125A and FIG.125B provide an overlay plot of XRPD patterns from salt screen experiments for 1-acetyl LSD
  • FIG.126 provides an overlay of XRPD patterns of crystalline LSD salts.
  • FIG.127 provides an overlay plot of the 1P-LSD Maleate Form 1 XRPD pattern calculated from single-crystal data with a pattern obtained from the bulk sample.
  • FIG.128 illustrates functional whole-brain network partition.
  • FIG.129 illustrates dense Global Brain Connectivity (GBC) maps showing the difference in GBC ( ⁇ GBC) for the ketanserin (Ket) + LSD-treated subjects vs placebo (Pla) + Pla contrast at the early time point (75-minute) after treatment.
  • FIG.130 illustrates dense GBC maps showing the difference in GBC ( ⁇ GBC) for the placebo + LSD-treated subjects vs placebo + placebo contrast at the early time point (75-minute) after treatment.
  • FIG.131 illustrates dense GBC maps showing the difference in GBC ( ⁇ GBC) for the ketanserin + LSD-treated subjects vs placebo + placebo contrast at the late time point (300- minute) after treatment.
  • FIG.132 illustrates dense GBC maps showing the difference in GBC ( ⁇ GBC) for the placebo + LSD-treated subjects vs placebo + placebo contrast at the late time point (300-minute) after treatment.
  • FIG.133 illustrates a collection of panels showing early session time point (75-minute) results and late session time point (300-minute) results for the difference in Functional Connectivity ( ⁇ FC) between the test conditions. The left of each row indicates the test conditions and the top of each column indicates the time points. Positive and negative contrasts are rendered, respectively, in red and blue hues. Nodes along the edges indicate (cortical and subcortical) parcels of the CAP-NP parcellation.
  • FIG.134 illustrates related effects of Ket+LSD and Pla+LSD on parcels’ GBC values.
  • Panels show 2d-histograms across parcels, indicating how pretreatment+treatment effects for Ket+LSD and Pla+LSD (relative to the placebo+placebo condition) were related.
  • the bulk of the distribution scattered around 0 effects, but some parcels with strong effects (bottom right) led to a net negative correlation.
  • the late time point (right panel; 300 minutes), a strong positive correlation was observed.
  • Table 130 also shows correlations between GBC changes in parcels induced by Pla+LSD and Ket+LSD (relative to Pla+Pla).
  • FIG.135 illustrates related effects of Ket+LSD and Pla+LSD on parcels’ Functional Connectivity (FC) values.
  • FIG.136 illustrates ⁇ GBC confidence intervals for the early time point. Confidence intervals were calculated assuming a t-distribution.
  • the CAP-NP network to which a parcel belongs is indicated by labels on the row.
  • FIG.137 illustrates ⁇ GBC confidence intervals for the late time point. Confidence intervals were calculated assuming a t-distribution. The CAP-NP network to which a parcel belongs is indicated by labels on the row. Additionally, a confidence interval was plotted in a desaturated (light) shade of grayscale if the FDR-BH corrected p-value is ⁇ 0.05.
  • FIG.138 illustrates network FC contrasts. For each pair of networks, all connection contrasts (i.e. ⁇ FC values) between these two networks were averaged resulting in a network ⁇ network FC contrast matrix. Networks are defined in the CAP-NP atlas. The contrasts shown here are average contrasts for a given network pair (left column of panels: 75 minutes after treatment; right column of panels: 300 minutes after treatment).
  • FIG.139 illustrates the time course of subjective drug effects for the labeled subject groups.
  • the fourth graph indicates that at no time point is there a significant presentation of self-reported altered states of consciousness in the Ket+LSD test subject group compared with the other graphs.
  • This figure is reprinted from eLife Preller 2018. (Preller et al. eLife.2018 Oct 25;7:e35082. Changes in global and thalamic brain connectivity in LSD-induced altered states of consciousness are attributable to the 5-HT2A receptor, PMID: 30355445).
  • FIG.140 illustrates chord plot showing the difference in connectivity ( ⁇ FC) between the Pla+LSD Vs Pla+Pla conditions (top) Ket+LSD Vs Pla+Pla (middle) and Pla+LSD Vs Ket+LSD (Bottom) at 75min and at 300m.
  • FIG.141 illustrates chord plot for Pla+LSD vs Pla+Pla contrast for the 75 minute time point. This chord plot visualizes the difference in connectivity ( ⁇ FC) between the two conditions. Positive and negative contrasts are rendered, respectively, in red and blue hues.
  • FIG.142 illustrates chord plot for Ket+LSD vs Pla+Pla contrast for the 75 minute time point. This chord plot visualizes the difference in connectivity ( ⁇ FC) between the two conditions. Positive and negative contrasts are rendered, respectively, in red and blue hues. Positive and negative contrasts are shown in separate panels. FC values that are very similar in both conditions are shown in gray hues.
  • FIG.143 illustrates chord plot for Pla+LSD vs Ket+LSD contrast for the 75 minute time point. This chord plot visualizes the difference in connectivity ( ⁇ FC) between the two conditions. Positive and negative contrasts are rendered, respectively, in red and blue hues. Positive and negative contrasts are shown in separate panels. FC values that are very similar in both conditions are shown in gray hues. Moreover, thicker lines indicate stronger differences in FC between the two respective conditions.
  • FIG.144 illustrates chord plot for Pla+LSD vs Pla+Pla contrast for the 300 minute time point. This chord plot visualizes the difference in connectivity ( ⁇ FC) between the two conditions. Positive and negative contrasts are rendered, respectively, in red and blue hues. Positive and negative contrasts are shown in separate panels. FC values that are very similar in both conditions are shown in gray hues. Moreover, thicker lines indicate stronger differences in FC between the two respective conditions. Nodes along the perimeter indicate left hemisphere cortical parcels of the CAP-NP parcellation.
  • FIG.145 illustrates chord plot for Ket+LSD vs Pla+Pla contrast for the 300 minute time point.
  • This chord plot visualizes the difference in connectivity ( ⁇ FC) between the two conditions. Positive and negative contrasts are rendered, respectively, in red and blue hues. Positive and negative contrasts are shown in separate panels. FC values that are very similar in both conditions are shown in gray hues. Moreover, thicker lines indicate stronger differences in FC between the two respective conditions. Nodes along the perimeter indicate left hemisphere cortical parcels of the CAP-NP parcellation.
  • FIG.146 illustrates chord plot for Pla+LSD vs Ket+LSD contrast for the 300 minute time point. This chord plot visualizes the difference in connectivity ( ⁇ FC) between the two conditions. Positive and negative contrasts are rendered, respectively, in red and blue hues. Positive and negative contrasts are shown in separate panels. FC values that are very similar in both conditions are shown in gray hues. Moreover, thicker lines indicate stronger differences in FC between the two respective conditions. Nodes along the perimeter indicate left hemisphere cortical parcels of the CAP-NP parcellation.
  • FIG.147 illustrates contrasts for Visual1 network ( ⁇ FC) between the Pla+LSD Vs Pla+Pla conditions (top) Ket+LSD Vs Pla+Pla (middle) and Pla+LSD Vs Ket+LSD (Bottom) at 75min and at 300m.
  • FIG.148 illustrates contrasts for Visual2 network ( ⁇ FC) between the Pla+LSD Vs Pla+Pla conditions (top) Ket+LSD Vs Pla+Pla (middle) and Pla+LSD Vs Ket+LSD (Bottom) at 75min and at 300m.
  • ⁇ FC Visual2 network
  • Positive and negative contrasts are rendered, respectively, in red and blue hues. Positive and negative contrasts are overlayed in the same panel.
  • FIG.149 illustrates contrasts for Somatomotor network ( ⁇ FC) between the Pla+LSD Vs Pla+Pla conditions (top) Ket+LSD Vs Pla+Pla (middle) and Pla+LSD Vs Ket+LSD (Bottom) at 75min and at 300m. Visualizes the difference in connectivity ( ⁇ FC) specifically for connections with the Somatomotor network.
  • Positive and negative contrasts are rendered, respectively, in red and blue hues. Positive and negative contrasts are overlayed in the same panel. FC values that are very similar in both conditions are shown in gray hues. Moreover, thicker lines indicate stronger differences in FC between the two respective conditions. Nodes along the perimeter indicate left hemisphere cortical parcels of the CAP-NP parcellation. The guide to the different regions are listed on the right (this guide reprinted from Ji et al., NeuroImage (2019)).
  • FIG.150 illustrates contrasts for Cingulo-Opercular network ( ⁇ FC) between the Pla+LSD Vs Pla+Pla conditions (top) Ket+LSD Vs Pla+Pla (middle) and Pla+LSD Vs Ket+LSD (Bottom) at 75min and at 300m.
  • Positive and negative contrasts are rendered, respectively, in red and blue hues.
  • Positive and negative contrasts are overlayed in the same panel.
  • FC values that are very similar in both conditions are shown in gray hues. Moreover, thicker lines indicate stronger differences in FC between the two respective conditions.
  • FIG.151 illustrates contrasts for Dorsal-Attention network ( ⁇ FC) between the Pla+LSD Vs Pla+Pla conditions (top) Ket+LSD Vs Pla+Pla (middle) and Pla+LSD Vs Ket+LSD (Bottom) at 75min and at 300m.
  • ⁇ FC Dorsal-Attention network
  • FIG.152 illustrates contrasts for Language network ( ⁇ FC) between the Pla+LSD Vs Pla+Pla conditions (top) Ket+LSD Vs Pla+Pla (middle) and Pla+LSD Vs Ket+LSD (Bottom) at 75min and at 300m. Visualizes the difference in connectivity ( ⁇ FC) specifically for connections with the Language network.
  • ⁇ FC Language network
  • Positive and negative contrasts are rendered, respectively, in red and blue hues. Positive and negative contrasts are overlayed in the same panel. FC values that are very similar in both conditions are shown in gray hues. Moreover, thicker lines indicate stronger differences in FC between the two respective conditions. Nodes along the perimeter indicate left hemisphere cortical parcels of the CAP-NP parcellation. The guide to the different regions are listed on the right (this guide reprinted from Ji et al., NeuroImage (2019)).
  • FIG.153 illustrates contrasts for Frontoparietal network ( ⁇ FC) between the Pla+LSD Vs Pla+Pla conditions (top) Ket+LSD Vs Pla+Pla (middle) and Pla+LSD Vs Ket+LSD (Bottom) at 75min and at 300m.
  • Positive and negative contrasts are rendered, respectively, in red and blue hues.
  • Positive and negative contrasts are overlayed in the same panel.
  • FC values that are very similar in both conditions are shown in gray hues.
  • thicker lines indicate stronger differences in FC between the two respective conditions. Nodes along the perimeter indicate left hemisphere cortical parcels of the CAP-NP parcellation.
  • FIG.154 illustrates contrasts for Auditory network ( ⁇ FC) between the Pla+LSD Vs Pla+Pla conditions (top) Ket+LSD Vs Pla+Pla (middle) and Pla+LSD Vs Ket+LSD (Bottom) at 75min and at 300m.
  • ⁇ FC Auditory network
  • Positive and negative contrasts are rendered, respectively, in red and blue hues.
  • Positive and negative contrasts are overlayed in the same panel.
  • FC values that are very similar in both conditions are shown in gray hues. Moreover, thicker lines indicate stronger differences in FC between the two respective conditions.
  • FIG.155 illustrates contrasts for Default network ( ⁇ FC) between the Pla+LSD Vs Pla+Pla conditions (top) Ket+LSD Vs Pla+Pla (middle) and Pla+LSD Vs Ket+LSD (Bottom) at 75min and at 300m.
  • ⁇ FC Default network
  • FIG.156 illustrates contrasts for Posterior-Multimodal network ( ⁇ FC) between the Pla+LSD Vs Pla+Pla conditions (top) Ket+LSD Vs Pla+Pla (middle) and Pla+LSD Vs Ket+LSD (Bottom) at 75min and at 300m. Visualizes the difference in connectivity ( ⁇ FC) specifically for connections with the Posterior-Multimodal network.
  • Positive and negative contrasts are rendered, respectively, in red and blue hues. Positive and negative contrasts are overlayed in the same panel. FC values that are very similar in both conditions are shown in gray hues. Moreover, thicker lines indicate stronger differences in FC between the two respective conditions. Nodes along the perimeter indicate left hemisphere cortical parcels of the CAP-NP parcellation. The guide to the different regions are listed on the right (this guide reprinted from Ji et al., NeuroImage (2019)).
  • FIG.157 illustrates contrasts for Ventral-Multimodal ( ⁇ FC) between the Pla+LSD Vs Pla+Pla conditions (top) Ket+LSD Vs Pla+Pla (middle) and Pla+LSD Vs Ket+LSD (Bottom) at 75min and at 300m.
  • Positive and negative contrasts are rendered, respectively, in red and blue hues.
  • Positive and negative contrasts are overlayed in the same panel.
  • FC values that are very similar in both conditions are shown in gray hues.
  • thicker lines indicate stronger differences in FC between the two respective conditions. Nodes along the perimeter indicate left hemisphere cortical parcels of the CAP-NP parcellation.
  • FIG.158 illustrates contrasts for Orbito-Affective network ( ⁇ FC) between the Pla+LSD Vs Pla+Pla conditions (top) Ket+LSD Vs Pla+Pla (middle) and Pla+LSD Vs Ket+LSD (Bottom) at 75min and at 300m.
  • ⁇ FC Orbito-Affective network
  • FIG.159 illustrates ⁇ GBCz contrast maps at 75min. Left: Placebo+LSD Vs Ket+LSD ⁇ GBCz contrast map at 75 minutes. Right: The same ⁇ GBCz contrast map but thresholded such that only the bottom and top 10% of parcels are visualized.
  • FIG.160 illustrates Placebo+LSD vs Ket+LSD seed connectivity maps averaged across all parcels of the Visual (left) and Cingulo-Opercular (right) networks at 75 minutes. Seed connectivity contrasts averaged across parcels of the visual networks were strongly positive with superior temporal regions, whereas seed connectivity contrasts averaged across parcels of the cingulo-opercular network were strongly positive with visual regions and strongly negative with regions of the anterior cingulate cortex.
  • FIG.161 illustrates ⁇ GBCz contrast maps for Pla+LSD vs Ket+LSD at 300min Left: ⁇ GBCz contrast map at 300 minutes. Right: The same ⁇ GBCz contrast map but thresholded such that only the bottom and top 10% of parcels are visualized.
  • the Pla+LSD vs Ket+LSD contrast for the ⁇ GBCz metric shows strong positive contrasts in parcels of the visual network and strong negative contrasts in parcels of the cingulo-opercular network.
  • FIG.162 illustrates seed connectivity maps for Placebo+LSD vs Ket+LSD averaged across all parcels of the Visual (left) and Cingulo-Opercular networks (right) at 300 minutes.
  • FIG.163 illustrates ⁇ GBCz contrast map at different timepoints for Ket+LSD vs Pla+Pla. Top: ⁇ GBCz contrast map at 75 minutes (left) 300 minutes (middle), and 300 minutes vs 75 minutes (right). Bottom: The same ⁇ GBCz contrast maps but thresholded such that only the bottom and top 10% of parcels are visualized.
  • FIG.164 illustrates seed connectivity maps for Ket+LSD vs Pla+Pla averaged across all parcels of the Visual (left) and Cingulo-Opercular (right) networks between 75 minute and 300 minute timepoints. Seed connectivity contrasts averaged across parcels of visual networks were strongly positive with somatomotor and superior temporal regions (left). Seed connectivity contrasts averaged across parcels of the cingulo-opercular network were strongly positive with visual regions and strongly negative with somatomotor and anterior cingulate regions (right).
  • FIG.165 illustrates the pattern of changes between the 300 min and 75 min time point for Ket+LSD vs Pla+Pla contrast and the Pla+LSD vs Ket+LSD contrast at 75min for ⁇ FC (left) and for ⁇ GBCz (right).
  • the Pla+LSD vs Ket+LSD contrast, here at 75 min, is an approximation for the neural effect that Ket blocks.
  • the changes between the 75 min and 300 min time points for the Ket+LSD vs Pla+Pla contrast resemble this pattern, both at the level of ⁇ FC (left) and ⁇ GBCz (right).
  • FIG.166 illustrates alignment of gene expression maps with contrast maps.
  • FIG.167 shows XRPD analysis of small scale and scale-up samples of 1P-LSD Maleate.
  • FIG.168 shows XRPD patterns of 1P-LSD Maleate 1 and non-crystalline material.
  • FIG.169 shows a TGA profile of 1P-LSD Maleate non-crystalline material.
  • FIG.170 shows a mDSC profile of 1P-LSD Maleate non-crystalline material.
  • FIG.171 shows DVS analysis of 1P-LSD Maleate non-crystalline material.
  • FIG.172 shows DVS analysis of 1P-LSD Maleate non-crystalline material.
  • FIG.173 shows XRPD analysis of RH stressed non-crystalline material.
  • FIG.174 shows XRPD analysis of LSD Maleate 1.
  • FIG.175 shows XRPD patterns of LSD maleate polymorphs 1, 2, and 3.
  • FIG.176 shows XRPD patterns of LSD Maleate 2 before and after heating at 110 °C.
  • FIG.177 shows XRPD patterns of LSD Maleate 2 before and after heating at 110 °C.
  • FIG.178 shows a 1 H NMR spectrum of non-crystalline LSD maleate.
  • FIG.179 shows TGA and DSC profiles of non-crystalline LSD maleate.
  • FIG.180 shows a mDSC profile of non-crystalline LSD maleate.
  • FIG.181 shows a mDSC profile of non-crystalline LSD maleate.
  • FIG.182 shows DVS analysis of non-crystalline LSD maleate.
  • FIG.183 shows an overlay plot of XRPD patterns: salt screen experiments for 1-acetyl LSD.
  • FIG.184 shows an overlay plot of the XRPD pattern calculated from single-crystal data (1-acetyl LSD phosphate salt-cocrystal) with a pattern obtained for 1-acetyl LSD phosphate (bulk sample).
  • FIG.185 shows overlay plot of XRPD patterns: precipitation (pcn) vs. grinding.
  • FIG.186 shows an overlay of DSC and TGA data for non-crystalline 1A-LSD tosylate salt.
  • FIG.187 shows modulated DSC analysis for non-crystalline 1A-LSD tosylate salt: 1 st step (not shown): heating to desolvate at 70° C.
  • FIG.188 shows modulated DSC analysis for non-crystalline 1A-LSD tosylate salt: 1 st step (not shown): heating to desolvate at 90° C.
  • FIG.189 shows modulated DSC analysis for non-crystalline 1A-LSD tosylate salt: no prior heating step to remove volatiles.
  • FIG.190 shows overlay of DSC and TGA data for non-crystalline 1A-LSD tosylate salt.
  • FIG.191 Modulated DSC analysis for non-crystalline 1A-LSD tosylate salt: hermetically sealed pan with laser pinhole.
  • FIG.192 shows Modulated DSC analysis for non-crystalline 1A-LSD tosylate salt: hermetically sealed pan (no pinhole).
  • FIG.193 shows an XRPD pattern of non-crystalline 1A-LSD tosylate.
  • FIG.194 shows a 1 H NMR spectrum of non-crystalline 1A-LSD tosylate salt.
  • FIG.195 shows a XRPD pattern of non-crystalline LSD maleate.
  • FIG.196 shows a 1 H NMR of non-crystalline 1P-LSD maleate.
  • FIG.197 illustrate dose-dependent effects of a single i.p. injection of LSD (0.1 or 0.32 mg/kg) and saline on head-twitch responses in mice.
  • Data is represented as a bar chart
  • Data is represented as a bar chart
  • Data is represented as a bar chart
  • Data is represented as a graph.
  • Data is represented as a bar chart
  • Data is represented as a graph
  • FIG.211 provides a calculated XRPD diffractogram of 1A-LSD Phosphate Form A.
  • FIG.212 provides a calculated XRPD diffractogram of 1A-LSD Gentisate Form A
  • FIG.213 provides a calculated XRPD diffractogram of 1A-LSD Freebase Form
  • FIG.214 provides overlaid XRPD diffractograms of the XRPD of LSD Maleate Form 1 calculated from single crystal data (top trace) with a pattern obtained from bulk material (bottom trace).
  • DETAILED DESCRIPTION Definitions The following explanations of terms and methods are provided to better describe the present disclosure and to guide those of ordinary skill in the art in the practice of the present disclosure.
  • the singular forms “a,” “an,” and “the” refer to one or more than one, unless the context clearly dictates otherwise.
  • administering refers to any suitable mode of administration, including, oral administration, administration as a suppository, topical contact, parenteral, intravenous, intraperitoneal, intramuscular, intralesional, intranasal or subcutaneous administration, intrathecal administration, or the implantation of a slow-release device e.g., a mini-osmotic pump, to the subject.
  • a slow-release device e.g., a mini-osmotic pump
  • “Lysergic acid diethylamide” refers to the compound (6aR,9R)-N,N-diethyl-7-methyl- 6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide.
  • the compound may also be referred to as lysergide, D-lysergic acid diethylamide, N,N-diethyllysergamide, or LSD.
  • Lysergic acid diethylamide “1-Acetyl LSD” refers to the compound (6aR,9R)-4-acetyl-N,N-diethyl-7-methyl- 6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide.
  • the compound may also be referred to as 1-acetyllysergic acid diethylamide, D-1-acetyl lysergic acid diethylamide, 1-acetyl-N,N- diethyllysergamide, or 1-acetyl-LSD.
  • 2-Bromolysergic acid diethyl amide refers to the compound (6aR,9R)-5-bromo-N,N- diethyl-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide.
  • the compound may also be referred to as bromolysergide, bromolysergic acid diethylamide, D-2-bromolysergic acid diethylamide, 2-bromo-LSD or 2-Br-LSD.
  • 2-Bromolysergic acid diethyl amide 2-bromo-LSD
  • 1P-LSD refers to the compound (6aR,9R)-N,N-diethyl-7-methyl-4-propanoyl-6,6a,8,9- tetrahydroindolo[4,3-fg]quinoline-9-carboxamide.
  • the compound may also be referred to as 1- propionyl-lysergic acid diethylamide, 1-propionyl LSD, or 1P-LAD.
  • Subject refers to an animal, such as a mammal, including, but not limited to, primates (e.g., humans), cows, sheep, goats, horses, dogs, cats, rabbits, rats, mice and the like. In certain embodiments, the subject is a human subject. “Therapeutically effective amount” or “therapeutically sufficient amount” or “effective or sufficient amount” refers to a dose that produces therapeutic effects for which it is administered.
  • the exact dose will depend on the purpose of the treatment, and will be ascertainable by one skilled in the art using known techniques (see, e.g., Lieberman, Pharmaceutical Dosage Forms (vols.1-3, 1992); Lloyd, The Art, Science and Technology of Pharmaceutical Compounding (1999); Pickar, Dosage Calculations (1999); and Remington: The Science and Practice of Pharmacy, 20th Edition, 2003, Gennaro, Ed., Lippincott, Williams & Wilkins).
  • the therapeutically effective dose can often be lower than the conventional therapeutically effective dose for non-sensitized cells.
  • Neurovascular plasticity refers to the ability of the brain to change its structure and/or function continuously throughout a subject’s life.
  • Brain disorder refers to a neurological disorder which affects the brain’s structure and function. Brain disorders can include, but are not limited to, Alzheimer’s, Parkinson’s disease, psychological disorder, depression, treatment resistant depression, addiction, anxiety, post- traumatic stress disorder, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, stroke, traumatic brain injury, and substance use disorder.
  • “Combination therapy” refers to a method of treating a disease or disorder, wherein two or more different pharmaceutical agents are administered in overlapping regimens so that the subject is simultaneously exposed to both agents.
  • the compounds of the present disclosure can be used in combination with other pharmaceutically active compounds.
  • the compounds of the disclosure can be administered simultaneously (as a single preparation or separate preparation) or sequentially to the other pharmaceutically active compound.
  • a combination therapy envisions administration of two or more pharmaceutical agents during a single cycle or course of therapy.
  • Neurotrophic factors refers to a family of soluble peptides or proteins which support the survival, growth, and differentiation of developing and mature neurons.
  • Modulate or “modulating” or “modulation” refers to an increase or decrease in the amount, quality, or effect of a particular activity, function or molecule.
  • agonists, partial agonists, antagonists, and allosteric modulators e.g., a positive allosteric modulator
  • G protein-coupled receptor e.g., 5HT2A
  • Agonism refers to the activation of a receptor or enzyme by a modulator, or agonist, to produce a biological response.
  • Ant refers to a modulator that binds to a receptor or enzyme and activates the receptor to produce a biological response.
  • 5HT 2A agonist can be used to refer to a compound that exhibits an EC50 with respect to 5HT2A activity of no more than about 100 mM.
  • the term “agonist” includes full agonists or partial agonists.
  • Full agonist refers to a modulator that binds to and activates a receptor with the maximum response that an agonist can elicit at the receptor.
  • Partial agonist refers to a modulator that binds to and activates a given receptor, but has partial efficacy, that is, less than the maximal response, at the receptor relative to a full agonist.
  • “Positive allosteric modulator” refers to a modulator that binds to a site distinct from the orthosteric binding site and enhances or amplifies the effect of an agonist. “Antagonism” refers to the inactivation of a receptor or enzyme by a modulator, or antagonist. Antagonism of a receptor, for example, is when a molecule binds to the receptor and does not allow activity to occur. “Antagonist” or “neutral antagonist” refers to a modulator that binds to a receptor or enzyme and blocks a biological response. An antagonist has no activity in the absence of an agonist or inverse agonist but can block the activity of either, causing no change in the biological response.
  • composition refers to a product comprising the specified ingredients in the specified amounts, as well as any product, which results, directly or indirectly, from combination of the specified ingredients in the specified amounts.
  • pharmaceutically acceptable it is meant the carrier, diluent or excipient must be compatible with the other ingredients of the formulation.
  • “Pharmaceutically acceptable excipient” refers to a substance that aids the administration of an active agent to and absorption by a subject.
  • Pharmaceutical excipients useful in the present disclosure include, but are not limited to, binders, fillers, disintegrants, lubricants, coatings, sweeteners, flavors and colors.
  • binders fillers, disintegrants, lubricants, coatings, sweeteners, flavors and colors.
  • Solid forms of lysergic acid diethylamide (LSD), 1-acetyl-LSD (1A- LSD), 1-propionyl-LSD (1P-LSD), and 2-bromo-LSD (2-Br-LSD) that are useful to treat various disorders, such as brain disorders.
  • methods for making the solid forms of LSD, 1-acetyl-LSD, 1-propionyl-LSD, and/or 2-bromo-LSD and methods of administering a solid forms of LSD, 1-acetyl-LSD, 1-propionyl-LSD, and/or 2-bromo-LSD.
  • the solid form of the compound is a crystalline form of LSD, 1- acetyl-LSD, 1-propionyl-LSD, or 2-bromo-LSD.
  • the solid form of the compound is a salt of the compound.
  • the solid form of LSD, 1-acetyl- LSD, 1-propionyl-LSD, or 2-bromo-LSD is a polymorph of LSD, 1-acetyl-LSD, 1-propionyl- LSD, or 2-bromo-LSD, such as a polymorph of the free base compound or a polymorph of the salt.
  • the solid form of the compound is a crystalline salt form of the compound, such as an acid addition salt form.
  • the solid form of LSD comprises a salt of LSD. Suitable salts include a pharmaceutically acceptable salt of LSD. In some embodiments, the salt is not a hydrochloride salt of LSD. In some embodiments, the solid form of 1-acetyl LSD comprises a salt of 1-acetyl LSD. Suitable salts include a pharmaceutically acceptable salt of 1-acetyl LSD. In some embodiments, the salt is not a hydrochloride salt of 1-acetyl LSD. In some embodiments, the solid form of 2-bromo-LSD comprises a salt of 2-bromo-LSD. Suitable salts include a pharmaceutically acceptable salt of 2-bromo-LSD.
  • the salt is not a hydrochloride salt of 2-bromo-LSD.
  • the solid form of 1P-LSD comprises a salt of 1P-LSD.
  • Suitable salts include a pharmaceutically acceptable salt of 1P-LSD.
  • the salt is not a hydrochloride salt of 1P-LSD.
  • the salt of LSD, 1-acetyl-LSD, 1-propionyl-LSD, or 2-bromo-LSD may be formed from a suitable pharmaceutically acceptable acid, including, without limitation, inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, and the like, as well as organic acids such as formic acid, acetic acid, trifluoroacetic acid, propionic acid, glycolic acid, pyruvic acid, oxalic acid, maleic acid, malonic acid, succinic acid, tartaric acid, citric acid, benzoic acid, cinnamic acid, mandelic acid, benzene sulfonic acid, isethionic acid, methanesulfonic acid, ethanesulfonic acid, p-toluenesulfonic acid, salicylic acid, xinafoic acid and the like.
  • inorganic acids such as hydrochloric acid, hydrobro
  • the salt of LSD, 1-acetyl-LSD, 1-propionyl-LSD, and/or 2-bromo- LSD may be formed from a suitable pharmaceutically acceptable base, including, without limitation, inorganic bases such as sodium, potassium, lithium, ammonium, calcium, magnesium, iron, zinc, copper, manganese, aluminum salts and the like.
  • Salts derived from pharmaceutically acceptable organic bases include, but are not limited to, salts of primary, secondary, and tertiary amines, substituted amines including naturally occurring substituted amines, cyclic amines and basic ion exchange resins, such as isopropylamine, trimethylamine, diethylamine, triethylamine, tripropylamine, tris(hydroxymethyl)aminomethane (Tris), ethanolamine, 2- dimethylaminoethanol, 2-diethylaminoethanol, dicyclohexylamine, lysine, arginine, histidine, caffeine, procaine, hydrabamine, choline, betaine, ethylenediamine, glucosamine, methylglucamine, theobromine, purines, piperazine, piperidine, N-ethylpiperidine, polyamine resins, and the like.
  • Tris tris(hydroxymethyl)aminomethane
  • ethanolamine 2- dimethylaminoethanol
  • the salt may be formed using an acid from Table 1.
  • the acid is not hydrochloric acid.
  • the acid salts of LSD, 1-acetyl-LSD, 1-propionyl-LSD, or 2-bromo-LSD disclosed herein can have any suitable stoichiometric ratio of acid to LSD, 1-acetyl-LSD, 1-propionyl- LSD, or 2-bromo-LSD.
  • the molar ratio of acid to LSD, 1-acetyl-LSD, 1- propionyl-LSD, or 2-bromo-LSD is from about 0.4 to about 2.2, such as forms wherein the salt has a stoichiometric ratio of acid to LSD, 1-acetyl-LSD, 1-propionyl-LSD, or 2-bromo-LSD of from about 0.5 to about 2, such as about 0.5, about 1 or about 2.
  • Solid forms Some embodiments of LSD, 1-acetyl-LSD, 1-propionyl-LSD, and/or 2-bromo-LSD of the present disclosure are in a solid form.
  • the solid form may be a crystalline form or an amorphous form.
  • the solid form is a crystalline form, such as a polymorph.
  • the solid form of LSD, 1-acetyl-LSD, 1-propionyl-LSD, and/or 2-bromo-LSD is a salt.
  • the solid form of LSD, 1-acetyl-LSD, 1- propionyl-LSD, and/or 2-bromo-LSD is an acid addition salt.
  • the salt is a 0.5:1 LSD, 1- acetyl-LSD, 1-propionyl-LSD, or 2-bromo-LSD:counterion salt. In some embodiments, the salt is a 1:0.5 LSD, 1-acetyl-LSD, 1-propionyl-LSD, or 2-bromo-LSD. In some embodiments, the salt is a 3:1 LSD, 1-acetyl-LSD, 1-propionyl-LSD, or 2-bromo-LSD.
  • the salt is a 1:3 LSD, 1-acetyl-LSD, 1-propionyl-LSD, or 2-bromo-LSD
  • the solid form is a crystalline salt form of the compound.
  • solid forms of LSD, 1-acetyl-LSD, 1-propionyl-LSD, and/or 2-bromo-LSD such as crystalline forms including salt and non-salt crystalline forms of LSD, 1-acetyl-LSD, 1-propionyl-LSD, and/or 2-bromo-LSD, may exist in more than one crystal form. Such different forms are referred to as polymorphs.
  • the disclosed compounds are particular polymorphs of LSD, 1-acetyl-LSD, 1- propionyl-LSD, and/or 2-bromo-LSD or LSD, 1-acetyl-LSD, 1-propionyl-LSD, and/or 2-bromo- LSD salts.
  • the crystalline polymorphs are characterized herein by XRPD signals. All XRPD signals described herein are in ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD, 1-acetyl-LSD, 1-propionyl-LSD, and/or 2- bromo-LSD disclosed herein is selected to be a crystalline form, such as a particular polymorph of a crystalline form of LSD, 1-acetyl-LSD, 1-propionyl-LSD, and/or 2-bromo-LSD that provides one or more desired properties.
  • the crystalline form offers advantages over the amorphous form of the molecule.
  • the disclosed polymorph offers improved properties as compared to another polymorph of LSD, 1-acetyl-LSD, 1-propionyl-LSD, and/or 2-bromo-LSD.
  • the LSD, 1-acetyl-LSD, 1-propionyl-LSD, and/or 2- bromo-LSD may be a salt or free base compound.
  • the one or more desired properties may include, but are not limited to, physical properties, including but not limited to, melting point, glass transition temperature, flowability, and/or stability, such as thermal stability, mechanical stability, shelf life, stability against polymorphic transition, etc.; chemical properties, such as, but not limited to, hygroscopic properties, solubility in water and/or organic solvents, reactivity, compatibility with excipients and/or delivery vehicles; and/or pharmacokinetic properties, such as, but not limited to, bioavailability, absorption, distribution, metabolism, excretion, toxicity including cytotoxicity, dissolution rate, and/or half-life.
  • the desired polymorph may be produced by techniques known to persons of ordinary skill in the art. Such techniques include, but are not limited to, crystallization in particular solvents and/or at particular temperatures, supersaturation, using a precipitation agent, such as a salt, glycol, alcohol, etc., co-crystallization, lyophilization, spray drying, freeze drying, and/or complexing with an inert agent.
