US20230202998A1 - Phenethylamine compounds salts, polymorphic forms and methods of use thereof - Google Patents

Phenethylamine compounds salts, polymorphic forms and methods of use thereof Download PDF

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US20230202998A1
US20230202998A1 US17/989,673 US202217989673A US2023202998A1 US 20230202998 A1 US20230202998 A1 US 20230202998A1 US 202217989673 A US202217989673 A US 202217989673A US 2023202998 A1 US2023202998 A1 US 2023202998A1
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mdma
mbdb
radiation
crystalline
solid form
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Matthew Duncton
Samuel Clark
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Terran Biosciences Inc
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Terran Biosciences Inc
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Priority claimed from PCT/US2022/079413 external-priority patent/WO2023081897A1/fr
Priority claimed from PCT/US2022/079411 external-priority patent/WO2023081895A1/fr
Priority claimed from PCT/US2022/079415 external-priority patent/WO2023081899A1/fr
Application filed by Terran Biosciences Inc filed Critical Terran Biosciences Inc
Priority to US17/989,673 priority Critical patent/US20230202998A1/en
Priority to US18/176,441 priority patent/US11958821B2/en
Publication of US20230202998A1 publication Critical patent/US20230202998A1/en
Priority to US18/418,122 priority patent/US20240327371A1/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

Definitions

  • Ketamine is a member of a class of compounds known as psychoplastogens.
  • Psychoplastogens promote neuronal growth through a mechanism involving the activation of AMPA receptors, the tropomyosin receptor kinase B (TrkB), and the mammalian target of rapamycin (mTOR).
  • TrkB tropomyosin receptor kinase B
  • mTOR mammalian target of rapamycin
  • N-methyl-3,4-methylenedioxyamphetamine (MDMA), (R)-MDMA, (S)-MDMA, N-ethyl-3,4-methylenedioxyamphetamine hydrochloride (MDE), 5,6-methylenedioxy-2-aminoindane (MDAI), N-methyl-1,3-benzodioxolylbutanamine (MBDB), 5-Methoxy-2-aminoindane (MEAI), and 5,6-Dimethoxy-2-aminoindane are synthetic analogues of the psychedelic phenethylamine class of compounds.
  • Solid forms of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane including salts, crystalline forms of the compounds and salts, as well as polymorphs of the solid forms.
  • the solid forms of (R)-MDMA and (S)-MDMA may have an enantiomeric excess of at least 70%, such as an enantiomeric excess of at least 90%, or at least 98%, or about 100%.
  • the solid forms made by the disclosed methods may have at least one improved property compared to known forms of the same compound.
  • the solid forms of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane are polymorphs of the free base forms.
  • the solid forms of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane are salt forms, such as a pharmaceutically acceptable salt.
  • the salt may be provided in a solid form.
  • the solid forms of these salts can be amorphous or crystalline.
  • the hydrochloride salt solid forms disclosed herein are crystalline forms that have an improved property relative to the amorphous forms.
  • a crystalline form disclosed herein is a polymorph of the hydrochloride salt.
  • a disclosed polymorph has an improved property over one or more other solid forms.
  • the at least one improved property of the solid form of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane, or salts thereof disclosed herein may comprise a physical property, chemical property, pharmacokinetic property, or a combination thereof.
  • the at least one improved property comprises a melting point, glass transition temperature, flowability, thermal 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, that is improved compared to an amorphous sample of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane and salts thereof.
  • the salt may be formed from an acid selected from 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, cinnamic acid, maleic acid
  • a stoichiometric ratio of acid to MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane 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 solvate such as a hydrate, or a combination thereof.
  • the crystalline solid may be substantially a single form, such as a polymorph form.
  • the solid form can be selected as described herein 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, that is improved compared to an amorphous sample and/or a previously known crystalline form.
  • compositions comprising a solid form of a disclosed compound or a salt thereof, and a pharmaceutically acceptable excipient.
  • a method for administering the solid form of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane and salts thereof also is disclosed herein.
  • the method comprises administering to a subject an effective amount of a solid form MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane, salts thereof, 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-HT 2A antagonist to the subject.
  • the 5-HT 2A antagonist may be selected from 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
  • administering the solid form of the compound comprises oral, parenteral, or topical administration.
  • oral administration is used, but in other particular embodiments, administration is by injection, inhalation, intraocular, intravaginal, intrarectal or transdermal routes.
  • FIG. 1 provides an XRPD diffractogram of a sample comprising crystalline MDMA ⁇ fumarate.
  • FIG. 2 provides an XRPD diffractogram of a sample comprising crystalline MDMA ⁇ maleate.
  • FIG. 3 provides an XRPD diffractogram of a sample comprising crystalline MDMA freebase.
  • FIG. 4 provides an XRPD diffractogram of a sample comprising crystalline MDMA ⁇ phosphate.
  • FIG. 5 provides an XRPD diffractogram of a sample comprising crystalline MDMA ⁇ L-tartrate.
  • FIG. 6 provides an XRPD diffractogram of a sample comprising crystalline MDMA ⁇ L-malate.
  • FIG. 7 provides an XRPD diffractogram of a sample comprising crystalline MDMA ⁇ galactarate (mucate).
  • FIG. 8 provides an XRPD diffractogram of a sample comprising crystalline MDMA ⁇ succinate.
  • FIG. 9 provides an XRPD diffractogram of a sample comprising crystalline MDMA ⁇ toluenesulfonate (tosylate).
  • FIG. 10 provides an XRPD diffractogram of a sample comprising crystalline MDMA ⁇ fumarate Form 2.
  • FIG. 11 provides an XRPD diffractogram of a sample comprising crystalline MDMA ⁇ maleate Form 2.
  • FIG. 12 provides an XRPD diffractogram of a sample comprising a mixture of crystalline MDMA ⁇ tartrate Form 1 and Form 2.
  • FIG. 13 is a plot of intensity versus 2theta, illustrating a stacked X-ray diffractogram plot of an exemplary solid form of (S)-3,4-methylenedioxymethamphetamine, crystalline (S)-3,4-methylenedioxymethamphetamine ⁇ hydrochloride, with the data normalized to 10,000 counts.
  • FIG. 14 is a plot of intensity versus 2theta, illustrating an expanded view of the 2theta region from 3° to 33° of the plot in FIG. 13 .
  • FIG. 15 is a plot of intensity versus 2theta, illustrating a stacked X-ray diffractogram plot of an exemplary solid form of (R)-3,4-methylenedioxymethamphetamine, crystalline (R)-3,4-methylenedioxymethamphetamine ⁇ hydrochloride, with the data normalized to 10,000 counts.
  • FIG. 16 is a plot of intensity versus 2theta, illustrating an expanded view of the 2theta region from 3° to 33° of the plot in FIG. 15 .
  • FIG. 17 provides an XRPD diffractogram of N-ethyl-3,4-methylenedioxyamphetamine hydrochloride.
  • FIG. 18 provides an expanded section of the XRPD diffractogram provided in FIG. 17 .
  • FIG. 19 provides an XRPD diffractogram of S-MDE tosylate.
  • FIG. 20 provides an expanded section of the XRPD diffractogram provided in FIG. 19 .
  • FIG. 21 provides a 1 H NMR spectrum of the S-MDE tosylate salt in d 4 -methanol.
  • FIG. 22 is a plot of intensity versus 2theta, illustrating a stacked X-ray diffractogram plot of a first exemplary solid form of 5,6-methylenedioxy-2-aminoindane hydrochloride, crystalline 5,6-methylenedioxy-2-aminoindane hydrochloride, with the data normalized to 10,000 counts.
  • FIG. 23 is a plot of intensity versus 2theta, illustrating an expanded view of the 2theta region from 3° to 33° of the plot in FIG. 22 .
  • FIG. 24 is a plot of intensity versus 2theta, illustrating a stacked X-ray diffractogram plot of a second exemplary solid form of 5,6-methylenedioxy-2-aminoindane hydrochloride, crystalline 5,6-methylenedioxy-2-aminoindane hydrochloride, with the data normalized to 10,000 counts.
  • FIG. 25 is a plot of intensity versus 2theta, illustrating an expanded view of the 2theta region from 3° to 33° of the plot in FIG. 24 .
  • FIG. 26 provides an XRPD diffractogram of crystalline MBDB ⁇ citrate.
  • FIG. 27 provides an XRPD diffractogram of crystalline MBDB ⁇ fumarate.
  • FIG. 28 provides an XRPD diffractogram of crystalline MBDB ⁇ galactarate.
  • FIG. 29 provides an XRPD diffractogram of crystalline MBDB ⁇ maleate (Form 1).
  • FIG. 30 provides an XRPD diffractogram of crystalline MBDB ⁇ phosphate.
  • FIG. 31 provides an XRPD diffractogram of crystalline MBDB ⁇ succinate.
  • FIG. 32 provides an XRPD diffractogram of crystalline MBDB ⁇ sulfate.
  • FIG. 33 provides an XRPD diffractogram of crystalline MBDB ⁇ tartrate.
  • FIG. 34 provides an XRPD pattern calculated (bottom trace) from the single-crystal data is overlaid with a pattern obtained from the bulk material in FIG. 32 .
  • FIG. 35 provides an XRPD diffractogram of crystalline MBDB ⁇ malonate.
  • FIG. 36 provides an XRPD diffractogram of crystalline MBDB ⁇ succinate (form 2).
  • FIG. 37 provides an XRPD diffractogram of crystalline MBDB ⁇ tosylate.
  • FIG. 38 provides an XRPD diffractogram of a sample comprising crystalline MBDB ⁇ HCl form A.
  • FIG. 39 provides an XRPD diffractogram of a sample comprising crystalline MBDB ⁇ HCl form B.
  • FIG. 40 is a plot of intensity versus 2theta, illustrating a stacked X-ray diffractogram plot of an exemplary solid form of 5-methoxy-2-aminoindane hydrochloride, crystalline 5-methoxy-2-aminoindane hydrochloride, with the data normalized to 10,000 counts.
  • FIG. 41 is a plot of intensity versus 2theta, illustrating an expanded view of the 2theta region from 3° to 33° of the plot in FIG. 40 .
  • FIG. 42 is a plot of intensity versus 2theta, illustrating a stacked X-ray diffractogram plot of an exemplary solid form of 5,6-dimethoxy-2-aminoindane hydrochloride, crystalline 5,6-dimethoxy-2-aminoindane hydrochloride, with the data normalized to 10,000 counts.
  • FIG. 43 is a plot of intensity versus 2theta, illustrating an expanded view of the 2theta region from 3° to 33° of the plot in FIG. 42 .
  • FIG. 44 provides a 1 H NMR spectrum for MDMA fumarate Form 1.
  • FIG. 45 provides TGA and DSC profiles for MDMA fumarate Form 1.
  • FIG. 46 provides an XRPD diffractogram of crystalline MDMA ⁇ galactarate (mucate).
  • FIG. 47 provides an XRPD diffractogram of crystalline MDMA ⁇ phosphate.
  • FIG. 48 provides an XRPD diffractogram of crystalline MDMA ⁇ HCl.
  • FIG. 49 provides a 1 H NMR spectrum for MDMA L-malate.
  • FIG. 50 provides TGA and DSC profiles for MDMA L-malate.
  • FIG. 51 provides a 1 H NMR spectrum for MDMA maleate Form 1.
  • FIG. 52 provides TGA and DSC profiles for MDMA maleate Form 1.
  • FIG. 53 provides a 1 H NMR spectrum for MDMA maleate Form 2.
  • FIG. 54 provides TGA and DSC profiles for MDMA maleate Form 2.
  • FIG. 55 provides a 1 H NMR spectrum for MDMA galactarate (mucate).
  • FIG. 56 provides TGA and DSC profiles for MDMA galactarate (mucate).
  • FIG. 57 provides a 1 H NMR spectrum for MDMA phosphate.
  • FIG. 58 provides TGA and DSC profiles for MDMA phosphate.
  • FIG. 59 provides a 1 H NMR spectrum for MDMA succinate.
  • FIG. 60 provides TGA and DSC profiles for MDMA succinate.
  • FIG. 61 provides a 1 H NMR spectrum for MDMA L-tartrate Form 1.
  • FIG. 62 provides TGA and DSC profiles for MDMA L-tartrate Form 1.
  • FIG. 63 provides a 1 H NMR spectrum for MDMA tosylate (toluenesulfonate).
  • FIG. 64 provides TGA and DSC profiles for MDMA tosylate (toluenesulfonate).
  • FIG. 65 provides a 1 H NMR spectrum for MBDB citrate.
  • FIG. 66 provides TGA and DSC profiles for MBDB citrate.
  • FIG. 67 provides a 1 H NMR spectrum for MBDB fumarate.
  • FIG. 68 provides TGA and DSC profiles for MBDB fumarate.
  • FIG. 69 provides a 1 H NMR spectrum for MBDB galactarate (mucate).
  • FIG. 70 provides TGA and DSC profiles for MBDB galactarate (mucate).
  • FIG. 71 provides a 1 H NMR spectrum for MBDB maleate (Form 1).
  • FIG. 72 provides TGA and DSC profiles for MBDB maleate (Form 1).
  • FIG. 73 provides a 1 H NMR spectrum for MBDB malonate.
  • FIG. 74 provides TGA and DSC profiles for MBDB malonate.
  • FIG. 75 provides a 1 H NMR spectrum for MBDB phosphate.
  • FIG. 76 provides TGA and DSC profiles for MBDB phosphate.
  • FIG. 77 provides a 1 H NMR spectrum for MBDB succinate Form 1.
  • FIG. 78 provides TGA and DSC profiles for MBDB succinate Form 1.
  • FIG. 79 provides a 1 H NMR spectrum for MBDB succinate Form 2.
  • FIG. 80 provides TGA and DSC profiles for MBDB succinate Form 2.
  • FIG. 81 provides TGA and DSC profiles for MBDB sulfate.
  • FIG. 82 provides a 1 H NMR spectrum for MBDB tosylate (toluenesulfonate).
  • FIG. 83 provides TGA and DSC profiles for MBDB tosylate (toluenesulfonate).
  • FIG. 84 provides an XRPD diffractogram of crystalline MBDB ⁇ citrate.
  • FIG. 85 provides an XRPD diffractogram of crystalline MBDB ⁇ fumarate.
  • FIG. 86 provides an XRPD diffractogram of crystalline MBDB ⁇ HCl Form A.
  • FIG. 87 provides an XRPD diffractogram of crystalline MBDB ⁇ HCl Form B.
  • FIG. 88 provides an XRPD diffractogram of crystalline MBDB ⁇ maleate Form 1.
  • FIG. 89 provides an XRPD diffractogram of crystalline MBDB ⁇ galactarate (mucate).
  • FIG. 90 provides a 1 H NMR spectrum for MBDB HCl Form A.
  • FIG. 91 provides TGA and DSC profiles for MBDB HCl Form A.
  • FIG. 92 provides a cyclic DSC profile for MBDB HCl Form A
  • FIG. 93 provides a 1 H NMR spectrum for MBDB HCl Form B.
  • FIG. 94 provides TGA and DSC profiles for MBDB HCl Form B.
  • FIG. 95 provides a 1 H NMR spectrum for MDMA HCl.
  • FIG. 96 provides an XRPD diffractogram of crystalline MBDB ⁇ maleate Form 2.
  • FIG. 97 provides an XRPD diffractogram of crystalline MBDB ⁇ maleate Form 3.
  • FIG. 98 provides a 1 H NMR spectrum for MBDB maleate (Form 2).
  • FIG. 99 provides a 1 H NMR spectrum for MBDB maleate (Form 3).
  • FIG. 100 provides TGA and DSC profiles for MBDB maleate (Form 2).
  • FIG. 101 provides TGA and DSC profiles for MBDB maleate (Form 3).
  • FIG. 102 provides an XRPD diffractogram of crystalline (R)-MDE HCl.
  • FIG. 103 provides an XRPD diffractogram of crystalline (S)-MDE HCl.
  • FIG. 104 provides an XRPD diffractogram of crystalline (R)-MBDB HCl.
  • FIG. 105 provides an XRPD diffractogram of crystalline (S)-MBDB HCl.
  • FIG. 106 provides an XRPD diffractogram of crystalline MBDB HCl.
  • FIG. 107 provides an XRPD diffractogram of crystalline MDAI HCl.
  • FIG. 108 provides an XRPD diffractogram of crystalline MDE HCl.
  • FIG. 109 provides TGA and DSC profiles for crystalline MDMA hemifumarate Form A.
  • FIG. 110 provides a DVS spectrum of crystalline MDMA hemifumarate Form A.
  • FIG. 111 provides a post-DVS XRPD diffractogram of crystalline MDMA hemifumarate Form A.
  • FIG. 112 provides an optical microscopy (OM) of crystalline MDMA hemifumarate Form A.
  • FIG. 113 provides an scanning electron microscope image of crystalline MDMA hemifumarate Form A.
  • FIG. 114 provides 1H NMR of crystalline MDMA hemifumarate Form A.
  • FIG. 115 provides an XRPD diffractogram of crystalline MDMA hemifumarate Form A.
  • FIG. 116 provides an XRPD diffractogram of crystalline MDMA hemifumarate Form A.
  • FIG. 117 illustrates the percentage of time spent in the open arms after racemic MDE compared to vehicle and chlordiazepoxide control on the elevated zero maze.
  • FIG. 118 illustrates the percentage of time spent in the open arms after R-MDE compared to vehicle and chlordiazepoxide control on the elevated zero maze.
  • FIG. 119 illustrates the percentage of time spent in the open arms after S-MDE compared to vehicle and chlordiazepoxide control on the elevated zero maze.
  • FIG. 120 illustrates the frequency of SAPs after racemic MDE compared to vehicle and chlordiazepoxide control on the elevated zero maze.
  • FIG. 121 illustrates the frequency of SAPs after R-MDE compared to vehicle and chlordiazepoxide control on the elevated zero maze.
  • FIG. 122 illustrates the frequency of SAPs after S-MDE compared to vehicle and chlordiazepoxide control on the elevated zero maze.
  • FIG. 123 illustrates the frequency of stretched attend postures (SAPs) after racemic MBDB, R-MBDB, and S-MBDB compared to vehicle and chlordiazepoxide control on the elevated zero maze.
  • FIG. 124 illustrates the percentage of time spent in the open arms after MDAI compared to vehicle and chlordiazepoxide control on the elevated zero maze.
  • FIG. 125 illustrates the total open arm entries after MDAI compared to vehicle and chlordiazepoxide control on the elevated zero maze.
  • FIG. 126 illustrates the total line crossings after MDAI compared to vehicle and chlordiazepoxide control on the elevated zero maze.
  • FIG. 127 illustrates the frequency of HDIPS after MDAI compared to vehicle and chlordiazepoxide control on the elevated zero maze.
  • FIG. 128 provides an overlay plot of the XRPD diffractogram of MBDB Maleate Form 1 and the XRPD diffractogram calculated from a single crystal of MBDB Maleate Form 1.
  • 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
  • 3,4-methylenedioxymethamphetamine refers to the racemic compound 1-(benzo[d][1,3]dioxol-5-yl)-N-methylpropan-2-amine.
  • the compound may also be referred to as MDMA, or N-methyl-3,4-methylenedioxyamphetamine.
  • (R)-3,4-methylenedioxymethamphetamine refers to the compound (R)-1-(benzo[d][1,3]dioxol-5-yl)-N-methylpropan-2-amine.
  • the compound may also be referred to as (R)-MDMA, or (R)—N-methyl-3,4-methylenedioxyamphetamine.
  • (S)-3,4-methylenedioxymethamphetamine refers to the compound (S)-1-(benzo[d][1,3]dioxol-5-yl)-N-methylpropan-2-amine.
  • the compound may also be referred to as (S)-MDMA, or (S)—N-methyl-3,4-methylenedioxyamphetamine.
  • N-ethyl-3,4-methylenedioxyamphetamine hydrochloride refers to the compound
  • MDE MDEA
  • N-ethyl-3,4-methylenedioxyamphetamine hydrochloride “N-ethyl-3,4-methylenedioxyamphetamine HCl,” and “MDE HCl” each refer to the hydrochloric acid salt of N-ethyl-3,4-methylenedioxyamphetamine.