  • a precipitation agent such as a salt, glycol, alcohol, etc.
  • co-crystallization such as a salt, glycol, alcohol, etc.
  • lyophilization such as a salt, glycol, alcohol, etc.
  • spray drying such as g., freeze drying, and/or complexing with an inert agent.
  • Solid forms of LSD, 1P-LSD, 1A-LSD, and 2-Br-LSD LSD Freebase Form A solid forms of LSD freebase Form A, e.g., crystalline forms of LSD freebase Form A.
  • the LSD freebase Form A XRPD pattern is substantially similar to that shown in any one of FIGs.1 or 46.
  • the LSD freebase Form A 1 H NMR spectrum is substantially similar to that shown in FIG.87.
  • the LSD freebase Form A TGA profile is substantially similar to that shown in FIG.88.
  • the LSD freebase Form A DSC profile is substantially similar to that shown in FIG.88.
  • the solid form of LSD is crystalline LSD freebase Form A characterized by two, or three XRPD signals selected from the group consisting of 7.3 °2 ⁇ , 16.3 °2 ⁇ , and 17.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by XRPD signals at 7.3 °2 ⁇ , 16.3 °2 ⁇ , and 17.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.3 °2 ⁇ , 16.3 °2 ⁇ , 17.3 °2 ⁇ , 20.2 °2 ⁇ , and 25.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by XRPD signals at 7.3 °2 ⁇ , 16.3 °2 ⁇ , 17.3 °2 ⁇ , 20.2 °2 ⁇ , and 25.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by two, or three XRPD signals selected from the group consisting of 7.3 °2 ⁇ , 11.5 °2 ⁇ , and 13.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by XRPD signals at 7.3 °2 ⁇ , 11.5 °2 ⁇ , and 13.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.3 °2 ⁇ , 11.5 °2 ⁇ , 13.2 °2 ⁇ , 16.3 °2 ⁇ , and 17.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by XRPD signals at 7.3 °2 ⁇ , 11.5 °2 ⁇ , 13.2 °2 ⁇ , 16.3 °2 ⁇ , and 17.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.3 °2 ⁇ , 16.3 °2 ⁇ , 17.3 °2 ⁇ , 20.2 °2 ⁇ , and 25.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by XRPD signals at 7.3 °2 ⁇ , 16.3 °2 ⁇ , 17.3 °2 ⁇ , 20.2 °2 ⁇ , and 25.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.3 °2 ⁇ , 16.3 °2 ⁇ , 17.3 °2 ⁇ , 20.2 °2 ⁇ , 25.0 °2 ⁇ , 16.0 °2 ⁇ , and 23.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by XRPD signals at 7.3 °2 ⁇ , 16.3 °2 ⁇ , 17.3 °2 ⁇ , 20.2 °2 ⁇ , and 25.0 °2 ⁇ , 16.0 °2 ⁇ , and 23.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.3 °2 ⁇ , 16.3 °2 ⁇ , 17.3 °2 ⁇ , 20.2 °2 ⁇ , 25.0 °2 ⁇ , 16.0 °2 ⁇ , 23.3 °2 ⁇ , 22.7 °2 ⁇ , 19.4 °2 ⁇ and 13.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by XRPD signals at 7.3 °2 ⁇ , 16.3 °2 ⁇ , 17.3 °2 ⁇ , 20.2 °2 ⁇ , 25.0 °2 ⁇ , 16.0 °2 ⁇ , 23.3 °2 ⁇ , 22.7 °2 ⁇ , 19.4 °2 ⁇ and 13.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD freebase Form A is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, or twenty-eight XRPD signals selected from those set forth in Table 2. Table 2.
  • the solid form of LSD is crystalline LSD freebase Form A characterized by two, or three XRPD signals selected from the group consisting of 7.3 °2 ⁇ , 11.6 °2 ⁇ , and 13.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by XRPD signals at 7.3 °2 ⁇ , 11.6 °2 ⁇ , and 13.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.3 °2 ⁇ , 11.6 °2 ⁇ , 13.3 °2 ⁇ , 16.3 °2 ⁇ , and 17.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by XRPD signals at 7.3 °2 ⁇ , 11.6 °2 ⁇ , 13.3 °2 ⁇ , 16.3 °2 ⁇ , and 17.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by two, or three XRPD signals selected from the group consisting of 7.3 °2 ⁇ , 17.4 °2 ⁇ , and 16.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by XRPD signals at 7.3 °2 ⁇ , 17.4 °2 ⁇ , and 16.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.3 °2 ⁇ , 17.4 °2 ⁇ , 16.3 °2 ⁇ , 20.2 °2 ⁇ , and 25.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by XRPD signals at 7.3 °2 ⁇ , 17.4 °2 ⁇ , 16.3 °2 ⁇ , 20.2 °2 ⁇ , and 25.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.3 °2 ⁇ , 17.4 °2 ⁇ , 16.3 °2 ⁇ , 20.2 °2 ⁇ , 25.1 °2 ⁇ , 23.4 °2 ⁇ , and 22.8 °2 ⁇ and 16.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by XRPD signals at 7.3 °2 ⁇ , 17.4 °2 ⁇ , 16.3 °2 ⁇ , 20.2 °2 ⁇ , 25.1 °2 ⁇ , 23.4 °2 ⁇ , 22.8 °2 ⁇ , and 16.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.3 °2 ⁇ , 17.4 °2 ⁇ , 16.3 °2 ⁇ , 20.2 °2 ⁇ , 25.1 °2 ⁇ , 23.4 °2 ⁇ , 22.8 °2 ⁇ , 16.0 °2 ⁇ , 13.3 °2 ⁇ and 22.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form A characterized by XRPD signals at 7.3 °2 ⁇ , 17.4 °2 ⁇ , 16.3 °2 ⁇ , 20.2 °2 ⁇ , 25.1 °2 ⁇ , 23.4 °2 ⁇ , 22.8 °2 ⁇ , 16.0 °2 ⁇ , 13.3 °2 ⁇ and 22.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD freebase Form A is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, or thirty-four XRPD signals selected from those set forth in Table 3.
  • Table 3 XRPD Signals for LSD Freebase Form A LSD Form A LSD Freebase Form B
  • the present disclosure provides solid forms of LSD freebase Form B, e.g., crystalline forms of LSD freebase Form B.
  • the LSD freebase Form B XRPD pattern is substantially similar to that shown in FIG.12.
  • the LSD freebase Form B TGA profile is substantially similar to that shown in FIG.118.
  • the LSD freebase Form B DSC profile is substantially similar to that shown in FIG.118.
  • the solid form of LSD is crystalline LSD freebase Form B characterized by two, or three XRPD signals selected from the group consisting of 7.5 °2 ⁇ , 9.8 °2 ⁇ , and 13.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form B characterized by XRPD signals at 7.5 °2 ⁇ , 9.8 °2 ⁇ , and 13.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form B characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.5 °2 ⁇ , 9.8 °2 ⁇ , 13.4 °2 ⁇ , 15.9 °2 ⁇ , and 17.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form B characterized by XRPD signals at 7.5 °2 ⁇ , 9.8 °2 ⁇ , 13.4 °2 ⁇ , 15.9 °2 ⁇ , and 17.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form B characterized by two, or three XRPD signals selected from the group consisting of 15.9 °2 ⁇ , 19.3 °2 ⁇ , and 13.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form B characterized by XRPD signals at 15.9 °2 ⁇ , 19.3 °2 ⁇ , and 13.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form B characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.9 °2 ⁇ , 19.3 °2 ⁇ , 13.4 °2 ⁇ , 17.8 °2 ⁇ , and 23.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form B characterized by XRPD signals at 15.9 °2 ⁇ , 19.3 °2 ⁇ , 13.4 °2 ⁇ , 17.8 °2 ⁇ , and 23.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form B characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.9 °2 ⁇ , 19.3 °2 ⁇ , 13.4 °2 ⁇ , 17.8 °2 ⁇ , 23.0 °2 ⁇ , 21.0 °2 ⁇ , and 25.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form B characterized by XRPD signals at 15.9 °2 ⁇ , 19.3 °2 ⁇ , 13.4 °2 ⁇ , 17.8 °2 ⁇ , 23.0 °2 ⁇ , 21.0 °2 ⁇ , and 25.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form B characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.9 °2 ⁇ , 19.3 °2 ⁇ , 13.4 °2 ⁇ , 17.8 °2 ⁇ , 23.0 °2 ⁇ , 21.0 °2 ⁇ , 25.6 °2 ⁇ , 9.8 °2 ⁇ , 7.5 °2 ⁇ and 27.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form B characterized by XRPD signals at 15.9 °2 ⁇ , 19.3 °2 ⁇ , 13.4 °2 ⁇ , 17.8 °2 ⁇ , 23.0 °2 ⁇ , 21.0 °2 ⁇ , 25.6 °2 ⁇ , 9.8 °2 ⁇ , 7.5 °2 ⁇ and 27.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD freebase Form B is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty- five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, or thirty-two XRPD signals selected from those set forth in Table 4.
  • Table 4 XRPD Signals for LSD Freebase Form B
  • the present disclosure provides solid forms of LSD freebase Form C, e.g., crystalline forms of LSD freebase Form C.
  • an XRPD pattern of LSD freebase Form C XRPD pattern that includes XRPD signals that correspond to aspartic acid is provided in FIG. 13.
  • the solid form of LSD is crystalline LSD freebase Form C characterized by two,or three XRPD signals selected from the group consisting of 7.9 °2 ⁇ , 8.5 °2 ⁇ , and 12.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form C characterized by XRPD signals at 7.9 °2 ⁇ , 8.5 °2 ⁇ , and 12.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form C characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.9 °2 ⁇ , 8.5 °2 ⁇ , 12.5 °2 ⁇ , 15.8 °2 ⁇ , and 17.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form C characterized by XRPD signals at 7.9 °2 ⁇ , 8.5 °2 ⁇ , 12.5 °2 ⁇ , 15.8 °2 ⁇ , and 17.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form C characterized by two, or three XRPD signals selected from the group consisting of 7.9 °2 ⁇ , 15.8 °2 ⁇ , and 8.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form C characterized by XRPD signals at 7.9 °2 ⁇ , 15.8 °2 ⁇ , and 8.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form C characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.9 °2 ⁇ , 15.8 °2 ⁇ , 8.5 °2 ⁇ , 17.6 °2 ⁇ , and 37.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form C characterized by XRPD signals at 7.9 °2 ⁇ , 15.8 °2 ⁇ , 8.5 °2 ⁇ , 17.6 °2 ⁇ , and 37.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form C characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.9 °2 ⁇ , 15.8 °2 ⁇ , 8.5 °2 ⁇ , 17.6 °2 ⁇ , 37.3 °2 ⁇ , and 12.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form C characterized by XRPD signals at 7.9 °2 ⁇ , 15.8 °2 ⁇ , 8.5 °2 ⁇ , 17.6 °2 ⁇ , 37.3 °2 ⁇ , and 12.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form C is characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.9 °2 ⁇ , 15.8 °2 ⁇ , 8.5 °2 ⁇ , 17.6 °2 ⁇ , 37.3 °2 ⁇ , 12.5 °2 ⁇ , 22.6 °2 ⁇ , 21.0 °2 ⁇ and 18.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD freebase Form C characterized by XRPD signals at 7.9 °2 ⁇ , 15.8 °2 ⁇ , 8.5 °2 ⁇ , 17.6 °2 ⁇ , 37.3 °2 ⁇ , 12.5 °2 ⁇ , 22.6 °2 ⁇ , 21.0 °2 ⁇ and 18.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD freebase Form C is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, or twenty-one XRPD signals selected from those set forth in Table 5.
  • Table 5 XRPD Signals for LSD Freebase Form C
  • LSD Gentisate Form 1 the present disclosure provides solid forms of gentisate salts of LSD, e.g., crystalline forms of LSD gentisate Form 1.
  • the LSD gentisate Form 1 XRPD pattern is substantially similar to that shown in FIG.3
  • the solid form of LSD is crystalline LSD gentisate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 5.5 °2 ⁇ , 6.8 °2 ⁇ , and 11.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 1 characterized by XRPD signals at 5.5 °2 ⁇ , 6.8 °2 ⁇ , and 11.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.5 °2 ⁇ , 6.8 °2 ⁇ , 11.2 °2 ⁇ , 13.2 °2 ⁇ , and 14.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 1 characterized by XRPD signals at 5.5 °2 ⁇ , 6.8 °2 ⁇ , 11.2 °2 ⁇ , 13.2 °2 ⁇ , and 14.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 16.0 °2 ⁇ , 20.8 °2 ⁇ , and 19.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 1 characterized by XRPD signals at 16.0 °2 ⁇ , 20.8 °2 ⁇ , and 19.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.0 °2 ⁇ , 20.8 °2 ⁇ , 19.5 °2 ⁇ , 19.2 °2 ⁇ , and 15.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 1 characterized by XRPD signals at 16.0 °2 ⁇ , 20.8 °2 ⁇ , 19.5 °2 ⁇ , 19.2 °2 ⁇ , and 15.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.0 °2 ⁇ , 20.8 °2 ⁇ , 19.5 °2 ⁇ , 19.2 °2 ⁇ , 15.2 °2 ⁇ , 5.5 °2 ⁇ , and 16.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 1 characterized by XRPD signals at 16.0 °2 ⁇ , 20.8 °2 ⁇ , 19.5 °2 ⁇ , 19.2 °2 ⁇ , 15.2 °2 ⁇ , 5.5 °2 ⁇ , and 16.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.0 °2 ⁇ , 20.8 °2 ⁇ , 19.5 °2 ⁇ , 19.2 °2 ⁇ , 15.2 °2 ⁇ , 5.5 °2 ⁇ , 16.5 °2 ⁇ , 15.6 °2 ⁇ , 14.1 °2 ⁇ and 22.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 1 characterized by XRPD signals at 16.0 °2 ⁇ , 20.8 °2 ⁇ , 19.5 °2 ⁇ , 19.2 °2 ⁇ , 15.2 °2 ⁇ , 5.5 °2 ⁇ , 16.5 °2 ⁇ , 15.6 °2 ⁇ , 14.1 °2 ⁇ and 22.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD gentisate Form 1 is characterized by two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five or thirty-six XRPD signals selected from those set forth in Table 6.
  • the present disclosure provides solid forms of gentisate salts of LSD, e.g., crystalline forms of LSD gentisate Form 2.
  • the LSD gentisate Form 2 XRPD pattern is substantially similar to that shown in FIG.4.
  • the LSD gentisate Form 2 1 H NMR spectrum is substantially similar to that shown in FIG.116.
  • the LSD gentisate Form 2 TGA profile is substantially similar to that shown in FIG.117.
  • the LSD gentisate Form 2 DSC profile is substantially similar to that shown in FIG.117.
  • the solid form of LSD is crystalline LSD gentisate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 6.8 °2 ⁇ , 9.7 °2 ⁇ , and 11.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 2 characterized by XRPD signals at 6.8 °2 ⁇ , 9.7 °2 ⁇ , 11.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.8 °2 ⁇ , 9.7 °2 ⁇ , 11.7 °2 ⁇ , 13.6 °2 ⁇ , and 15.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 2 characterized by XRPD signals at 6.8 °2 ⁇ , 9.7 °2 ⁇ , 11.7 °2 ⁇ , 13.6 °2 ⁇ , and 15.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 19.2 °2 ⁇ , 25.1 °2 ⁇ , and 20.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 2 characterized by XRPD signals at 19.2 °2 ⁇ , 25.1 °2 ⁇ , and 20.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.2 °2 ⁇ , 25.1 °2 ⁇ , 20.1 °2 ⁇ , 22.8 °2 ⁇ and 2.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 2 characterized by XRPD signals at 19.2 °2 ⁇ , 25.1 °2 ⁇ , 20.1 °2 ⁇ , 22.8 °2 ⁇ and 2.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.2 °2 ⁇ , 25.1 °2 ⁇ , 20.1 °2 ⁇ , 22.8 °2 ⁇ , 2.7 °2 ⁇ , 13.6 °2 ⁇ , and 20.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 2 characterized by XRPD signals at 19.2 °2 ⁇ , 25.1 °2 ⁇ , 20.1 °2 ⁇ , 22.8 °2 ⁇ , 2.7 °2 ⁇ , 13.6 °2 ⁇ , and 20.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.2 °2 ⁇ , 25.1 °2 ⁇ , 20.1 °2 ⁇ , 22.8 °2 ⁇ , 2.7 °2 ⁇ , 13.6 °2 ⁇ , 20.4 °2 ⁇ , 22.2 °2 ⁇ , 3.2 °2 ⁇ and 22.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 2 characterized by XRPD signals at 19.2 °2 ⁇ , 25.1 °2 ⁇ , 20.1 °2 ⁇ , 22.8 °2 ⁇ , 2.7 °2 ⁇ , 13.6 °2 ⁇ , 20.4 °2 ⁇ , 22.2 °2 ⁇ , 3.2 °2 ⁇ and 22.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD gentisate Form 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four , thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty- one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty- fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six, fifty-seven, fifty-eight, fifty- nine, sixty, sixty-one, or sixty-two XRPD signals selected from those set forth in Table 7.
  • the present disclosure provides solid forms of gentisate salts of LSD, e.g., crystalline forms of LSD gentisate Form 3.
  • the LSD gentisate Form 3 XRPD pattern is substantially similar to that shown in any one of FIGs.15 or 47.
  • the LSD gentisate Form 3 1 H NMR spectrum is substantially similar to that shown in FIG.85.
  • the LSD gentisate Form 3 TGA profile is substantially similar to that shown in FIG.86.
  • the LSD gentisate Form 3 DSC profile is substantially similar to that shown in FIG.86.
  • the solid form of LSD is crystalline LSD gentisate Form 3characterized by two, or three XRPD signals selected from the group consisting of 7.0 °2 ⁇ , 10.0 °2 ⁇ , and 11.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by XRPD signals at 7.0 °2 ⁇ , 10.0 °2 ⁇ , and 11.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.0 °2 ⁇ , 10.0 °2 ⁇ , 11.1 °2 ⁇ , 13.2 °2 ⁇ , and 13.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by XRPD signals at 7.0 °2 ⁇ , 10.0 °2 ⁇ , 11.1 °2 ⁇ , 13.2 °2 ⁇ , and 13.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by two, or three XRPD signals selected from the group consisting of 19.0 °2 ⁇ , 7.0 °2 ⁇ , and 20.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by XRPD signals at 19.0 °2 ⁇ , 7.0 °2 ⁇ , and 20.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.0 °2 ⁇ , 7.0 °2 ⁇ , 20.4 °2 ⁇ , 13.9 °2 ⁇ and 22.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by XRPD signals at 19.0 °2 ⁇ , 7.0 °2 ⁇ , 20.4 °2 ⁇ , 13.9 °2 ⁇ and 22.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.0 °2 ⁇ , 7.0 °2 ⁇ , 20.4 °2 ⁇ , 13.9 °2 ⁇ , 22.7 °2 ⁇ , 13.2 °2 ⁇ , and 15.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by XRPD signals at 19.0 °2 ⁇ , 7.0 °2 ⁇ , 20.4 °2 ⁇ , 13.9 °2 ⁇ , 22.7 °2 ⁇ , 13.2 °2 ⁇ , and 15.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.0 °2 ⁇ , 7.0 °2 ⁇ , 20.4 °2 ⁇ , 13.9 °2 ⁇ , 22.7 °2 ⁇ , 13.2 °2 ⁇ , 15.5 °2 ⁇ , 25.8 °2 ⁇ , 10.0 °2 ⁇ and 20.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by XRPD signals at 19.0 °2 ⁇ , 7.0 °2 ⁇ , 20.4 °2 ⁇ , 13.9 °2 ⁇ , 22.7 °2 ⁇ , 13.2 °2 ⁇ , 15.5 °2 ⁇ , 25.8 °2 ⁇ , 10.0 °2 ⁇ and 20.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD gentisate Form 3 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty- one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty, or fifty-one XRPD signals selected from those set forth in Table 8.
  • the present disclosure provides solid forms of glycolate salts of LSD, e.g., crystalline forms of LSD glycolate Form 1.
  • the LSD glycolate Form 1XRPD pattern is substantially similar to that shown in FIG.10.
  • the solid form of LSD is crystalline LSD glycolate Form 1characterized by two, or three XRPD signals selected from the group consisting of 4.3 °2 ⁇ , 7.3 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD glycolate Form 1characterized by XRPD signals at 4.3 °2 ⁇ , 7.3 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD glycolate Form 1characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.3 °2 ⁇ , 5.3 °2 ⁇ , 7.3 °2 ⁇ , 8.5 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is LSD glycolate Form 1characterized by XRPD signals at 4.3 °2 ⁇ , 5.3 °2 ⁇ , 7.3 °2 ⁇ , 8.5 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD glycolate Form 1characterized by two, or three XRPD signals selected from the group consisting of 4.3 °2 ⁇ , 7.3 °2 ⁇ , and 5.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD glycolate Form 1characterized by XRPD signals at 4.3 °2 ⁇ , 7.3 °2 ⁇ , and 5.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD glycolate Form 1characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.3 °2 ⁇ , 7.3 °2 ⁇ , 5.3 °2 ⁇ , 18.0 °2 ⁇ and 8.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD glycolate Form 1characterized by XRPD signals at 4.3 °2 ⁇ , 7.3 °2 ⁇ , 5.3 °2 ⁇ , 18.0 °2 ⁇ and 8.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD glycolate Form 1characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.3 °2 ⁇ , 7.3 °2 ⁇ , 5.3 °2 ⁇ , 18.0 °2 ⁇ , 8.5 °2 ⁇ , 17.7 °2 ⁇ , and 16.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD glycolate Form 1characterized by XRPD signals at 4.3 °2 ⁇ , 7.3 °2 ⁇ , 5.3 °2 ⁇ , 18.0 °2 ⁇ , 8.5 °2 ⁇ , 17.7 °2 ⁇ , and 16.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD glycolate Form 1characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.3 °2 ⁇ , 7.3 °2 ⁇ , 5.3 °2 ⁇ , 18.0 °2 ⁇ , 8.5 °2 ⁇ , 17.7 °2 ⁇ , 16.2 °2 ⁇ , 11.6 °2 ⁇ , 19.2 °2 ⁇ and 20.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD glycolate Form 1characterized by XRPD signals at 4.3 °2 ⁇ , 7.3 °2 ⁇ , 5.3 °2 ⁇ , 18.0 °2 ⁇ , 8.5 °2 ⁇ , 17.7 °2 ⁇ , 16.2 °2 ⁇ , 11.6 °2 ⁇ , 19.2 °2 ⁇ and 20.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD glycolate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, or twenty-three XRPD signals selected from those set forth in Table 9.
  • Table 9 XRPD Signals for LSD Glycolate Form 1 LSD HCl
  • the present disclosure provides solid forms of hydrochloride salts of LSD, e.g., crystalline forms of LSD hydrochloride .
  • the LSD hydrochloride XRPD pattern is substantially similar to that shown in any one of FIG.48.
  • the solid form of LSD is crystalline LSD hydrochloride characterized by two, or three XRPD signals selected from the group consisting of 10.2 °2 ⁇ , 25.5 °2 ⁇ , and 31.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD hydrochloride characterized by XRPD signals at 10.2 °2 ⁇ , 25.5 °2 ⁇ , and 31.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD hydrochloride characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.0 °2 ⁇ , 7.0 °2 ⁇ , 10.2 °2 ⁇ , 14.3 °2 ⁇ , 18.0 °2 ⁇ , 25.5 °2 ⁇ , and 31.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is LSD hydrochloride characterized by XRPD signals at 5.0 °2 ⁇ , 7.0 °2 ⁇ , 10.2 °2 ⁇ , 14.3 °2 ⁇ , 18.0 °2 ⁇ , 25.5 °2 ⁇ , and 31.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD hydrochloride characterized by two, or three XRPD signals selected from the group consisting of 5.0 °2 ⁇ , 25.5 °2 ⁇ , and 7.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD hydrochloride characterized by XRPD signals at 5.0 °2 ⁇ , 25.5 °2 ⁇ , and 7.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD hydrochloride characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.0 °2 ⁇ , 25.5 °2 ⁇ , 7.0 °2 ⁇ , 18.0 °2 ⁇ and 10.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD hydrochloride characterized by XRPD signals at 5.0 °2 ⁇ , 25.5 °2 ⁇ , 7.0 °2 ⁇ , 18.0 °2 ⁇ and 10.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD hydrochloride characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.0 °2 ⁇ , 25.5 °2 ⁇ , 7.0 °2 ⁇ , 18.0 °2 ⁇ , 10.2 °2 ⁇ , 14.3 °2 ⁇ , and 31.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD hydrochloride characterized by XRPD signals at 5.0 °2 ⁇ , 25.5 °2 ⁇ , 7.0 °2 ⁇ , 18.0 °2 ⁇ , 10.2 °2 ⁇ , 14.3 °2 ⁇ , and 31.72 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD hydrochloride is characterized by one, two, three, four, five, six, or seven XRPD signals selected from those set forth in Table 10.
  • the present disclosure provides solid forms of L-tartrate salts of LSD, e.g., crystalline forms of LSD L-tartrate .
  • the LSD L-tartrate XRPD pattern is substantially similar to that shown in FIG.49.
  • the solid form of LSD is crystalline LSD L-tartrate characterized by two, or three XRPD signals selected from the group consisting of 15.6 °2 ⁇ , 17.1 °2 ⁇ , and 17.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD L-tartrate characterized by XRPD signals at 15.6 °2 ⁇ , 17.1 °2 ⁇ , and 17.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD L-tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.5 °2 ⁇ , 15.6 °2 ⁇ , 17.1 °2 ⁇ , 17.9 °2 ⁇ , 18.7 °2 ⁇ , 19.2 °2 ⁇ , 20.2 °2 ⁇ , 20.7 °2 ⁇ , and 22.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is LSD L-tartrate characterized by XRPD signals at 9.5 °2 ⁇ , 15.6 °2 ⁇ , 17.1 °2 ⁇ , 17.9 °2 ⁇ , 18.7 °2 ⁇ , 19.2 °2 ⁇ , 20.2 °2 ⁇ , 20.7 °2 ⁇ , and 22.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD L-tartrate characterized by two, or three XRPD signals selected from the group consisting of 17.9 °2 ⁇ , 15.6 °2 ⁇ , and 18.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD L-tartrate characterized by XRPD signals at 17.9 °2 ⁇ , 15.6 °2 ⁇ , and 18.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD L-tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.9 °2 ⁇ , 15.6 °2 ⁇ , 18.7 °2 ⁇ , 20.7 °2 ⁇ and 19.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD L-tartrate characterized by XRPD signals at 17.9 °2 ⁇ , 15.6 °2 ⁇ , 18.7 °2 ⁇ , 20.7 °2 ⁇ and 19.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD L-tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.9 °2 ⁇ , 15.6 °2 ⁇ , 18.7 °2 ⁇ , 20.7 °2 ⁇ , 19.2 °2 ⁇ , 20.2 °2 ⁇ , and 22.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD L-tartrate characterized by XRPD signals at 17.9 °2 ⁇ , 15.6 °2 ⁇ , 18.7 °2 ⁇ , 20.7 °2 ⁇ , 19.2 °2 ⁇ , 20.2 °2 ⁇ , and 22.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD L-tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.9 °2 ⁇ , 15.6 °2 ⁇ , 18.7 °2 ⁇ , 20.7 °2 ⁇ , 19.2 °2 ⁇ , 20.2 °2 ⁇ , 22.2 °2 ⁇ , 17.1 °2 ⁇ , and 9.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD L-tartrate characterized by XRPD signals at 17.9 °2 ⁇ , 15.6 °2 ⁇ , 18.7 °2 ⁇ , 20.7 °2 ⁇ , 19.2 °2 ⁇ , 20.2 °2 ⁇ , 22.2 °2 ⁇ , 17.1 °2 ⁇ , and 9.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD L-tartrate is characterized by one, two, three, four, five, six, seven, eight, or nine XRPD signals selected from those set forth in Table 11.
  • the present disclosure provides non-crystalline LSD maleate salts.
  • the non-crystalline LSD maleate salt is characterized by a glass transition temperature of about 88.0 °C.
  • the non-crystalline LSD maleate salt is characterized by a DSC endotherm of about 61 oC.
  • the non-crystalline LSD maleate salt is a unary LSD maleate salt.
  • the non-crystalline LSD maleate salt is characterized by a TG thermogram showing about 1.9% weight loss from ambient to 109 oC.
  • the non-crystalline LSD maleate salt is characterized by a 1 H NMR spectra substantially similar to that shown in FIG.178. In some embodiments, the non- crystalline LSD maleate salt is characterized by a TGA profile substantially similar to that shown in FIG.179. In some embodiments, the non-crystalline LSD maleate salt is characterized by a DSC profile substantially similar to that shown in FIG.179. In some embodiments, the non- crystalline LSD maleate salt is characterized by a mDSC profile substantially similar to that shown in FIG.180 or 181. In some embodiments, the non-crystalline LSD maleate salt is characterized by a DVS profile substantially similar to that shown in FIG.182.
  • the present disclosure provides solid forms of Maleate Form 1 salts of LSD, e.g., crystalline forms of LSD Maleate Form 1.
  • the LSD Maleate Form 1 XRPD pattern is substantially similar to that shown in any one of FIGs.6 or 50.
  • the LSD Maleate Form 1 1 H NMR spectrum is substantially similar to that shown in FIG.83 or 97.
  • the LSD Maleate Form 1 TGA profile is substantially similar to that shown in any one of FIGs.84 or 98.
  • the LSD Maleate Form 1 DSC profile is substantially similar to that shown in any one of FIGs.84 or 98.
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 8.9 °2 ⁇ , 10.8 °2 ⁇ , and 13.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by XRPD signals at 8.9 °2 ⁇ , 10.8 °2 ⁇ , and 13.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2 ⁇ , 10.8 °2 ⁇ , 13.0 °2 ⁇ , 14.3 °2 ⁇ , and 15.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is LSD Maleate Form 1 characterized by XRPD signals at 8.9 °2 ⁇ , 10.8 °2 ⁇ , 13.0 °2 ⁇ , 14.3 °2 ⁇ , and 15.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 8.9 °2 ⁇ , 25.0 °2 ⁇ , and 16.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by XRPD signals at 8.9 °2 ⁇ , 25.0 °2 ⁇ , and 16.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2 ⁇ , 25.0 °2 ⁇ , 16.3 °2 ⁇ , 20.1 °2 ⁇ and 18.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by XRPD signals at 8.9 °2 ⁇ , 25.0 °2 ⁇ , 16.3 °2 ⁇ , 20.1 °2 ⁇ and 18.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2 ⁇ , 25.0 °2 ⁇ , 16.3 °2 ⁇ , 20.1 °2 ⁇ , 18.8 °2 ⁇ , 17.4 °2 ⁇ , and 21.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by XRPD signals at 8.9 °2 ⁇ , 25.0 °2 ⁇ , 16.3 °2 ⁇ , 20.1 °2 ⁇ , 18.8 °2 ⁇ , 17.4 °2 ⁇ , and 21.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2 ⁇ , 25.0 °2 ⁇ , 16.3 °2 ⁇ , 20.1 °2 ⁇ , 18.8 °2 ⁇ , 17.4 °2 ⁇ , 21.5 °2 ⁇ , 21.6 °2 ⁇ , 14.3 °2 ⁇ and 17.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by XRPD signals at 8.9 °2 ⁇ , 25.0 °2 ⁇ , 16.3 °2 ⁇ , 20.1 °2 ⁇ , 18.8 °2 ⁇ , 17.4 °2 ⁇ , 21.5 °2 ⁇ , 21.6 °2 ⁇ , 14.3 °2 ⁇ and 17.8 °2 ⁇ ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD Maleate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty- one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty, fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six, fifty-seven, fifty-eight, fifty- nine, sixty, sixty-one, sixty-two or sixty-three XRPD signals selected from those set forth in Table 12.
  • the present disclosure provides solid forms of Maleate Form 2 salts of LSD, e.g., crystalline forms of LSD Maleate Form 2.
  • the LSD Maleate Form 2 XRPD pattern is substantially similar to that shown in FIG.51.
  • the solid form of LSD is crystalline LSD Maleate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 6.4 °2 ⁇ , 7.7 °2 ⁇ , and 10.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 2 characterized by XRPD signals at 6.4 °2 ⁇ , 7.7 °2 ⁇ , and 10.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.4 °2 ⁇ , 7.7 °2 ⁇ , 9.6 °2 ⁇ , 10.0 °2 ⁇ , and 15.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is LSD Maleate Form 2 characterized by XRPD signals at 6.4 °2 ⁇ , 7.7 °2 ⁇ , 9.6 °2 ⁇ , 10.0 °2 ⁇ , and 15.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 18.5 °2 ⁇ , 11.6 °2 ⁇ , and 15.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 2 characterized by XRPD signals at18.5 °2 ⁇ , 11.6 °2 ⁇ , and 15.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 18.5 °2 ⁇ , 11.6 °2 ⁇ , 15.5 °2 ⁇ , 17.3 °2 ⁇ and 7.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 2 characterized by XRPD signals at 18.5 °2 ⁇ , 11.6 °2 ⁇ , 15.5 °2 ⁇ , 17.3 °2 ⁇ , and 7.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 18.5 °2 ⁇ , 11.6 °2 ⁇ , 15.5 °2 ⁇ , 17.3 °2 ⁇ , 7.7 °2 ⁇ , 10.0 °2 ⁇ , and 20.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 2 characterized by XRPD signals at 18.5 °2 ⁇ , 11.6 °2 ⁇ , 15.5 °2 ⁇ , 17.3 °2 ⁇ , 7.7 °2 ⁇ , 10.0 °2 ⁇ , and 20.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 18.5 °2 ⁇ , 11.6 °2 ⁇ , 15.5 °2 ⁇ , 17.3 °2 ⁇ , 7.7 °2 ⁇ , 10.0 °2 ⁇ , 20.1 °2 ⁇ , 19.3 °2 ⁇ , 23.4 °2 ⁇ and 16.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 2 characterized by XRPD signals at 18.5 °2 ⁇ , 11.6 °2 ⁇ , 15.5 °2 ⁇ , 17.3 °2 ⁇ , 7.7 °2 ⁇ , 10.0 °2 ⁇ , 20.1 °2 ⁇ , 19.3 °2 ⁇ , 23.4 °2 ⁇ and 16.2 °2 ⁇ ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD Maleate Form 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, or thirty-seven XRPD signals selected from those set forth in Table 13.