  • S-MDE S-MDEA
  • MDAI which also may be referred to as, “MDAI.”
  • 5,6-methylenedioxy-2-aminoindane hydrochloride refers to the hydrochloric acid salt of 5,6-methylenedioxy-2-aminoindane:
  • N-methyl-1,3-benzodioxolylbutanamine refers to the compound
  • MBDB MBDB
  • 1-(benzo[d][1,3]dioxol-5-yl)-N-methylbutan-2-amine MBDB
  • N-methyl-1,3-benzodioxolylbutanamine hydrochloride or “MBDB ⁇ HCl” refers to the hydrochloric acid salt of N-methyl-1,3-benzodioxolylbutanamine.
  • 5-Methoxy-2-aminoindane hydrochloride refers to the racemic compound 5-methoxy-2,3-dihydro-1H-inden-2-amine hydrochloride.
  • the compound also may be referred to as 2-amino-5-methoxyindan hydrochloride, 5-methoxyindan-2-ylamine hydrochloride, MEAI HCl, or 5-MeO-AI HCl.
  • 5,6-Dimethoxy-2-aminoindane hydrochloride refers to the compound 5,6-dimethoxy-2,3-dihydro-1H-inden-2-amine hydrochloride.
  • the compound also may be referred to as 5,6-dimethoxyindan-2-amine hydrochloride, 2-amino-5,6-dimethoxyindan hydrochloride, or 5,6-dimethoxyindan-2-ylamine hydrochloride.
  • 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). In sensitized cells, the therapeutically effective dose can often be lower than the conventional therapeutically effective dose for non-sensitized cells.
  • Neuronal plasticity refers to the ability of the brain to change its structure and/or function continuously throughout a subject's life. Examples of the changes to the brain include, but are not limited to, the ability to adapt or respond to internal and/or external stimuli, such as due to an injury, and the ability to produce new neurites, dendritic spines, and synapses.
  • 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 present disclosure can be administered simultaneously (as a single preparation or separate preparation) or sequentially to the other drug therapy.
  • a combination therapy envisions administration of two or more drugs 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
  • a G protein-coupled receptor e.g., 5HT 2A
  • Agonism refers to the activation of a receptor or enzyme by a modulator, or agonist, to produce a biological response.
  • “Agonist” 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 EC 50 with respect to 5HT 2A 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 include, but are not limited to, binders, fillers, disintegrants, lubricants, coatings, sweeteners, flavors and colors.
  • Racemic or “racemic mixture” refers to a compound which comprises equal proportions of the dextrorotatory and levorotatory forms of a compound or salt thereof, such that the racemic compound is not optically active.
  • Enantiomeric excess refers to the degree to which a sample contains one enantiomer in greater amounts than the other.
  • a racemic mixture has an e.e. of 0% (i.e., there is no excess of one enantiomer compared to another), while a single completely pure enantiomer has an e.e. of 100%.
  • the compound is synthesized and/or purified to be in at least a 70% enantiomeric excess, at least a 75% enantiomeric excess, at least 80% enantiomeric excess, at least an 85% enantiomeric excess, at least a 90% enantiomeric excess, at least a 95% enantiomeric excess, at least a 97% enantiomeric excess, at least a 98% enantiomeric excess, at least a 99% enantiomeric excess, or even in greater than a 99% enantiomeric excess, such as in a substantially enantiopure form (substantially 100% enantiomeric excess), compared to the amount of the corresponding (S)-enantiomer.
  • the compound is synthesized and/or purified to be in at least a 70% enantiomeric excess, at least a 75% enantiomeric excess, at least 80% enantiomeric excess, at least an 85% enantiomeric excess, at least a 90% enantiomeric excess, at least a 95% enantiomeric excess, at least a 97% enantiomeric excess, at least a 98% enantiomeric excess, at least a 99% enantiomeric excess, or even in greater than a 99% enantiomeric excess, such as in a substantially enantiopure form (substantially 100% enantiomeric excess), compared to the amount of the corresponding (R)-enantiomer.
  • the disclosed forms are useful to treat various disorders, such as brain disorders. Also disclosed are methods for making the solid forms of these compounds and methods of administering the same.
  • the solid form of the compound is a crystalline form of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane.
  • the solid form of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, and/or 5,6-Dimethoxy-2-aminoindane is a crystalline polymorph of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, and/or 5,6-Dimethoxy-2-aminoindane such as a polymorph of the free base compound or a polymorph of the salt.
  • the solid form of the compound is a salt of the compound.
  • the solid form of the compound is a crystalline salt form of the compound, such as an acid addition salt form.
  • the salt is a salt formed from 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, glycolic 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, 2-hydroxy ethane-2-sulfonic
  • the stoichiometric ratio of acid to free base is 1:1. In some embodiments, the stoichiometric ratio of acid to free base is 1:2. In some embodiments, the stoichiometric ratio of acid to free base is 2:1. In some embodiments, the solid form of the compound is a polymorph of the compound, such as a novel polymorph that is not previously known in the art.
  • the solid form of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane comprises a salt of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane.
  • Suitable salts include pharmaceutically acceptable salts of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane.
  • the salt is provided as a solid form of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane that is not, and does not comprise, a hydrochloride salt.
  • the salt forms of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane 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, fumaric acid, tartaric acid, citric acid, benzoic acid, cinnamic acid, mandelic acid, benzene sulfonic acid, isethionic acid, methanesulfonic acid, ethanesulfonic acid,
  • the salt forms of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane 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. Additional information concerning pharmaceutically acceptable salts can be found in, for example, S. M. Berge, et
  • the disclosed salt forms may be formed using an acid from Table 1.
  • 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 cinnamic acid maleic acid adipic acid phosphoric acid sebacic acid ethanesulfonic acid (+)-camphoric acid glutamic acid acetic acid pamoic (embonic) acid nico
  • the acid salts of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane disclosed herein can have any suitable stoichiometric ratio of acid to free base.
  • the molar ratio of acid to MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane is from about 0.4 to about 2.2, such as forms wherein the salt has a stoichiometric ratio of acid to MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane of from about 0.5 to about 2, such as about 0.5, about 1 or about 2.
  • Embodiments of the compounds 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 MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane is a salt.
  • the solid form is a crystalline salt form of the compound.
  • a solid form of a salt may be a crystalline form or an amorphous form.
  • solid forms of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane, such as crystalline forms including salt and non-salt crystalline forms, may exist in more than one crystal form. Such different forms are referred to as polymorphs.
  • the disclosed compounds are particular polymorphs of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane or salts thereof.
  • the solid form of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane or salts thereof disclosed herein is selected to be a crystalline form, such as a particular polymorph of a crystalline form of MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane, e.g., 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 MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane.
  • the MDMA, (R)-MDMA, (S)-MDMA, MDE, S-MDE, R-MDE, MDAI, MBDB, S-MBDB, R-MBDB, MEAI, or 5,6-Dimethoxy-2-aminoindane 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.
  • 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
  • the desired polymorph may be produced by techniques as described herein and also are 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 freeze drying, and/or complexing with an inert agent.
  • Techniques to identify a particular solid form of a compound are described herein and are also known to persons of ordinary skill in the art, and include, but are not limited to, X-ray crystallography, X-ray diffraction, electron crystallography, powder diffraction, including X-ray, neutron, or electron diffraction, X-ray fiber diffraction, small-angle X-ray scattering, and/or melting point.
  • MDMA MDMA, (R)-MDMA, (S)-MDMA, MDE, (S)-MDE, (R)-MDE, MDAI, MBDB, (S)-MBDB, (R)-MBDB, MEAI, or 5,6-Dimethoxy-2-Aminoindane and Salts and Solid Forms Thereof
  • the present disclosure provides solid forms of MDMA fumarate Form 1, e.g., crystalline forms of MDMA fumarate Form 1.
  • the MDMA fumarate Form 1 XRPD profile is substantially similar to that shown in FIG. 1 .
  • the MDMA fumarate Form 1 1 H NMR spectrum is substantially similar to that shown in FIG. 44 .
  • the MDMA fumarate Form 1 TGA profile is substantially similar to that shown in FIG. 45 .
  • the MDMA fumarate Form 1 DSC profile is substantially similar to that shown in FIG. 45 .
  • the solid form of MDMA fumarate Form 1 is crystalline MDMA fumarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.3°2 ⁇ , 18.6°2 ⁇ , and 21.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA fumarate Form 1 is crystalline MDMA fumarate Form 1 characterized by XRPD signals at 17.3°2 ⁇ , 18.6°2 ⁇ , and 21.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA fumarate Form 1 is crystalline MDMA fumarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.7°2 ⁇ , 17.3°2 ⁇ , 18.6°2 ⁇ , 19.2°2 ⁇ , and 21.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA fumarate Form 1 is MDMA fumarate Form 1 characterized by XRPD signals at 16.7°2 ⁇ , 17.3°2 ⁇ , 18.6°2 ⁇ , 19.2°2 ⁇ , and 21.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA fumarate Form 1 is crystalline MDMA fumarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 10.9°2 ⁇ , 13.1°2 ⁇ , and 16.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA fumarate Form 1 is crystalline MDMA fumarate Form 1 characterized by XRPD signals at 10.9°2 ⁇ , 13.1°2 ⁇ , and 16.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA fumarate Form 1 is crystalline MDMA fumarate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 10.9°2 ⁇ , 13.1°2 ⁇ , 16.7°2 ⁇ , 17.3°2 ⁇ , and 18.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA fumarate Form 1 is MDMA fumarate Form 1 characterized by XRPD signals at 10.9°2 ⁇ , 13.1°2 ⁇ , 16.7°2 ⁇ , 17.3°2 ⁇ , and 18.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDMA fumarate 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, or forty-six XRPD signals selected from those set forth in Table 2.
  • the present disclosure provides solid forms of MDMA maleate Form 1, e.g., crystalline forms of MDMA maleate Form 1.
  • the MDMA maleate Form 1 XRPD profile is substantially similar to that shown in FIG. 2 .
  • the MDMA maleate Form 1 1 H NMR spectrum is substantially similar to that shown in FIG. 51 .
  • the MDMA maleate Form 1 TGA profile is substantially similar to that shown in FIG. 52 .
  • the MDMA maleate Form 1 DSC profile is substantially similar to that shown in FIG. 52 .
  • the solid form of MDMA maleate Form 1 is crystalline MDMA maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.9°2 ⁇ , 18.1°2 ⁇ , and 25.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA maleate Form 1 is crystalline MDMA maleate Form 1 characterized by XRPD signals at 14.9°2 ⁇ , 18.1°2 ⁇ , and 25.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA maleate Form 1 is crystalline MDMA maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.9°2 ⁇ , 18.1°2 ⁇ , 25.0°2 ⁇ , 25.3°2 ⁇ , and 29.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA maleate Form 1 is MDMA maleate Form 1 characterized by XRPD signals at 14.9°2 ⁇ , 18.1°2 ⁇ , 25.0°2 ⁇ , 25.3°2 ⁇ , and 29.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA maleate Form 1 is crystalline MDMA maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 10.1°2 ⁇ , 14.9°2 ⁇ , and 18.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA maleate Form 1 is crystalline MDMA maleate Form 1 characterized by XRPD signals at 10.1°2 ⁇ , 14.9°2 ⁇ , and 18.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA maleate Form 1 is crystalline MDMA maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 10.1°2 ⁇ , 14.9°2 ⁇ , 18.1°2 ⁇ , 25.0°2 ⁇ , and 28.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA maleate Form 1 is MDMA maleate Form 1 characterized by XRPD signals at 10.1°2 ⁇ , 14.9°2 ⁇ , 18.1°2 ⁇ , 25.0°2 ⁇ , and 28.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDMA 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, or thirty-nine XRPD signals selected from those set forth in Table 3.
  • the present disclosure provides solid forms of MDMA phosphate, e.g., crystalline forms of MDMA phosphate.
  • the MDMA phosphate XRPD profile is substantially similar to that shown in any one of FIG. 4 or 47 .
  • the MDMA phosphate 1 H NMR spectrum is substantially similar to that shown in FIG. 57 .
  • the MDMA phosphate TGA profile is substantially similar to that shown in FIG. 58 .
  • the MDMA phosphate DSC profile is substantially similar to that shown in FIG. 58 .
  • the solid form of MDMA phosphate is crystalline MDMA phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.4°2 ⁇ , 19.0°2 ⁇ , and 22.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA phosphate is crystalline MDMA phosphate characterized by XRPD signals at 12.4°2 ⁇ , 19.0°2 ⁇ , and 22.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA phosphate is crystalline MDMA phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.2°2 ⁇ , 12.4°2 ⁇ , 18.8°2 ⁇ , 19.0°2 ⁇ , and 22.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA phosphate is MDMA phosphate characterized by XRPD signals at 6.2°2 ⁇ , 12.4°2 ⁇ , 18.8°2 ⁇ , 19.0°2 ⁇ , and 22.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA phosphate is crystalline MDMA phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.2°2 ⁇ , 12.4°2 ⁇ , and 22.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA phosphate is crystalline MDMA phosphate characterized by XRPD signals at 6.2°2 ⁇ , 12.4°2 ⁇ , and 22.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA phosphate is crystalline MDMA phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.2°2 ⁇ , 12.4°2 ⁇ , 17.9°2 ⁇ , 19.3°2 ⁇ , and 22.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA phosphate is MDMA phosphate characterized by XRPD signals at 6.2°2 ⁇ , 12.4°2 ⁇ , 17.9°2 ⁇ , 19.3°2 ⁇ , and 22.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDMA phosphate 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 4.
  • the solid form of MDMA phosphate is crystalline MDMA phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.3°2 ⁇ , 12.5°2 ⁇ , and 22.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA phosphate is crystalline MDMA phosphate characterized by XRPD signals at 6.3°2 ⁇ , 12.5°2 ⁇ , and 22.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA phosphate is crystalline MDMA phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.3°2 ⁇ , 12.5°2 ⁇ , 19.0°2 ⁇ , 22.0°2 ⁇ , and 23.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA phosphate is MDMA phosphate characterized by XRPD signals at 6.3°2 ⁇ , 12.5°2 ⁇ , 19.0°2 ⁇ , 22.0°2 ⁇ , and 23.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA phosphate is crystalline MDMA phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.3°2 ⁇ , 12.5°2 ⁇ , 17.9°2 ⁇ , 19.4°2 ⁇ , and 22.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA phosphate is MDMA phosphate characterized by XRPD signals at 6.3°2 ⁇ , 12.5°2 ⁇ , 17.9°2 ⁇ , 19.4°2 ⁇ , and 22.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDMA phosphate 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 5.
  • the present disclosure provides solid forms of MDMA tartrate Form 1, e.g., crystalline forms of MDMA tartrate Form 1.
  • the MDMA tartrate Form 1 XRPD profile is substantially similar to that shown in FIG. 5 .
  • the MDMA tartrate Form 1 1 H NMR spectrum is substantially similar to that shown in FIG. 61 .
  • the MDMA tartrate Form 1 TGA profile is substantially similar to that shown in FIG. 62 .
  • the MDMA tartrate Form 1 DSC profile is substantially similar to that shown in FIG. 62 .
  • the solid form of MDMA tartrate Form 1 is crystalline MDMA tartrate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.5°2 ⁇ , 18.0°2 ⁇ , and 18.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tartrate Form 1 is crystalline MDMA tartrate Form 1 characterized by XRPD signals at 12.5°2 ⁇ , 18.0°2 ⁇ , and 18.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tartrate Form 1 is crystalline MDMA tartrate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.3°2 ⁇ , 12.5°2 ⁇ , 18.0°2 ⁇ , 18.3°2 ⁇ , and 18.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tartrate Form 1 is MDMA tartrate Form 1 characterized by XRPD signals at 6.3°2 ⁇ , 12.5°2 ⁇ , 18.0°2 ⁇ , 18.3°2 ⁇ , and 18.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tartrate Form 1 is crystalline MDMA tartrate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.3°2 ⁇ , 11.7°2 ⁇ , and 12.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tartrate Form 1 is crystalline MDMA tartrate Form 1 characterized by XRPD signals at 6.3°2 ⁇ , 11.7°2 ⁇ , and 12.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tartrate Form 1 is crystalline MDMA tartrate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.3°2 ⁇ , 11.7°2 ⁇ , 12.5°2 ⁇ , 17.2°2 ⁇ , and 18.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tartrate Form 1 is MDMA tartrate Form 1 characterized by XRPD signals at 6.3°2 ⁇ , 11.7°2 ⁇ , 12.5°2 ⁇ , 17.2°2 ⁇ , and 18.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDMA tartrate 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, or forty-four XRPD signals selected from those set forth in Table 6.
  • the present disclosure provides solid forms of MDMA malate, e.g., crystalline forms of MDMA malate.
  • the MDMA malate XRPD profile is substantially similar to that shown in FIG. 6 .
  • the MDMA malate 1 H NMR spectrum is substantially similar to that shown in FIG. 49 .
  • the MDMA malate TGA profile is substantially similar to that shown in FIG. 50 .
  • the MDMA malate DSC profile is substantially similar to that shown in FIG. 50 .
  • the solid form of MDMA malate is crystalline MDMA malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.2°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 MDMA malate is crystalline MDMA malate characterized by XRPD signals at 17.2°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 MDMA malate is crystalline MDMA malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.2°2 ⁇ , 18.0°2 ⁇ , 19.2°2 ⁇ , 20.8°2 ⁇ , and 24.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA malate is MDMA malate characterized by XRPD signals at 17.2°2 ⁇ , 18.0°2 ⁇ , 19.2°2 ⁇ , 20.8°2 ⁇ , and 24.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA malate is crystalline MDMA malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.9°2 ⁇ , 13.1°2 ⁇ , and 13.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA malate is crystalline MDMA malate characterized by XRPD signals at 11.9°2 ⁇ , 13.1°2 ⁇ , and 13.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA malate is crystalline MDMA malate characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.9°2 ⁇ , 13.1°2 ⁇ , 13.7°2 ⁇ , 17.2°2 ⁇ , and 18.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA malate is MDMA malate characterized by XRPD signals at 11.9°2 ⁇ , 13.1°2 ⁇ , 13.7°2 ⁇ , 17.2°2 ⁇ , and 18.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDMA 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, or forty-five XRPD signals selected from those set forth in Table 7.
  • the present disclosure provides solid forms of MDMA galactarate (mucate), e.g., crystalline forms of MDMA galactarate (mucate).
  • the MDMA galactarate (mucate) XRPD profile is substantially similar to that shown in any one of FIG. 7 or 46 .
  • the MDMA galactarate (mucate) 1 H NMR spectrum is substantially similar to that shown in FIG. 55 .
  • the MDMA galactarate (mucate) TGA profile is substantially similar to that shown in FIG. 56 .
  • the MDMA galactarate (mucate) DSC profile is substantially similar to that shown in FIG. 56 .
  • the solid form of MDMA galactarate (mucate) is crystalline MDMA galactarate (mucate) characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6°2 ⁇ , 18.8°2 ⁇ , and 19.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA galactarate (mucate) is crystalline MDMA galactarate (mucate) characterized by XRPD signals at 4.6°2 ⁇ , 18.8°2 ⁇ , and 19.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA galactarate is crystalline MDMA galactarate (mucate) characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6°2 ⁇ , 18.4°2 ⁇ , 18.8°2 ⁇ , 19.6°2 ⁇ , and 30.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA galactarate is MDMA galactarate (mucate) characterized by XRPD signals at 4.6°2 ⁇ , 18.4°2 ⁇ , 18.8°2 ⁇ , 19.6°2 ⁇ , and 30.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA galactarate (mucate) is crystalline MDMA galactarate (mucate) characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6°2 ⁇ , 9.0°2 ⁇ , and 13.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA galactarate (mucate) is crystalline MDMA galactarate (mucate) characterized by XRPD signals at 4.6°2 ⁇ , 9.0°2 ⁇ , and 13.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA galactarate is crystalline MDMA galactarate (mucate) characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6°2 ⁇ , 9.0°2 ⁇ , 13.6°2 ⁇ , 18.4°2 ⁇ , and 18.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA galactarate is MDMA galactarate (mucate) characterized by XRPD signals at 4.6°2 ⁇ , 9.0°2 ⁇ , 13.6°2 ⁇ , 18.4°2 ⁇ , and 18.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDMA galactarate 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 8.