  • the present disclosure provides solid forms of Maleate Form 3 salts of LSD, e.g., crystalline forms of LSD Maleate Form 3.
  • the LSD Maleate Form 3 XRPD pattern is substantially similar to that shown in FIG.52.
  • the solid form of LSD is crystalline LSD Maleate Form 3 characterized by two, or three XRPD signals selected from the group consisting of 8.0 °2 ⁇ , 8.9 °2 ⁇ , and 9.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 3 characterized by XRPD signals at 8.0 °2 ⁇ , 8.9 °2 ⁇ , and 9.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.2 °2 ⁇ , 8.0 °2 ⁇ , 8.9 °2 ⁇ , 9.8 °2 ⁇ , and 12.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is LSD Maleate Form 3 characterized by XRPD signals at 5.2 °2 ⁇ , 8.0 °2 ⁇ , 8.9 °2 ⁇ , 9.8 °2 ⁇ , and 12.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 3 characterized by two, or three XRPD signals selected from the group consisting of 8.9 °2 ⁇ , 17.8 °2 ⁇ , and 15.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 3 characterized by XRPD signals at 8.9 °2 ⁇ , 17.8 °2 ⁇ , and 15.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2 ⁇ , 17.8 °2 ⁇ , 15.9 °2 ⁇ , 9.8 °2 ⁇ and 13.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 3 characterized by XRPD signals at 8.9 °2 ⁇ , 17.8 °2 ⁇ , 15.9 °2 ⁇ , 9.8 °2 ⁇ and 13.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2 ⁇ , 17.8 °2 ⁇ , 15.9 °2 ⁇ , 9.8 °2 ⁇ , 13.0 °2 ⁇ , 24.3 °2 ⁇ , and 5.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 3 characterized by XRPD signals at 8.9 °2 ⁇ , 17.8 °2 ⁇ , 15.9 °2 ⁇ , 9.8 °2 ⁇ , 13.0 °2 ⁇ , 24.3 °2 ⁇ , and 5.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2 ⁇ , 17.8 °2 ⁇ , 15.9 °2 ⁇ , 9.8 °2 ⁇ , 13.0 °2 ⁇ , 24.3 °2 ⁇ , 5.2 °2 ⁇ , 8.0 °2 ⁇ , 12.1 °2 ⁇ and 22.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 3 characterized by XRPD signals at 8.9 °2 ⁇ , 17.8 °2 ⁇ , 15.9 °2 ⁇ , 9.8 °2 ⁇ , 13.0 °2 ⁇ , 24.3 °2 ⁇ , 5.2 °2 ⁇ , 8.0 °2 ⁇ , 12.1 °2 ⁇ and 22.5 °2 ⁇ ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD Maleate Form 3 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, or fourteen XRPD signals selected from those set forth in Table 14.
  • the present disclosure provides solid forms of Mesylate Form 1 salts of LSD, e.g., crystalline forms of LSD Mesylate Form 1.
  • the LSD Mesylate Form 1 XRPD pattern is substantially similar to that shown in FIG.7.
  • the LSD Mesylate Form 1 1 H NMR spectrum is substantially similar to that shown in FIG.106.
  • the LSD Mesylate Form 1 TGA profile is substantially similar to that shown in FIG.107.
  • the LSD Mesylate Form 1 DSC profile is substantially similar to that shown in FIG.107.
  • the solid form of LSD is crystalline LSD Mesylate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 7.5 °2 ⁇ , 9.9 °2 ⁇ , and 11.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mesylate Form 1 characterized by XRPD signals at 7.5 °2 ⁇ , 9.9 °2 ⁇ , and 11.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mesylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.5 °2 ⁇ , 9.9 °2 ⁇ , 11.3 °2 ⁇ , 13.5 °2 ⁇ , and 15.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is LSD Mesylate Form 1 characterized by XRPD signals at 7.5 °2 ⁇ , 9.9 °2 ⁇ , 11.3 °2 ⁇ , 13.5 °2 ⁇ , and 15.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mesylate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 15.9 °2 ⁇ , 19.6 °2 ⁇ , and 22.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mesylate Form 1 characterized by XRPD signals at 15.9 °2 ⁇ , 19.6 °2 ⁇ , and 22.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mesylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.9 °2 ⁇ , 19.6 °2 ⁇ , 22.6 °2 ⁇ , 13.5 °2 ⁇ and 7.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mesylate Form 1 characterized by XRPD signals at 15.9 °2 ⁇ , 19.6 °2 ⁇ , 22.6 °2 ⁇ , 13.5 °2 ⁇ and 7.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mesylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.9 °2 ⁇ , 19.6 °2 ⁇ , 22.6 °2 ⁇ , 13.5 °2 ⁇ , 7.5 °2 ⁇ , 20.8 °2 ⁇ , and 25.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mesylate Form 1 characterized by XRPD signals at 15.9 °2 ⁇ , 19.6 °2 ⁇ , 22.6 °2 ⁇ , 13.5 °2 ⁇ , 7.5 °2 ⁇ , 20.8 °2 ⁇ , and 25.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mesylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.9 °2 ⁇ , 19.6 °2 ⁇ , 22.6 °2 ⁇ , 13.5 °2 ⁇ , 7.5 °2 ⁇ , 20.8 °2 ⁇ , 25.3 °2 ⁇ , 24.5 °2 ⁇ , 11.3 °2 ⁇ and 17.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mesylate Form 1 characterized by XRPD signals at 15.9 °2 ⁇ , 19.6 °2 ⁇ , 22.6 °2 ⁇ , 13.5 °2 ⁇ , 7.5 °2 ⁇ , 20.8 °2 ⁇ , 25.3 °2 ⁇ , 24.5 °2 ⁇ , 11.3 °2 ⁇ and 17.8 °2 ⁇ ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD Mesylate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, or thirty-five XRPD signals selected from those set forth in Table 15.
  • Table 15 XRPD Signals for LSD Mesylate Form 1 LSD Mucate Form 1
  • the present disclosure provides solid forms of Mucate Form 1 salts of LSD, e.g., crystalline forms of LSD Mucate Form 1.
  • the LSD Mucate Form 1 XRPD pattern is substantially similar to that shown in FIG.8.
  • the LSD Mucate Form 1 1 H NMR spectrum is substantially similar to that shown in FIG.101.
  • the solid form of LSD is crystalline LSD Mucate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 3.9 °2 ⁇ , 7.2 °2 ⁇ , and 7.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mucate Form 1 characterized by XRPD signals at 3.9 °2 ⁇ , 7.2 °2 ⁇ , and 7.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mucate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.9 °2 ⁇ , 7.2 °2 ⁇ , 7.8 °2 ⁇ , 14.2 °2 ⁇ , and 15.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is LSD Mucate Form 1 characterized by XRPD signals at 3.9 °2 ⁇ , 7.2 °2 ⁇ , 7.8 °2 ⁇ , 14.2 °2 ⁇ , and 15.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mucate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 7.8 °2 ⁇ , 14.2 °2 ⁇ , and 3.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mucate Form 1 characterized by XRPD signals at 7.8 °2 ⁇ , 14.2 °2 ⁇ , and 3.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mucate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.8 °2 ⁇ , 14.2 °2 ⁇ , 3.9 °2 ⁇ , 7.2 °2 ⁇ and 18.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mucate Form 1 characterized by XRPD signals at 7.8 °2 ⁇ , 14.2 °2 ⁇ , 3.9 °2 ⁇ , 7.2 °2 ⁇ and 18.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mucate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.8 °2 ⁇ , 14.2 °2 ⁇ , 3.9 °2 ⁇ , 7.2 °2 ⁇ , 18.0 °2 ⁇ , 15.7 °2 ⁇ , and 14.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mucate Form 1 characterized by XRPD signals at 7.8 °2 ⁇ , 14.2 °2 ⁇ , 3.9 °2 ⁇ , 7.2 °2 ⁇ , 18.0 °2 ⁇ , 15.7 °2 ⁇ , and 14.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mucate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.8 °2 ⁇ , 14.2 °2 ⁇ , 3.9 °2 ⁇ , 7.2 °2 ⁇ , 18.0 °2 ⁇ , 15.7 °2 ⁇ , 14.8 °2 ⁇ , 19.7 °2 ⁇ , 19.5 °2 ⁇ and 17.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Mucate Form 1 characterized by XRPD signals at 7.8 °2 ⁇ , 14.2 °2 ⁇ , 3.9 °2 ⁇ , 7.2 °2 ⁇ , 18.0 °2 ⁇ , 15.7 °2 ⁇ , 14.8 °2 ⁇ , 19.7 °2 ⁇ , 19.5 °2 ⁇ and 17.7 °2 ⁇ ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD Mucate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, or thirty-four XRPD signals selected from those set forth in Table 16.
  • Table 16 XRPD Signals for LSD Mucate Form 1 LSD Phosphate Form 1
  • the present disclosure provides solid forms of Phosphate Form 1 salts of LSD, e.g., crystalline forms of LSD Phosphate Form 1.
  • the LSD Phosphate Form 1 XRPD pattern is substantially similar to that shown in any one of FIGs.5 or 53.
  • the LSD Phosphate Form 1 1 H NMR spectrum is substantially similar to that shown in any one of FIGs 81 or 119..
  • the LSD Phosphate Form 1 TGA profile is substantially similar to that shown in any one of FIGs.82 or 120.
  • the LSD Phosphate Form 1 DSC profile is substantially similar to that shown in any one of FIGs.82 or 120.
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 7.9 °2 ⁇ , 8.6 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by XRPD signals at 7.9 °2 ⁇ , 8.6 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.9 °2 ⁇ , 8.6 °2 ⁇ , 11.6 °2 ⁇ , 12.9 °2 ⁇ , and 15.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is LSD Phosphate Form 1 characterized by XRPD signals at 7.9 °2 ⁇ , 8.6 °2 ⁇ , 11.6 °2 ⁇ , 12.9 °2 ⁇ , and 15.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 15.1 °2 ⁇ , 21.1 °2 ⁇ , and 8.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by XRPD signals at 15.1 °2 ⁇ , 21.1 °2 ⁇ , and 8.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.1 °2 ⁇ , 21.1 °2 ⁇ , 8.6 °2 ⁇ , 7.9 °2 ⁇ and 12.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by XRPD signals at 15.1 °2 ⁇ , 21.1 °2 ⁇ , 8.6 °2 ⁇ , 7.9 °2 ⁇ and 12.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.1 °2 ⁇ , 21.1 °2 ⁇ , 8.6 °2 ⁇ , 7.9 °2 ⁇ , 12.9 °2 ⁇ , 22.0 °2 ⁇ , and 18.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by XRPD signals at 15.1 °2 ⁇ , 21.1 °2 ⁇ , 8.6 °2 ⁇ , 7.9 °2 ⁇ , 12.9 °2 ⁇ , 22.0 °2 ⁇ , and 18.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.1 °2 ⁇ , 21.1 °2 ⁇ , 8.6 °2 ⁇ , 7.9 °2 ⁇ , 12.9 °2 ⁇ , 22.0 °2 ⁇ , 18.6 °2 ⁇ , 23.0 °2 ⁇ , 26.8 °2 ⁇ and 25.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by XRPD signals at 15.1 °2 ⁇ , 21.1 °2 ⁇ , 8.6 °2 ⁇ , 7.9 °2 ⁇ , 12.9 °2 ⁇ , 22.0 °2 ⁇ , 18.6 °2 ⁇ , 23.0 °2 ⁇ , 26.8 °2 ⁇ and 25.9 °2 ⁇ ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD Phosphate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty- four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, or thirty XRPD signals selected from those set forth in Table 17.
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 7.9 °2 ⁇ , 8.6 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by XRPD signals at 7.9 °2 ⁇ , 8.6 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.9 °2 ⁇ , 8.6 °2 ⁇ , 11.6 °2 ⁇ , 12.9 °2 ⁇ , and 15.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is LSD Phosphate Form 1 characterized by XRPD signals at 7.9 °2 ⁇ , 8.6 °2 ⁇ , 11.6 °2 ⁇ , 12.9 °2 ⁇ , and 15.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 15.1 °2 ⁇ , 21.1 °2 ⁇ , and 8.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by XRPD signals at 15.1 °2 ⁇ , 21.1 °2 ⁇ , and 8.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.1 °2 ⁇ , 21.1 °2 ⁇ , 8.6 °2 ⁇ , 18.1 °2 ⁇ and 7.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by XRPD signals at 15.1 °2 ⁇ , 21.1 °2 ⁇ , 8.6 °2 ⁇ , 18.1 °2 ⁇ , and 7.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.1 °2 ⁇ , 21.1 °2 ⁇ , 8.6 °2 ⁇ , 18.1 °2 ⁇ , 7.9 °2 ⁇ , 12.9 °2 ⁇ , and 18.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by XRPD signals at 15.1 °2 ⁇ , 21.1 °2 ⁇ , 8.6 °2 ⁇ , 18.1 °2 ⁇ , 7.9 °2 ⁇ , 12.9 °2 ⁇ , and 18.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.1 °2 ⁇ , 21.1 °2 ⁇ , 8.6 °2 ⁇ , 18.1 °2 ⁇ , 7.9 °2 ⁇ , 12.9 °2 ⁇ , 18.6 °2 ⁇ , 21.9 °2 ⁇ , 23.1 °2 ⁇ and 26.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Phosphate Form 1 characterized by XRPD signals at 15.1 °2 ⁇ , 21.1 °2 ⁇ , 8.6 °2 ⁇ , 18.1 °2 ⁇ , 7.9 °2 ⁇ , 12.9 °2 ⁇ , 18.6 °2 ⁇ , 21.9 °2 ⁇ , 23.1 °2 ⁇ and 26.9 °2 ⁇ ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD Phosphate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty- four, twenty-five, twenty-six, twenty-seven, or twenty-eight XRPD signals selected from those set forth in Table 18.
  • Table 18 XRPD Signals for LSD Phosphate Form 1 LSD Xinafoate Form 1
  • the present disclosure provides solid forms of Xinafoate Form 1 salts of LSD, e.g., crystalline forms of LSD Xinafoate Form 1.
  • the LSD Xinafoate Form 1 XRPD pattern is substantially similar to that shown in FIG.9.
  • the LSD Xinafoate Form 1 1 H NMR spectrum is substantially similar to that shown in FIG.121.
  • the LSD Xinafoate Form 1 TGA profile is substantially similar to that shown in FIG.122.
  • the LSD Xinafoate Form 1 DSC profile is substantially similar to that shown in FIG.122.
  • the solid form of LSD is crystalline LSD Xinafoate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 6.0 °2 ⁇ , 9.8 °2 ⁇ , and 14.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 1 characterized by XRPD signals at 6.0 °2 ⁇ , 9.8 °2 ⁇ , and 14.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.0 °2 ⁇ , 9.8 °2 ⁇ , 14.3 °2 ⁇ , 15.8 °2 ⁇ , and 16.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is LSD Xinafoate Form 1 characterized by XRPD signals at 6.0 °2 ⁇ , 9.8 °2 ⁇ , 14.3 °2 ⁇ , 15.8 °2 ⁇ , and 16.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 19.5 °2 ⁇ , 20.9 °2 ⁇ , and 16.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 1 characterized by XRPD signals at 19.5 °2 ⁇ , 20.9 °2 ⁇ , and 16.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.5 °2 ⁇ , 20.9 °2 ⁇ , 16.7 °2 ⁇ , 15.8 °2 ⁇ and 14.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 1 characterized by XRPD signals at 19.5 °2 ⁇ , 20.9 °2 ⁇ , 16.7 °2 ⁇ , 15.8 °2 ⁇ , and 14.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.5 °2 ⁇ , 20.9 °2 ⁇ , 16.7 °2 ⁇ , 15.8 °2 ⁇ , 14.9 °2 ⁇ , 6.0 °2 ⁇ , and 14.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 1 characterized by XRPD signals at 19.5 °2 ⁇ , 20.9 °2 ⁇ , 16.7 °2 ⁇ , 15.8 °2 ⁇ , 14.9 °2 ⁇ , 6.0 °2 ⁇ , and 14.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.5 °2 ⁇ , 20.9 °2 ⁇ , 16.7 °2 ⁇ , 15.8 °2 ⁇ , 14.9 °2 ⁇ , 6.0 °2 ⁇ , 14.3 °2 ⁇ , 9.8 °2 ⁇ , 24.6 °2 ⁇ and 26.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 1 characterized by XRPD signals at 19.5 °2 ⁇ , 20.9 °2 ⁇ , 16.7 °2 ⁇ , 15.8 °2 ⁇ , 14.9 °2 ⁇ , 6.0 °2 ⁇ , 14.3 °2 ⁇ , 9.8 °2 ⁇ , 24.6 °2 ⁇ and 26.1 °2 ⁇ ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD Xinafoate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty- four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty- two, or thirty-three XRPD signals selected from those set forth in Table 19.
  • Table 19 XRPD Signals for LSD Xinafoate Form 1 LSD Xinafoate Form 2
  • the present disclosure provides solid forms of Xinafoate Form 2 salts of LSD, e.g., crystalline forms of LSD Xinafoate Form 2.
  • the LSD Xinafoate Form 2 XRPD pattern is substantially similar to that shown in any one of FIGs.11 or 54.
  • the LSD Xinafoate Form 2 1 H NMR spectrum is substantially similar to that shown in FIG.79.
  • the LSD Xinafoate Form 2 TGA profile is substantially similar to that shown in FIG.80.
  • the LSD Xinafoate Form 2 DSC profile is substantially similar to that shown in FIG.80.
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 9.0 °2 ⁇ , 10.2 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by XRPD signals at 9.0 °2 ⁇ , 10.2 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.4 °2 ⁇ , 9.0 °2 ⁇ , 10.2 °2 ⁇ , 11.6 °2 ⁇ , and 13.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is LSD Xinafoate Form 2 characterized by XRPD signals at 7.4 °2 ⁇ , 9.0 °2 ⁇ , 10.2 °2 ⁇ , 11.6 °2 ⁇ , and 13.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 21.5 °2 ⁇ , 15.5 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by XRPD signals at 21.5 °2 ⁇ , 15.5 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 21.5 °2 ⁇ , 15.5 °2 ⁇ , 11.6 °2 ⁇ , 13.3 °2 ⁇ , and 18.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by XRPD signals at 21.5 °2 ⁇ , 15.5 °2 ⁇ , 11.6 °2 ⁇ , 13.3 °2 ⁇ , and 18.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 21.5 °2 ⁇ , 15.5 °2 ⁇ , 11.6 °2 ⁇ , 13.3 °2 ⁇ , 18.4 °2 ⁇ , 16.3 °2 ⁇ , and 24.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by XRPD signals at 21.5 °2 ⁇ , 15.5 °2 ⁇ , 11.6 °2 ⁇ , 13.3 °2 ⁇ , 18.4 °2 ⁇ , 16.3 °2 ⁇ , and 24.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 21.5 °2 ⁇ , 15.5 °2 ⁇ , 11.6 °2 ⁇ , 13.3 °2 ⁇ , 18.4 °2 ⁇ , 16.3 °2 ⁇ , 24.0 °2 ⁇ , 10.2 °2 ⁇ , 19.9 °2 ⁇ and 18.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by XRPD signals at 21.5 °2 ⁇ , 15.5 °2 ⁇ , 11.6 °2 ⁇ , 13.3 °2 ⁇ , 18.4 °2 ⁇ , 16.3 °2 ⁇ , 24.0 °2 ⁇ , 10.2 °2 ⁇ , 19.9 °2 ⁇ and 18.0 °2 ⁇ ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD Xinafoate Form 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty- four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty- two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty- nine, fifty, fifty-one, fifty-two, fifty-three, fifty-four, or fifty-five XRPD signals selected from those set forth in Table 20.
  • the present disclosure provides solid forms of Fumarate Form 1 salts of LSD, e.g., crystalline forms of LSD Fumarate Form 1.
  • the LSD Fumarate Form 1 XRPD pattern is substantially similar to that shown in FIG.2.
  • the solid form of LSD is crystalline LSD Fumarate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 8.8 °2 ⁇ , 10.0 °2 ⁇ , and 12.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 1 characterized by XRPD signals at 8.8 °2 ⁇ , 10.0 °2 ⁇ , and 12.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.8 °2 ⁇ , 10.0 °2 ⁇ , 12.3 °2 ⁇ , 21.3 °2 ⁇ , and 24.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is LSD Fumarate Form 1 characterized by XRPD signals at 8.8 °2 ⁇ , 10.0 °2 ⁇ , 12.3 °2 ⁇ , 21.3 °2 ⁇ , and 24.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 8.8 °2 ⁇ , 24.7 °2 ⁇ , and 21.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 1 characterized by XRPD signals at 8.8 °2 ⁇ , 24.7 °2 ⁇ , and 21.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.8 °2 ⁇ , 24.7 °2 ⁇ , 21.3 °2 ⁇ , 17.6 °2 ⁇ , and 22.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 1 characterized by XRPD signals at 8.8 °2 ⁇ , 24.7 °2 ⁇ , 21.3 °2 ⁇ , 17.6 °2 ⁇ , and 22.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.8 °2 ⁇ , 24.7 °2 ⁇ , 21.3 °2 ⁇ , 17.6 °2 ⁇ , 22.3 °2 ⁇ , 10.0 °2 ⁇ , and 17.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 1 characterized by XRPD signals at 8.8 °2 ⁇ , 24.7 °2 ⁇ , 21.3 °2 ⁇ , 17.6 °2 ⁇ , 22.3 °2 ⁇ , 10.0 °2 ⁇ , and 17.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.8 °2 ⁇ , 24.7 °2 ⁇ , 21.3 °2 ⁇ , 17.6 °2 ⁇ , 22.3 °2 ⁇ , 10.0 °2 ⁇ , 17.1 °2 ⁇ , 20.9 °2 ⁇ , 15.2 °2 ⁇ and 12.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 1 characterized by XRPD signals at 8.8 °2 ⁇ , 24.7 °2 ⁇ , 21.3 °2 ⁇ , 17.6 °2 ⁇ , 22.3 °2 ⁇ , 10.0 °2 ⁇ , 17.1 °2 ⁇ , 20.9 °2 ⁇ , 15.2 °2 ⁇ and 12.3 °2 ⁇ ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD Fumarate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, or nineteen XRPD signals selected from those set forth in Table 21.
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 8.9 °2 ⁇ , 10.8 °2 ⁇ , and 13.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1characterized by XRPD signals at 8.9 °2 ⁇ , 10.8 °2 ⁇ , and 13.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2 ⁇ , 10.8 °2 ⁇ , 13.0 °2 ⁇ , 14.3 °2 ⁇ , and 15.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is LSD Maleate Form 1 characterized by XRPD signals at 8.9 °2 ⁇ , 10.8 °2 ⁇ , 13.0 °2 ⁇ , 14.3 °2 ⁇ , and 15.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 8.9 °2 ⁇ , 16.3 °2 ⁇ , and 25.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by XRPD signals at 8.9 °2 ⁇ , 16.3 °2 ⁇ , and 25.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2 ⁇ , 16.3 °2 ⁇ , 25.0 °2 ⁇ , 20.1 °2 ⁇ , and 18.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by XRPD signals at 8.9 °2 ⁇ , 16.3 °2 ⁇ , 25.0 °2 ⁇ , 20.1 °2 ⁇ , and 18.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2 ⁇ , 16.3 °2 ⁇ , 25.0 °2 ⁇ , 20.1 °2 ⁇ , 18.7 °2 ⁇ , 21.6 °2 ⁇ , and 17.4°2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by XRPD signals at 8.9 °2 ⁇ , 16.3 °2 ⁇ , 25.0 °2 ⁇ , 20.1 °2 ⁇ , 18.7 °2 ⁇ , 21.6 °2 ⁇ , and 17.4°2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2 ⁇ , 16.3 °2 ⁇ , 25.0 °2 ⁇ , 20.1 °2 ⁇ , 18.7 °2 ⁇ , 21.6 °2 ⁇ , 17.4°2 ⁇ , 14.3°2 ⁇ , 17.8°2 ⁇ and 15.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Maleate Form 1 characterized by XRPD signals at 8.9 °2 ⁇ , 16.3 °2 ⁇ , 25.0 °2 ⁇ , 20.1 °2 ⁇ , 18.7 °2 ⁇ , 21.6 °2 ⁇ , 17.4°2 ⁇ , 14.3°2 ⁇ , 17.8°2 ⁇ and 15.5 ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD Maleate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, or forty-one XRPD signals selected from those set forth in Table 22.
  • the solid form of LSD maleate Form 1 is crystalline LSD maleate characterized by two or more, or three XRPD signals selected from the group consisting of 5.5 °2 ⁇ , 9.0 °2 ⁇ , and 13.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD maleate Form 1 is crystalline LSD maleate characterized by XRPD signals at 5.5 °2 ⁇ , 9.0 °2 ⁇ , and 13.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD maleate Form 1 is crystalline LSD maleate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.5 °2 ⁇ , 9.0 °2 ⁇ , 13.1 °2 ⁇ , 14.4 °2 ⁇ , and 15.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD maleate Form 1 is crystalline LSD maleate characterized by XRPD signals at 5.5 °2 ⁇ , 9.0 °2 ⁇ , 13.1 °2 ⁇ , 14.4 °2 ⁇ , and 15.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD maleate Form 1 is crystalline LSD maleate characterized by two or more, or three XRPD signals selected from the group consisting of 9.0 °2 ⁇ , 25.2 °2 ⁇ , and 20.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD maleate Form 1 is crystalline LSD maleate characterized by XRPD signals at 9.0 °2 ⁇ , 25.2 °2 ⁇ , and 20.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD maleate Form 1 is crystalline LSD maleate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.0 °2 ⁇ , 25.2 °2 ⁇ , 20.3 °2 ⁇ , 18.9 °2 ⁇ , and 17.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD maleate Form 1 is crystalline LSD maleate characterized by XRPD signals at 9.0 °2 ⁇ , 25.2 °2 ⁇ , 20.3 °2 ⁇ , 18.9 °2 ⁇ , and 17.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD maleate Form 1 is crystalline LSD maleate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.0 °2 ⁇ , 25.2 °2 ⁇ , 20.3 °2 ⁇ , 18.9 °2 ⁇ , 17.5 °2 ⁇ , 16.4 °2 ⁇ , and 21.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD maleate Form 1 is crystalline LSD maleate characterized by XRPD signals at 9.0 °2 ⁇ , 25.2 °2 ⁇ , 20.3 °2 ⁇ , 18.9 °2 ⁇ , 17.5 °2 ⁇ , 16.4 °2 ⁇ , and 21.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD maleate is crystalline LSD maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.0 °2 ⁇ , 25.2 °2 ⁇ , 20.3 °2 ⁇ , 18.9 °2 ⁇ , 17.5 °2 ⁇ , 16.4 °2 ⁇ , 21.7 °2 ⁇ , 21.8 °2 ⁇ , 14.4 °2 ⁇ , and 25.8°2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD maleate is crystalline LSD maleate Form 1 characterized by XRPD signals at 9.0 °2 ⁇ , 25.2 °2 ⁇ , 20.3 °2 ⁇ , 18.9 °2 ⁇ , 17.5 °2 ⁇ , 16.4 °2 ⁇ , 21.7 °2 ⁇ , 21.8 °2 ⁇ , 14.4 °2 ⁇ , and 25.8°2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD maleate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty- one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty, fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six, fifty-seven, fifty-eight, fifty- nine, sixty, sixty-one, sixty-two, sixty-three, sixty-four, sixty-five, sixty-six, sixty
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 8.9 °2 ⁇ , 11.6 °2 ⁇ , and 13.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by XRPD signals at 8.9 °2 ⁇ , 11.6 °2 ⁇ , and 13.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.9 °2 ⁇ , 11.6 °2 ⁇ , 13.2 °2 ⁇ , 21.4 °2 ⁇ , and 24.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is LSD Xinafoate Form 2 characterized by XRPD signals at 8.9 °2 ⁇ , 11.6 °2 ⁇ , 13.2 °2 ⁇ , 21.4 °2 ⁇ , and 24.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 21.4 °2 ⁇ , 31.7 °2 ⁇ , and 8.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by XRPD signals at 21.4 °2 ⁇ , 31.7 °2 ⁇ , and 8.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 21.4 °2 ⁇ , 31.7 °2 ⁇ , 8.9 °2 ⁇ , 15.5 °2 ⁇ , and 24.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by XRPD signals at 21.4 °2 ⁇ , 31.7 °2 ⁇ , 8.9 °2 ⁇ , 15.5 °2 ⁇ , and 24.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 21.4 °2 ⁇ , 31.7 °2 ⁇ , 8.9 °2 ⁇ , 15.5 °2 ⁇ , 24.0 °2 ⁇ , 18.3 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by XRPD signals at 21.4 °2 ⁇ , 31.7 °2 ⁇ , 8.9 °2 ⁇ , 15.5 °2 ⁇ , 24.0 °2 ⁇ , 18.3 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 21.4 °2 ⁇ , 31.7 °2 ⁇ , 8.9 °2 ⁇ , 15.5 °2 ⁇ , 24.0 °2 ⁇ , 18.3 °2 ⁇ , 11.6 °2 ⁇ , 10.2 °2 ⁇ , 16.2 °2 ⁇ and 13.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Xinafoate Form 2 characterized by XRPD signals at 21.4 °2 ⁇ , 31.7 °2 ⁇ , 8.9 °2 ⁇ , 15.5 °2 ⁇ , 24.0 °2 ⁇ , 18.3 °2 ⁇ , 11.6 °2 ⁇ , 10.2 °2 ⁇ , 16.2 °2 ⁇ and 13.2 °2 ⁇ ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD Xinafoate Form 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty- four, twenty-five, or twenty-six XRPD signals selected from those set forth in Table 23.
  • Table 23 XRPD Signals for LSD Xinafoate Form 2
  • the present disclosure provides solid forms of Fumarate Form 2 salts of LSD, e.g., crystalline forms of LSD Fumarate Form 2.
  • an XRPD pattern of LSD fumarate Form 2 that includes XRPD signals that correspond to LSD Fumarate Form 1 is provided in Fig.14.
  • the solid form of LSD is crystalline LSD Fumarate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 7.7 °2 ⁇ , 8.1 °2 ⁇ , and 11.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 2 characterized by XRPD signals at 7.7 °2 ⁇ , 8.1 °2 ⁇ , and 11.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.7 °2 ⁇ , 8.1 °2 ⁇ , 11.2 °2 ⁇ , 12.0 °2 ⁇ , and 14.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 2 characterized by XRPD signals at 7.7 °2 ⁇ , 8.1 °2 ⁇ , 11.2 °2 ⁇ , 12.0 °2 ⁇ , and 14.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 7.7 °2 ⁇ , 28.8 °2 ⁇ , and 22.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline Fumarate Form 2 characterized by XRPD signals at 7.7 °2 ⁇ , 28.8 °2 ⁇ , and 22.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.7 °2 ⁇ , 28.8 °2 ⁇ , 22.8 °2 ⁇ , 11.2 °2 ⁇ , and 8.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 2 characterized by XRPD signals at 7.7 °2 ⁇ , 28.8 °2 ⁇ , 22.8 °2 ⁇ , 11.2 °2 ⁇ , and 8.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.7 °2 ⁇ , 28.8 °2 ⁇ , 22.8 °2 ⁇ , 11.2 °2 ⁇ , 8.1 °2 ⁇ , 29.4 °2 ⁇ , and 21.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 2 characterized by XRPD signals at 7.7 °2 ⁇ , 28.8 °2 ⁇ , 22.8 °2 ⁇ , 11.2 °2 ⁇ , 8.1 °2 ⁇ , 29.4 °2 ⁇ , and 21.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.7 °2 ⁇ , 28.8 °2 ⁇ , 22.8 °2 ⁇ , 11.2 °2 ⁇ , 8.1 °2 ⁇ , 29.4 °2 ⁇ , 21.7 °2 ⁇ , 18.6 °2 ⁇ , 12.0 °2 ⁇ , and 14.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Form 2 characterized by XRPD signals at 7.7 °2 ⁇ , 28.8 °2 ⁇ , 22.8 °2 ⁇ , 11.2 °2 ⁇ , 8.1 °2 ⁇ , 29.4 °2 ⁇ , 21.7 °2 ⁇ , 18.6 °2 ⁇ , 12.0 °2 ⁇ , and 14.8 °2 ⁇ ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • Table 35 Table 35.
  • LSD Fumarate Forms 1 and 2 LSD Fumarate Forms 1 and 2
  • the present disclosure provides solid forms of Fumarate Forms 1 and 2 salts of LSD, e.g., crystalline forms of LSD Fumarate Forms 1 and 2.
  • the LSD Fumarate Forms 1 and 2 XRPD pattern is substantially similar to that shown in FIG.14.
  • the solid form of LSD is crystalline LSD Fumarate Forms 1 and 2 characterized by two, or three XRPD signals selected from the group consisting of 7.7 °2 ⁇ , 8.1 °2 ⁇ , and 10.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Forms 1 and 2 characterized by XRPD signals at 7.7 °2 ⁇ , 8.1 °2 ⁇ , and 10.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Forms 1 and 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.7 °2 ⁇ , 8.1 °2 ⁇ , 10.0 °2 ⁇ , 11.2 °2 ⁇ , and 12.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is LSD Fumarate Forms 1 and 2 characterized by XRPD signals at 7.7 °2 ⁇ , 8.1 °2 ⁇ , 10.0 °2 ⁇ , 11.2 °2 ⁇ , and 12.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Forms 1 and 2 characterized by two, or three XRPD signals selected from the group consisting of 7.7 °2 ⁇ , 28.8 °2 ⁇ , and 22.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Forms 1 and 2 characterized by XRPD signals at 7.7 °2 ⁇ , 28.8 °2 ⁇ , and 22.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Forms 1 and 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.7 °2 ⁇ , 28.8 °2 ⁇ , 22.8 °2 ⁇ , 21.3 °2 ⁇ , and 11.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Forms 1 and 2 characterized by XRPD signals at 7.7 °2 ⁇ , 28.8 °2 ⁇ , 22.8 °2 ⁇ , 21.3 °2 ⁇ , and 11.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Forms 1 and 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.7 °2 ⁇ , 28.8 °2 ⁇ , 22.8 °2 ⁇ , 21.3 °2 ⁇ , 11.2 °2 ⁇ , 8.1 °2 ⁇ , and 24.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Forms 1 and 2 characterized by XRPD signals at 7.7 °2 ⁇ , 28.8 °2 ⁇ , 22.8 °2 ⁇ , 21.3 °2 ⁇ , 11.2 °2 ⁇ , 8.1 °2 ⁇ , and 24.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Forms 1 and 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.7 °2 ⁇ , 28.8 °2 ⁇ , 22.8 °2 ⁇ , 21.3 °2 ⁇ , 11.2 °2 ⁇ , 8.1 °2 ⁇ , 24.7 °2 ⁇ , 29.4 °2 ⁇ , 21.7 °2 ⁇ and 18.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Fumarate Forms 1 and 2 characterized by XRPD signals at 7.7 °2 ⁇ , 28.8 °2 ⁇ , 22.8 °2 ⁇ , 21.3 °2 ⁇ , 11.2 °2 ⁇ , 8.1 °2 ⁇ , 24.7 °2 ⁇ , 29.4 °2 ⁇ , 21.7 °2 ⁇ and 18.6 °2 ⁇ ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation)
  • the crystalline LSD Fumarate Forms 1 and 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty- four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty- two, or thirty
  • the solid form of LSD is crystalline LSD Gentisate Form 3 characterized by two, or three XRPD signals selected from the group consisting of 7.0 °2 ⁇ , 10.0 °2 ⁇ , and 11.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Gentisate Form 3 characterized by XRPD signals at 7.0 °2 ⁇ , 10.0 °2 ⁇ , and 11.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Gentisate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.0 °2 ⁇ , 10.0 °2 ⁇ , 11.2 °2 ⁇ , 13.2 °2 ⁇ , and 14.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD Gentisate Form 3 characterized by XRPD signals at 7.0 °2 ⁇ , 10.0 °2 ⁇ , 11.2 °2 ⁇ , 13.2 °2 ⁇ , and 14.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by two, or three XRPD signals selected from the group consisting of 19.1 °2 ⁇ , 7.0 °2 ⁇ , and 20.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by XRPD signals at 19.1 °2 ⁇ , 7.0 °2 ⁇ , and 20.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.1 °2 ⁇ , 7.0 °2 ⁇ , 20.5 °2 ⁇ , 14.0 °2 ⁇ and 22.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by XRPD signals at 19.1 °2 ⁇ , 7.0 °2 ⁇ , 20.5 °2 ⁇ , 14.0 °2 ⁇ and 22.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.1 °2 ⁇ , 7.0 °2 ⁇ , 20.5 °2 ⁇ , 14.0 °2 ⁇ , 22.7 °2 ⁇ , 13.2 °2 ⁇ , and 22.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by XRPD signals at 19.1 °2 ⁇ , 7.0 °2 ⁇ , 20.5 °2 ⁇ , 14.0 °2 ⁇ , 22.7 °2 ⁇ , 13.2 °2 ⁇ , and 22.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.1 °2 ⁇ , 7.0 °2 ⁇ , 20.5 °2 ⁇ , 14.0 °2 ⁇ , 22.7 °2 ⁇ , 13.2 °2 ⁇ , 22.3 °2 ⁇ , 14.2 °2 ⁇ , 25.8 °2 ⁇ and 19.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline LSD gentisate Form 3 characterized by XRPD signals at 19.1 °2 ⁇ , 7.0 °2 ⁇ , 20.5 °2 ⁇ , 14.0 °2 ⁇ , 22.7 °2 ⁇ , 13.2 °2 ⁇ , 22.3 °2 ⁇ , 14.2 °2 ⁇ , 25.8 °2 ⁇ and 19.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline LSD Gentisate Form 3 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty- one, forty-two, or forty-three XRPD signals selected from those set forth in Table 25.
  • Table 25 XRPD Signals for LSD Gentisate Form 3
  • 1-acetyl-LSD Citrate the present disclosure provides solid forms of Citrate salts of 1- acetyl-LSD, e.g., crystalline forms of 1-acetyl-LSD Citrate .
  • the 1-acetyl- LSD Citrate XRPD pattern is substantially similar to that shown in FIG.55.
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Citrate characterized by two, or three XRPD signals selected from the group consisting of 3.1 °2 ⁇ , 5.7 °2 ⁇ , and 14.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Citrate characterized by XRPD signals at 3.1 °2 ⁇ , 5.7 °2 ⁇ , and 14.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Citrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.1 °2 ⁇ , 5.7 °2 ⁇ , 14.4 °2 ⁇ , 17.6 °2 ⁇ , and 24.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Citrate characterized by XRPD signals at 3.1 °2 ⁇ , 5.7 °2 ⁇ , 14.4 °2 ⁇ , 17.6 °2 ⁇ , and 24.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline LSD 1-acetyl-LSD Citrate characterized by two, or three XRPD signals selected from the group consisting of 14.4 °2 ⁇ , 17.6 °2 ⁇ , and 24.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Citrate characterized by XRPD signals at 14.4 °2 ⁇ , 17.6 °2 ⁇ , and 24.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Citrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.4 °2 ⁇ , 17.6 °2 ⁇ , 24.3 °2 ⁇ , 5.7 °2 ⁇ , and 3.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Citrate characterized by XRPD signals at 14.4 °2 ⁇ , 17.6 °2 ⁇ , 24.3 °2 ⁇ , 5.7 °2 ⁇ , and 3.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-acetyl-LSD Citrate is characterized by one, two, three, four, or five XRPD signals selected from those set forth in Table 26.
  • Table 26 XRPD Signals for 1-acetyl-LSD Citrate 1-acetyl-LSD Free base Form A
  • the present disclosure provides solid forms of 1-acetyl-LSD freebase Form A, e.g., crystalline forms of 1-acetyl-LSD freebase Form A.
  • the 1-acetyl-LSD freebase Form A XRPD pattern is substantially similar to that shown in any one of FIGs.1621, or 213.
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD freebase Form A characterized by two or three XRPD signals selected from the group consisting of 9.6 °2 ⁇ , 10.2 °2 ⁇ , and 12.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD freebase Form A characterized by XRPD signals at 9.6 °2 ⁇ , 10.2 °2 ⁇ , and 12.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.6 °2 ⁇ , 10.2 °2 ⁇ , 12.7 °2 ⁇ , 13.2 °2 ⁇ , and 15.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl- LSD freebase Form A characterized by XRPD signals at 9.6 °2 ⁇ , 10.2 °2 ⁇ , 12.7 °2 ⁇ , 13.2 °2 ⁇ , and 15.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD freebase Form A characterized by two, or three XRPD signals selected from the group consisting of 19.3 °2 ⁇ , 12.7 °2 ⁇ , and 15.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline 1-acetyl-LSD freebase Form A characterized by XRPD signals at 19.3 °2 ⁇ , 12.7 °2 ⁇ , and 15.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.3 °2 ⁇ , 12.7 °2 ⁇ , 15.5 °2 ⁇ , 24.1 °2 ⁇ , and 17.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl- LSD freebase Form A characterized by XRPD signals at 19.3 °2 ⁇ , 12.7 °2 ⁇ , 15.5 °2 ⁇ , 24.1 °2 ⁇ , and 17.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.3 °2 ⁇ , 12.7 °2 ⁇ , 15.5 °2 ⁇ , 24.1 °2 ⁇ , 17.3 °2 ⁇ , 19.6 °2 ⁇ , and 21.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD freebase Form A characterized by XRPD signals at 19.3 °2 ⁇ , 12.7 °2 ⁇ , 15.5 °2 ⁇ , 24.1 °2 ⁇ , 17.3 °2 ⁇ , 19.6 °2 ⁇ , and 21.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.3 °2 ⁇ , 12.7 °2 ⁇ , 15.5 °2 ⁇ , 24.1 °2 ⁇ , 17.3 °2 ⁇ , 19.6 °2 ⁇ , 21.2 °2 ⁇ , 20.5 °2 ⁇ , 13.2 °2 ⁇ and 9.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD freebase Form A characterized by XRPD signals at 19.3 °2 ⁇ , 12.7 °2 ⁇ , 15.5 °2 ⁇ , 24.1 °2 ⁇ , 17.3 °2 ⁇ , 19.6 °2 ⁇ , 21.2 °2 ⁇ , 20.5 °2 ⁇ , 13.2 °2 ⁇ and 9.6 °2 ⁇ ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • crystalline 1-acetyl-LSD freebase Form A is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty- four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty- two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, or forty-five XRPD signals selected from those set forth in Table 27.
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD freebase Form A characterized by two, or three XRPD signals selected from the group consisting of 9.6 °2 ⁇ , 10.2 °2 ⁇ , and 12.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD freebase Form A characterized by XRPD signals at 9.6 °2 ⁇ , 10.2 °2 ⁇ , and 12.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.6 °2 ⁇ , 10.2 °2 ⁇ , 12.8 °2 ⁇ , 13.3 °2 ⁇ , and 15.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD freebase Form A characterized by XRPD signals at 9.6 °2 ⁇ , 10.2 °2 ⁇ , 12.8 °2 ⁇ , 13.3 °2 ⁇ , and 15.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD freebase Form A characterized by two, or three XRPD signals selected from the group consisting of 12.8 °2 ⁇ , 19.4 °2 ⁇ , and 24.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD freebase Form A characterized by XRPD signals at 12.8 °2 ⁇ , 19.4 °2 ⁇ , and 24.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.8 °2 ⁇ , 19.4 °2 ⁇ , 24.3 °2 ⁇ , 15.6 °2 ⁇ , and 9.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD freebase Form A characterized by XRPD signals at 12.8 °2 ⁇ , 19.4 °2 ⁇ , 24.3 °2 ⁇ , 15.6 °2 ⁇ , and 9.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.8 °2 ⁇ , 19.4 °2 ⁇ , 24.3 °2 ⁇ , 15.6 °2 ⁇ , 9.6 °2 ⁇ , 17.4 °2 ⁇ , and 19.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1- acetyl-LSD freebase Form A characterized by XRPD signals at 12.8 °2 ⁇ , 19.4 °2 ⁇ , 24.3 °2 ⁇ , 15.6 °2 ⁇ , 9.6 °2 ⁇ , 17.4 °2 ⁇ , and 19.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.8 °2 ⁇ , 19.4 °2 ⁇ , 24.3 °2 ⁇ , 15.6 °2 ⁇ , 9.6 °2 ⁇ , 17.4 °2 ⁇ , 19.8 °2 ⁇ , 20.6 °2 ⁇ , 21.4 °2 ⁇ and 13.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD freebase Form A characterized by XRPD signals at 12.8 °2 ⁇ , 19.4 °2 ⁇ , 24.3 °2 ⁇ , 15.6 °2 ⁇ , 9.6 °2 ⁇ , 17.4 °2 ⁇ , 19.8 °2 ⁇ , 20.6 °2 ⁇ , 21.4 °2 ⁇ and 13.3 °2 ⁇ ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-acetyl-LSD freebase Form A is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty- four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty- two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty- nine, fifty, fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six, fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two, sixty-three, sixty-four, sixty-five,
  • Table 28 Calculated XRPD Signals for 1-acetyl-LSD Freebase Form A 1-acetyl-LSD Fumarate
  • the present disclosure provides solid forms of Fumarate salts of 1- acetyl-LSD, e.g., crystalline forms of 1-acetyl-LSD Fumarate.
  • the 1- acetyl-LSD Fumarate XRPD pattern is substantially similar to that shown in FIG.56.
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Fumarate characterized by two, or three XRPD signals selected from the group consisting of 4.1 °2 ⁇ , 5.2 °2 ⁇ , and 6.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Fumarate characterized by XRPD signals at 4.1 °2 ⁇ , 5.2 °2 ⁇ , and 6.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Fumarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.1 °2 ⁇ , 5.2 °2 ⁇ , 6.0 °2 ⁇ , 10.8 °2 ⁇ , and 15.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Fumarate characterized by XRPD signals at 4.1 °2 ⁇ , 5.2 °2 ⁇ , 6.0 °2 ⁇ , 10.8 °2 ⁇ , and 15.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Fumarate characterized by two, or three XRPD signals selected from the group consisting of 5.2 °2 ⁇ , 6.0 °2 ⁇ , and 15.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Fumarate characterized by XRPD signals at 5.2 °2 ⁇ , 6.0 °2 ⁇ , and 15.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Fumarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.2 °2 ⁇ , 6.0 °2 ⁇ , 15.0 °2 ⁇ , 14.4 °2 ⁇ , and 21.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Fumarate characterized by XRPD signals at 5.2 °2 ⁇ , 6.0 °2 ⁇ , 15.0 °2 ⁇ , 14.4 °2 ⁇ , and 21.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Fumarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.2 °2 ⁇ , 6.0 °2 ⁇ , 15.0 °2 ⁇ , 14.4 °2 ⁇ , 21.8 °2 ⁇ , 4.1 °2 ⁇ , and 10.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1- acetyl-LSD Fumarate characterized by XRPD signals at 5.2 °2 ⁇ , 6.0 °2 ⁇ , 15.0 °2 ⁇ , 14.4 °2 ⁇ , 21.8 °2 ⁇ , 4.1 °2 ⁇ , and 10.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Fumarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.2 °2 ⁇ , 6.0 °2 ⁇ , 15.0 °2 ⁇ , 14.4 °2 ⁇ , 21.8 °2 ⁇ , 4.1 °2 ⁇ , 10.8 °2 ⁇ , 13.4 °2 ⁇ , 24.3 °2 ⁇ and 20.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Fumarate characterized by XRPD signals at 5.2 °2 ⁇ , 6.0 °2 ⁇ , 15.0 °2 ⁇ , 14.4 °2 ⁇ , 21.8 °2 ⁇ , 4.1 °2 ⁇ , 10.8 °2 ⁇ , 13.4 °2 ⁇ , 24.3 °2 ⁇ and 20.6 °2 ⁇ ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-acetyl-LSD Fumarate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, or sixteen XRPD signals selected from those set forth in Table 29.
  • Table 29 XRPD Signals for 1-acetyl-LSD Fumarate 1-acetyl-LSD Gentisate Form A
  • the present disclosure provides solid forms of Gentisate salts of 1- acetyl-LSD, e.g., crystalline forms of 1-acetyl-LSD Gentisate Form A.
  • the 1-acetyl-LSD Gentisate Form A XRPD pattern is substantially similar to that shown in any one of FIGs.2022, or 212.
  • the 1-acetyl-LSD Gentisate Form A TGA profile is substantially similar to that shown in FIG.115.
  • the 1-acetyl- LSD Gentisate Form A DSC profile is substantially similar to that shown in FIG.115.
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Gentisate Form A characterized by two, or three XRPD signals selected from the group consisting of 5.4 °2 ⁇ , 6.7 °2 ⁇ , and 8.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Gentisate Form A characterized by XRPD signals at 5.4 °2 ⁇ , 6.7 °2 ⁇ , and 8.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Gentisate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.4 °2 ⁇ , 6.7 °2 ⁇ , 8.3 °2 ⁇ , 11.4 °2 ⁇ , and 12.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Gentisate Form A characterized by XRPD signals at 5.4 °2 ⁇ , 6.7 °2 ⁇ , 8.3 °2 ⁇ , 11.4 °2 ⁇ , and 12.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Gentisate Form A characterized by two, or three XRPD signals selected from the group consisting of 8.3 °2 ⁇ , 24.0 °2 ⁇ , and 5.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Gentisate Form A characterized by XRPD signals at 8.3 °2 ⁇ , 24.0 °2 ⁇ , and 5.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Gentisate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.3 °2 ⁇ , 24.0 °2 ⁇ , 5.4 °2 ⁇ , 16.4 °2 ⁇ , and 24.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Gentisate Form A characterized by XRPD signals at 8.3 °2 ⁇ , 24.0 °2 ⁇ , 5.4 °2 ⁇ , 16.4 °2 ⁇ , and 24.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Gentisate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.3 °2 ⁇ , 24.0 °2 ⁇ , 5.4 °2 ⁇ , 16.4 °2 ⁇ , 24.7 °2 ⁇ , 23.6 °2 ⁇ , and 17.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl- LSD Gentisate Form A characterized by XRPD signals at 8.3 °2 ⁇ , 24.0 °2 ⁇ , 5.4 °2 ⁇ , 16.4 °2 ⁇ , 24.7 °2 ⁇ , 23.6 °2 ⁇ , and 17.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Gentisate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.3 °2 ⁇ , 24.0 °2 ⁇ , 5.4 °2 ⁇ , 16.4 °2 ⁇ , 24.7 °2 ⁇ , 23.6 °2 ⁇ , 17.6 °2 ⁇ , 20.2 °2 ⁇ , 16.6 °2 ⁇ and 24.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Gentisate Form A characterized by XRPD signals at 8.3 °2 ⁇ , 24.0 °2 ⁇ , 5.4 °2 ⁇ , 16.4 °2 ⁇ , 24.7 °2 ⁇ , 23.6 °2 ⁇ , 17.6 °2 ⁇ , 20.2 °2 ⁇ , 16.6 °2 ⁇ and 24.8 °2 ⁇ ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-acetyl-LSD Gentisate Form A is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty- four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty- two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty- nine, fifty, fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six, fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two, sixty-three, sixty-four, sixty-five
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Gentisate Form A characterized by two, or three XRPD signals selected from the group consisting of 5.4 °2 ⁇ , 6.7 °2 ⁇ , and 8.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Gentisate Form A characterized by XRPD signals at 5.4 °2 ⁇ , 6.7 °2 ⁇ , and 8.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Gentisate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.4 °2 ⁇ , 6.7 °2 ⁇ , 8.4 °2 ⁇ , 11.5 °2 ⁇ , and 12.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Gentisate Form A characterized by XRPD signals at 5.4 °2 ⁇ , 6.7 °2 ⁇ , 8.4 °2 ⁇ , 11.5 °2 ⁇ , and 12.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Gentisate Form A characterized by two, or three XRPD signals selected from the group consisting of 8.4 °2 ⁇ , 5.4 °2 ⁇ , and 24.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline 1-acetyl-LSD Gentisate Form A characterized by XRPD signals at 8.4 °2 ⁇ , 5.4 °2 ⁇ , and 24.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Gentisate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.4 °2 ⁇ , 5.4 °2 ⁇ , 24.2 °2 ⁇ , 16.6 °2 ⁇ , and 17.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is 1-acetyl-LSD Gentisate Form A characterized by XRPD signals at 8.4 °2 ⁇ , 5.4 °2 ⁇ , 24.2 °2 ⁇ , 16.6 °2 ⁇ , and 17.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Gentisate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.4 °2 ⁇ , 5.4 °2 ⁇ , 24.2 °2 ⁇ , 16.6 °2 ⁇ , 17.8 °2 ⁇ , 16.7 °2 ⁇ , and 24.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is 1-acetyl-LSD Gentisate Form A characterized by XRPD signals at 8.4 °2 ⁇ , 5.4 °2 ⁇ , 24.2 °2 ⁇ , 16.6 °2 ⁇ , 17.8 °2 ⁇ , 16.7 °2 ⁇ , and 24.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Gentisate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.4 °2 ⁇ , 5.4 °2 ⁇ , 24.2 °2 ⁇ , 16.6 °2 ⁇ , 17.8 °2 ⁇ , 16.7 °2 ⁇ , 24.9 °2 ⁇ , 23.7 °2 ⁇ , 6.7 °2 ⁇ and 20.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline 1-acetyl-LSD Gentisate Form A characterized by XRPD signals at 8.4 °2 ⁇ , 5.4 °2 ⁇ , 24.2 °2 ⁇ , 16.6 °2 ⁇ , 17.8 °2 ⁇ , 16.7 °2 ⁇ , 24.9 °2 ⁇ , 23.7 °2 ⁇ , 6.7 °2 ⁇ and 20.3 °2 ⁇ ( ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-acetyl-LSD Gentisate Form A is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty- four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty- two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty- nine, fifty, fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six, fifty-seven, fifty-eight, fifty-nine, sixty, sixty-one, sixty-two, sixty-three, sixty-four, sixty-five
  • Table 31 Calculated XRPD Signals for 1-acetyl-LSD Gentisate Form A 1-acetyl-LSD HCl Form A
  • the present disclosure provides solid forms of Hydrochloride salts of 1-acetyl-LSD, e.g., crystalline forms of 1-acetyl-LSD Hydrochloride Form A.
  • the 1-acetyl-LSD Hydrochloride Form A XRPD pattern is substantially similar to that shown in any one of FIGs.18 or 24.
  • the 1-acetyl-LSD Hydrochloride Form A NMR spectrum is substantially similar to that shown in FIG.113.
  • the 1-acetyl-LSD Hydrochloride TGA profile is substantially similar to that shown in FIG.114.
  • the 1-acetyl-LSD Hydrochloride Form A DSC profile is substantially similar to that shown in FIG.114.
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Hydrochloride Form A characterized by two, or three XRPD signals selected from the group consisting of 5.3 °2 ⁇ , 5.9 °2 ⁇ , and 7.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Hydrochloride Form A characterized by XRPD signals at 5.3 °2 ⁇ , 5.9 °2 ⁇ , and 7.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Hydrochloride Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.3 °2 ⁇ , 5.9 °2 ⁇ , 7.4 °2 ⁇ , 9.2 °2 ⁇ , and 13.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Hydrochloride Form A characterized by XRPD signals at 5.3 °2 ⁇ , 5.9 °2 ⁇ , 7.4 °2 ⁇ , 9.2 °2 ⁇ , and 13.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Hydrochloride Form A characterized by two, or three XRPD signals selected from the group consisting of 7.4 °2 ⁇ , 5.9 °2 ⁇ , and 17.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Hydrochloride Form A characterized by XRPD signals at 7.4 °2 ⁇ , 5.9 °2 ⁇ , and 17.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Hydrochloride Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.4 °2 ⁇ , 5.9 °2 ⁇ , 17.6 °2 ⁇ , 13.4 °2 ⁇ , and 17.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl- LSD Hydrochloride Form A characterized by XRPD signals at 7.4 °2 ⁇ , 5.9 °2 ⁇ , 17.6 °2 ⁇ , 13.4 °2 ⁇ , and 17.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Hydrochloride Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.4 °2 ⁇ , 5.9 °2 ⁇ , 17.6 °2 ⁇ , 13.4 °2 ⁇ , 17.4 °2 ⁇ , 5.3 °2 ⁇ , and 24.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1- acetyl-LSD Hydrochloride Form A characterized by XRPD signals at 7.4 °2 ⁇ , 5.9 °2 ⁇ , 17.6 °2 ⁇ , 13.4 °2 ⁇ , 17.4 °2 ⁇ , 5.3 °2 ⁇ , and 24.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Hydrochloride Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.4 °2 ⁇ , 5.9 °2 ⁇ , 17.6 °2 ⁇ , 13.4 °2 ⁇ , 17.4 °2 ⁇ , 5.3 °2 ⁇ , 24.8 °2 ⁇ , 9.2 °2 ⁇ , 22.0 °2 ⁇ and 19.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Hydrochloride Form A characterized by XRPD signals at 7.4 °2 ⁇ , 5.9 °2 ⁇ , 17.6 °2 ⁇ , 13.4 °2 ⁇ , 17.4 °2 ⁇ , 5.3 °2 ⁇ , 24.8 °2 ⁇ , 9.2 °2 ⁇ , 22.0 °2 ⁇ and 19.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-acetyl-LSD Hydrochloride Form A is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty- three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, or forty-six XRPD signals selected from those set forth in Table 32.
  • Table 32 XRPD Signals for 1-acetyl-LSD HCl Form A 1-acetyl-LSD L-malate
  • the present disclosure provides solid forms of L-malate salts of 1- acetyl-LSD, e.g., crystalline forms of 1-acetyl-LSD L-malate .
  • the 1- acetyl-LSD L-malate XRPD pattern is substantially similar to that shown in FIG.57.
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD L-malate characterized by two, or three XRPD signals selected from the group consisting of 4.8 °2 ⁇ , 5.6 °2 ⁇ , and 9.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD L-malate characterized by XRPD signals at 4.8 °2 ⁇ , 5.6 °2 ⁇ , and 9.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD L-malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.8 °2 ⁇ , 5.6 °2 ⁇ , 9.4 °2 ⁇ , 10.2 °2 ⁇ , and 11.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD L-malate characterized by XRPD signals at 4.8 °2 ⁇ , 5.6 °2 ⁇ , 9.4 °2 ⁇ , 10.2 °2 ⁇ , and 11.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD L-malate characterized by two, or three XRPD signals selected from the group consisting of 4.8 °2 ⁇ , 24.5 °2 ⁇ , and 5.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD L-malate characterized by XRPD signals at 4.8 °2 ⁇ , 24.5 °2 ⁇ , and 5.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD L-malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.8 °2 ⁇ , 24.5 °2 ⁇ , 5.6 °2 ⁇ , 14.0 °2 ⁇ , and 24.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD L-malate characterized by XRPD signals at 4.8 °2 ⁇ , 24.5 °2 ⁇ , 5.6 °2 ⁇ , 14.0 °2 ⁇ , and 24.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD L-malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.8 °2 ⁇ , 24.5 °2 ⁇ , 5.6 °2 ⁇ , 14.0 °2 ⁇ , 24.8 °2 ⁇ , 24.0 °2 ⁇ , and 13.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl- LSD L-malate characterized by XRPD signals at 4.8 °2 ⁇ , 24.5 °2 ⁇ , 5.6 °2 ⁇ , 14.0 °2 ⁇ , 24.8 °2 ⁇ , 24.0 °2 ⁇ , and 13.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD L-malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.8 °2 ⁇ , 24.5 °2 ⁇ , 5.6 °2 ⁇ , 14.0 °2 ⁇ , 24.8 °2 ⁇ , 24.0 °2 ⁇ , 13.5 °2 ⁇ , 20.4 °2 ⁇ , 20.2 °2 ⁇ and 18.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD L-malate characterized by XRPD signals at 4.8 °2 ⁇ , 24.5 °2 ⁇ , 5.6 °2 ⁇ , 14.0 °2 ⁇ , 24.8 °2 ⁇ , 24.0 °2 ⁇ , 13.5 °2 ⁇ , 20.4 °2 ⁇ , 20.2 °2 ⁇ and 18.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-acetyl-LSD L-malate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty- four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty- two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty- nine, fifty, fifty-one, or fifty-two XRPD signals selected from those set forth in Table 33.
  • Table 33 XRPD Signals for 1-acetyl-LSD L-malate 1-acetyl-LSD Phosphate Form A
  • the present disclosure provides solid forms of Phosphate salts of 1-acetyl-LSD, e.g., crystalline forms of 1-acetyl-LSD Phosphate Form A .
  • the 1-acetyl-LSD Phosphate Form A XRPD pattern is substantially similar to that shown in any one of FIGs.1925, or 211.
  • the 1-acetyl-LSD Phosphate Form A 1 H NMR spectrum is substantially similar to that shown in FIG.111.
  • the 1-acetyl- LSD Phosphate Form A TGA profile is substantially similar to that shown in FIG.112.
  • the 1-acetyl-LSD Phosphate Form A DSC profile is substantially similar to that shown in FIG.112.
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Phosphate Form A characterized by two, or three XRPD signals selected from the group consisting of 4.6 °2 ⁇ , 5.7 °2 ⁇ , and 9.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Phosphate Form A characterized by XRPD signals at 4.6 °2 ⁇ , 5.7 °2 ⁇ , and 9.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Phosphate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6 °2 ⁇ , 5.7 °2 ⁇ , 8.1 °2 ⁇ , 9.2 °2 ⁇ , and 9.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Phosphate Form A characterized by XRPD signals at 4.6 °2 ⁇ , 5.7 °2 ⁇ , 8.1 °2 ⁇ , 9.2 °2 ⁇ , and 9.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Phosphate Form A characterized by two, or three XRPD signals selected from the group consisting of 4.6 °2 ⁇ , 22.5 °2 ⁇ , and 13.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Phosphate Form A characterized by XRPD signals at 4.6 °2 ⁇ , 22.5 °2 ⁇ , and 13.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Phosphate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6 °2 ⁇ , 22.5 °2 ⁇ , 13.7 °2 ⁇ , 5.7 °2 ⁇ , and 9.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl- LSD Phosphate Form A characterized by XRPD signals at 4.6 °2 ⁇ , 22.5 °2 ⁇ , 13.7 °2 ⁇ , 5.7 °2 ⁇ , and 9.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 11-acetyl-LSD Phosphate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6 °2 ⁇ , 22.5 °2 ⁇ , 13.7 °2 ⁇ , 5.7 °2 ⁇ , 9.2 °2 ⁇ , 18.1 °2 ⁇ , and 23.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Phosphate Form A characterized by XRPD signals at 4.6 °2 ⁇ , 22.5 °2 ⁇ , 13.7 °2 ⁇ , 5.7 °2 ⁇ , 9.2 °2 ⁇ , 18.1 °2 ⁇ , and 23.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Phosphate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6 °2 ⁇ , 22.5 °2 ⁇ , 13.7 °2 ⁇ , 5.7 °2 ⁇ , 9.2 °2 ⁇ , 18.1 °2 ⁇ , 23.9 °2 ⁇ , 24.1 °2 ⁇ , 13.5 °2 ⁇ and 18.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Phosphate Form A characterized by XRPD signals at 4.6 °2 ⁇ , 22.5 °2 ⁇ , 13.7 °2 ⁇ , 5.7 °2 ⁇ , 9.2 °2 ⁇ , 18.1 °2 ⁇ , 23.9 °2 ⁇ , 24.1 °2 ⁇ , 13.5 °2 ⁇ and 18.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-acetyl-LSD Phosphate Form A is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, or forty-one XRPD signals selected from those set forth in Table 34.
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Phosphate Form A characterized by two, or three XRPD signals selected from the group consisting of 4.6 °2 ⁇ , 5.5 °2 ⁇ , and 9.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Phosphate Form A characterized by XRPD signals at 4.6 °2 ⁇ , 5.5 °2 ⁇ , and 9.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Phosphate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6 °2 ⁇ , 5.5 °2 ⁇ , 7.5 °2 ⁇ , 9.1 °2 ⁇ , and 10.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Phosphate Form A characterized by XRPD signals at 4.6 °2 ⁇ , 5.5 °2 ⁇ , 7.5 °2 ⁇ , 9.1 °2 ⁇ , and 10.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Phosphate Form A characterized by two, or three XRPD signals selected from the group consisting of 5.5 °2 ⁇ , 4.6 °2 ⁇ , and 24.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Phosphate Form A characterized by XRPD signals at 5.5 °2 ⁇ , 4.6 °2 ⁇ , and 24.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Phosphate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.5 °2 ⁇ , 4.6 °2 ⁇ , 24.3 °2 ⁇ , 24.6 °2 ⁇ , and 19.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl- LSD Phosphate Form A characterized by XRPD signals at 5.5 °2 ⁇ , 4.6 °2 ⁇ , 24.3 °2 ⁇ , 24.6 °2 ⁇ , and 19.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Phosphate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.5 °2 ⁇ , 4.6 °2 ⁇ , 24.3 °2 ⁇ , 24.6 °2 ⁇ , 19.8 °2 ⁇ , 13.5 °2 ⁇ , and 11.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl- LSD Phosphate Form A characterized by XRPD signals at 5.5 °2 ⁇ , 4.6 °2 ⁇ , 24.3 °2 ⁇ , 24.6 °2 ⁇ , 19.8 °2 ⁇ , 13.5 °2 ⁇ , and 11.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Phosphate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.5 °2 ⁇ , 4.6 °2 ⁇ , 24.3 °2 ⁇ , 24.6 °2 ⁇ , 19.8 °2 ⁇ , 13.5 °2 ⁇ , 11.0 °2 ⁇ , 24.0 °2 ⁇ , 23.0 °2 ⁇ and 7.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Phosphate Form A characterized by XRPD signals at 5.5 °2 ⁇ , 4.6 °2 ⁇ , 24.3 °2 ⁇ , 24.6 °2 ⁇ , 19.8 °2 ⁇ , 13.5 °2 ⁇ , 11.0 °2 ⁇ , 24.0 °2 ⁇ , 23.0 °2 ⁇ and 7.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-acetyl-LSD Phosphate Form A is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty, fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six, fifty-seven, fifty- eight, fifty-nine, sixty, sixty-one, sixty-two, sixty-three, sixty-four, sixty
  • Table 36 Calculated XRPD Signals for 1-acetyl-LSD Phosphate Form A 1-acetyl-LSD Succinate
  • the present disclosure provides solid forms of Succinate salts of 1- acetyl-LSD, e.g., crystalline forms of 1-acetyl-LSD Succinate.
  • the 1- acetyl-LSD Succinate XRPD pattern is substantially similar to that shown in FIG.58.