  • the solid form of MDMA galactarate (mucate) is crystalline MDMA galactarate (mucate) characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6°2 ⁇ , 18.3°2 ⁇ , and 18.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA galactarate (mucate) is crystalline MDMA galactarate (mucate) characterized by XRPD signals at 4.6°2 ⁇ , 18.3°2 ⁇ , and 18.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA galactarate is crystalline MDMA galactarate (mucate) characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6°2 ⁇ , 9.1°2 ⁇ , 13.6°2 ⁇ , 18.3°2 ⁇ , and 18.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA galactarate is MDMA galactarate (mucate) characterized by XRPD signals at 4.6°2 ⁇ , 9.1°2 ⁇ , 13.6°2 ⁇ , 18.3°2 ⁇ , and 18.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA galactarate (mucate) is crystalline MDMA galactarate (mucate) characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6°2 ⁇ , 9.1°2 ⁇ , and 13.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA galactarate (mucate) is crystalline MDMA galactarate (mucate) characterized by XRPD signals at 4.6°2 ⁇ , 9.1°2 ⁇ , and 13.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDMA galactarate 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 9.
  • the present disclosure provides solid forms of MDMA succinate, e.g., crystalline forms of MDMA succinate.
  • the MDMA succinate XRPD profile is substantially similar to that shown in FIG. 8 .
  • the MDMA succinate 1 H NMR spectrum is substantially similar to that shown in FIG. 59 .
  • the MDMA succinate TGA profile is substantially similar to that shown in FIG. 60 .
  • the MDMA succinate DSC profile is substantially similar to that shown in FIG. 60 .
  • the solid form of MDMA succinate is crystalline MDMA succinate characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.0°2 ⁇ , 21.8°2 ⁇ , and 22.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA succinate is crystalline MDMA succinate characterized by XRPD signals at 13.0°2 ⁇ , 21.8°2 ⁇ , and 22.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA succinate is crystalline MDMA succinate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.5°2 ⁇ , 13.0°2 ⁇ , 18.9°2 ⁇ , 21.8°2 ⁇ , and 22.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA succinate is MDMA succinate characterized by XRPD signals at 6.5°2 ⁇ , 13.0°2 ⁇ , 18.9°2 ⁇ , 21.8°2 ⁇ , and 22.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA succinate is crystalline MDMA succinate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.5°2 ⁇ , 12.6°2 ⁇ , and 13.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA succinate is crystalline MDMA succinate characterized by XRPD signals at 6.5°2 ⁇ , 12.6°2 ⁇ , and 13.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA succinate is crystalline MDMA succinate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.5°2 ⁇ , 12.6°2 ⁇ , 13.0°2 ⁇ , 17.1°2 ⁇ , and 18.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA succinate is MDMA succinate characterized by XRPD signals at 6.5°2 ⁇ , 12.6°2 ⁇ , 13.0°2 ⁇ , 17.1°2 ⁇ , and 18.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDMA 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, twenty-seven, twenty-eight, twenty-nine, or thirty XRPD signals selected from those set forth in Table 10.
  • the present disclosure provides solid forms of MDMA tosylate, e.g., crystalline forms of MDMA tosylate.
  • the MDMA tosylate XRPD profile is substantially similar to that shown in FIG. 9 .
  • the MDMA tosylate 1 H NMR spectrum is substantially similar to that shown in FIG. 63 .
  • the MDMA tosylate TGA profile is substantially similar to that shown in FIG. 64 .
  • the MDMA tosylate DSC profile is substantially similar to that shown in FIG. 64 .
  • the solid form of MDMA tosylate is crystalline MDMA tosylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.4°2 ⁇ , 20.5°2 ⁇ , and 21.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tosylate is crystalline MDMA tosylate characterized by XRPD signals at 15.4°2 ⁇ , 20.5°2 ⁇ , and 21.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tosylate is crystalline MDMA tosylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.6°2 ⁇ , 15.4°2 ⁇ , 20.5°2 ⁇ , 21.3°2 ⁇ , and 21.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tosylate is MDMA tosylate characterized by XRPD signals at 13.6°2 ⁇ , 15.4°2 ⁇ , 20.5°2 ⁇ , 21.3°2 ⁇ , and 21.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; 20 ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tosylate is crystalline MDMA tosylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.0°2 ⁇ , 12.3°2 ⁇ , and 13.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tosylate is crystalline MDMA tosylate characterized by XRPD signals at 8.0°2 ⁇ , 12.3°2 ⁇ , and 13.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tosylate is crystalline MDMA tosylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.0°2 ⁇ , 12.3°2 ⁇ , 13.6°2 ⁇ , 15.4°2 ⁇ , and 20.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tosylate is MDMA tosylate characterized by XRPD signals at 8.0°2 ⁇ , 12.3°2 ⁇ , 13.6°2 ⁇ , 15.4°2 ⁇ , and 20.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDMA 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, 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, or forty-seven XRPD signals selected from those set forth in Table 11.
  • the present disclosure provides solid forms of MDMA fumarate Form 2, e.g., crystalline forms of MDMA fumarate Form 2.
  • a mixture of MDMA fumarate Forms 1 and 2 has an XRPD profile substantially similar to that shown in FIG. 10 .
  • the solid form of MDMA fumarate Form 2 is crystalline MDMA fumarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.5°2 ⁇ , 22.2°2 ⁇ , and 27.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA fumarate Form 2 is crystalline MDMA fumarate Form 2 characterized by XRPD signals at 14.5°2 ⁇ , 22.2°2 ⁇ , and 27.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA fumarate Form 2 is crystalline MDMA fumarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.5°2 ⁇ , 17.8°2 ⁇ , 22.2°2 ⁇ , 25.7°2 ⁇ , and 27.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA fumarate Form 2 is MDMA fumarate Form 2 characterized by XRPD signals at 14.5°2 ⁇ , 17.8°2 ⁇ , 22.2°2 ⁇ , 25.7°2 ⁇ , and 27.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA fumarate Form 2 is crystalline MDMA fumarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.2°2 ⁇ , 12.8°2 ⁇ , and 14.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA fumarate Form 2 is crystalline MDMA fumarate Form 2 characterized by XRPD signals at 12.2°2 ⁇ , 12.8°2 ⁇ , and 14.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA fumarate Form 2 is crystalline MDMA fumarate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.2°2 ⁇ , 12.8°2 ⁇ , 14.5°2 ⁇ , 16.0°2 ⁇ , and 16.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA fumarate Form 2 is MDMA fumarate Form 2 characterized by XRPD signals at 12.2°2 ⁇ , 12.8°2 ⁇ , 14.5°2 ⁇ , 16.0°2 ⁇ , and 16.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDMA fumarate 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, or thirty-five XRPD signals selected from those set forth in Table 12.
  • the present disclosure provides solid forms of MDMA maleate Form 2, e.g., crystalline forms of MDMA maleate Form 2.
  • the MDMA maleate Form 2 XRPD profile is substantially similar to that shown in FIG. 11 .
  • the MDMA maleate Form 2 1 H NMR spectrum is substantially similar to that shown in FIG. 53 .
  • the MDMA maleate Form 2 TGA profile is substantially similar to that shown in FIG. 54 .
  • the MDMA maleate Form 2 DSC profile is substantially similar to that shown in FIG. 54 .
  • the solid form of MDMA maleate Form 2 is crystalline MDMA maleate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.4°2 ⁇ , 18.5°2 ⁇ , and 26.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA maleate Form 2 is crystalline MDMA maleate Form 2 characterized by XRPD signals at 9.4°2 ⁇ , 18.5°2 ⁇ , and 26.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA maleate Form 2 is crystalline MDMA maleate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.4°2 ⁇ , 15.6°2 ⁇ , 15.9°2 ⁇ , 18.5°2 ⁇ , and 26.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA maleate Form 2 is MDMA maleate Form 2 characterized by XRPD signals at 9.4°2 ⁇ , 15.6°2 ⁇ , 15.9°2 ⁇ , 18.5°2 ⁇ , and 26.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA maleate Form 2 is crystalline MDMA maleate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.4°2 ⁇ , 13.8°2 ⁇ , and 14.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA maleate Form 2 is crystalline MDMA maleate Form 2 characterized by XRPD signals at 9.4°2 ⁇ , 13.8°2 ⁇ , and 14.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA maleate Form 2 is crystalline MDMA maleate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.4°2 ⁇ , 13.8°2 ⁇ , 14.8°2 ⁇ , 18.5°2 ⁇ , and 26.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA maleate Form 2 is MDMA maleate Form 2 characterized by XRPD signals at 9.4°2 ⁇ , 13.8°2 ⁇ , 14.8°2 ⁇ , 18.5°2 ⁇ , and 26.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDMA 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, thirty-seven, thirty-eight, thirty-nine, forty, or forty-one XRPD signals selected from those set forth in Table 13.
  • the present disclosure provides solid forms of MDMA tartrate Form 2, e.g., crystalline forms of MDMA tartrate Form 2.
  • a mixture of MDMA tartrate Forms 1 and 2 has an XRPD profile substantially similar to that shown in FIG. 12 .
  • the solid form of MDMA tartrate Form 2 is crystalline MDMA tartrate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.2°2 ⁇ , 18.9°2 ⁇ , and 19.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tartrate Form 2 is crystalline MDMA tartrate Form 2 characterized by XRPD signals at 5.2°2 ⁇ , 18.9°2 ⁇ , and 19.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tartrate Form 2 is crystalline MDMA tartrate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.2°2 ⁇ , 11.7°2 ⁇ , 15.4°2 ⁇ , 18.9°2 ⁇ , and 19.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tartrate Form 2 is MDMA tartrate Form 2 characterized by XRPD signals at 5.2°2 ⁇ , 11.7°2 ⁇ , 15.4°2 ⁇ , 18.9°2 ⁇ , and 19.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tartrate Form 2 is crystalline MDMA tartrate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.2°2 ⁇ , 10.3°2 ⁇ , and 11.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tartrate Form 2 is crystalline MDMA tartrate Form 2 characterized by XRPD signals at 5.2°2 ⁇ , 10.3°2 ⁇ , and 11.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tartrate Form 2 is crystalline MDMA tartrate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.2°2 ⁇ , 10.3°2 ⁇ , 11.7°2 ⁇ , 15.4°2 ⁇ , and 19.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA tartrate Form 2 is MDMA tartrate Form 2 characterized by XRPD signals at 5.2°2 ⁇ , 10.3°2 ⁇ , 11.7°2 ⁇ , 15.4°2 ⁇ , and 19.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDMA tartrate Form 2 is characterized by one, two, three, four, five, six, seven, eight, nine, ten, or eleven XRPD signals selected from those set forth in Table 14.