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Succinate characterized by two, or three XRPD signals selected from the group consisting of 4.9 °2 ⁇ , 5.6 °2 ⁇ , and 10.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Succinate characterized by XRPD signals at 4.9 °2 ⁇ , 5.6 °2 ⁇ , and 10.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Succinate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.9 °2 ⁇ , 5.6 °2 ⁇ , 7.4 °2 ⁇ , 9.4 °2 ⁇ , and 10.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Succinate characterized by XRPD signals at 4.9 °2 ⁇ , 5.6 °2 ⁇ , 7.4 °2 ⁇ , 9.4 °2 ⁇ , and 10.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Succinate characterized by two, or three XRPD signals selected from the group consisting of 4.9 °2 ⁇ , 5.6 °2 ⁇ , and 24.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Succinate characterized by XRPD signals at 4.9 °2 ⁇ , 5.6 °2 ⁇ , and 24.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Succinate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.9 °2 ⁇ , 5.6 °2 ⁇ , 24.5 °2 ⁇ , 24.0 °2 ⁇ , and 14.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Succinate characterized by XRPD signals at 4.9 °2 ⁇ , 5.6 °2 ⁇ , 24.5 °2 ⁇ , 24.0 °2 ⁇ , and 14.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is 1-acetyl-LSD Succinate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.9 °2 ⁇ , 5.6 °2 ⁇ , 24.5 °2 ⁇ , 24.0 °2 ⁇ , 14.0 °2 ⁇ , 10.2 °2 ⁇ , and 9.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is 1-acetyl-LSD Succinate characterized by XRPD signals at 4.9 °2 ⁇ , 5.6 °2 ⁇ , 24.5 °2 ⁇ , 24.0 °2 ⁇ , 14.0 °2 ⁇ , 10.2 °2 ⁇ , and 9.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Succinate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.9 °2 ⁇ , 5.6 °2 ⁇ , 24.5 °2 ⁇ , 24.0 °2 ⁇ , 14.0 °2 ⁇ , 10.2 °2 ⁇ , 9.4 °2 ⁇ , 20.5 °2 ⁇ , 25.4 °2 ⁇ and 21.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Succinate characterized by XRPD signals at 4.9 °2 ⁇ , 5.6 °2 ⁇ , 24.5 °2 ⁇ , 24.0 °2 ⁇ , 14.0 °2 ⁇ , 10.2 °2 ⁇ , 9.4 °2 ⁇ , 20.5 °2 ⁇ , 25.4 °2 ⁇ , and 21.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-acetyl-LSD Succinate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty- four, twenty-five, twenty-six, or twenty-seven XRPD signals selected from those set forth in Table 37.
  • Table 37 XRPD Signals for 1-acetyl-LSD Succinate 1-acetyl-LSD Sulfate
  • the present disclosure provides solid forms of Sulfate salts of 1- acetyl-LSD, e.g., crystalline forms of 1-acetyl-LSD Sulfate.
  • the 1-acetyl- LSD Sulfate XRPD pattern is substantially similar to that shown in FIG.59.
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Sulfate characterized by two, or three XRPD signals selected from the group consisting of 3.1 °2 ⁇ , 5.7 °2 ⁇ , and 14.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Sulfate characterized by XRPD signals at 3.1 °2 ⁇ , 5.7 °2 ⁇ , and 14.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.1 °2 ⁇ , 5.7 °2 ⁇ , 14.0 °2 ⁇ , 22.0 °2 ⁇ , and 24.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Sulfate characterized by XRPD signals at 3.1 °2 ⁇ , 5.7 °2 ⁇ , 14.0 °2 ⁇ , 22.0 °2 ⁇ , and 24.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Sulfate characterized by two, or three XRPD signals selected from the group consisting of 5.7 °2 ⁇ , 3.1 °2 ⁇ , and 6.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Sulfate characterized by XRPD signals at 5.7 °2 ⁇ , 3.1 °2 ⁇ , and 6.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.7 °2 ⁇ , 3.1 °2 ⁇ , 6.5 °2 ⁇ , 14.0 °2 ⁇ , and 22.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Sulfate characterized by XRPD signals at 45.7 °2 ⁇ , 3.1 °2 ⁇ , 6.5 °2 ⁇ , 14.0 °2 ⁇ , and 22.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.7 °2 ⁇ , 3.1 °2 ⁇ , 6.5 °2 ⁇ , 14.0 °2 ⁇ , 22.0 °2 ⁇ , 24.2 °2 ⁇ , and 12.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Sulfate characterized by XRPD signals at 5.7 °2 ⁇ , 3.1 °2 ⁇ , 6.5 °2 ⁇ , 14.0 °2 ⁇ , 22.0 °2 ⁇ , 24.2 °2 ⁇ , and 12.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.7 °2 ⁇ , 3.1 °2 ⁇ , 6.5 °2 ⁇ , 14.0 °2 ⁇ , 22.0 °2 ⁇ , 24.2 °2 ⁇ , 12.2 °2 ⁇ , 18.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Sulfate characterized by XRPD signals at 5.7 °2 ⁇ , 3.1 °2 ⁇ , 6.5 °2 ⁇ , 14.0 °2 ⁇ , 22.0 °2 ⁇ , 24.2 °2 ⁇ , 12.2 °2 ⁇ , and 18.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-acetyl-LSD Sulfate is characterized by one, two, three, four, five, six, seven, or eight XRPD signals selected from those set forth in Table 38.
  • Table 38 XRPD Signals for 1-acetyl-LSD Sulfate 1-acetyl-LSD L-tartrate
  • the present disclosure provides solid forms of L-tartrate salts of 1- acetyl-LSD, e.g., crystalline forms of 1-acetyl-LSD L-tartrate.
  • the 1- acetyl-LSD L-tartrate XRPD pattern is substantially similar to that shown in FIG.60.
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD L- tartrate characterized by two, or three XRPD signals selected from the group consisting of 5.6 °2 ⁇ , 18.3 °2 ⁇ , and 24.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD L-tartrate characterized by XRPD signals at 5.6 °2 ⁇ , 18.3 °2 ⁇ , and 24.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD L- tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.6 °2 ⁇ , 13.7 °2 ⁇ , 17.0 °2 ⁇ , 18.3 °2 ⁇ , and 24.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD L- tartrate characterized by XRPD signals at 5.6 °2 ⁇ , 13.7 °2 ⁇ , 17.0 °2 ⁇ , 18.3 °2 ⁇ , and 24.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD L- tartrate characterized by two, or three XRPD signals selected from the group consisting of 24.9 °2 ⁇ , 18.3 °2 ⁇ , and 5.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD L-tartrate characterized by XRPD signals at 24.9 °2 ⁇ , 18.3 °2 ⁇ , and 5.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD L- tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 24.9 °2 ⁇ , 18.3 °2 ⁇ , 5.6 °2 ⁇ , 21.1 °2 ⁇ , and 13.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD L- tartrate characterized by XRPD signals at 24.9 °2 ⁇ , 18.3 °2 ⁇ , 5.6 °2 ⁇ , 21.1 °2 ⁇ , and 13.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD L-tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 24.9 °2 ⁇ , 18.3 °2 ⁇ , 5.6 °2 ⁇ , 21.1 °2 ⁇ , 13.7 °2 ⁇ , 17.0 °2 ⁇ , and 29.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl- LSD L-tartrate characterized by XRPD signals at 24.9 °2 ⁇ , 18.3 °2 ⁇ , 5.6 °2 ⁇ , 21.1 °2 ⁇ , 13.7 °2 ⁇ , 17.0 °2 ⁇ , and 29.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD L- tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 24.9 °2 ⁇ , 18.3 °2 ⁇ , 5.6 °2 ⁇ , 21.1 °2 ⁇ , 13.7 °2 ⁇ , 17.0 °2 ⁇ , 29.9 °2 ⁇ , and 28.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl- LSD is crystalline 1-acetyl-LSD L-tartrate characterized by XRPD signals at 24.9 °2 ⁇ , 18.3 °2 ⁇ , 5.6 °2 ⁇ , 21.1 °2 ⁇ , 13.7 °2 ⁇ , 17.0 °2 ⁇ , 29.9 °2 ⁇ , and 28.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-acetyl-LSD L-tartrate is characterized by one, two, three, four, five, six, seven, or eight XRPD signals selected from those set forth in Table 39.
  • the present disclosure provides non-crystalline 1A-LSD tosylate salts.
  • the non-crystalline 1A-LSD tosylate salt is characterized by a glass transition temperature of about 88.0 °C.
  • the non-crystalline 1A-LSD tosylate salt is characterized by a DSC profile with endotherms at about 72 oC, about 142o, and about 232 oC, or by a DSC profile with endotherms at about 71 oC, 145 oC, and about 230 oC.
  • the non-crystalline 1A-LSD tosylate salt is characterized by a TGA thermogram showing about 6.2% weight loss from ambient to 125 oC and about 1.2% weight loss from 125 oC to 210 oC, or by a TGA thermogram showing about 4.4% weight loss from ambient to 125 oC and about 1.2% weight loss from 125 oC to 210 oC.
  • the non-crystalline 1A-LSD tosylate salt is characterized by a 1 H NMR spectra substantially similar to that shown in FIG.194.
  • the non-crystalline 1A-LSD tosylate salt is characterized by a TGA profile substantially similar to that shown in FIG.186 or FIG.190.
  • the non-crystalline 1A-LSD tosylate salt is characterized by a DSC profile substantially similar to that shown in FIG.186 or FIG.190. In some embodiments, the non- crystalline 1A-LSD tosylate salt is characterized by a mDSC profile substantially similar to that shown in any one of FIGs.187-189, 191, or 192.
  • 1-acetyl-LSD Tosylate Form A the present disclosure provides solid forms of Tosylate salts of 1- acetyl-LSD, e.g., crystalline forms of 1-acetyl-LSD Tosylate Form A.
  • the 1-acetyl-LSD Tosylate Form A XRPD pattern is substantially similar to that shown in any one of FIGs.17, 23, or 61.
  • the 1-acetyl-LSD Tosylate Form A 1 H NMR spectrum is substantially similar to that shown in FIG.77.
  • the 1-acetyl- LSD Tosylate Form A TGA profile is substantially similar to that shown in FIG.78.
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by two, or three XRPD signals selected from the group consisting of 7.5 °2 ⁇ , 11.2 °2 ⁇ , and 12.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by XRPD signals at 7.5 °2 ⁇ , 11.2 °2 ⁇ , and 12.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.5 °2 ⁇ , 11.2 °2 ⁇ , 12.3 °2 ⁇ , 13.5 °2 ⁇ , and 18.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Tosylate Form A characterized by XRPD signals at 7.5 °2 ⁇ , 11.2 °2 ⁇ , 12.3 °2 ⁇ , 13.5 °2 ⁇ , and 18.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by two, or three XRPD signals selected from the group consisting of 24.4 °2 ⁇ , 7.5 °2 ⁇ , and 18.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by XRPD signals at 24.4 °2 ⁇ , 7.5 °2 ⁇ , and 18.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 24.4 °2 ⁇ , 7.5 °2 ⁇ , 18.0 °2 ⁇ , 22.4 °2 ⁇ , and 15.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Tosylate Form A characterized by XRPD signals at 24.4 °2 ⁇ , 7.5 °2 ⁇ , 18.0 °2 ⁇ , 22.4 °2 ⁇ , and 15.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Tosylate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 24.4 °2 ⁇ , 7.5 °2 ⁇ , 18.0 °2 ⁇ , 22.4 °2 ⁇ , 15.6 °2 ⁇ , 12.5 °2 ⁇ , and 12.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl- LSD Tosylate Form A characterized by XRPD signals at 24.4 °2 ⁇ , 7.5 °2 ⁇ , 18.0 °2 ⁇ , 22.4 °2 ⁇ , 15.6 °2 ⁇ , 12.5 °2 ⁇ , and 12.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 24.4 °2 ⁇ , 7.5 °2 ⁇ , 18.0 °2 ⁇ , 22.4 °2 ⁇ , 15.6 °2 ⁇ , 12.5 °2 ⁇ , 12.3 °2 ⁇ , 15.7 °2 ⁇ , 27.2 °2 ⁇ , and 19.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by XRPD signals at 24.4 °2 ⁇ , 7.5 °2 ⁇ , 18.0 °2 ⁇ , 22.4 °2 ⁇ , 15.6 °2 ⁇ , 12.5 °2 ⁇ , 12.3 °2 ⁇ , 15.7 °2 ⁇ , 27.2 °2 ⁇ , and 19.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-acetyl-LSD Tosylate Form A is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty- four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, or thirty-one XRPD signals selected from those set forth in Table 40.
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by two, or three XRPD signals selected from the group consisting of 7.6 °2 ⁇ , 11.3 °2 ⁇ , and 12.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by XRPD signals at 7.6 °2 ⁇ , 11.3 °2 ⁇ , and 12.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.6 °2 ⁇ , 11.3 °2 ⁇ , 12.4 °2 ⁇ , 13.5 °2 ⁇ , and 18.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Tosylate Form A characterized by XRPD signals at 7.6 °2 ⁇ , 11.3 °2 ⁇ , 12.4 °2 ⁇ , 13.5 °2 ⁇ , and 18.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by two, or three XRPD signals selected from the group consisting of 7.6 °2 ⁇ , 12.4 °2 ⁇ , and 24.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by XRPD signals at 7.6 °2 ⁇ , 12.4 °2 ⁇ , and 24.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.6 °2 ⁇ , 12.4 °2 ⁇ , 24.5 °2 ⁇ , 15.6 °2 ⁇ , and 18.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Tosylate Form A characterized by XRPD signals at 7.6 °2 ⁇ , 12.4 °2 ⁇ , 24.5 °2 ⁇ , 15.6 °2 ⁇ , and 18.1°2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Tosylate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.6 °2 ⁇ , 12.4 °2 ⁇ , 24.5 °2 ⁇ , 15.6 °2 ⁇ , 18.1 °2 ⁇ , 15.7 °2 ⁇ , and 22.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl- LSD Tosylate Form A characterized by XRPD signals at 7.6 °2 ⁇ , 12.4 °2 ⁇ , 24.5 °2 ⁇ , 15.6 °2 ⁇ , 18.1 °2 ⁇ , 15.7 °2 ⁇ , and 22.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.6 °2 ⁇ , 12.4 °2 ⁇ , 24.5 °2 ⁇ , 15.6 °2 ⁇ , 18.1 °2 ⁇ , 15.7 °2 ⁇ , 22.6 °2 ⁇ , 27.5 °2 ⁇ , 19.4 °2 ⁇ , and 11.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by XRPD signals at 7.6 °2 ⁇ , 12.4 °2 ⁇ , 24.5 °2 ⁇ , 15.6 °2 ⁇ , 18.1 °2 ⁇ , 15.7 °2 ⁇ , 22.6 °2 ⁇ , 27.5 °2 ⁇ , 19.4 °2 ⁇ , and 11.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-acetyl-LSD Tosylate Form A is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty- four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty- two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty- nine, fifty, fifty-one, fifty-two, fifty-three, fifty-four, or fifty-five XRPD signals selected from those set forth in Table 41.
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by two, or three XRPD signals selected from the group consisting of 7.5 °2 ⁇ , 11.1 °2 ⁇ , and 12.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by XRPD signals at 7.5 °2 ⁇ , 11.1 °2 ⁇ , and 12.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.5 °2 ⁇ , 11.1 °2 ⁇ , 12.3 °2 ⁇ , 13.5 °2 ⁇ , and 18.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Tosylate Form A characterized by XRPD signals at ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by two, or three XRPD signals selected from the group consisting of 24.3 °2 ⁇ , 7.5 °2 ⁇ , and 15.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by XRPD signals at 24.3 °2 ⁇ , 7.5 °2 ⁇ , and 15.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 24.3 °2 ⁇ , 7.5 °2 ⁇ , 15.6 °2 ⁇ , 22.4 °2 ⁇ , and 18.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Tosylate Form A characterized by XRPD signals at 24.3 °2 ⁇ , 7.5 °2 ⁇ , 15.6 °2 ⁇ , 22.4 °2 ⁇ , and 18.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Tosylate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 24.3 °2 ⁇ , 7.5 °2 ⁇ , 15.6 °2 ⁇ , 22.4 °2 ⁇ , 18.0 °2 ⁇ , 12.5 °2 ⁇ , and 12.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl- LSD Tosylate Form A characterized by XRPD signals at 24.3 °2 ⁇ , 7.5 °2 ⁇ , 15.6 °2 ⁇ , 22.4 °2 ⁇ , 18.0 °2 ⁇ , 12.5 °2 ⁇ , and 12.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 24.3 °2 ⁇ , 7.5 °2 ⁇ , 15.6 °2 ⁇ , 22.4 °2 ⁇ , 18.0 °2 ⁇ , 12.5 °2 ⁇ , 12.3 °2 ⁇ , 15.7 °2 ⁇ , 27.2 °2 ⁇ , and 11.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Tosylate Form A characterized by XRPD signals at 24.3 °2 ⁇ , 7.5 °2 ⁇ , 15.6 °2 ⁇ , 22.4 °2 ⁇ , 18.0 °2 ⁇ , 12.5 °2 ⁇ , 12.3 °2 ⁇ , 15.7 °2 ⁇ , 27.2 °2 ⁇ , and 11.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-acetyl-LSD Tosylate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty- four, twenty-five, twenty-six, twenty-seven, or twenty-eight XRPD signals selected from those set forth in Table 42.
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Hydrochloride characterized by two, or three XRPD signals selected from the group consisting of 5.3 °2 ⁇ , 5.9 °2 ⁇ , and 7.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Hydrochloride characterized by XRPD signals at 5.3 °2 ⁇ , 5.9 °2 ⁇ , and 7.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Hydrochloride characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.3 °2 ⁇ , 5.9 °2 ⁇ , 7.4 °2 ⁇ , 9.2 °2 ⁇ , and 13.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Hydrochloride characterized by XRPD signals at 5.3 °2 ⁇ , 5.9 °2 ⁇ , 7.4 °2 ⁇ , 9.2 °2 ⁇ , and 13.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Hydrochloride characterized by two, or three XRPD signals selected from the group consisting of 5.9 °2 ⁇ , 7,4 °2 ⁇ , and 17.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Hydrochloride characterized by XRPD signals at 7.4 °2 ⁇ , 5.9 °2 ⁇ , and 17.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Hydrochloride characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.4 °2 ⁇ , 5.9 °2 ⁇ , 17.6 °2 ⁇ , 5.3 °2 ⁇ , and 13.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Hydrochloride characterized by XRPD signals at 7.4 °2 ⁇ , 5.9 °2 ⁇ , 17.6 °2 ⁇ , 5.3 °2 ⁇ , and 13.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Hydrochloride characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.4 °2 ⁇ , 5.9 °2 ⁇ , 17.6 °2 ⁇ , 5.3 °2 ⁇ , 13.4 °2 ⁇ , 9.2 °2 ⁇ , and 24.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is 1-acetyl-LSD Hydrochloride characterized by XRPD signals at 7.4 °2 ⁇ , 5.9 °2 ⁇ , 17.6 °2 ⁇ , 5.3 °2 ⁇ , 13.4 °2 ⁇ , 9.2 °2 ⁇ , and 24.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Hydrochloride characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.4 °2 ⁇ , 5.9 °2 ⁇ , 17.6 °2 ⁇ , 5.3 °2 ⁇ , 13.4 °2 ⁇ , 9.2 °2 ⁇ , 24.9 °2 ⁇ , 17.4 °2 ⁇ , 22.0 °2 ⁇ and 26.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-acetyl-LSD is crystalline 1-acetyl-LSD Hydrochloride characterized by XRPD signals at 7.4 °2 ⁇ , 5.9 °2 ⁇ , 17.6 °2 ⁇ , 5.3 °2 ⁇ , 13.4 °2 ⁇ , 9.2 °2 ⁇ , 24.9 °2 ⁇ , 17.4 °2 ⁇ , 22.0 °2 ⁇ and 26.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-acetyl-LSD Hydrochloride is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty- four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty- two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, or forty-nine XRPD signals selected from those set forth in Table 43.
  • Table 43 XRPD Signals for 1-acetyl-LSD Hydrochloride Form A 1-propionyl-LSD Citrate Form 1
  • the present disclosure provides solid forms of Citrate salts of 1- propionyl-LSD, e.g., crystalline forms of 1-propionyl-LSD Citrate.
  • the 1- propionyl-LSD Citrate XRPD pattern is substantially similar to that shown in FIG.62.
  • the 1-propionyl-LSD Citrate 1 H NMR spectrum is substantially similar to that shown in FIG.76.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Citrate characterized by two, or three XRPD signals selected from the group consisting of 4.9 °2 ⁇ , 5.7 °2 ⁇ , and 10.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Citrate characterized by XRPD signals at 4.9 °2 ⁇ , 5.7 °2 ⁇ , and 10.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Citrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.9 °2 ⁇ , 5.7 °2 ⁇ , 10.2 °2 ⁇ , 14.1 °2 ⁇ , and 15.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Citrate characterized by XRPD signals at 4.9 °2 ⁇ , 5.7 °2 ⁇ , 10.2 °2 ⁇ , 14.1 °2 ⁇ , and 15.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Citrate characterized by two, or three XRPD signals selected from the group consisting of 4.9 °2 ⁇ , 5.7 °2 ⁇ , and 14.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Citrate characterized by XRPD signals at 4.9 °2 ⁇ , 5.7 °2 ⁇ , and 14.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Citrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.9 °2 ⁇ , 5.7 °2 ⁇ , 14.1 °2 ⁇ , 15.8 °2 ⁇ , and 10.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Citrate characterized by XRPD signals at 4.9 °2 ⁇ , 5.7 °2 ⁇ , 14.1 °2 ⁇ , 15.8 °2 ⁇ , and 10.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Citrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.9 °2 ⁇ , 5.7 °2 ⁇ , 14.1 °2 ⁇ , 15.8 °2 ⁇ , 10.2 °2 ⁇ , 22.4 °2 ⁇ , and 22.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1- propionyl-LSD Citrate characterized by XRPD signals at 4.9 °2 ⁇ , 5.7 °2 ⁇ , 14.1 °2 ⁇ , 15.8 °2 ⁇ , 10.2 °2 ⁇ , 22.4 °2 ⁇ , and 22.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Citrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.9 °2 ⁇ , 5.7 °2 ⁇ , 14.1 °2 ⁇ , 15.8 °2 ⁇ , 10.2 °2 ⁇ , 22.4 °2 ⁇ , 22.7 °2 ⁇ , 9.9 °2 ⁇ , 15.1 °2 ⁇ , and 16.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Citrate characterized by XRPD signals at 4.9 °2 ⁇ , 5.7 °2 ⁇ , 14.1 °2 ⁇ , 15.8 °2 ⁇ , 10.2 °2 ⁇ , 22.4 °2 ⁇ , 22.7 °2 ⁇ , 9.9 °2 ⁇ , 15.1 °2 ⁇ , and 16.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD Citrate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, or fourteen XRPD signals selected from those set forth in Table 44.
  • Table 44 XRPD Signals for 1-proionyl-LSD Citrate 1-propionyl-LSD Ethanesulfonate (Esylate) Form 1
  • the present disclosure provides solid forms of Esylate Form 1 salts of 1-propionyl-LSD, e.g., crystalline forms of 1-propionyl-LSD Esylate Form 1.
  • the 1-propionyl-LSD Esylate Form 1 XRPD pattern is substantially similar to that shown in FIG.63.
  • the 1-propionyl-LSD Esylate Form 1 1 H NMR spectrum is substantially similar to that shown in FIG.74.
  • the 1- propionyl-LSD Esylate Form 1 TGA profile is substantially similar to that shown in FIG.75.
  • the 1-propionyl-LSD Esylate Form 1 DSC profile is substantially similar to that shown in FIG.75.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Esylate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 7.2 °2 ⁇ , 10.2 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Esylate Form 1 characterized by XRPD signals at 7.2 °2 ⁇ , 10.2 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Esylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.2 °2 ⁇ , 10.2 °2 ⁇ , 11.6 °2 ⁇ , 17.8 °2 ⁇ , and 21.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD Esylate Form 1 characterized by XRPD signals at 7.2 °2 ⁇ , 10.2 °2 ⁇ , 11.6 °2 ⁇ , 17.8 °2 ⁇ , and 21.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Esylate Form 1 characterized by two, or three or more XRPD signals selected from the group consisting of 17.8 °2 ⁇ , 7.2 °2 ⁇ , and 21.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Esylate Form 1 characterized by XRPD signals at 17.8 °2 ⁇ , 7.2 °2 ⁇ , and 21.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Esylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.8 °2 ⁇ , 7.2 °2 ⁇ , 21.5 °2 ⁇ , 10.2 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD Esylate Form 1 characterized by XRPD signals at 17.8 °2 ⁇ , 7.2 °2 ⁇ , 21.5 °2 ⁇ , 10.2 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Esylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.8 °2 ⁇ , 7.2 °2 ⁇ , 21.5 °2 ⁇ , 10.2 °2 ⁇ , 11.6 °2 ⁇ , 17.1 °2 ⁇ , and 16.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Esylate Form 1 characterized by XRPD signals at 17.8 °2 ⁇ , 7.2 °2 ⁇ , 21.5 °2 ⁇ , 10.2 °2 ⁇ , 11.6 °2 ⁇ , 17.1 °2 ⁇ , and 16.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Esylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.8 °2 ⁇ , 7.2 °2 ⁇ , 21.5 °2 ⁇ , 10.2 °2 ⁇ , 11.6 °2 ⁇ , 17.1 °2 ⁇ , 16.2 °2 ⁇ , 23.5 °2 ⁇ , 16.3 °2 ⁇ , and 22.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Esylate Form 1 characterized by XRPD signals at 17.8 °2 ⁇ , 7.2 °2 ⁇ , 21.5 °2 ⁇ , 10.2 °2 ⁇ , 11.6 °2 ⁇ , 17.1 °2 ⁇ , 16.2 °2 ⁇ , 23.5 °2 ⁇ , 16.3 °2 ⁇ , and 22.3°2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD Esylate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, or thirty-four XRPD signals selected from those set forth in Table 45.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Esylate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 7.2 °2 ⁇ , 10.2 °2 ⁇ , 11.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Esylate Form 1 characterized by XRPD signals at 7.2 °2 ⁇ , 10.2 °2 ⁇ , 11.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Esylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.2 °2 ⁇ , 10.2 °2 ⁇ , 11.5 °2 ⁇ , 17.8 °2 ⁇ , and 21.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD Esylate Form 1 characterized by XRPD signals at 7.2 °2 ⁇ , 10.2 °2 ⁇ , 11.5 °2 ⁇ , 17.8 °2 ⁇ , and 21.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Esylate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 7.2 °2 ⁇ , 17.8 °2 ⁇ , and 10.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Esylate Form 1 characterized by XRPD signals at 7.2 °2 ⁇ , 17.8 °2 ⁇ , and 10.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Esylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.2 °2 ⁇ , 17.8 °2 ⁇ , 10.2 °2 ⁇ , 21.5 °2 ⁇ , and 22.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD Esylate Form 1 characterized by XRPD signals at 7.2 °2 ⁇ , 17.8 °2 ⁇ , 10.2 °2 ⁇ , 21.5 °2 ⁇ , and 22.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Esylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.2 °2 ⁇ , 17.8 °2 ⁇ , 10.2 °2 ⁇ , 21.5 °2 ⁇ , 22.3 °2 ⁇ , 23.4 °2 ⁇ , and 16.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Esylate Form 1 characterized by XRPD signals at 7.2 °2 ⁇ , 17.8 °2 ⁇ , 10.2 °2 ⁇ , 21.5 °2 ⁇ , 22.3 °2 ⁇ , 23.4 °2 ⁇ , and 16.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Esylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.2 °2 ⁇ , 17.8 °2 ⁇ , 10.2 °2 ⁇ , 21.5 °2 ⁇ , 22.3 °2 ⁇ , 23.4 °2 ⁇ , 16.2 °2 ⁇ , 17.1 °2 ⁇ , 16.9 °2 ⁇ , and 24.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Esylate Form 1 characterized by XRPD signals at 7.2 °2 ⁇ , 17.8 °2 ⁇ , 10.2 °2 ⁇ , 21.5 °2 ⁇ , 22.3 °2 ⁇ , 23.4 °2 ⁇ , 16.2 °2 ⁇ , 17.1 °2 ⁇ , 16.9 °2 ⁇ , and 24.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD Esylate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, or twenty-nine XRPD signals selected from those set forth in Table 46.
  • Table 46 XRPD Signals for 1-propionyl-LSD Esylate Form 1 1-propionyl-LSD Freebase Form A
  • the present disclosure provides solid forms of 1-propionyl-LSD freebase Form A, e.g., crystalline forms of 1-propionyl-LSD freebase Form A.
  • the 1-propionyl-LSD freebase Form A XRPD pattern is substantially similar to that shown in any one of FIGs.28 or 29.
  • the 1-propionyl-LSD freebase Form A 1 H NMR spectrum is substantially similar to that shown in any one of FIGs.30 or 87.
  • the 1-propionyl-LSD freebase Form A TGA profile is substantially similar to that shown in FIG.88.
  • the 1-propionyl-LSD freebase Form A DSC profile is substantially similar to that shown in FIG.88.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD freebase Form A characterized by two, or three XRPD signals selected from the group consisting of 9.4 °2 ⁇ , 10.3 °2 ⁇ , 12.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD freebase Form A characterized by XRPD signals at 9.4 °2 ⁇ , 10.3 °2 ⁇ , 12.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD freebase Form A characterized by two, or three XRPD signals selected from the group consisting of 9.4 °2 ⁇ , 10.3 °2 ⁇ , 12.5 °2 ⁇ , 16.6 °2 ⁇ , and 17.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl- LSD freebase Form A characterized by XRPD signals at 9.4 °2 ⁇ , 10.3 °2 ⁇ , 12.5 °2 ⁇ , 16.6 °2 ⁇ , and 17.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.5 °2 ⁇ , 19.2 °2 ⁇ , and 20.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl- LSD freebase Form A characterized by XRPD signals at 12.5 °2 ⁇ , 19.2 °2 ⁇ , and 20.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.5 °2 ⁇ , 19.2 °2 ⁇ , 20.6 °2 ⁇ , 17.3 °2 ⁇ , and 24.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1- propionyl-LSD freebase Form A characterized by XRPD signals at 12.5 °2 ⁇ , 19.2 °2 ⁇ , 20.6 °2 ⁇ , 17.3 °2 ⁇ , and 24.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.5 °2 ⁇ , 19.2 °2 ⁇ , 20.6 °2 ⁇ , 17.3 °2 ⁇ , 24.1 °2 ⁇ , 19.6 °2 ⁇ , and 23.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl- LSD is 1-propionyl-LSD freebase Form A characterized by XRPD signals at 12.5 °2 ⁇ , 19.2 °2 ⁇ , 20.6 °2 ⁇ , 17.3 °2 ⁇ , 24.1 °2 ⁇ , 19.6 °2 ⁇ , and 23.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.5 °2 ⁇ , 19.2 °2 ⁇ , 20.6 °2 ⁇ , 17.3 °2 ⁇ , 24.1 °2 ⁇ , 19.6 °2 ⁇ , 23.6 °2 ⁇ , 15.4 °2 ⁇ , 21.1 °2 ⁇ , and 22.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD freebase Form A characterized by XRPD signals at 12.5 °2 ⁇ , 19.2 °2 ⁇ , 20.6 °2 ⁇ , 17.3 °2 ⁇ , 24.1 °2 ⁇ , 19.6 °2 ⁇ , 23.6 °2 ⁇ , 15.4 °2 ⁇ , 21.1 °2 ⁇ , and 22.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • crystalline 1-propionyl-LSD freebase Form A is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty- four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty- two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, or forty-three XRPD signals selected from those set forth in Table 47.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD freebase Form A characterized by two, or three XRPD signals selected from the group consisting of 9.4 °2 ⁇ , 10.3 °2 ⁇ , and 12.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD freebase Form A characterized by XRPD signals at 9.4 °2 ⁇ , 10.3 °2 ⁇ , and 12.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.4 °2 ⁇ , 10.3 °2 ⁇ , 12.6 °2 ⁇ , 16.6 °2 ⁇ , and 17.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1- propionyl-LSD freebase Form A characterized by XRPD signals at 9.4 °2 ⁇ , 10.3 °2 ⁇ , 12.6 °2 ⁇ , 16.6 °2 ⁇ , and 17.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD freebase Form A characterized by two, or three XRPD signals selected from the group consisting of 19.3 °2 ⁇ , 12.6 °2 ⁇ , and 17.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD freebase Form A characterized by XRPD signals at 19.3 °2 ⁇ , 12.6 °2 ⁇ , and 17.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.3 °2 ⁇ , 12.6 °2 ⁇ , 17.4 °2 ⁇ , 19.6 °2 ⁇ , and 24.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1- propionyl-LSD freebase Form A characterized by XRPD signals at 19.3 °2 ⁇ , 12.6 °2 ⁇ , 17.4 °2 ⁇ , 19.6 °2 ⁇ , and 24.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.3 °2 ⁇ , 12.6 °2 ⁇ , 17.4 °2 ⁇ , 19.6 °2 ⁇ , 24.1 °2 ⁇ , 20.6 °2 ⁇ , and 15.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl- LSD is 1-propionyl-LSD freebase Form A characterized by XRPD signals at 19.3 °2 ⁇ , 12.6 °2 ⁇ , 17.4 °2 ⁇ , 19.6 °2 ⁇ , 24.1 °2 ⁇ , 20.6 °2 ⁇ , and 15.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD freebase Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.3 °2 ⁇ , 12.6 °2 ⁇ , 17.4 °2 ⁇ , 19.6 °2 ⁇ , 24.1 °2 ⁇ , 20.6 °2 ⁇ , 15.4 °2 ⁇ , 21.1 °2 ⁇ , 13.2 °2 ⁇ , and 10.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD freebase Form A characterized by XRPD signals at 19.3 °2 ⁇ , 12.6 °2 ⁇ , 17.4 °2 ⁇ , 19.6 °2 ⁇ , 24.1 °2 ⁇ , 20.6 °2 ⁇ , 15.4 °2 ⁇ , 21.1 °2 ⁇ , 13.2 °2 ⁇ , and 10.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • crystalline 1-propionyl-LSD freebase Form A is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty- four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty- two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, or forty-eight XRPD signals selected from those set forth in Table 48.
  • Table 48 XRPD Signals for 1-propionyl-LSD Freebase Form A 1-propionyl-LSD Fumarate Form 1
  • the present disclosure provides solid forms of Fumarate Form 1 salts of 1-propionyl-LSD, e.g., crystalline forms of 1-propionyl-LSD Fumarate Form 1.
  • the 1-propionyl-LSD Fumarate Form 1 XRPD pattern is substantially similar to that shown in FIG.64.
  • the 1-propionyl-LSD Fumarate Form 1 1 H NMR spectrum is substantially similar to that shown in FIG.73.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Fumarate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 3.0 °2 ⁇ , 5.2 °2 ⁇ , and 5.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Fumarate Form 1 characterized by XRPD signals at 3.0 °2 ⁇ , 5.2 °2 ⁇ , and 5.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Fumarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 3.0 °2 ⁇ , 5.2 °2 ⁇ , 5.9 °2 ⁇ , 10.7 °2 ⁇ , and 11.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD Fumarate Form 1 characterized by XRPD signals at 3.0 °2 ⁇ , 5.2 °2 ⁇ , 5.9 °2 ⁇ , 10.7 °2 ⁇ , and 11.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Fumarate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 5.2 °2 ⁇ , 5.9 °2 ⁇ , and 15.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Fumarate Form 1 characterized by XRPD signals at 5.2° 2 ⁇ , 5.9 °2 ⁇ , and 15.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Fumarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.2 °2 ⁇ , 5.9 °2 ⁇ , 15.4 °2 ⁇ , 3.0 °2 ⁇ , and 14.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD Fumarate Form 1characterized by XRPD signals at 5.2 °2 ⁇ , 5.9 °2 ⁇ , 15.4 °2 ⁇ , 3.0 °2 ⁇ , and 14.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Fumarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.2 °2 ⁇ , 5.9 °2 ⁇ , 15.4 °2 ⁇ , 3.0 °2 ⁇ , 14.7 °2 ⁇ , 10.7 °2 ⁇ , and 11.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Fumarate Form 1 characterized by XRPD signals at 5.2 °2 ⁇ , 5.9 °2 ⁇ , 15.4 °2 ⁇ , 3.0 °2 ⁇ , 14.7 °2 ⁇ , 10.7 °2 ⁇ , and 11.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Fumarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.2 °2 ⁇ , 5.9 °2 ⁇ , 15.4 °2 ⁇ , 3.0 °2 ⁇ , 14.7 °2 ⁇ , 10.7 °2 ⁇ , 11.9 °2 ⁇ , 10.3 °2 ⁇ , 12.6 °2 ⁇ , and 8.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Fumarate Form 1 characterized by XRPD signals at 5.2 °2 ⁇ , 5.9 °2 ⁇ , 15.4 °2 ⁇ , 3.0 °2 ⁇ , 14.7 °2 ⁇ , 10.7 °2 ⁇ , 11.9 °2 ⁇ , 10.3 °2 ⁇ , 12.6 °2 ⁇ , and 8.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD Fumarate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, or twelve XRPD signals selected from those set forth in Table 49.
  • Table 49 XRPD Signals for 1-propionyl-LSD Fumarate Form 1
  • 1-propionyl-LSD HCl Form 1 the present disclosure provides solid forms of Hydrochloride Form 1 salts of 1-propionyl-LSD, e.g., crystalline forms of 1-propionyl-LSD Hydrochloride Form 1.
  • the 1-propionyl-LSD Hydrochloride Form 1 XRPD pattern is substantially similar to that shown in FIG.31.
  • the 1-propionyl-LSD Hydrochloride Form 1 1 H NMR spectrum is substantially similar to that shown in FIG.108.
  • the 1-propionyl-LSD Hydrochloride Form A TGA profile is substantially similar to that shown in FIG.109.
  • the 1-propionyl-LSD Hydrochloride Form A DSC profile is substantially similar to that shown in FIG.109.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Hydrochloride Form 1 characterized by two, or three XRPD signals selected from the group consisting of 6.7 °2 ⁇ , 7.7 °2 ⁇ , and 11.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Hydrochloride Form 1 characterized by XRPD signals at 6.7 °2 ⁇ , 7.7 °2 ⁇ , and 11.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Hydrochloride Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.7 °2 ⁇ , 7.7 °2 ⁇ , 9.0 °2 ⁇ , 11.5 °2 ⁇ , and 12.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1- propionyl-LSD Hydrochloride Form 1 characterized by XRPD signals at 6.7 °2 ⁇ , 7.7 °2 ⁇ , 9.0 °2 ⁇ , 11.5 °2 ⁇ , and 12.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Hydrochloride Form 1 characterized by two, or three XRPD signals selected from the group consisting of 7.7 °2 ⁇ , 18.0 °2 ⁇ , and 19.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Hydrochloride Form 1 characterized by XRPD signals at 7.7 °2 ⁇ , 18.0 °2 ⁇ , and 19.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Hydrochloride Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.7 °2 ⁇ , 18.0 °2 ⁇ , 19.2 °2 ⁇ , 6.7 °2 ⁇ , and 11.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1- propionyl-LSD Hydrochloride Form 1 characterized by XRPD signals at 7.7 °2 ⁇ , 18.0 °2 ⁇ , 19.2 °2 ⁇ , 6.7 °2 ⁇ , and 11.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Hydrochloride Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.7 °2 ⁇ , 18.0 °2 ⁇ , 19.2 °2 ⁇ , 6.7 °2 ⁇ , 11.5 °2 ⁇ , 20.3 °2 ⁇ , and 23.2°2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1- propionyl-LSD is 1-propionyl-LSD Hydrochloride Form 1 characterized by XRPD signals at 7.7 °2 ⁇ , 18.0 °2 ⁇ , 19.2 °2 ⁇ , 6.7 °2 ⁇ , 11.5 °2 ⁇ , 20.3 °2 ⁇ , and 23.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Hydrochloride Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.7 °2 ⁇ , 18.0 °2 ⁇ , 19.2 °2 ⁇ , 6.7 °2 ⁇ , 11.5 °2 ⁇ , 20.3 °2 ⁇ , 23.2 °2 ⁇ , 12.1 °2 ⁇ , 15.4 °2 ⁇ , and 12.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Hydrochloride Form 1 characterized by XRPD signals at 7.7 °2 ⁇ , 18.0 °2 ⁇ , 19.2 °2 ⁇ , 6.7 °2 ⁇ , 11.5 °2 ⁇ , 20.3 °2 ⁇ , 23.2 °2 ⁇ , 12.1 °2 ⁇ , 15.4 °2 ⁇ , and 12.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD Hydrochloride Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty- three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, or twenty-nine XRPD signals selected from those set forth in Table 50.
  • Table 50 XRPD Signals for 1-propionyl-LSD Hydrochloride Form 1 1-propionyl-LSD HCl Form 2
  • the present disclosure provides solid forms of Hydrochloride Form 2 salts of 1-propionyl-LSD, e.g., crystalline forms of 1-propionyl-LSD Hydrochloride Form 2.
  • the 1-propionyl-LSD Hydrochloride Form 2 XRPD pattern is substantially similar to that shown in FIG.44.
  • the 1-propionyl-LSD Hydrochloride Form 2 1 H NMR spectrum is substantially similar to that shown in FIG.89.
  • the 1-propionyl-LSD Hydrochloride Form 2 TGA profile is substantially similar to that shown in FIG.90.
  • the 1-propionyl-LSD Hydrochloride Form 2 DSC profile is substantially similar to that shown in FIG.90.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Hydrochloride Form 2 characterized by two, or three XRPD signals selected from the group consisting of 6.5 °2 ⁇ , 7.5 °2 ⁇ , and 8.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Hydrochloride Form 2 characterized by XRPD signals at 6.5 °2 ⁇ , 7.5 °2 ⁇ , and 8.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Hydrochloride Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.5 °2 ⁇ , 7.5 °2 ⁇ , 8.6 °2 ⁇ , 11.3 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1- propionyl-LSD Hydrochloride Form 2 characterized by XRPD signals at 6.5 °2 ⁇ , 7.5 °2 ⁇ , 8.6 °2 ⁇ , 11.3 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Hydrochloride Form 2 characterized by two, or three XRPD signals selected from the group consisting of 6.5 °2 ⁇ , 7.5 °2 ⁇ , and 21.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Hydrochloride Form 2 characterized by XRPD signals at 6.5 °2 ⁇ , 7.5 °2 ⁇ , and 21.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Hydrochloride Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.5 °2 ⁇ , 7.5 °2 ⁇ , 21.3 °2 ⁇ , 8.6 °2 ⁇ , and 17.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1- propionyl-LSD Hydrochloride Form 2 characterized by XRPD signals at 6.5 °2 ⁇ , 7.5 °2 ⁇ , 21.3 °2 ⁇ , 8.6 °2 ⁇ , and 17.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Hydrochloride Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.5 °2 ⁇ , 7.5 °2 ⁇ , 21.3 °2 ⁇ , 8.6 °2 ⁇ , 17.3 °2 ⁇ , 22.6 °2 ⁇ , and 13.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1- propionyl-LSD is 1-propionyl-LSD Hydrochloride Form 2 characterized by XRPD signals at 6.5 °2 ⁇ , 7.5 °2 ⁇ , 21.3 °2 ⁇ , 8.6 °2 ⁇ , 17.3 °2 ⁇ , 22.6 °2 ⁇ , and 13.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Hydrochloride Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.5 °2 ⁇ , 7.5 °2 ⁇ , 21.3 °2 ⁇ , 8.6 °2 ⁇ , 17.3 °2 ⁇ , 22.6 °2 ⁇ , 13.1 °2 ⁇ , 23.5 °2 ⁇ , 15.1 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Hydrochloride Form 2 characterized by XRPD signals at 6.5 °2 ⁇ , 7.5 °2 ⁇ , 21.3 °2 ⁇ , 8.6 °2 ⁇ , 17.3 °2 ⁇ , 22.6 °2 ⁇ , 13.1 °2 ⁇ , 23.5 °2 ⁇ , 15.1 °2 ⁇ , and 11.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD Hydrochloride Form 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty- three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, or forty-one XRPD signals selected from those set forth in Table 51.
  • Table 51 XRPD Signals for 1-propionyl-LSD Hydrochloride Form 2
  • 1-propionyl-LSD L-Malate Form 1 the present disclosure provides solid forms of L-malate Form 1 salts of 1-propionyl-LSD, e.g., crystalline forms of 1-propionyl-LSD L-malate Form 1.
  • the 1-propionyl-LSD L-malate Form 1 XRPD pattern is substantially similar to that shown in FIG.33.
  • the 1-propionyl-LSD L-malate Form 1 1 H NMR spectrum is substantially similar to that shown in FIG.40.
  • the 1- propionyl-LSD L-malate Form 1 TGA profile is substantially similar to that shown in FIG.95.
  • the 1-propionyl-LSD L-malate Form 1 DSC profile is substantially similar to that shown in FIG.95.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD L-malate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 5.0 °2 ⁇ , 5.8 °2 ⁇ , and 10.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD L-malate Form 1 characterized by XRPD signals at 5.0 °2 ⁇ , 5.8 °2 ⁇ , and 10.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD L-malate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.0 °2 ⁇ , 5.8 °2 ⁇ , 10.0 °2 ⁇ , 10.5 °2 ⁇ , and 12.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD L-malate Form 1 characterized by XRPD signals at 5.0 °2 ⁇ , 5.8 °2 ⁇ , 10.0 °2 ⁇ , 10.5 °2 ⁇ , and 12.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD L-malate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 5.0 °2 ⁇ , 5.8 °2 ⁇ , and 15.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD L-malate Form 1 characterized by XRPD signals at 5.0 °2 ⁇ , 5.8 °2 ⁇ , and 15.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD L-malate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.0 °2 ⁇ , 5.8 °2 ⁇ , 15.3 °2 ⁇ , 16.1 °2 ⁇ , and 12.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1- propionyl-LSD L-malate Form 1 characterized by XRPD signals at 6.5.0 °2 ⁇ , 5.8 °2 ⁇ , 15.3 °2 ⁇ , 16.1 °2 ⁇ , and 12.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD L-malate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.0 °2 ⁇ , 5.8 °2 ⁇ , 15.3 °2 ⁇ , 16.1 °2 ⁇ , 12.6 °2 ⁇ , 13.3 °2 ⁇ , and 10.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl- LSD is crystalline 1-propionyl-LSD L-malate Form 1 characterized by XRPD signals at 5.0 °2 ⁇ , 5.8 °2 ⁇ , 15.3 °2 ⁇ , 16.1 °2 ⁇ , 12.6 °2 ⁇ , 13.3 °2 ⁇ , and 10.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD L-malate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.0 °2 ⁇ , 5.8 °2 ⁇ , 15.3 °2 ⁇ , 16.1 °2 ⁇ , 12.6 °2 ⁇ , 13.3 °2 ⁇ , 10.0 °2 ⁇ , 15.1 °2 ⁇ , 10.5 °2 ⁇ , and 20.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD L-malate Form 1 characterized by XRPD signals at 5.0 °2 ⁇ , 5.8 °2 ⁇ , 15.3 °2 ⁇ , 16.1 °2 ⁇ , 12.6 °2 ⁇ , 13.3 °2 ⁇ , 10.0 °2 ⁇ , 15.1 °2 ⁇ , 10.5 °2 ⁇ , and 20.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD L-malate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, or thirty XRPD signals selected from those set forth in Table 52.
  • Table 52 XRPD Signals for 1-propionyl-LSD L-malate Form 1 1-propionyl-LSD L-Tartrate Form 1
  • the present disclosure provides solid forms of L-Tartrate Form 1 salts of 1-propionyl-LSD, e.g., crystalline forms of 1-propionyl-LSD L-Tartrate Form 1.
  • the 1-propionyl-LSD L-Tartrate Form 1 XRPD pattern is substantially similar to that shown in FIG.39.
  • the 1-propionyl-LSD L-Tartrate Form 1 1 H NMR spectrum is substantially similar to that shown in FIG.96.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD L-Tartrate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 5.3 °2 ⁇ , 6.0 °2 ⁇ , and 10.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD L-Tartrate Form 1 characterized by XRPD signals at 5.3 °2 ⁇ , 6.0 °2 ⁇ , and 10.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD L-Tartrate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.3 °2 ⁇ , 6.0 °2 ⁇ , 10.4 °2 ⁇ , 10.8 °2 ⁇ , and 13.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD L-Tartrate Form 1 characterized by XRPD signals at 5.3 °2 ⁇ , 6.0 °2 ⁇ , 10.4 °2 ⁇ , 10.8 °2 ⁇ , and 13.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD L-Tartrate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 5.3 °2 ⁇ , 6.0 °2 ⁇ , and 10.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD L-Tartrate Form 1 characterized by XRPD signals at 5.3 °2 ⁇ , 6.0 °2 ⁇ , and 10.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD L-Tartrate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.3 °2 ⁇ , 6.0 °2 ⁇ , 10.8 °2 ⁇ , 10.4 °2 ⁇ , and 13.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1- propionyl-LSD L-Tartrate Form 1 characterized by XRPD signals at 5.3 °2 ⁇ , 6.0 °2 ⁇ , 10.8 °2 ⁇ , 10.4 °2 ⁇ , and 13.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD L-Tartrate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.3 °2 ⁇ , 6.0 °2 ⁇ , 10.8 °2 ⁇ , 10.4 °2 ⁇ , 13.8 °2 ⁇ , 15.2 °2 ⁇ , and 14.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl- LSD is crystalline 1-propionyl-LSD L-Tartrate Form 1 characterized by XRPD signals at 5.3 °2 ⁇ , 6.0 °2 ⁇ , 10.8 °2 ⁇ , 10.4 °2 ⁇ , 13.8 °2 ⁇ , 15.2 °2 ⁇ , and 14.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD L-Tartrate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.3 °2 ⁇ , 6.0 °2 ⁇ , 10.8 °2 ⁇ , 10.4 °2 ⁇ , 13.8 °2 ⁇ , 15.2 °2 ⁇ , 14.9 °2 ⁇ , 15.4 °2 ⁇ , 14.2 °2 ⁇ , and 13.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD L-Tartrate Form 1 characterized by XRPD signals at 5.3 °2 ⁇ , 6.0 °2 ⁇ , 10.8 °2 ⁇ , 10.4 °2 ⁇ , 13.8 °2 ⁇ , 15.2 °2 ⁇ , 14.9 °2 ⁇ , 15.4 °2 ⁇ , 14.2 °2 ⁇ , and 13.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD L-Tartrate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, or twelve XRPD signals selected from those set forth in Table 53.
  • Table 53 XRPD Signals for 1-propionyl-LSD L-Tartrate Form 1
  • Non-Crystalline 1-propionyl LSD Maleate the present disclosure provides non-crystalline 1P-LSD maleate salts.
  • the non-crystalline 1P-LSD maleate salt is characterized by a glass transition temperature of about 69.0 °C.
  • the non-crystalline 1P-LSD maleate salt is characterized by a TGA thermogram showing about 1.2% weight loss from ambient to 100 oC. In some embodiments, the non-crystalline 1P-LSD maleate salt is characterized by a 1 H NMR spectra substantially similar to that shown in FIG.196. In some embodiments, the non-crystalline 1P-LSD maleate salt is characterized by a TGA profile substantially similar to that shown in FIG.169. In some embodiments, the non-crystalline 1P- LSD maleate salt is characterized by a mDSC profile substantially similar to that shown in FIG. 170.
  • 1-propionyl-LSD Maleate Form 1 the present disclosure provides solid forms of Maleate Form 1 salts of 1-propionyl-LSD, e.g., crystalline forms of 1-propionyl-LSD Maleate Form 1.
  • the 1-propionyl-LSD Maleate Form 1 XRPD pattern is substantially similar to that shown in any one of FIGs.32 or 65.
  • the 1-propionyl-LSD Maleate Form 1 1 H NMR spectrum is substantially similar to that shown in FIG.71.
  • the 1-propionyl-LSD Maleate Form 1 TGA profile is substantially similar to that shown in FIG.72.
  • the 1-propionyl-LSD Maleate Form 1 DSC profile is substantially similar to that shown in FIG.72.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 9.6 °2 ⁇ , 10.6 °2 ⁇ , and 14.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by XRPD signals at 9.6 °2 ⁇ , 10.6 °2 ⁇ , and 14.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.6 °2 ⁇ , 10.6 °2 ⁇ , 14.6 °2 ⁇ , 16.9 °2 ⁇ , and 18.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD Maleate Form 1 characterized by XRPD signals at 9.6 °2 ⁇ , 10.6 °2 ⁇ , 14.6 °2 ⁇ , 16.9 °2 ⁇ , and 18.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Maleate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 14.6 °2 ⁇ , 16.9 °2 ⁇ , and 20.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by XRPD signals at 14.6 °2 ⁇ , 16.9 °2 ⁇ , and 20.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.6 °2 ⁇ , 16.9 °2 ⁇ , 20.1 °2 ⁇ , 24.1 °2 ⁇ , and 10.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by XRPD signals at 14.6 °2 ⁇ , 16.9 °2 ⁇ , 20.1 °2 ⁇ , 24.1 °2 ⁇ , and 10.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.6 °2 ⁇ , 16.9 °2 ⁇ , 20.1 °2 ⁇ , 24.1 °2 ⁇ , 10.6 °2 ⁇ , 18.2 °2 ⁇ , and 22.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1- propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by XRPD signals at 14.6 °2 ⁇ , 16.9 °2 ⁇ , 20.1 °2 ⁇ , 24.1 °2 ⁇ , 10.6 °2 ⁇ , 18.2 °2 ⁇ , and 22.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.6 °2 ⁇ , 16.9 °2 ⁇ , 20.1 °2 ⁇ , 24.1 °2 ⁇ , 10.6 °2 ⁇ , 18.2 °2 ⁇ , 22.1 °2 ⁇ , 17.3 °2 ⁇ , 18.0 °2 ⁇ , and 20.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 Form 1 characterized by XRPD signals at 14.6 °2 ⁇ , 16.9 °2 ⁇ , 20.1 °2 ⁇ , 24.1 °2 ⁇ , 10.6 °2 ⁇ , 18.2 °2 ⁇ , 22.1 °2 ⁇ , 17.3 °2 ⁇ , 18.0 °2 ⁇ , and 20.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD Maleate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, or forty-two XRPD signals selected from those set forth in Table 54.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 9.6 °2 ⁇ , 10.6 °2 ⁇ , and 14.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by XRPD signals at 9.6 °2 ⁇ , 10.6 °2 ⁇ , and 14.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.6 °2 ⁇ , 10.6 °2 ⁇ , 14.6 °2 ⁇ , 16.8 °2 ⁇ , and 18.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD Maleate Form 1 characterized by XRPD signals at 9.6 °2 ⁇ , 10.6 °2 ⁇ , 14.6 °2 ⁇ , 16.8 °2 ⁇ , and 18.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Maleate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 14.6 °2 ⁇ , 16.8 °2 ⁇ , and 20.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by XRPD signals at 14.6 °2 ⁇ , 16.8 °2 ⁇ , and 20.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.6 °2 ⁇ , 16.8 °2 ⁇ , 20.1 °2 ⁇ 24.1 °2 ⁇ , and 18.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by XRPD signals at 14.6 °2 ⁇ , 16.8 °2 ⁇ , 20.1 °2 ⁇ , 24.1 °2 ⁇ , and 18.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.6 °2 ⁇ , 16.8 °2 ⁇ , 20.1 °2 ⁇ , 24.1 °2 ⁇ , 18.2 °2 ⁇ , 10.6 °2 ⁇ , and 22.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1- propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by XRPD signals at 14.6 °2 ⁇ , 16.8 °2 ⁇ , 20.1 °2 ⁇ , 24.1 °2 ⁇ , 18.2 °2 ⁇ , 10.6 °2 ⁇ , and 22.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.6 °2 ⁇ , 16.8 °2 ⁇ , 20.1 °2 ⁇ , 24.1 °2 ⁇ , 18.2 °2 ⁇ , 10.6 °2 ⁇ , 22.1 °2 ⁇ , 18.0 °2 ⁇ , 17.3 °2 ⁇ , and 20.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 1 characterized by XRPD signals at14.6 °2 ⁇ , 16.8 °2 ⁇ , 20.1 °2 ⁇ , 24.1 °2 ⁇ , 18.2 °2 ⁇ , 10.6 °2 ⁇ , 22.1 °2 ⁇ , 18.0 °2 ⁇ , 17.3 °2 ⁇ , and 20.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD Maleate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, or forty-two XRPD signals selected from those set forth in Table 55.
  • the solid form of 1-propionyl LSD maleate is crystalline 1- propionyl LSD maleate Form 1 characterized by two or more, or three XRPD signals selected from the group consisting of 9.6 °2 ⁇ , 9.9 °2 ⁇ , and 10.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl LSD maleate is crystalline 1-propionyl LSD maleate Form 1characterized by XRPD signals at 9.6 °2 ⁇ , 9.9 °2 ⁇ , and 10.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl LSD maleate is crystalline 1- propionyl LSD maleate Form 1characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.6 °2 ⁇ , 9.9 °2 ⁇ , 10.6 °2 ⁇ , 13.4 °2 ⁇ , and 14.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl LSD maleate is crystalline 1-propionyl LSD maleate Form 1 characterized by XRPD signals at 14.7 °2 ⁇ , 9.6 °2 ⁇ , 9.9 °2 ⁇ , 10.6 °2 ⁇ , 13.4 °2 ⁇ , and 14.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl LSD maleate is crystalline 1- propionyl LSD maleate Form 1 characterized by two or more, or three XRPD signals selected from the group consisting of 14.7 °2 ⁇ , 16.9 °2 ⁇ , and 24.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl LSD maleate is crystalline 1-propionyl LSD maleate Form 1characterized by XRPD signals at 14.7 °2 ⁇ , 16.9 °2 ⁇ , and 24.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl LSD maleate is crystalline 1- propionyl LSD maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.7 °2 ⁇ , 16.9 °2 ⁇ , 24.4 °2 ⁇ , 10.6 °2 ⁇ , and 18.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1- propionyl LSD maleate is crystalline 1-propionyl LSD maleate Form 1 characterized by XRPD signals at 14.7 °2 ⁇ , 16.9 °2 ⁇ , 24.4 °2 ⁇ , 10.6 °2 ⁇ , and 18.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl LSD maleate is crystalline 1- propionyl LSD maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.7 °2 ⁇ , 16.9 °2 ⁇ , 24.4 °2 ⁇ , 10.6 °2 ⁇ , 18.4 °2 ⁇ , 22.4 °2 ⁇ , and 20.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl LSD maleate is crystalline 1-propionyl LSD maleate Form 1 characterized by XRPD signals at 14.7 °2 ⁇ , 16.9 °2 ⁇ , 24.4 °2 ⁇ , 10.6 °2 ⁇ , 18.4 °2 ⁇ , 22.4 °2 ⁇ , and 20.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl LSD maleate is crystalline 1- propionyl LSD maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.7 °2 ⁇ , 16.9 °2 ⁇ , 24.4 °2 ⁇ , 10.6 °2 ⁇ , 18.4 °2 ⁇ , 22.4 °2 ⁇ , 20.4 °2 ⁇ , 28.1 °2 ⁇ , 18.1 °2 ⁇ , and 17.4°2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl LSD maleate is crystalline 1-propionyl LSD maleate Form 1 characterized by XRPD signals at 14.7 °2 ⁇ , 16.9 °2 ⁇ , 24.4 °2 ⁇ , 10.6 °2 ⁇ , 18.4 °2 ⁇ , 22.4 °2 ⁇ , 20.4 °2 ⁇ , 28.1 °2 ⁇ , 18.1 °2 ⁇ , and 17.4°2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl LSD maleate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty, fifty-one, fifty-two, fifty-three, fifty-four, fifty-five, fifty-six, fifty-seven, fifty- eight, fifty-nine, sixty, or sixty-one XRPD signals selected from those set forth in Table 165.
  • Table 165 Calculated XRPD Signals for 1-propionyl LSD Maleate Form 1
  • 1-propionyl-LSD Maleate Form 2 the present disclosure provides solid forms of Maleate Form 2 salts of 1-propionyl-LSD, e.g., crystalline forms of 1-propionyl-LSD Maleate Form 2.
  • the 1-propionyl-LSD Maleate Form 2 XRPD pattern is substantially similar to that shown in FIG.45.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 5.4 °2 ⁇ , 8.1 °2 ⁇ , 11.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 2 characterized by XRPD signals at 5.4 °2 ⁇ , 8.1 °2 ⁇ , 11.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.4 °2 ⁇ , 8.1 °2 ⁇ , 11.8 °2 ⁇ , 16.7 °2 ⁇ , and 19.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD Maleate Form 2 characterized by XRPD signals at 5.4 °2 ⁇ , 8.1 °2 ⁇ , 11.8 °2 ⁇ , 16.7 °2 ⁇ , and 19.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is 1-propionyl-LSD Maleate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 5.4 °2 ⁇ , 8.1 °2 ⁇ , and 11.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of LSD is crystalline 1-propionyl-LSD Maleate Form 2 characterized by XRPD signals at 5.4 °2 ⁇ , 8.1 °2 ⁇ , and 11.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.4 °2 ⁇ , 8.1 °2 ⁇ , 11.8 °2 ⁇ , 5.6 °2 ⁇ , and 19.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1- propionyl-LSD Maleate Form 2 characterized by XRPD signals at 5.4 °2 ⁇ , 8.1 °2 ⁇ , 11.8 °2 ⁇ , 5.6 °2 ⁇ , and 19.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.4 °2 ⁇ , 8.1 °2 ⁇ , 11.8 °2 ⁇ , 5.6 °2 ⁇ , 19.9 °2 ⁇ , 16.7 °2 ⁇ , and 15.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl- LSD is crystalline 1-propionyl-LSD Maleate Form2 characterized by XRPD signals at 5.4 °2 ⁇ , 8.1 °2 ⁇ , 11.8 °2 ⁇ , 5.6 °2 ⁇ , 19.9 °2 ⁇ , 16.7 °2 ⁇ , and 15.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.4 °2 ⁇ , 8.1 °2 ⁇ , 11.8 °2 ⁇ , 5.6 °2 ⁇ , 19.9 °2 ⁇ , 16.7 °2 ⁇ , 15.5 °2 ⁇ , 17.9 °2 ⁇ , 15.3 °2 ⁇ , and 15.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Maleate Form 2 characterized by XRPD signals at 5.4 °2 ⁇ , 8.1 °2 ⁇ , 11.8 °2 ⁇ , 5.6 °2 ⁇ , 19.9 °2 ⁇ , 16.7 °2 ⁇ , 15.5 °2 ⁇ , 17.9 °2 ⁇ , 15.3 °2 ⁇ , and 15.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD Maleate Form 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, or sixteen XRPD signals selected from those set forth in Table 56.
  • Table 56 XRPD Signals for 1-propionyl-LSD Maleate Form 2
  • 1-propionyl-LSD Mesylate Form 1 the present disclosure provides solid forms of Mesylate Form 1 salts of 1-propionyl-LSD, e.g., crystalline forms of 1-propionyl-LSD Mesylate Form 1.
  • the 1-propionyl-LSD Mesylate Form 1 XRPD pattern is substantially similar to that shown in FIG.41.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Mesylate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 7.3 °2 ⁇ , 10.4 °2 ⁇ , and 16.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Mesylate Form 1 characterized by XRPD signals at 7.3 °2 ⁇ , 10.4 °2 ⁇ , and 16.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Mesylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.3 °2 ⁇ , 10.4 °2 ⁇ , 16.1 °2 ⁇ , 17.1 °2 ⁇ , and 18.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD Mesylate Form 1 characterized by XRPD signals at 7.3 °2 ⁇ , 10.4 °2 ⁇ , 16.1 °2 ⁇ , 17.1 °2 ⁇ , and 18.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Mesylate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 18.2 °2 ⁇ , 7.3 °2 ⁇ , and 10.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Mesylate Form 1 characterized by XRPD signals at 18.2 °2 ⁇ , 7.3 °2 ⁇ , and 10.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Mesylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 18.2 °2 ⁇ , 7.3 °2 ⁇ , 10.4 °2 ⁇ , 21.9 °2 ⁇ , and 17.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1- propionyl-LSD Mesylate Form 1 characterized by XRPD signals at 18.2 °2 ⁇ , 7.3 °2 ⁇ , 10.4 °2 ⁇ , 21.9 °2 ⁇ , and 17.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Mesylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 18.2 °2 ⁇ , 7.3 °2 ⁇ , 10.4 °2 ⁇ , 21.9 °2 ⁇ , 17.1 °2 ⁇ , 23.6 °2 ⁇ , and 17.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1- propionyl-LSD is crystalline 1-propionyl-LSD Mesylate Form 1 characterized by XRPD signals at 18.2 °2 ⁇ , 7.3 °2 ⁇ , 10.4 °2 ⁇ , 21.9 °2 ⁇ , 17.1 °2 ⁇ , 23.6 °2 ⁇ , and 17.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Mesylate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 18.2 °2 ⁇ , 7.3 °2 ⁇ , 10.4 °2 ⁇ , 21.9 °2 ⁇ , 17.1 °2 ⁇ , 23.6 °2 ⁇ , 17.4 °2 ⁇ , 22.3 °2 ⁇ , 16.8 °2 ⁇ , and 25.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Mesylate Form 1 characterized by XRPD signals at 18.2 °2 ⁇ , 7.3 °2 ⁇ , 10.4 °2 ⁇ , 21.9 °2 ⁇ , 17.1 °2 ⁇ , 23.6 °2 ⁇ , 17.4 °2 ⁇ , 22.3 °2 ⁇ , 16.8 °2 ⁇ , and 25.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD Mesylate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty-nine, or fifty XRPD signals selected from those set forth in Table 57.
  • Table 57 XRPD Signals for 1-proionyl-LSD Mesylate Form 1 1-propionyl-LSD Mesylate Form 2
  • the present disclosure provides solid forms of Mesylate Form 2 salts of 1-propionyl-LSD, e.g., crystalline forms of 1-propionyl-LSD Mesylate Form 2.
  • the 1-propionyl-LSD Mesylate Form 2 XRPD pattern is substantially similar to that shown in FIG.43.
  • the 1-propionyl-LSD Mesylate Form 2 1 H NMR spectrum is substantially similar to that shown in FIG.91.
  • the 1- propionyl-LSD Mesylate Form 2 TGA profile is substantially similar to that shown in FIG.92.
  • the 1-propionyl-LSD Mesylate Form 2 DSC profile is substantially similar to that shown in FIG.92.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Mesylate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 5.3 °2 ⁇ , 9.6 °2 ⁇ , and 10.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Mesylate Form 2 characterized by XRPD signals at 5.3 °2 ⁇ , 9.6 °2 ⁇ , and 10.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Mesylate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.3 °2 ⁇ , 7.0 °2 ⁇ , 9.2 °2 ⁇ , 9.6 °2 ⁇ , and 10.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD Mesylate Form 2 characterized by XRPD signals at 5.3 °2 ⁇ , 7.0 °2 ⁇ , 9.2 °2 ⁇ , 9.6 °2 ⁇ , and 10.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Mesylate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 5.3 °2 ⁇ , 18.5 °2 ⁇ , and 10.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Mesylate Form 2 characterized by XRPD signals at 5.3 °2 ⁇ , 18.5 °2 ⁇ , and 10.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Mesylate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.3 °2 ⁇ , 18.5 °2 ⁇ , 10.6 °2 ⁇ , 16.0 °2 ⁇ , and 9.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1- propionyl-LSD Mesylate Form 2 characterized by XRPD signals at 5.3 °2 ⁇ , 18.5 °2 ⁇ , 10.6 °2 ⁇ , 16.0 °2 ⁇ , and 9.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Mesylate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.3 °2 ⁇ , 18.5 °2 ⁇ , 10.6 °2 ⁇ , 16.0 °2 ⁇ , 9.6 °2 ⁇ , 24.5 °2 ⁇ , and 12.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl- LSD is crystalline 1-propionyl-LSD Mesylate Form 2 characterized by XRPD signals at 5.3 °2 ⁇ , 18.5 °2 ⁇ , 10.6 °2 ⁇ , 16.0 °2 ⁇ , 9.6 °2 ⁇ , 24.5 °2 ⁇ , and 12.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Mesylate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.3 °2 ⁇ , 18.5 °2 ⁇ , 10.6 °2 ⁇ , 16.0 °2 ⁇ , 9.6 °2 ⁇ , 24.5 °2 ⁇ , 12.0 °2 ⁇ , 23.4 °2 ⁇ , 24.8 °2 ⁇ , and 9.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Mesylate Form 2 characterized by XRPD signals at 5.3 °2 ⁇ , 18.5 °2 ⁇ , 10.6 °2 ⁇ , 16.0 °2 ⁇ , 9.6 °2 ⁇ , 24.5 °2 ⁇ , 12.0 °2 ⁇ , 23.4 °2 ⁇ , 24.8 °2 ⁇ , and 9.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD Mesylate Form 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, or forty-three XRPD signals selected from those set forth in Table 58.