  • the present disclosure provides solid forms of MDMA HCl, e.g., crystalline forms of MDMA HCl.
  • the MDMA HCl XRPD profile is substantially similar to that shown in FIG. 48 .
  • the MDMA HCl 1 H NMR spectrum is substantially similar to that shown in FIG. 95 .
  • the solid form of MDMA HCl is crystalline MDMA HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.9°2 ⁇ , 18.5°2 ⁇ , and 21.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA HCl is crystalline MDMA HCl characterized by XRPD signals at 15.9°2 ⁇ , 18.5°2 ⁇ , and 21.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA HCl is crystalline MDMA HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.9°2 ⁇ , 18.5°2 ⁇ , 19.5°2 ⁇ , 21.5°2 ⁇ , and 27.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA HCl is MDMA HCl characterized by XRPD signals at 15.9°2 ⁇ , 18.5°2 ⁇ , 19.5°2 ⁇ , 21.5°2 ⁇ , and 27.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA HCl is crystalline MDMA HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.8°2 ⁇ , 12.6°2 ⁇ , and 15.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA HCl is crystalline MDMA HCl characterized by XRPD signals at 9.8°2 ⁇ , 12.6°2 ⁇ , and 15.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA HCl is crystalline MDMA HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.8°2 ⁇ , 12.6°2 ⁇ , 15.9°2 ⁇ , 18.5°2 ⁇ , and 19.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA HCl is MDMA HCl characterized by XRPD signals at 9.8°2 ⁇ , 12.6°2 ⁇ , 15.9°2 ⁇ , 18.5°2 ⁇ , and 19.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDMA HCl 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, or thirty-six XRPD signals selected from those set forth in Table 15.
  • the present disclosure provides solid forms of MDE HCl, e.g., crystalline forms of MDE HCl.
  • the MDE HCl XRPD profile is substantially similar to that shown in FIG. 17 or 108 .
  • the solid form of MDE HCl is crystalline MDE HCl characterized by XRPD signals at 15.6°2 ⁇ and 21.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDE HCl is crystalline MDE HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.6°2 ⁇ , 21.6°2 ⁇ , 22.1°2 ⁇ , and 23.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDE HCl is MDE HCl characterized by XRPD signals at 15.6°2 ⁇ , 21.6°2 ⁇ , 22.1°2 ⁇ , and 23.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDE HCl is crystalline MDE HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.0°2 ⁇ , 14.4°2 ⁇ , and 23.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDE HCl is crystalline MDE HCl characterized by XRPD signals at 14.0°2 ⁇ , 14.4°2 ⁇ , and 23.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDE HCl is crystalline MDE HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.0°2 ⁇ , 14.4°2 ⁇ , 23.5°2 ⁇ , 24.9°2 ⁇ , and 28.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDE HCl is MDE HCl characterized by XRPD signals at 14.0°2 ⁇ , 14.4°2 ⁇ , 23.5°2 ⁇ , 24.9°2 ⁇ , and 28.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDE HCl 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 16.
  • the solid form of MDE HCl is crystalline MDE HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.1°2 ⁇ , 14.5°2 ⁇ , and 15.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDE HCl is crystalline MDE HCl characterized by XRPD signals at 14.1°2 ⁇ , 14.5°2 ⁇ , and 15.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDE HCl is crystalline MDE HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.1°2 ⁇ , 14.5°2 ⁇ , 15.7°2 ⁇ , 18.5°2 ⁇ , and 18.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDE HCl is MDE HCl characterized by XRPD signals at 14.1°2 ⁇ , 14.5°2 ⁇ , 15.7°2 ⁇ , 18.5°2 ⁇ , and 18.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDE HCl is crystalline MDE HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.5°2 ⁇ , 23.5°2 ⁇ , and 28.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDE HCl is crystalline MDE HCl characterized by XRPD signals at 14.5°2 ⁇ , 23.5°2 ⁇ , and 28.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDE HCl is crystalline MDE HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.1°2 ⁇ , 14.5°2 ⁇ , 23.5°2 ⁇ , 25.2°2 ⁇ , and 28.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDE HCl is MDE HCl characterized by XRPD signals at 14.1°2 ⁇ , 14.5°2 ⁇ , 23.5°2 ⁇ , 25.2°2 ⁇ , and 28.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDE 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 17.
  • the present disclosure provides solid forms of S-MDE tosylate, e.g., crystalline forms of S-MDE tosylate.
  • the S-MDE tosylate XRPD profile is substantially similar to that shown in FIG. 19 .
  • the solid form of S-MDE tosylate is crystalline S-MDE tosylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.1°2 ⁇ , 13.9°2 ⁇ , and 15.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of S-MDE tosylate is crystalline S-MDE tosylate characterized by XRPD signals at 12.1°2 ⁇ , 13.9°2 ⁇ , and 15.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of S-MDE tosylate is crystalline S-MDE tosylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.1°2 ⁇ , 13.9°2 ⁇ , 15.1°2 ⁇ , 15.6°2 ⁇ , and 16.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of S-MDE tosylate is S-MDE tosylate characterized by XRPD signals at 12.1°2 ⁇ , 13.9°2 ⁇ , 15.1°2 ⁇ , 15.6°2 ⁇ , and 16.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of S-MDE tosylate is crystalline S-MDE tosylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.9°2 ⁇ , 19.8°2 ⁇ , and 21.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of S-MDE tosylate is crystalline S-MDE tosylate characterized by XRPD signals at 13.9°2 ⁇ , 19.8°2 ⁇ , and 21.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of S-MDE tosylate is crystalline S-MDE tosylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.9°2 ⁇ , 19.8°2 ⁇ , 21.8°2 ⁇ , 24.3°2 ⁇ , and 26.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of S-MDE tosylate is S-MDE tosylate characterized by XRPD signals at 13.9°2 ⁇ , 19.8°2 ⁇ , 21.8°2 ⁇ , 24.3°2 ⁇ , and 26.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline S-MDE tosylate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, or twenty XRPD signals selected from those set forth in Table 18.
  • the present disclosure provides solid forms of MDAI HCl, e.g., crystalline forms of MDAI HCl.
  • the MDAI HCl XRPD profile is substantially similar to that shown in FIG. 22 .
  • the solid form of MDAI HCl is crystalline MDAI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.9°2 ⁇ , 23.6°2 ⁇ , and 24.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is crystalline MDAI HCl characterized by XRPD signals at 16.9°2 ⁇ , 23.6°2 ⁇ , and 24.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is crystalline MDAI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.9°2 ⁇ , 23.6°2 ⁇ , 24.2°2 ⁇ , 26.4°2 ⁇ , and 27.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is MDAI HCl characterized by XRPD signals at 16.9°2 ⁇ , 23.6°2 ⁇ , 24.2°2 ⁇ , 26.4°2 ⁇ , and 27.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is crystalline MDAI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 24.2°2 ⁇ , 27.2°2 ⁇ , and 45.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is crystalline MDAI HCl characterized by XRPD signals at 24.2°2 ⁇ , 27.2°2 ⁇ , and 45.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is crystalline MDAI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 23.6°2 ⁇ , 24.2°2 ⁇ , 26.4°2 ⁇ , 27.2°2 ⁇ , and 45.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is MDAI HCl characterized by XRPD signals at 23.6°2 ⁇ , 24.2°2 ⁇ , 26.4°2 ⁇ , 27.2°2 ⁇ , and 45.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDAI HCl is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, or thirteen XRPD signals selected from those set forth in Table 19.
  • the solid form of MDAI HCl is crystalline MDAI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.8°2 ⁇ , 23.2°2 ⁇ , and 24.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is crystalline MDAI HCl (Pattern #1) characterized by XRPD signals at 16.8°2 ⁇ , 23.2°2 ⁇ , and 24.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is crystalline MDAI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.8°2 ⁇ , 23.2°2 ⁇ , 24.2°2 ⁇ , 26.4°2 ⁇ , and 27.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is crystalline MDAI HCl characterized by XRPD signals at 16.8°2 ⁇ , 23.2°2 ⁇ , 24.2°2 ⁇ , 26.4°2 ⁇ , and 27.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is crystalline MDAI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 24.2°2 ⁇ , 45.8°2 ⁇ , and 27.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is crystalline MDAI HCl (Pattern #1) characterized by XRPD signals at 24.2°2 ⁇ , 45.8°2 ⁇ , and 27.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is crystalline MDAI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 24.2°2 ⁇ , 45.8°2 ⁇ , 27.1°2 ⁇ , 23.6°2 ⁇ , and 26.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is crystalline MDAI HCl characterized by XRPD signals at 24.2°2 ⁇ , 45.8°2 ⁇ , 27.1°2 ⁇ , 23.6°2 ⁇ , and 26.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDAI HCl is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, or fifteen XRPD signals selected from those set forth in Table 20.
  • the present disclosure provides solid forms of MBDB citrate, e.g., crystalline forms of MBDB citrate.
  • the MBDB citrate XRPD profile is substantially similar to that shown in any one of FIG. 26 or 84 .
  • the MBDB citrate 1 H NMR spectrum is substantially similar to that shown in FIG. 65 .
  • the MBDB citrate TGA profile is substantially similar to that shown in FIG. 66 .
  • the MBDB citrate DSC profile is substantially similar to that shown in FIG. 66 .