  • Table 58 XRPD Signals for 1-propionyl-LSD Mesylate Form 2
  • 1-propionyl-LSD Phosphate Form 1 the present disclosure provides solid forms of Phosphate Form 1 salts of 1-propionyl-LSD, e.g., crystalline forms of 1-propionyl-LSD Phosphate Form 1.
  • the 1-propionyl-LSD Phosphate Form 1 XRPD pattern is substantially similar to that shown in FIG.34.
  • the 1-propionyl-LSD Phosphate Form 1 1 H NMR spectrum is substantially similar to that shown in FIG.104.
  • the 1- propionyl-LSD Phosphate Form 1 TGA profile is substantially similar to that shown in FIG.105.
  • the 1-propionyl-LSD Phosphate Form 1 DSC profile is substantially similar to that shown in FIG.105.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Phosphate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 4.6 °2 ⁇ , 5.6 °2 ⁇ , and 8.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Phosphate Form 1 characterized by XRPD signals at 4.6 °2 ⁇ , 5.6 °2 ⁇ , and 8.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Phosphate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6 °2 ⁇ , 5.6 °2 ⁇ , 8.4 °2 ⁇ , 9.0 °2 ⁇ , and 11.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD Phosphate Form 1 characterized by XRPD signals at 4.6 °2 ⁇ , 5.6 °2 ⁇ , 8.4 °2 ⁇ , 9.0 °2 ⁇ , and 11.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Phosphate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 11.2 °2 ⁇ , 21.9 °2 ⁇ , and 13.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Phosphate Form 1 characterized by XRPD signals at 11.2 °2 ⁇ , 21.9 °2 ⁇ , and 13.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Phosphate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.2 °2 ⁇ , 21.9 °2 ⁇ , 13.5 °2 ⁇ , 8.4 °2 ⁇ , and 5.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1- propionyl-LSD Phosphate Form 1 characterized by XRPD signals at 11.2 °2 ⁇ , 21.9 °2 ⁇ , 13.5 °2 ⁇ , 8.4 °2 ⁇ , and 5.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Phosphate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.2 °2 ⁇ , 21.9 °2 ⁇ , 13.5 °2 ⁇ , 8.4 °2 ⁇ , 5.6 °2 ⁇ , 9.0 °2 ⁇ , and 5.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl- LSD is crystalline 1-propionyl-LSD Phosphate Form 1 characterized by XRPD signals at 11.2 °2 ⁇ , 21.9 °2 ⁇ , 13.5 °2 ⁇ , 8.4 °2 ⁇ , 5.6 °2 ⁇ , 9.0 °2 ⁇ , and 5.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Phosphate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.2 °2 ⁇ , 21.9 °2 ⁇ , 13.5 °2 ⁇ , 8.4 °2 ⁇ , 5.6 °2 ⁇ , 9.0 °2 ⁇ , 5.9 °2 ⁇ , 4.6 °2 ⁇ , 9.2 °2 ⁇ , and 10.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Phosphate Form 1 characterized by XRPD signals at 11.2 °2 ⁇ , 21.9 °2 ⁇ , 13.5 °2 ⁇ , 8.4 °2 ⁇ , 5.6 °2 ⁇ , 9.0 °2 ⁇ , 5.9 °2 ⁇ , 4.6 °2 ⁇ , 9.2 °2 ⁇ , and 10.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD Phosphate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty- three, twenty-four, twenty-five, or twenty-six XRPD signals selected from those set forth in Table 59.
  • Table 59 XRPD Signals for 1-proionyl-LSD Phosphate Form 1 1-propionyl-LSD Phosphate Form 2
  • the present disclosure provides solid forms of Phosphate Form 2 salts of 1-propionyl-LSD, e.g., crystalline forms of 1-propionyl-LSD Phosphate Form 2.
  • the 1-propionyl-LSD Phosphate Form 2 XRPD pattern is substantially similar to that shown in FIG.35.
  • the 1-propionyl-LSD Phosphate Form 2 1 H NMR spectrum is substantially similar to that shown in FIG.102.
  • the 1- propionyl-LSD Phosphate Form 2 TGA profile is substantially similar to that shown in FIG.103.
  • the 1-propionyl-LSD Phosphate Form 2 DSC profile is substantially similar to that shown in FIG.103.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Phosphate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 5.4 °2 ⁇ , 7.2 °2 ⁇ , and 10.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Phosphate Form 2 characterized by XRPD signals at 5.4 °2 ⁇ , 7.2 °2 ⁇ , and 10.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Phosphate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.4 °2 ⁇ , 6.6 °2 ⁇ , 7.2 °2 ⁇ , 10.5 °2 ⁇ , and 11.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD Phosphate Form 2 characterized by XRPD signals at 5.4 °2 ⁇ , 6.6 °2 ⁇ , 7.2 °2 ⁇ , 10.5 °2 ⁇ , and 11.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Phosphate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 5.4 °2 ⁇ , 22.7 °2 ⁇ , and 7.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Phosphate Form 2 characterized by XRPD signals at 5.4 °2 ⁇ , 22.7 °2 ⁇ , and 7.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Phosphate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.4 °2 ⁇ , 22.7 °2 ⁇ , 7.2 °2 ⁇ , 21.7 °2 ⁇ , and 11.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1- propionyl-LSD Phosphate Form 2 characterized by XRPD signals at 5.4 °2 ⁇ , 22.7 °2 ⁇ , 7.2 °2 ⁇ , 21.7 °2 ⁇ , and 11.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Phosphate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.4 °2 ⁇ , 22.7 °2 ⁇ , 7.2 °2 ⁇ , 21.7 °2 ⁇ , 11.3 °2 ⁇ , 10.5 °2 ⁇ , and 23.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl- LSD is crystalline 1-propionyl-LSD Phosphate Form 2 characterized by XRPD signals at 5.4 °2 ⁇ , 22.7 °2 ⁇ , 7.2 °2 ⁇ , 21.7 °2 ⁇ , 11.3 °2 ⁇ , 10.5 °2 ⁇ , and 23.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Phosphate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.4 °2 ⁇ , 22.7 °2 ⁇ , 7.2 °2 ⁇ , 21.7 °2 ⁇ , 11.3 °2 ⁇ , 10.5 °2 ⁇ , 23.8 °2 ⁇ , 24.3 °2 ⁇ , 19.5 °2 ⁇ , and 23.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Phosphate Form 2 characterized by XRPD signals at 5.4 °2 ⁇ , 22.7 °2 ⁇ , 7.2 °2 ⁇ , 21.7 °2 ⁇ , 11.3 °2 ⁇ , 10.5 °2 ⁇ , 23.8 °2 ⁇ , 24.3 °2 ⁇ , 19.5 °2 ⁇ , and 23.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD Phosphate Form 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty- three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, forty-one, forty-two, forty-three, forty-four, forty-five, forty-six, forty-seven, forty-eight, forty-nine, fifty, fifty-one, or fifty-two XRPD signals selected from those set forth in Table 60.
  • Table 60 XRPD Signals for 1-propionyl-LSD Phosphate Form 2
  • 1-propionyl-LSD Succinate Form 1 the present disclosure provides solid forms of Succinate Form 1 salts of 1-propionyl-LSD, e.g., crystalline forms of 1-propionyl-LSD Succinate Form 1.
  • the 1-propionyl-LSD Succinate Form 1 XRPD pattern is substantially similar to that shown in any one of FIGs.36 or 66.
  • the 1-propionyl-LSD Succinate Form 1 1 H NMR spectrum is substantially similar to that shown in FIG.70.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 5.0 °2 ⁇ , 5.5 °2 ⁇ , and 5.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by XRPD signals at 5.0 °2 ⁇ , 5.5 °2 ⁇ , and 5.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.8 °2 ⁇ , 5.0 °2 ⁇ , 5.5 °2 ⁇ , 5.8 °2 ⁇ , and 10.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD Succinate Form 1 characterized by XRPD signals at 4.8 °2 ⁇ , 5.0 °2 ⁇ , 5.5 °2 ⁇ , 5.8 °2 ⁇ , and 10.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Succinate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 5.0 °2 ⁇ , 5.8 °2 ⁇ , and 4.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by XRPD signals at 5.0 °2 ⁇ , 5.8 °2 ⁇ , and 4.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.0 °2 ⁇ , 5.8 °2 ⁇ , 4.8 °2 ⁇ , 5.5 °2 ⁇ , and 15.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by XRPD signals at 5.0 °2 ⁇ , 5.8 °2 ⁇ , 4.8 °2 ⁇ , 5.5 °2 ⁇ , and 15.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.0 °2 ⁇ , 5.8 °2 ⁇ , 4.8 °2 ⁇ , 5.5 °2 ⁇ , 15.3 °2 ⁇ , 12.6 °2 ⁇ , and 16.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl- LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by XRPD signals at 5.0 °2 ⁇ , 5.8 °2 ⁇ , 4.8 °2 ⁇ , 5.5 °2 ⁇ , 15.3 °2 ⁇ , 12.6 °2 ⁇ , and 16.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.0 °2 ⁇ , 5.8 °2 ⁇ , 4.8 °2 ⁇ , 5.5 °2 ⁇ , 15.3 °2 ⁇ , 12.6 °2 ⁇ , 16.1 °2 ⁇ , 12.7 °2 ⁇ , 14.5 °2 ⁇ , and 13.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by XRPD signals at 5.0 °2 ⁇ , 5.8 °2 ⁇ , 4.8 °2 ⁇ , 5.5 °2 ⁇ , 15.3 °2 ⁇ , 12.6 °2 ⁇ , 16.1 °2 ⁇ , 12.7 °2 ⁇ , 14.5 °2 ⁇ , and 13.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD Succinate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, or thirty-two XRPD signals selected from those set forth in Table 61.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 5.1 °2 ⁇ , 5.9 °2 ⁇ , and 12.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by XRPD signals at 5.1 °2 ⁇ , 5.9 °2 ⁇ , and 12.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.1 °2 ⁇ , 5.9 °2 ⁇ , 12.8 °2 ⁇ , 15.4 °2 ⁇ , and 16.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD Succinate Form 1 characterized by XRPD signals at 5.1 °2 ⁇ , 5.9 °2 ⁇ , 12.8 °2 ⁇ , 15.4 °2 ⁇ , and 16.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Succinate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 5.1 °2 ⁇ , 5.9 °2 ⁇ , and 15.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by XRPD signals at 5.1 °2 ⁇ , 5.9 °2 ⁇ , and 15.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.1 °2 ⁇ , 5.9 °2 ⁇ , 15.4 °2 ⁇ , 3.0 °2 ⁇ , and 12.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1- propionyl-LSD Succinate Form 1 characterized by XRPD signals at 5.1 °2 ⁇ , 5.9 °2 ⁇ , 15.4 °2 ⁇ , 3.0 °2 ⁇ , and 12.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.1 °2 ⁇ , 5.9 °2 ⁇ , 15.4 °2 ⁇ , 3.0 °2 ⁇ , 12.8 °2 ⁇ , 16.2 °2 ⁇ , and 13.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl- LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by XRPD signals at 5.1 °2 ⁇ , 5.9 °2 ⁇ , 15.4 °2 ⁇ , 3.0 °2 ⁇ , 12.8 °2 ⁇ , 16.2 °2 ⁇ , and 13.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.1 °2 ⁇ , 5.9 °2 ⁇ , 15.4 °2 ⁇ , 3.0 °2 ⁇ , 12.8 °2 ⁇ , 16.2 °2 ⁇ , 13.4 °2 ⁇ , 14.7 °2 ⁇ , 21.9 °2 ⁇ , and 10.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Succinate Form 1 characterized by XRPD signals at 5.1 °2 ⁇ , 5.9 °2 ⁇ , 15.4 °2 ⁇ , 3.0 °2 ⁇ , 12.8 °2 ⁇ , 16.2 °2 ⁇ , 13.4 °2 ⁇ , 14.7 °2 ⁇ , 21.9 °2 ⁇ , and 10.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD Succinate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, or eighteen XRPD signals selected from those set forth in Table 62.
  • Table 62 XRPD Signals for 1-propionyl-LSD Succinate Form 1
  • 1-propionyl-LSD Sulfate Form 1 1-propionyl-LSD Sulfate Form 1
  • the present disclosure provides solid forms of Sulfate Form 1 salts of 1-propionyl-LSD, e.g., crystalline forms of 1-propionyl-LSD Sulfate Form 1.
  • the 1-propionyl-LSD Sulfate Form 1 XRPD pattern is substantially similar to that shown in FIG.37.
  • the 1-propionyl-LSD Sulfate Form 1 1 H NMR spectrum is substantially similar to that shown in FIG.99.
  • the 1-propionyl-LSD Sulfate Form 1 TGA profile is substantially similar to that shown in FIG.100.
  • the 1-propionyl-LSD Sulfate Form 1 DSC profile is substantially similar to that shown in FIG.100.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 9.3 °2 ⁇ , 9.7 °2 ⁇ , and 12.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 1 characterized by XRPD signals at 9.3 °2 ⁇ , 9.7 °2 ⁇ , and 12.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.1 °2 ⁇ , 9.3 °2 ⁇ , 9.7 °2 ⁇ , 12.0 °2 ⁇ , and 12.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD Sulfate Form 1 characterized by XRPD signals at 6.1 °2 ⁇ , 9.3 °2 ⁇ , 9.7 °2 ⁇ , 12.0 °2 ⁇ , and 12.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Sulfate Form 1 characterized by two, or three XRPD signals selected from the group consisting of 12.3 °2 ⁇ , 9.7 °2 ⁇ , and 9.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 1 characterized by XRPD signals at 12.3 °2 ⁇ , 9.7 °2 ⁇ , and 9.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.3 °2 ⁇ , 9.7 °2 ⁇ , 9.3 °2 ⁇ , 12.0 °2 ⁇ , and 18.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1- propionyl-LSD Sulfate Form 1 characterized by XRPD signals at 12.3 °2 ⁇ , 9.7 °2 ⁇ , 9.3 °2 ⁇ , 12.0 °2 ⁇ , and 18.8 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.3 °2 ⁇ , 9.7 °2 ⁇ , 9.3 °2 ⁇ , 12.0 °2 ⁇ , 18.8 °2 ⁇ , 21.4 °2 ⁇ , and 20.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl- LSD is crystalline 1-propionyl-LSD Sulfate Form 1 characterized by XRPD signals at 12.3 °2 ⁇ , 9.7 °2 ⁇ , 9.3 °2 ⁇ , 12.0 °2 ⁇ , 18.8 °2 ⁇ , 21.4 °2 ⁇ , and 20.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.3 °2 ⁇ , 9.7 °2 ⁇ , 9.3 °2 ⁇ , 12.0 °2 ⁇ , 18.8 °2 ⁇ , 21.4 °2 ⁇ , 20.9 °2 ⁇ , 21.8 °2 ⁇ , 21.6 °2 ⁇ , and 6.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 1 characterized by XRPD signals at 12.3 °2 ⁇ , 9.7 °2 ⁇ , 9.3 °2 ⁇ , 12.0 °2 ⁇ , 18.8 °2 ⁇ , 21.4 °2 ⁇ , 20.9 °2 ⁇ , 21.8 °2 ⁇ , 21.6 °2 ⁇ , and 6.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD Sulfate Form 1 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, or thirty-seven XRPD signals selected from those set forth in Table 63.
  • Table 63 XRPD Signals for 1-propionyl-LSD Sulfate Form 1 1-propionyl-LSD Sulfate Form 2
  • the present disclosure provides solid forms of Sulfate Form 2 salts of 1-propionyl-LSD, e.g., crystalline forms of 1-propionyl-LSD Sulfate Form 2.
  • the 1-propionyl-LSD Sulfate Form 2 XRPD pattern is substantially similar to that shown in any one of FIGs.38 or 67.
  • the 1-propionyl-LSD Sulfate Form 2 1 H NMR spectrum is substantially similar to that shown in FIG.68.
  • the 1- propionyl-LSD Sulfate Form 2 TGA profile is substantially similar to that shown in FIG.69.
  • the 1-propionyl-LSD Sulfate Form 2 DSC profile is substantially similar to that shown FIG.69.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 6.2 °2 ⁇ , 12.1 °2 ⁇ , and 18.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 2 characterized by XRPD signals at 6.2 °2 ⁇ , 12.1 °2 ⁇ , and 18.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.2 °2 ⁇ , 9.9 °2 ⁇ , 12.1 °2 ⁇ , 15.6 °2 ⁇ , and 18.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD Sulfate Form 2 characterized by XRPD signals at 6.2 °2 ⁇ , 9.9 °2 ⁇ , 12.1 °2 ⁇ , 15.6 °2 ⁇ , and 18.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl-LSD Sulfate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 12.1 °2 ⁇ , 18.1 °2 ⁇ , and 6.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 2 characterized by XRPD signals at 12.1 °2 ⁇ , 18.1 °2 ⁇ , and 6.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.1 °2 ⁇ , 18.1 °2 ⁇ , 6.2 °2 ⁇ , 22.0 °2 ⁇ , and 20.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1- propionyl-LSD Sulfate Form 2 characterized by XRPD signals at 12.1 °2 ⁇ , 18.1 °2 ⁇ , 6.2 °2 ⁇ , 22.0 °2 ⁇ , and 20.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.1 °2 ⁇ , 18.1 °2 ⁇ , 6.2 °2 ⁇ , 22.0 °2 ⁇ , 20.2 °2 ⁇ , 14.7 °2 ⁇ , and 19.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1- propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 2 characterized by XRPD signals at 12.1 °2 ⁇ , 18.1 °2 ⁇ , 6.2 °2 ⁇ , 22.0 °2 ⁇ , 20.2 °2 ⁇ , 14.7 °2 ⁇ , and 19.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.1 °2 ⁇ , 18.1 °2 ⁇ , 6.2 °2 ⁇ , 22.0 °2 ⁇ , 20.2 °2 ⁇ , 14.7 °2 ⁇ , 19.9 °2 ⁇ , 15.6 °2 ⁇ , 25.9 °2 ⁇ , and 25.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 2 characterized by XRPD signals at 12.1 °2 ⁇ , 18.1 °2 ⁇ , 6.2 °2 ⁇ , 22.0 °2 ⁇ , 20.2 °2 ⁇ , 14.7 °2 ⁇ , 19.9 °2 ⁇ , 15.6 °2 ⁇ , 25.9 °2 ⁇ , and 25.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD Sulfate Form 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, or thirty-nine XRPD signals selected from those set forth in Table 64.
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 2 characterized by two, or three XRPD signals selected from the group consisting of 6.2 °2 ⁇ , 12.1 °2 ⁇ , and 18.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 2 characterized by XRPD signals at 6.2 °2 ⁇ , 12.1 °2 ⁇ , and 18.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.2 °2 ⁇ , 9.9 °2 ⁇ , 12.1 °2 ⁇ , 15.5 °2 ⁇ , and 18.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is 1-propionyl- LSD Sulfate Form 2 characterized by XRPD signals at 6.2 °2 ⁇ , 9.9 °2 ⁇ , 12.1 °2 ⁇ , 15.5 °2 ⁇ , and 18.1 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.1 °2 ⁇ , 18.1 °2 ⁇ , 6.2 °2 ⁇ , 22.0 °2 ⁇ , and 20.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1- propionyl-LSD Sulfate Form 2 characterized by XRPD signals at 12.1 °2 ⁇ , 18.1 °2 ⁇ , 6.2 °2 ⁇ , 22.0 °2 ⁇ , and 20.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.1 °2 ⁇ , 18.1 °2 ⁇ , 6.2 °2 ⁇ , 22.0 °2 ⁇ , 20.2 °2 ⁇ , 14.7 °2 ⁇ , and 25.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1- propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 2 characterized by XRPD signals at 12.1 °2 ⁇ , 18.1 °2 ⁇ , 6.2 °2 ⁇ , 22.0 °2 ⁇ , 20.2 °2 ⁇ , 14.7 °2 ⁇ , and 25.9 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.1 °2 ⁇ , 18.1 °2 ⁇ , 6.2 °2 ⁇ , 22.0 °2 ⁇ , 20.2 °2 ⁇ , 14.7 °2 ⁇ , 25.9 °2 ⁇ , 19.9 °2 ⁇ , 25.1 °2 ⁇ , and 15.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 1-propionyl-LSD is crystalline 1-propionyl-LSD Sulfate Form 2 characterized by XRPD signals at 12.1 °2 ⁇ , 18.1 °2 ⁇ , 6.2 °2 ⁇ , 22.0 °2 ⁇ , 20.2 °2 ⁇ , 14.7 °2 ⁇ , 25.9 °2 ⁇ , 19.9 °2 ⁇ , 25.1 °2 ⁇ , and 15.5 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 1-propionyl-LSD Sulfate Form 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, twenty-five, twenty-six, twenty-seven, twenty-eight, twenty-nine, thirty, thirty-one, thirty-two, thirty-three, thirty-four, thirty-five, thirty-six, thirty-seven, thirty-eight, thirty-nine, forty, or forty-one XRPD signals selected from those set forth in Table 65.
  • Table 65 XRPD Signals for 1-propionyl-LSD Sulfate Form 2 2-Bromo-LSD Hydrochloride
  • the present disclosure provides solid forms of hydrochloride salts of 2-bromo-LSD, e.g., crystalline forms of 2-bromo-LSD HCl.
  • the 2- bromo-LSD HCl XRPD pattern is substantially similar to that shown in any one of FIG.26 or 27.
  • the solid form of 2-bromo-LSD is crystalline 2-bromo-LSD HCl characterized by two or more, or three XRPD signals selected from the group consisting of 10.3 °2 ⁇ , 12.0 °2 ⁇ , and 17.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 2-bromo-LSD is crystalline 2-bromo-LSD HCl characterized by XRPD signals at 10.3 °2 ⁇ , 12.0 °2 ⁇ , and 17.7 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 2-bromo-LSD is crystalline 2-bromo-LSD HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 10.3 °2 ⁇ , 12.0 °2 ⁇ , 17.7 °2 ⁇ , 18.4 °2 ⁇ , and 19.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 2-bromo-LSD is crystalline 2-bromo-LSD HCl characterized by XRPD signals at 10.3 °2 ⁇ , 12.0 °2 ⁇ , 17.7 °2 ⁇ , 18.4 °2 ⁇ , and 19.2 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 2-bromo-LSD is crystalline 2-bromo-LSD HCl characterized by two or more, or three XRPD signals selected from the group consisting of 24.9 °2 ⁇ , 19.2 °2 ⁇ , and 5.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 2-bromo-LSD is crystalline 2-bromo-LSD HCl characterized by XRPD signals at 24.9 °2 ⁇ , 19.2 °2 ⁇ , and 5.4 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 2-bromo-LSD is crystalline 2-bromo-LSD HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 24.9 °2 ⁇ , 19.2 °2 ⁇ , 5.4 °2 ⁇ , 26.3 °2 ⁇ , and 10.3 ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 2-bromo-LSD is crystalline 2-bromo-LSD HCl characterized by XRPD signals at 24.9 °2 ⁇ , 19.2 °2 ⁇ , 5.4 °2 ⁇ , 26.3 °2 ⁇ , and 10.3 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 2-bromo-LSD is crystalline 2-bromo-LSD HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 24.9 °2 ⁇ , 19.2 °2 ⁇ , 5.4 °2 ⁇ , 26.3 °2 ⁇ , 10.3 °2 ⁇ , 19.9 °2 ⁇ , and 12.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 2-bromo-LSD is crystalline 2-bromo-LSD HCl characterized by XRPD signals at 24.9 °2 ⁇ , 19.2 °2 ⁇ , 5.4 °2 ⁇ , 26.3 °2 ⁇ , 10.3 °2 ⁇ , 19.9 °2 ⁇ , and 12.0 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 2-bromo-LSD is crystalline 2-bromo-LSD HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 24.9 °2 ⁇ , 19.2 °2 ⁇ , 5.4 °2 ⁇ , 26.3 °2 ⁇ , 10.3 °2 ⁇ , 19.9 °2 ⁇ , 12.0 °2 ⁇ , 13.3 °2 ⁇ , 18.4 °2 ⁇ , and 25.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 2-bromo-LSD is crystalline 2-bromo-LSD HCl characterized by XRPD signals at 24.9 °2 ⁇ , 19.2 °2 ⁇ , 5.4 °2 ⁇ , 26.3 °2 ⁇ , 10.3 °2 ⁇ , 19.9 °2 ⁇ , 12.0 °2 ⁇ , 13.3 °2 ⁇ , 18.4 °2 ⁇ , and 25.6 °2 ⁇ ( ⁇ 0.2 °2 ⁇ ; ⁇ 0.1 °2 ⁇ ; or ⁇ 0.0 °2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 2-bromo-LSD HCl is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, or seventeen XRPD signals selected from those set forth in Table 66.
  • Table 66 XRPD Signals for 2-Bromo-LSD Hydrochloride
  • the present disclosure provides a pharmaceutical composition comprising one or more of the solid forms of LSD, 1-acetyl-LSD, 2-bromo-LSD, and/or 1- propionyl LSD, illustrated above, and a pharmaceutically acceptable excipient.
  • Such compositions are suitable for administration to a subject, such as a human subject.
  • compositions of the present disclosure can be prepared in a wide variety of oral, parenteral and topical dosage forms.
  • Oral preparations include tablets, pills, powder, capsules, lozenges, cachets, slurries, suspensions, etc., suitable for ingestion by the patient.
  • the compositions of the present disclosure can also be administered by injection, that is, intravenously, intramuscularly, intracutaneously, subcutaneously, intraduodenally, or intraperitoneally.
  • the compositions described herein can be administered by inhalation, for example, intranasally. Additionally, the compositions of the present disclosure can be administered transdermally.
  • compositions of this disclosure can also be administered by intraocular, intravaginal, and intrarectal routes including suppositories, insufflation, powders and aerosol formulations (for examples of steroid inhalants, see Rohatagi, J. Clin. Pharmacol. 35:1187-1193, 1995; Tjwa, Ann. Allergy Asthma Immunol.75:107-111, 1995).
  • the present disclosure also provides pharmaceutical compositions including a pharmaceutically acceptable carrier or excipient and the solid form of LSD, 1-acetyl-LSD, 1-propionyl-LSD, and/or 2-bromo-LSD of the present disclosure.
  • pharmaceutically acceptable carriers can be either solid or liquid.
  • Solid form preparations include powders, tablets, pills, capsules, cachets, suppositories, and dispersible granules.
  • a solid carrier can be one or more substances, which may also act as diluents, flavoring agents, binders, preservatives, tablet disintegrating agents, or an encapsulating material. Details on techniques for formulation and administration are well described in the scientific and patent literature, see, e.g., the latest edition of Remington's Pharmaceutical Sciences, Mack Publishing Co, Easton PA ("Remington's").
  • the carrier is a finely divided solid, which is in a mixture with the finely divided active component.
  • the active component is mixed with the carrier having the necessary binding properties in suitable proportions and compacted in the shape and size desired.
  • the powders and tablets preferably contain from 5% to 70% or 10% to 70% of the compounds of the present disclosure.
  • suitable solid excipients include, but are not limited to, magnesium carbonate; magnesium stearate; talc; pectin; dextrin; starch; tragacanth; a low melting wax; cocoa butter; carbohydrates; sugars including, but not limited to, lactose, sucrose, mannitol, or sorbitol, starch from com, wheat, rice, potato, or other plants; cellulose such as methyl cellulose, hydroxypropylmethyl-cellulose, or sodium carboxymethylcellulose; and gums including arabic and tragacanth; as well as proteins including, but not limited to, gelatin and collagen.
  • disintegrating or solubilizing agents may be added, such as the cross-linked polyvinyl pyrrolidone, agar, alginic acid, or a salt thereof, such as sodium alginate.
  • a low melting wax such as a mixture of fatty acid glycerides or cocoa butter
  • the molten homogeneous mixture is then poured into convenient sized molds, allowed to cool, and thereby to solidify.
  • Liquid form preparations include suspensions, for example, water or water/propylene glycol suspensions.
  • Aqueous suspensions suitable for oral use can be made by dispersing the finely divided active component in water with viscous material, such as natural or synthetic gums, resins, methylcellulose, sodium carboxymethylcellulose, hydroxypropylmethylcellulose, sodium alginate, polyvinylpyrrolidone, gum tragacanth and gum acacia, and dispersing or wetting agents such as a naturally occurring phosphatide (e.g., lecithin), a condensation product of an alkylene oxide with a fatty acid (e.g., polyoxyethylene stearate), a condensation product of ethylene oxide with a long chain aliphatic alcohol (e.g., heptadecaethylene oxycetanol), a condensation product of ethylene oxide with a partial ester derived from a fatty acid and a hexitol (e.g., polyoxyethylene sorbitol mono-oleate), or a condensation product of ethylene oxide with a partial ester derived from fatty
  • the aqueous suspension can also contain one or more preservatives such as ethyl or n-propyl p-hydroxybenzoate, one or more coloring agents, one or more flavoring agents and one or more sweetening agents, such as sucrose, aspartame or saccharin.
  • preservatives such as ethyl or n-propyl p-hydroxybenzoate
  • coloring agents such as ethyl or n-propyl p-hydroxybenzoate
  • flavoring agents such as sucrose, aspartame or saccharin.
  • sweetening agents such as sucrose, aspartame or saccharin.
  • Formulations can be adjusted for osmolarity.
  • solid form preparations which are intended to be converted, shortly before use, to liquid form preparations for oral administration.
  • Such liquid forms include suspensions.
  • These preparations may contain, in addition to the active component, colorants, flavors, stabilizers, buffers, artificial and natural sweeteners, dispersants, thicken
  • Oil suspensions can be formulated by suspending the compound of the present disclosure in a vegetable oil, such as arachis oil, olive oil, sesame oil or coconut oil, or in a mineral oil such as liquid paraffin; or a mixture of these.
  • the oil suspensions can contain a thickening agent, such as beeswax, hard paraffin or cetyl alcohol.
  • Sweetening agents can be added to provide a palatable oral preparation, such as glycerol, sorbitol or sucrose.
  • These formulations can be preserved by the addition of an antioxidant such as ascorbic acid.
  • an injectable oil vehicle see Minto, J. Pharmacol. Exp. Ther.281:93-102, 1997.
  • the pharmaceutical formulations of the disclosure can also be in the form of oil-in-water emulsions.
  • the oily phase can be a vegetable oil or a mineral oil, described above, or a mixture of these.
  • Suitable emulsifying agents include naturally-occurring gums, such as gum acacia and gum tragacanth, naturally occurring phosphatides, such as soybean lecithin, esters or partial esters derived from fatty acids and hexitol anhydrides, such as sorbitan mono-oleate, and condensation products of these partial esters with ethylene oxide, such as polyoxyethylene sorbitan mono-oleate.
  • the emulsion can also contain sweetening agents and flavoring agents, as in the formulation of syrups and elixirs.
  • compositions of the present disclosure can also be delivered as microspheres for slow release in the body.
  • microspheres can be formulated for administration via intradermal injection of drug- containing microspheres, which slowly release subcutaneously (see Rao, J. Biomater Sci. Polym. Ed.7:623-645, 1995; as biodegradable and injectable gel formulations (see, e.g., Gao Pharm. Res.12:857-863, 1995); or, as microspheres for oral administration (see, e.g., Eyles, J. Pharm. Pharmacol.49:669-674, 1997).
  • the pharmaceutical compositions of the present disclosure can be formulated for parenteral administration, such as intravenous (IV) administration or administration into a body cavity or lumen of an organ.
  • parenteral administration such as intravenous (IV) administration or administration into a body cavity or lumen of an organ.
  • the formulations for administration will commonly comprise a solution or suspension of the compositions of the present disclosure dissolved or suspended in a pharmaceutically acceptable carrier.
  • acceptable vehicles and solvents that can be employed are water and Ringer's solution, an isotonic sodium chloride.
  • sterile fixed oils can conventionally be employed as a solvent or suspending medium.
  • any bland fixed oil can be employed including synthetic mono- or diglycerides.
  • fatty acids such as oleic acid can likewise be used in the preparation of injectables. These solutions or suspensions are sterile and generally free of undesirable matter.
  • These formulations may be sterilized by conventional, well known sterilization techniques.
  • the formulations may contain pharmaceutically acceptable auxiliary substances as required to approximate physiological conditions such as pH adjusting and buffering agents, toxicity adjusting agents, e.g., sodium acetate, sodium chloride, potassium chloride, calcium chloride, sodium lactate and the like.
  • concentration of the compositions of the present disclosure in these formulations can vary widely, and will be selected primarily based on fluid volumes, viscosities, body weight, and the like, in accordance with the particular mode of administration selected and the patient's needs.
  • the formulation can be a sterile injectable preparation, such as a sterile injectable aqueous or oleaginous suspension.
  • This suspension can be formulated according to the known art using those suitable dispersing or wetting agents and suspending agents.
  • the sterile injectable preparation can also be a sterile injectable solution or suspension in a nontoxic parenterally-acceptable diluent or solvent, such as a solution of 1,3- butanediol.
  • the formulations of the compositions of the present disclosure can be delivered by the use of liposomes which fuse with the cellular membrane or are endocytosed, for example, by employing ligands attached to the liposome, or attached directly to the oligonucleotide, that bind to surface membrane protein receptors of the cell resulting in endocytosis.
  • liposomes particularly where the liposome surface carries ligands specific for target cells, or are otherwise preferentially directed to a specific organ, one can focus the delivery of the compositions of the present disclosure into the target cells in vivo. (See, e.g., Al- Muhammed, J. Microencapsul.13:293-306, 1996; Chonn, Curr. Opin.
  • compositions of the present disclosure can be administered by any suitable means, including oral, parenteral and topical methods.
  • Transdermal administration methods by a topical route, can be formulated as applicator sticks, suspensions, creams, ointments, pastes, jellies, paints, powders, and aerosols.
  • the pharmaceutical preparation is in unit dosage form. In such form the preparation is subdivided into unit doses containing appropriate quantities of the compounds of the present disclosure.
  • the unit dosage form can be a packaged preparation, the package containing discrete quantities of preparation, such as packeted tablets, capsules, and powders in vials or ampoules. Also, the unit dosage form can be a capsule, tablet, cachet, or lozenge itself, or it can be the appropriate number of any of these in packaged form.
  • the compound of the present disclosure can be present in any suitable amount, and can depend on various factors including, but not limited to, weight and age of the subject, state of the disease, and the like as is known to those of ordinary skill in the art.
  • the LSD, 1P-LSD, and 1- acetyl-LSD (ALD-52)forms administered herein typically are administered to provide between about 1 microgram to about 400 micrograms, or about 50 micrograms to about 200 micrograms of the free base equivalent of the molecule.
  • the 2-bromo-LSD forms of the present invention can be present in any suitable amount, and can depend on various factors including, but not limited to, weight and age of the subject, state of the disease, and the like as is known to those of ordinary skill in the art.
  • Suitable dosage ranges for the 2-bromo-LSD forms disclosed herein include from about 10 micrograms to 1.0mg or about 1.8mg or about 30 micrograms per kg or about 0.1 mg to about 50 mg or about 1 mg to about 20 mg or 20mg to about 30mg.
  • Suitable dosages for the compound of the present invention include about 0.1 mg, 0.5, 1, 2, 3, 4, 5, 10, 15, 20, 30, 40, or 50 mg.
  • the compounds of the present disclosure can be co-administered with a second active agent. In some embodiments, co-administration can be accomplished by co-formulation, such as by preparing a single pharmaceutical composition including both the compound of the present disclosure and a second active agent. In other embodiments, the compound of the present disclosure and the second active agent can be formulated separately.
  • the solid forms of LSD, 1-acetyl-LSD, 1-propionyl LSD, and/or 2-bromo-LSD of the present disclosure can be used for increasing neuronal plasticity.
  • the compounds of the present disclosure can also be used to treat any brain disease.
  • the compounds of the present disclosure can also be used for increasing at least one of translation, transcription or secretion of neurotrophic factors.
  • the methods described herein are for treating a disease or disorder that is a brain disease or disorder.
  • the methods described herein are for increasing at least one of translation, transcription or secretion of neurotrophic factors.
  • the compositions provided herein have, for example, anti- addictive properties, antidepressant properties, anxiolytic properties, or a combination thereof.
  • the brain disorder is a neuropsychiatric disease.
  • the methods described herein are for treating a disease or disorder that is a neuropsychiatric disease.
  • the neuropsychiatric disease is a mood or anxiety disorder.
  • brain disorders include, for example, migraine, cluster headache, post-traumatic stress disorder (PTSD), anxiety, depression, panic disorder, suicidality, schizophrenia, and addiction (e.g., substance abuse disorder).
  • brain disorders include, for example, migraines, addiction (e.g., substance use disorder for example alcohol abuse, opiate addition, or abuse), depression, and anxiety.
  • the brain disease or disorder is a neurodegenerative disorder, Alzheimer’s disease or Parkinson’s disease.
  • the brain disease or disorder is psychological disorder, depression, addiction, anxiety, or a post-traumatic stress disorder.
  • the brain disorder is depression.
  • the brain disorder is addiction.
  • the brain disorder is treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, stroke, traumatic brain injury or substance use disorder.
  • the brain disorder is treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, or substance use disorder.
  • the brain disorder is stroke or traumatic brain injury.
  • the brain disorder is treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, or substance use disorder.
  • the brain disorder is schizophrenia.
  • the brain disorder is alcohol use disorder.
  • the methods described herein are for treating a disease or disorder that is a neurological disease.
  • a compound provided herein can exhibit, anti- addictive properties, antidepressant properties, anxiolytic properties, or a combination thereof.
  • the neurological disease is a neuropsychiatric disease.
  • the neuropsychiatric disease is a mood or anxiety disorder.
  • the neurological disease is a migraine, headaches (e.g., cluster headache), post-traumatic stress disorder (PTSD), anxiety, depression, neurodegenerative disorder, Alzheimer’s disease, Parkinson’s disease, psychological disorder, treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, stroke, hypoxic brain injury, Chronic traumatic encephalopathy (CTE), traumatic brain injury, dementia, and addiction (e.g., substance use disorder).
  • the neurological disease is a migraine or cluster headache.
  • the neurological disease is a neurodegenerative disorder, dementia, Alzheimer’s disease, or Parkinson’s disease.
  • the neurological disease is dementia.
  • the neurological disease is a psychological disorder, treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, post-traumatic stress disorder (PTSD), addiction (e.g., substance use disorder), depression, or anxiety.
  • the neuropsychiatric disease is a psychological disorder, treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, post-traumatic stress disorder (PTSD), addiction (e.g., substance use disorder), depression, or anxiety.
  • the neuropsychiatric disease or neurological disease is post-traumatic stress disorder (PTSD), addiction (e.g., substance use disorder), schizophrenia, depression, or anxiety.
  • the neuropsychiatric disease or neurological disease is addiction (e.g., substance use disorder). In some embodiments, the neuropsychiatric disease or neurological disease is depression. In some embodiments, the neuropsychiatric disease or neurological disease is anxiety. In some embodiments, the neuropsychiatric disease or neurological disease is post-traumatic stress disorder (PTSD). In some embodiments, the neurological disease is stroke or traumatic brain injury. In some embodiments, the neuropsychiatric disease or neurological disease is schizophrenia. In some embodiments, a compound of the present disclosure is used to treat neurological diseases. In some embodiments, the compounds have, for example, anti- addictive properties, antidepressant properties, anxiolytic properties, or a combination thereof.
  • the neurological disease is a neuropsychiatric disease.
  • the neuropsychiatric disease is a mood or anxiety disorder.
  • the neurological disease is a migraine, headaches (e.g., cluster headache), post-traumatic stress disorder (PTSD), anxiety, depression, neurodegenerative disorder, Alzheimer’s disease, Parkinson’s disease, psychological disorder, treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, stroke, traumatic brain injury, and addiction (e.g., substance use disorder).
  • the neurological disease is a migraine or cluster headache.
  • the neurological disease is a neurodegenerative disorder, Alzheimer’s disease, or Parkinson’s disease.
  • the neurological disease is a psychological disorder, treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, post-traumatic stress disorder (PTSD), addiction (e.g., substance use disorder), depression, or anxiety.
  • the methods described herein are for increasing neuronal plasticity and has, for example, anti-addictive properties, antidepressant properties, anxiolytic properties, or a combination thereof.
  • decreased neuronal plasticity is associated with a neuropsychiatric disease.
  • a compound of the present disclosure is used for increasing neuronal plasticity.
  • the compounds described herein are used for treating a brain disorder.
  • the compounds described herein are used for increasing at least one of translation, transcription, or secretion of neurotrophic factors.
  • the present disclosure provides a method of treating a disease, including administering to a subject in need thereof, a therapeutically effective amount of a compound of the present disclosure.
  • the disease is a musculoskeletal pain disorder including fibromyalgia, muscle pain, joint stiffness, osteoarthritis, rheumatoid arthritis, and muscle cramps.
  • the present disclosure provides a method of treating a disease of women’s reproductive health including premenstrual dysphoric disorder (PMDD), premenstrual syndrome (PMS), post-partum depression, and menopause.
  • the disease or disorder is depression or a disease or disorder related to depression.
  • the disease or disorder is post-traumatic stress disorder.
  • the disease or disorder is fibromyalgia.
  • Diseases of particular interest include depression and related conditions.
  • the disease or disorder treated herein is depression or a disease or disorder related to depression.
  • the depression is major depressive disorder, persistent depressive disorder, bipolar disorder, treatment resistant depression (TRD), postpartum depression, premenstrual dysphoric disorder, or seasonal affective disorder.
  • the disease or disorder related to depression is anxiety.
  • methods of treating depression or a disease or disorder related to depression comprise treating the symptoms associated with the depression or the disease or disorder related to depression.
  • the depression is major depressive disorder, persistent depressive disorder, bipolar disorder, treatment resistant depression (TRD), postpartum depression, premenstrual dysphoric disorder, or seasonal affective disorder.
  • the disease or disorder related to depression is anxiety.
  • methods of treating depression or a disease or disorder related to depression comprise treating the symptoms associated with the depression or the disease or disorder related to depression.
  • methods of treating fibromyalgia or a disease or disorder related to chronic widespread pain, fatigue or hypersensitivity comprising administering to the subject a therapeutically effective amount of a compound described herein.
  • the LSD, 1-acetyl-LSD, 1-propionyl-LSD, and/or 2-bromo-LSD forms of the present disclosure have activity as 5-HT2A modulators.
  • the compounds of the present disclosure elicit a biological response by activating the 5-HT 2A receptor (e.g., allosteric modulation or modulation of a biological target that activates the 5-HT 2A receptor).
  • 5-HT2A agonism has been correlated with the promotion of neural plasticity (Ly et al., 2018).5-HT 2A antagonists abrogate the neuritogenesis and spinogenesis effects of hallucinogenic compounds with 5-HT 2A agonist activity, for example, DMT, and DOI.
  • the compounds of the present disclosure are 5-HT2A modulators and promote neural plasticity (e.g., cortical structural plasticity).
  • the compounds of the present disclosure are selective 5-HT 2A modulators and promote neural plasticity (e.g., cortical structural plasticity).
  • promotion of neural plasticity includes, for example, increased dendritic spine growth, increased synthesis of synaptic proteins, strengthened synaptic responses, increased dendritic arbor complexity, increased dendritic branch content, increased spinogenesis, increased neuritogenesis, or any combination thereof.
  • increased neural plasticity includes, for example, increased cortical structural plasticity in the anterior parts of the brain.
  • the 5-HT 2A modulators e.g., 5-HT 2A agonists
  • non-hallucinogenic 5-HT2A modulators e.g., 5-HT2A agonists
  • the hallucinogenic potential of the compounds described herein is assessed in vitro.
  • the hallucinogenic potential assessed in vitro of the compounds described herein is compared to the hallucinogenic potential assessed in vitro of hallucinogenic homologs.
  • the compounds described herein elicit less hallucinogenic potential in vitro than the hallucinogenic homologs.
  • serotonin receptor modulators such as modulators of serotonin receptor 2A (5-HT2A modulators, e.g., 5-HT2A agonists), are used to treat a brain disorder.
  • the presently disclosed compounds can function as 5-HT 2A agonists alone, or in combination with a second therapeutic agent that also is a 5-HT 2A modulator.
  • the second therapeutic agent can be an agonist or an antagonist.
  • Serotonin receptor modulators useful as second therapeutic agents for combination therapy as described herein are known to those of skill in the art and include, without limitation, ketanserin, volinanserin (MDL-100907), eplivanserin (SR-46349), pimavanserin (ACP-103), glemanserin (MDL-11939), ritanserin, flibanserin, nelotanserin, blonanserin, mianserin, mirtazapine, roluperiodone (CYR-101, MIN-101), quetiapine, olanzapine, altanserin, acepromazine, nefazodone, risperidone, pruvanserin, AC-90179, AC-279, adatanserin, fananserin, HY10275, benanserin, butanserin, manserin, iferanserin, lidanserin, pelanserin, seganserin, tropanserin, lorcaserin,
  • the serotonin receptor modulator for combination with the presently disclosed compounds is selected from, glemanserin (MDL-11,939), eplivanserin (SR- 46,349), ketanserin, ritanserin, altanserin, acepromazine, mianserin, mirtazapine, quetiapine, SB204741, SB206553, SB242084, LY272015, SB243213, blonanserin, SB200646, RS102221, nefazodone, volinanserin (MDL-100,907), pimavanserin (ACO-103), nelotanserin, lorcaserin, flibanserin, roluperiodone or a pharmaceutically acceptable salt, solvate, metabolite, deuterated analog, derivative, prodrug, or combinations thereof.
  • glemanserin MDL-11,939
  • eplivanserin SR- 46,349
  • ketanserin ritanserin,
  • the serotonin receptor modulator comprises eplivanserin (SR-46,349), ketanserin, ritanserin, altanserin, acepromazine, mianserin, mirtazapine, quetiapine, SB204741, SB206553, SB242084, LY272015, SB243213, blonanserin, SB200646, RS102221, nefazodone, MDL-100,907, pimavanserin, nelotanserin or lorcaserin.
  • eplivanserin SR-46,349
  • ketanserin ritanserin, altanserin
  • acepromazine mianserin
  • mirtazapine mirtazapine
  • quetiapine quetiapine
  • SB204741, SB206553, SB242084 LY272015, SB243213, blonanserin, SB200646, RS102221, nefazodone, MDL-100
  • the serotonin receptor modulator is selected from the group consisting of altanserin, blonanserin, eplivanserin, glemanserin, volinanserin, ketanserin, ritanserin, pimavanserin, nelotanserin, pruvanserin, and flibanserin. In one embodiment, the serotonin receptor modulator is selected from the group consisting of eplivanserin, volinanserin, ketanserin, ritanserin, pimavanserin, nelotanserin, pruvanserin, flibanserin, olanzapine, quetiapine, and risperidone.
  • the serotonin receptor modulator is ketanserin or a pharmaceutically acceptable salt, solvate, metabolite, deuterated analog, derivative, or prodrug thereof.
  • the serotonin receptor modulator is pimavanserin or a pharmaceutically acceptable salt, solvate, metabolite, deuterated analog, derivative, or prodrug thereof.
  • the serotonin receptor modulator is eplivanserin or a pharmaceutically acceptable salt, solvate, metabolite, deuterated analog, derivative, or prodrug thereof.
  • the serotonin receptor modulator is flibanserin or a pharmaceutically acceptable salt, solvate, metabolite, deuterated analog, derivative, or prodrug thereof. In some embodiments, the serotonin receptor modulator is roluperiodone or a pharmaceutically acceptable salt, solvate, metabolite, deuterated analog, derivative, or prodrug thereof. In some embodiments, the serotonin receptor modulator is administered prior to a compound disclosed herein, such as about one to about three hours prior to administration of a compound disclosed herein. In some embodiments, the serotonin receptor modulator is administered at most about one hour prior to the presently disclosed compound.
  • the serotonin receptor modulator is administered after to a compound disclosed herein, such as from about one to about three hours after administration of a compound disclosed herein.
  • the second therapeutic agent is a serotonin receptor modulator.
  • the disease or disorder is depression or a disease or disorder related to depression.
  • the disease or disorder is post-traumatic stress disorder.
  • the disease or disorder is fibromyalgia.
  • non-hallucinogenic 5-HT2A modulators e.g., 5-HT2A agonists
  • the neurological diseases comprise decreased neural plasticity, decreased cortical structural plasticity, decreased 5-HT 2A receptor content, decreased dendritic arbor complexity, loss of dendritic spines, decreased dendritic branch content, decreased spinogenesis, decreased neuritogenesis, retraction of neurites, or any combination thereof.
  • non-hallucinogenic 5-HT 2A modulators e.g., 5-HT 2A agonists
  • non-hallucinogenic 5-HT2A modulators are used for treating a brain disorder.
  • non-hallucinogenic 5-HT 2A modulators are used for increasing at least one of translation, transcription, or secretion of neurotrophic factors.
  • Methods for Increasing Neuronal Plasticity refers to the ability of the brain to change structure and/or function throughout a subject’s life. New neurons can be produced and integrated into the central nervous system throughout the subject’s life. Increasing neuronal plasticity includes, but is not limited to, promoting neuronal growth, promoting neuritogenesis, promoting synaptogenesis, promoting dendritogenesis, increasing dendritic arbor complexity, increasing dendritic spine density, and increasing excitatory synapsis in the brain.
  • increasing neuronal plasticity comprises promoting neuronal growth, promoting neuritogenesis, promoting synaptogenesis, promoting dendritogenesis, increasing dendritic arbor complexity, and increasing dendritic spine density.
  • increasing neuronal plasticity by treating a subject with one or more of the disclosed compound can treat neurodegenerative disorder, Alzheimer’s, Parkinson’s disease, psychological disorder, depression, addiction, anxiety, post-traumatic stress disorder, treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, stroke, traumatic brain injury, or substance use disorder.
  • the present disclosure provides methods for increasing neuronal plasticity, comprising contacting a neuronal cell with a compound of the present disclosure.
  • increasing neuronal plasticity improves a brain disorder described herein.
  • a compound of the present disclosure is used to increase neuronal plasticity.
  • the compounds and solid forms thereof (e.g., salts and crystalline polymorphs) used to increase neuronal plasticity have, for example, anti- addictive properties, antidepressant properties, anxiolytic properties, or a combination thereof.
  • decreased neuronal plasticity is associated with a neuropsychiatric disease.
  • the neuropsychiatric disease is a mood or anxiety disorder.
  • the neuropsychiatric disease includes, for example, migraine, cluster headache, post-traumatic stress disorder (PTSD), schizophrenia, anxiety, depression, and addiction (e.g., substance abuse disorder).
  • brain disorders include, for example, migraines, addiction (e.g., substance use disorder), depression, and anxiety.
  • the experiment or assay to determine increased neuronal plasticity of any compound of the present disclosure is a phenotypic assay, a dendritogenesis assay, a spinogenesis assay, a synaptogenesis assay, a Sholl analysis, a concentration-response experiment, a 5-HT2A agonist assay, a 5-HT2A antagonist assay, a 5-HT2A binding assay, or a 5- HT 2A blocking experiment (e.g., ketanserin blocking experiments).
  • the experiment or assay to determine the hallucinogenic potential of any compound of the present disclosure is a mouse head-twitch response (HTR) assay.
  • HTR mouse head-twitch response
  • the present disclosure provides a method for increasing neuronal plasticity, comprising contacting a neuronal cell with a compound disclosed herein.
  • Methods of Treating a Brain Disorder the present disclosure provides a method of treating a disease, including administering to a subject in need thereof, a therapeutically effective amount of LSD, 1-acetyl LSD, 1-propionyl LSD, and/or 2-bromo LSD of the present disclosure.
  • the disease is a musculoskeletal pain disorder including fibromyalgia, muscle pain, joint stiffness, osteoarthritis, rheumatoid arthritis, and muscle cramps.
  • the present disclosure provides a method of treating a disease of women’s reproductive health including premenstrual dysphoric disorder (PMDD), premenstrual syndrome (PMS), post-partum depression, and menopause.
  • PMDD premenstrual dysphoric disorder
  • PMS premenstrual syndrome
  • the present disclosure provides a method of treating a brain disorder, including administering to a subject in need thereof, a therapeutically effective amount of a compound of the present disclosure.
  • the present disclosure provides a method of treating a brain disorder with combination therapy, including administering to a subject in need thereof, a therapeutically effective amount of a compound of the present disclosure and at least one additional therapeutic agent.
  • 5-HT 2A modulators e.g., 5-HT 2A agonists
  • the brain disorders comprise decreased neural plasticity, decreased cortical structural plasticity, decreased 5-HT2A receptor content, decreased dendritic arbor complexity, loss of dendritic spines, decreased dendritic branch content, decreased spinogenesis, decreased neuritogenesis, retraction of neurites, or any combination thereof.
  • a compound of the present disclosure is used to treat brain disorders.
  • the compounds have, for example, anti- addictive properties, antidepressant properties, anxiolytic properties, or a combination thereof.
  • the brain disorder is a neuropsychiatric disease.
  • the neuropsychiatric disease is a mood or anxiety disorder.
  • brain disorders include, for example, migraine, cluster headache, post-traumatic stress disorder (PTSD), anxiety, depression, panic disorder, suicidality, schizophrenia, and addiction (e.g., substance abuse disorder).
  • brain disorders include, for example, migraines, addiction (e.g., substance use disorder), depression, and anxiety.
  • the present disclosure provides a method of treating a brain disorder, comprising administering to a subject in need thereof a therapeutically effective amount of a compound disclosed herein.
  • the brain disorder is a neurodegenerative disorder, Alzheimer’s, Parkinson’s disease, psychological disorder, depression, addiction, anxiety, post-traumatic stress disorder, treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, stroke, traumatic brain injury, or substance use disorder.
  • the brain disorder is a neurodegenerative disorder, Alzheimer’s, or Parkinson’s disease.
  • the brain disorder is a psychological disorder, depression, addiction, anxiety, or a post-traumatic stress disorder.
  • the brain disorder is depression.
  • the brain disorder is addiction.
  • the brain disorder is treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, stroke, traumatic brain injury or substance use disorder.
  • the brain disorder is treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, or substance use disorder.
  • the brain disorder is stroke or traumatic brain injury.
  • the brain disorder is treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, or substance use disorder.
  • the brain disorder is schizophrenia.
  • the brain disorder is alcohol use disorder.
  • the method further comprises administering one or more additional therapeutic agent that is lithium, olanzapine (Zyprexa), quetiapine (Seroquel), risperidone (Risperdal), ariprazole (Abilify), ziprasidone (Geodon), clozapine (Clozaril), divalproex sodium (Depakote), lamotrigine (Lamictal), valproic acid (Depakene), carbamazepine (Equetro), topiramate (Topamax), levomilnacipran (Fetzima), duloxetine (Cymbalta, Yentreve), venlafaxine (Effexor), citalopram (Celexa), fluvoxamine (Luvox), escitalopram (Lexapro), fluoxetine (Prozac), paroxetine (Paxil), sertraline (Zoloft), clomipramine (Anafranil),
  • a second therapeutic agent that is an empathogenic agent is administered.
  • suitable empathogenic agents for use in combination with the present solid forms include phenethylamines, such as 3,4-methylene- dioxymethamphetamine (MDMA), and analogs thereof.
  • Suitable empathogenic agents for use in combination with the presently disclosed compounds include, without limitation, N-Allyl-3,4-methylenedioxy-amphetamine (MDAL), N-Butyl-3,4-methylenedioxyamphetamine (MDBU), N-Benzyl-3,4-methylenedioxyamphetamine (MDBZ), N-Cyclopropylmethyl-3,4-methylenedioxyamphetamine (MDCPM), N,N-Dimethyl-3,4-methylenedioxyamphetamine (MDDM), N-Ethyl-3,4-methylenedioxyamphetamine (MDE; MDEA), N-(2-Hydroxyethyl)-3,4-methylenedioxy amphetamine (MDHOET), N-Isopropyl-3,4-methylenedioxyamphetamine (MDIP), N-Methyl-3,4-ethylenedioxyamphetamine (MDMC), N-Methoxy-3,4-methylenedioxyamphet
  • the compounds of the present disclosure are used in combination with the standard of care therapy for a neurological disease described herein.
  • the standard of care therapies may include, for example, lithium, olanzapine, quetiapine, risperidone, ariprazole, ziprasidone, clozapine, divalproex sodium, lamotrigine, valproic acid, carbamazepine, topiramate, levomilnacipran, duloxetine, venlafaxine, citalopram, fluvoxamine, escitalopram, fluoxetine, paroxetine, sertraline, clomipramine, amitriptyline, desipramine, imipramine, nortriptyline, phenelzine, tranylcypromine, diazepam, alprazolam, clonazepam, or any combination thereof.
  • Nonlimiting examples of standard of care therapy for depression are sertraline, fluoxetine, escitalopram, venlafaxine, or aripiprazole.
  • Non-limiting examples of standard of care therapy for depression are citralopram, escitalopram, fluoxetine, paroxetine, diazepam, or sertraline. Additional examples of standard of care therapeutics are known to those of ordinary skill in the art.
  • Methods of increasing at least one of translation, transcription, or secretion of neurotrophic factors refer to a family of soluble peptides or proteins which support the survival, growth, and differentiation of developing and mature neurons.
  • Increasing at least one of translation, transcription, or secretion of neurotrophic factors can be useful for, but not limited to, increasing neuronal plasticity, promoting neuronal growth, promoting neuritogenesis, promoting synaptogenesis, promoting dendritogenesis, increasing dendritic arbor complexity, increasing dendritic spine density, and increasing excitatory synapsis in the brain.
  • increasing at least one of translation, transcription, or secretion of neurotrophic factors can increasing neuronal plasticity.
  • increasing at least one of translation, transcription, or secretion of neurotrophic factors can promoting neuronal growth, promoting neuritogenesis, promoting synaptogenesis, promoting dendritogenesis, increasing dendritic arbor complexity, and/or increasing dendritic spine density.
  • 5-HT2A modulators e.g., 5-HT2A agonists
  • a compound of the present disclosure is used to increase at least one of translation, transcription, or secretion of neurotrophic factors.
  • increasing at least one of translation, transcription or secretion of neurotrophic factors treats a migraine, headaches (e.g., cluster headache), post-traumatic stress disorder (PTSD), anxiety, depression, neurodegenerative disorder, Alzheimer’s disease, Parkinson’s disease, psychological disorder, treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, stroke, traumatic brain injury, and addiction (e.g., substance use disorder).
  • the experiment or assay used to determine increase translation of neurotrophic factors includes ELISA, western blot, immunofluorescence assays, proteomic experiments, and mass spectrometry.
  • the experiment or assay used to determine increase transcription of neurotrophic factors includes gene expression assays, PCR, and microarrays. In some embodiments, the experiment or assay used to determine increase secretion of neurotrophic factors includes ELISA, western blot, immunofluorescence assays, proteomic experiments, and mass spectrometry. In some embodiments, the present disclosure provides a method for increasing at least one of translation, transcription or secretion of neurotrophic factors, comprising contacting a neuronal cell with a compound disclosed herein. Combination therapy In particular embodiments of treating the disorders described above, combination therapy is used as described herein.
  • a form of LSD, 1P-LSD, 1A-LSD, or 2-BR-LSD described herein is administered in combination with a serotonin receptor modulator.
  • the serotonin receptor modulator is selected from the group consisting of altanserin, blonanserin, eplivanserin, glemanserin, volinanserin, ketanserin, ritanserin, pimavanserin, nelotanserin, pruvanserin, and flibanserin.
  • the serotonin receptor modulator is selected from the group consisting of serotonin receptor modulator is selected from the group consisting of eplivanserin, volinanserin, ketanserin, ritanserin, pimavanserin, nelotanserin, pruvanserin, flibanserin, olanzapine, quetiapine, risperidone, cariprazine, clozapine, chlorpromazine, sertindole, iloperidone, paliperidone, asenapine, amisulpride, aripiprazole, brexpiprazole, lurasidone, ziprasidone, lumateperone, zotepine, buspirone, and xanomeline.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is LSD, 1P-LSD, or 1A-LSD, wherein the eplivanserin is present in about 1 mg to about 40 mg, or about 5 mg to about 10 mg, and the LSD, 1P-LSD, or 1A-LSD is present between about 1 microgram to about 400 micrograms, about 50 micrograms to about 200 micrograms, about 100 micrograms, about 150 micrograms, or about 250 micrograms.
  • the serotonin receptor modulator is volinanserin and the psychedelic is LSD, 1P-LSD, or 1A-LSD, wherein the volinanserin is present in about 1 mg to about 60 mg, or about 5 mg to about 20 mg, and the LSD, 1P-LSD, or 1A-LSD is present between about 1 microgram to about 400 micrograms, about 50 micrograms to about 200 micrograms, about 100 micrograms, about 150 micrograms, or about 250 micrograms.
  • the serotonin receptor modulator is ketanserin and the psychedelic is LSD, 1P-LSD, or 1A-LSD, wherein the ketanserin is present in about 10 mg to about 80 mg, about 30 mg to about 50 mg, or about 40 mg and the LSD, 1P-LSD, or 1A-LSD is present between about 1 microgram to about 400 micrograms, about 50 micrograms to about 200 micrograms, about 100 micrograms, about 150 micrograms, or about 250 micrograms.
  • the serotonin receptor modulator is ritanserin and the psychedelic is LSD, 1P-LSD, or 1A-LSD, wherein the ritanserin is present in about 1 mg to about 40 mg, or about 2.5 mg to about 10 mg, and the LSD, 1P-LSD, or 1A-LSD is present between about 1 microgram to about 400 micrograms, about 50 micrograms to about 200 micrograms, about 100 micrograms, about 150 micrograms, or about 250 micrograms.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is LSD, 1P-LSD, or 1A-LSD, wherein the pimavanserin is present in about 1 mg to about 60 mg, or about 17 mg to about 34 mg, and the LSD, 1P-LSD, or 1A-LSD is present between about 1 microgram to about 400 micrograms, about 50 micrograms to about 200 micrograms, about 100 micrograms, about 150 micrograms, or about 250 micrograms.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is LSD, 1P-LSD, or 1A-LSD, wherein the nelotanserin is present in about 1 mg to about 80 mg, or about 40 mg to about 80 mg, and the LSD, 1P-LSD, or 1A-LSD is present between about 1 microgram to about 400 micrograms, about 50 micrograms to about 200 micrograms, about 100 micrograms, about 150 micrograms, or about 250 micrograms.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is LSD, 1P-LSD, or 1A-LSD, wherein the pruvanserin is present in about 1 mg to about 40 mg, or about 3 mg to about 10 mg, and the LSD, 1P-LSD, or 1A-LSD is present between about 1 microgram to about 400 micrograms, about 50 micrograms to about 200 micrograms, about 100 micrograms, about 150 micrograms, or about 250 micrograms.
  • the serotonin receptor modulator is flibanserin and the psychedelic is LSD, 1P-LSD, or 1A-LSD, wherein the flibanserin is present in about 10 mg to about 200 mg, or about 80 mg to about 120 mg, or about 100 mg and LSD, 1P-LSD, or 1A-LSD is present between about 1 microgram to about 400 micrograms, about 50 micrograms to about 200 micrograms, about 100 micrograms, about 150 micrograms, or about 250 micrograms.
  • the serotonin receptor modulator is olanzapine and the psychedelic is LSD, 1P-LSD, or 1A-LSD, wherein the olanzapine is present in about 2.5 mg to about 30 mg, or about 5 mg or about 10 mg, or about 20 mg or about 25 mg and the LSD, 1P- LSD, or 1A-LSD is present between about 1 microgram to about 400 micrograms, about 50 micrograms to about 200 micrograms, about 100 micrograms, about 150 micrograms, or about 250 micrograms.
  • the serotonin receptor modulator is an extended-release form of olanzapine (e.g., ZYPREXA RELPREVV) and the psychedelic is LSD, 1P-LSD, or 1A-LSD, wherein the extended-release form of olanzapine (e.g., ZYPREXA RELPREVV) is present in about 50 mg to about 450 mg, or about 150 mg or about 210 mg, or about 300 mg or about 405 mg and the LSD, 1P-LSD, or 1A-LSD is present between about 1 microgram to about 400 micrograms, about 50 micrograms to about 200 micrograms, about 100 micrograms, about 150 micrograms, or about 250 micrograms.
  • olanzapine e.g., ZYPREXA RELPREVV
  • the psychedelic is LSD, 1P-LSD, or 1A-LSD
  • the extended-release form of olanzapine e.g.
  • the serotonin receptor modulator is quetiapine and the psychedelic is LSD, 1P-LSD, or 1A-LSD, wherein the quetiapine is present in about 25 mg to about 800 mg, or about 50 mg to about 100 mg, or about 150 mg or about 200 mg or about 250 mg or about 300 mg and the LSD, 1P-LSD, or 1A-LSD is present between about 1 microgram to about 400 micrograms, about 50 micrograms to about 200 micrograms, about 100 micrograms, about 150 micrograms, or about 250 micrograms.
  • the serotonin receptor modulator is an extended-release form of quetiapine and the psychedelic is LSD, 1P-LSD, or 1A-LSD, wherein the extended-release form of quetiapine is present in about 50 mg to about 300 mg, or about 50 mg or about 100 mg or about 200 mg, or about 300 mg and the LSD, 1P-LSD, or 1A-LSD is present between about 1 microgram to about 400 micrograms, about 50 micrograms to about 200 micrograms, about 100 micrograms, about 150 micrograms, or about 250 micrograms.
  • the serotonin receptor modulator is risperidone and the psychedelic is LSD, 1P-LSD, or 1A-LSD, wherein the risperidone is present in about 0.5 mg to about 20 mg or about .5 mg, or about 1mg, or about 2 mg, or about 3 mg or about 4 mg or about 5 mg or about 7.5 mg or about 10 mg or about 16 mg and the LSD, 1P-LSD, or 1A-LSD is present between about 1 microgram to about 400 micrograms, about 50 micrograms to about 200 micrograms, about 100 micrograms, about 150 micrograms, or about 250 micrograms.

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Abstract

L'invention concerne des sels et des formes solides de LSD, de 1-acétyl-LSD, de 1-propionyl-LSd et de 2-bromo-LSD. La forme solide peut être un sel et/ou une forme cristalline du LSD, du 1-acétyl-LSD, du 1-propionyl-LSd ou du 2-bromo-LSD, tel qu'un polymorphe de LSD, de 1-acétyl-LSD, de 1-propionyl-LSd ou de 2-bromo-LSD ou un sel de ceux-ci. L'invention concerne également des procédés de fabrication des formes solides et des procédés d'administration des formes solides. Les formes solides selon l'invention du LSD, du 1-acétyl-LSD, du 1-propionyl-LSd et du 2-bromo-LSD sont utiles pour traiter une maladie neurologique et/ou un trouble psychiatrique chez un patient.
PCT/US2022/081041 2021-12-06 2022-12-06 Formes salines et solides du diéthylamide de l'acide lysergique (lsd) et analogues WO2023107966A1 (fr)

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