  • the solid form of MBDB citrate is crystalline MBDB citrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.3°2 ⁇ , 19.0°2 ⁇ , and 25.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB citrate is crystalline MBDB citrate characterized by XRPD signals at 6.3°2 ⁇ , 19.0°2 ⁇ , and 25.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB citrate is crystalline MBDB citrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.3°2 ⁇ , 12.6°2 ⁇ , 19.0°2 ⁇ , 21.4°2 ⁇ , and 25.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB citrate is MBDB citrate characterized by XRPD signals at 6.3°2 ⁇ , 12.6°2 ⁇ , 19.0°2 ⁇ , 21.4°2 ⁇ , and 25.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB citrate is crystalline MBDB citrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.3°2 ⁇ , 12.6°2 ⁇ , and 19.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB citrate is crystalline MBDB citrate characterized by XRPD signals at 6.3°2 ⁇ , 12.6°2 ⁇ , and 19.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB citrate 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 21.
  • the solid form of MBDB citrate is crystalline MBDB citrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.3°2 ⁇ , 19.0°2 ⁇ , and 25.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB citrate is crystalline MBDB citrate characterized by XRPD signals at 6.3°2 ⁇ , 19.0°2 ⁇ , and 25.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB citrate is crystalline MBDB citrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.3°2 ⁇ , 15.9°2 ⁇ , 17.1°2 ⁇ , 19.0°2 ⁇ , and 25.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB citrate is MBDB citrate characterized by XRPD signals at 6.3°2 ⁇ , 15.9°2 ⁇ , 17.1°2 ⁇ , 19.0°2 ⁇ , and 25.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB citrate is crystalline MBDB citrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.3°2 ⁇ , 11.7°2 ⁇ , and 12.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB citrate is crystalline MBDB citrate characterized by XRPD signals at 6.3°2 ⁇ , 11.7°2 ⁇ , and 12.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB citrate is crystalline MBDB citrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.3°2 ⁇ , 11.7°2 ⁇ , 12.7°2 ⁇ , 15.9°2 ⁇ , and 17.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB citrate is MBDB citrate characterized by XRPD signals at 6.3°2 ⁇ , 11.7°2 ⁇ , 12.7°2 ⁇ , 15.9°2 ⁇ , and 17.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB citrate 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 22.
  • the present disclosure provides solid forms of MBDB fumarate, e.g., crystalline forms of MBDB fumarate.
  • the MBDB fumarate XRPD profile is substantially similar to that shown in any one of FIG. 27 or 85 .
  • the MBDB fumarate 1 H NMR spectrum is substantially similar to that shown in FIG. 67 .
  • the MBDB fumarate TGA profile is substantially similar to that shown in FIG. 68 .
  • the MBDB fumarate DSC profile is substantially similar to that shown in FIG. 68 .
  • the solid form of MBDB fumarate is crystalline MBDB fumarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.9°2 ⁇ , 20.2°2 ⁇ , and 20.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB fumarate is crystalline MBDB fumarate characterized by XRPD signals at 12.9°2 ⁇ , 20.2°2 ⁇ , and 20.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB fumarate is crystalline MBDB fumarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.9°2 ⁇ , 20.2°2 ⁇ , 20.5°2 ⁇ , 22.5°2 ⁇ , and 26.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB fumarate is MBDB fumarate characterized by XRPD signals at 12.9°2 ⁇ , 20.2°2 ⁇ , 20.5°2 ⁇ , 22.5°2 ⁇ , and 26.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB fumarate is crystalline MBDB fumarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.7°2 ⁇ , 12.9°2 ⁇ , 20.2°2 ⁇ , 20.5°2 ⁇ , and 26.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB fumarate is MBDB fumarate characterized by XRPD signals at 11.7°2 ⁇ , 12.9°2 ⁇ , 20.2°2 ⁇ , 20.5°2 ⁇ , and 26.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB fumarate 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 23.
  • the solid form of MBDB fumarate is crystalline MBDB fumarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.9°2 ⁇ , 21.6°2 ⁇ , and 22.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB fumarate is crystalline MBDB fumarate characterized by XRPD signals at 12.9°2 ⁇ , 21.6°2 ⁇ , and 22.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB fumarate is crystalline MBDB fumarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.8°2 ⁇ , 12.9°2 ⁇ , 20.2°2 ⁇ , 21.6°2 ⁇ , and 22.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB fumarate is MBDB fumarate characterized by XRPD signals at 11.8°2 ⁇ , 12.9°2 ⁇ , 20.2°2 ⁇ , 21.6°2 ⁇ , and 22.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB fumarate is crystalline MBDB fumarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.8°2 ⁇ , 12.9°2 ⁇ , and 21.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB fumarate is crystalline MBDB fumarate characterized by XRPD signals at 11.8°2 ⁇ , 12.9°2 ⁇ , and 21.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB fumarate is crystalline MBDB fumarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.8°2 ⁇ , 12.9°2 ⁇ , 20.2°2 ⁇ , 20.5°2 ⁇ , and 21.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB fumarate is MBDB fumarate characterized by XRPD signals at 11.8°2 ⁇ , 12.9°2 ⁇ , 20.2°2 ⁇ , 20.5°2 ⁇ , and 21.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB fumarate 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 24.
  • the present disclosure provides solid forms of MBDB galactarate (mucate), e.g., crystalline forms of MBDB galactarate.
  • the MBDB galactarate XRPD profile is substantially similar to that shown in any one of FIG. 28 or 89 .
  • the MBDB galactarate 1 H NMR spectrum is substantially similar to that shown in FIG. 69 .
  • the MBDB galactarate TGA profile is substantially similar to that shown in FIG. 70 .
  • the MBDB galactarate DSC profile is substantially similar to that shown in FIG. 70 .
  • the solid form of MBDB galactarate is crystalline MBDB galactarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.2°2 ⁇ , 19.6°2 ⁇ , and 23.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB galactarate is crystalline MBDB galactarate characterized by XRPD signals at 9.2°2 ⁇ , 19.6°2 ⁇ , and 23.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB galactarate is crystalline MBDB galactarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6°2 ⁇ , 9.2°2 ⁇ , 19.6°2 ⁇ , 23.1°2 ⁇ , and 30.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB galactarate is MBDB galactarate characterized by XRPD signals at 4.6°2 ⁇ , 9.2°2 ⁇ , 19.6°2 ⁇ , 23.1°2 ⁇ , and 30.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB galactarate is crystalline MBDB galactarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6°2 ⁇ , 9.2°2 ⁇ , and 19.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB galactarate is crystalline MBDB galactarate characterized by XRPD signals at 4.6°2 ⁇ , 9.2°2 ⁇ , and 19.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB galactarate is crystalline MBDB galactarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6°2 ⁇ , 9.2°2 ⁇ , 18.5°2 ⁇ , 19.6°2 ⁇ , and 23.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB galactarate is MBDB galactarate characterized by XRPD signals at 4.6°2 ⁇ , 9.2°2 ⁇ , 18.5°2 ⁇ , 19.6°2 ⁇ , and 23.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB galactarate 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, or twenty-four XRPD signals selected from those set forth in Table 25.
  • the solid form of MBDB galactarate is crystalline MBDB galactarate (mucate) characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6°2 ⁇ , 9.2°2 ⁇ , and 19.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB galactarate is crystalline MBDB galactarate characterized by XRPD signals at 4.6°2 ⁇ , 9.2°2 ⁇ , and 19.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB galactarate is crystalline MBDB galactarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6°2 ⁇ , 9.2°2 ⁇ , 19.6°2 ⁇ , 23.1°2 ⁇ , and 30.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB galactarate is MBDB galactarate characterized by XRPD signals at 4.6°2 ⁇ , 9.2°2 ⁇ , 19.6°2 ⁇ , 23.1°2 ⁇ , and 30.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB galactarate is crystalline MBDB galactarate characterized by two or more, or three or more XRPD signals selected from the group consisting of 4.6°2 ⁇ , 9.2°2 ⁇ , 17.7°2 ⁇ , 18.1°2 ⁇ , and 19.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB galactarate is MBDB galactarate characterized by XRPD signals at 4.6°2 ⁇ , 9.2°2 ⁇ , 17.7°2 ⁇ , 18.1°2 ⁇ , and 19.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB galactarate 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 26.
  • the present disclosure provides solid forms of MBDB maleate Form 1, e.g., crystalline forms of MBDB maleate Form 1.
  • the MBDB maleate Form 1 XRPD profile is substantially similar to that shown in any one of FIG. 29 or 88 .
  • the MBDB maleate Form 1 1 H NMR spectrum is substantially similar to that shown in FIG. 71 .
  • the MBDB maleate Form 1 TGA profile is substantially similar to that shown in FIG. 72 .
  • the MBDB maleate Form 1 DSC profile is substantially similar to that shown in FIG. 72 .
  • the solid form of MBDB maleate Form 1 is crystalline MBDB maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.8°2 ⁇ , 22.4°2 ⁇ , and 23.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 1 is crystalline MBDB maleate Form 1 characterized by XRPD signals at 13.8°2 ⁇ , 22.4°2 ⁇ , and 23.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 1 is crystalline MBDB maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6°2 ⁇ , 13.8°2 ⁇ , 15.2°2 ⁇ , 22.4°2 ⁇ , and 23.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 1 is MBDB maleate Form 1 characterized by XRPD signals at 12.6°2 ⁇ , 13.8°2 ⁇ , 15.2°2 ⁇ , 22.4°2 ⁇ , and 23.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 1 is crystalline MBDB maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6°2 ⁇ , 13.8°2 ⁇ , and 15.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 1 is crystalline MBDB maleate Form 1 characterized by XRPD signals at 12.6°2 ⁇ , 13.8°2 ⁇ , and 15.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 1 is crystalline MBDB maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6°2 ⁇ , 13.8°2 ⁇ , 15.2°2 ⁇ , 16.2°2 ⁇ , and 18.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 1 is MBDB maleate Form 1 characterized by XRPD signals at 12.6°2 ⁇ , 13.8°2 ⁇ , 15.2°2 ⁇ , 16.2°2 ⁇ , and 18.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB 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, or thirty-four XRPD signals selected from those set forth in Table 27.
  • the solid form of MBDB maleate Form 1 is crystalline MBDB maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.8°2 ⁇ , 23.6°2 ⁇ , and 23.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 1 is crystalline MBDB maleate Form 1 characterized by XRPD signals at 13.8°2 ⁇ , 23.6°2 ⁇ , and 23.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 1 is crystalline MBDB maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.8°2 ⁇ , 21.5°2 ⁇ , 22.4°2 ⁇ , 23.6°2 ⁇ , and 23.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 1 is MBDB maleate Form 1 characterized by XRPD signals at 13.8°2 ⁇ , 21.5°2 ⁇ , 22.4°2 ⁇ , 23.6°2 ⁇ , and 23.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 1 is crystalline MBDB maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6°2 ⁇ , 13.8°2 ⁇ , and 15.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 1 is crystalline MBDB maleate Form 1 characterized by XRPD signals at 12.6°2 ⁇ , 13.8°2 ⁇ , and 15.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 1 is crystalline MBDB maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6°2 ⁇ , 13.8°2 ⁇ , and 15.2°2 ⁇ , 16.2°2 ⁇ , and 18.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 1 is MBDB maleate Form 1 characterized by XRPD signals at 12.6°2 ⁇ , 13.8°2 ⁇ , and 15.2°2 ⁇ , 16.2°2 ⁇ , and 18.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB 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, or thirty-five XRPD signals selected from those set forth in Table 28.
  • the solid form of MBDB maleate Form 1 is crystalline MBDB maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6°2 ⁇ , 13.9°2 ⁇ , and 15.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 1 is crystalline MBDB maleate Form 1 characterized by XRPD signals at 12.6°2 ⁇ , 13.9°2 ⁇ , and 15.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 1 is crystalline MBDB maleate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 12.6°2 ⁇ , 13.9°2 ⁇ , 15.3°2 ⁇ , 18.4°2 ⁇ , and 19.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 1 is MBDB maleate Form 1 characterized by XRPD signals at 12.6°2 ⁇ , 13.9°2 ⁇ , 15.3°2 ⁇ , 18.4°2 ⁇ , and 19.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB 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, or fifty-seven XRPD signals selected from those set forth in Table 28A.
  • the present disclosure provides solid forms of MBDB phosphate, e.g., crystalline forms of MBDB phosphate.
  • the MBDB phosphate XRPD profile is substantially similar to that shown in FIG. 30 .
  • the MBDB phosphate 1 H NMR spectrum is substantially similar to that shown in FIG. 75 .
  • the MBDB phosphate TGA profile is substantially similar to that shown in FIG. 76 .
  • the MBDB phosphate DSC profile is substantially similar to that shown in FIG. 76 .
  • the solid form of MBDB phosphate is crystalline MBDB phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.4°2 ⁇ , 12.7°2 ⁇ , and 21.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB phosphate is crystalline MBDB phosphate characterized by XRPD signals at 6.4°2 ⁇ , 12.7°2 ⁇ , and 21.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB phosphate is crystalline MBDB phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.4°2 ⁇ , 12.7°2 ⁇ , 17.3°2 ⁇ , 18.4°2 ⁇ , and 21.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB phosphate is MBDB phosphate characterized by XRPD signals at 6.4°2 ⁇ , 12.7°2 ⁇ , 17.3°2 ⁇ , 18.4°2 ⁇ , and 21.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB phosphate is crystalline MBDB phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.4°2 ⁇ , 12.7°2 ⁇ , and 14.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB phosphate is crystalline MBDB phosphate characterized by XRPD signals at 6.4°2 ⁇ , 12.7°2 ⁇ , and 14.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB phosphate is crystalline MBDB phosphate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.4°2 ⁇ , 12.7°2 ⁇ , 14.5°2 ⁇ , 14.8°2 ⁇ , and 17.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB phosphate is MBDB phosphate characterized by XRPD signals at 6.4°2 ⁇ , 12.7°2 ⁇ , 14.5°2 ⁇ , 14.8°2 ⁇ , and 17.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB phosphate 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, or forty-four XRPD signals selected from those set forth in Table 29.
  • the present disclosure provides solid forms of MBDB succinate Form 1, e.g., crystalline forms of MBDB succinate Form 1.
  • the MBDB succinate Form 1 XRPD profile is substantially similar to that shown in FIG. 31 .
  • the MBDB succinate Form 1 1 H NMR spectrum is substantially similar to that shown in FIG. 77 .
  • the MBDB succinate Form 1 TGA profile is substantially similar to that shown in FIG. 78 .
  • the MBDB succinate Form 1 DSC profile is substantially similar to that shown in FIG. 78 .
  • the solid form of MBDB succinate Form 1 is crystalline MBDB succinate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.1°2 ⁇ , 20.5°2 ⁇ , and 21.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB succinate Form 1 is crystalline MBDB succinate Form 1 characterized by XRPD signals at 13.1°2 ⁇ , 20.5°2 ⁇ , and 21.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB succinate Form 1 is crystalline MBDB succinate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.1°2 ⁇ , 20.5°2 ⁇ , 21.9°2 ⁇ , 22.9°2 ⁇ , and 26.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB succinate Form 1 is MBDB succinate Form 1 characterized by XRPD signals at 13.1°2 ⁇ , 20.5°2 ⁇ , 21.9°2 ⁇ , 22.9°2 ⁇ , and 26.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB succinate Form 1 is crystalline MBDB succinate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.7°2 ⁇ , 13.1°2 ⁇ , and 20.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB succinate Form 1 is crystalline MBDB succinate Form 1 characterized by XRPD signals at 11.7°2 ⁇ , 13.1°2 ⁇ , and 20.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB succinate Form 1 is crystalline MBDB succinate Form 1 characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.7°2 ⁇ , 13.1°2 ⁇ , 20.5°2 ⁇ , 21.9°2 ⁇ , and 22.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB succinate Form 1 is MBDB succinate Form 1 characterized by XRPD signals at 11.7°2 ⁇ , 13.1°2 ⁇ , 20.5°2 ⁇ , 21.9°2 ⁇ , and 22.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB succinate 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 30.
  • the present disclosure provides solid forms of MBDB sulfate, e.g., crystalline forms of MBDB sulfate.
  • the MBDB sulfate XRPD profile is substantially similar to that shown in any one of FIG. 32 or 34 .
  • the MBDB sulfate TGA profile is substantially similar to that shown in FIG. 81 .
  • the MBDB sulfate DSC profile is substantially similar to that shown in FIG. 81 .
  • the solid form of MBDB sulfate is crystalline MBDB sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.8°2 ⁇ , 17.5°2 ⁇ , and 26.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB sulfate is crystalline MBDB sulfate characterized by XRPD signals at 8.8°2 ⁇ , 17.5°2 ⁇ , and 26.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB sulfate is crystalline MBDB sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.8°2 ⁇ , 13.7°2 ⁇ , 17.5°2 ⁇ , 21.0°2 ⁇ , and 26.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB sulfate is MBDB sulfate characterized by XRPD signals at 8.8°2 ⁇ , 13.7°2 ⁇ , 17.5°2 ⁇ , 21.0°2 ⁇ , and 26.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB sulfate is crystalline MBDB sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.8°2 ⁇ , 15.0°2 ⁇ , 17.5°2 ⁇ , 22.3°2 ⁇ , and 26.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB sulfate is MBDB sulfate characterized by XRPD signals at 8.8°2 ⁇ , 15.0°2 ⁇ , 17.5°2 ⁇ , 22.3°2 ⁇ , and 26.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB sulfate is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, or twenty XRPD signals selected from those set forth in Table 31.
  • the solid form of MBDB sulfate is crystalline MBDB sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.4°2 ⁇ , 22.4°2 ⁇ , and 24.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB sulfate is crystalline MBDB sulfate characterized by XRPD signals at 17.4°2 ⁇ , 22.4°2 ⁇ , and 24.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB sulfate is crystalline MBDB sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.4°2 ⁇ , 18.9°2 ⁇ , 21.5°2 ⁇ , 22.4°2 ⁇ , and 24.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB sulfate is MBDB sulfate characterized by XRPD signals at 17.4°2 ⁇ , 18.9°2 ⁇ , 21.5°2 ⁇ , 22.4°2 ⁇ , and 24.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB sulfate is crystalline MBDB sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.8°2 ⁇ , 17.4°2 ⁇ , and 18.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB sulfate is crystalline MBDB sulfate characterized by XRPD signals at 8.8°2 ⁇ , 17.4°2 ⁇ , and 18.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB sulfate is crystalline MBDB sulfate characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.8°2 ⁇ , 17.4°2 ⁇ , 18.9°2 ⁇ , 21.1°2 ⁇ , and 22.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB sulfate is MBDB sulfate characterized by XRPD signals at 8.8°2 ⁇ , 17.4°2 ⁇ , 18.9°2 ⁇ , 21.1°2 ⁇ , and 22.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB sulfate 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, or sixty-
  • the present disclosure provides solid forms of MBDB tartrate, e.g., crystalline forms of MBDB tartrate.
  • the MBDB tartrate XRPD profile is substantially similar to FIG. 33 .
  • the solid form of MBDB tartrate is crystalline MBDB tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.8°2 ⁇ , 11.5°2 ⁇ , and 17.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB tartrate is crystalline MBDB tartrate characterized by XRPD signals at 5.8°2 ⁇ , 11.5°2 ⁇ , and 17.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB tartrate is crystalline MBDB tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.8°2 ⁇ , 11.5°2 ⁇ , 17.2°2 ⁇ , 18.7°2 ⁇ , and 24.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB tartrate is MBDB tartrate characterized by XRPD signals at 5.8°2 ⁇ , 11.5°2 ⁇ , 17.2°2 ⁇ , 18.7°2 ⁇ , and 24.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB tartrate is crystalline MBDB tartrate characterized by two or more, or three or more XRPD signals selected from the group consisting of 5.8°2 ⁇ , 8.6°2 ⁇ , 11.5°2 ⁇ , 17.2°2 ⁇ , and 18.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB tartrate is MBDB tartrate characterized by XRPD signals at 5.8°2 ⁇ , 8.6°2 ⁇ , 11.5°2 ⁇ , 17.2°2 ⁇ , and 18.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB tartrate 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 33.
  • the present disclosure provides solid forms of MBDB malonate, e.g., crystalline forms of MBDB malonate.
  • the MBDB malonate XRPD profile is substantially similar to FIG. 35 .
  • the MBDB malonate 1 H NMR spectrum is substantially similar to that shown in FIG. 73 .
  • the MBDB malonate TGA profile is substantially similar to that shown in FIG. 74 .
  • the MBDB malonate DSC profile is substantially similar to that shown in FIG. 74 .
  • the solid form of MBDB malonate is crystalline MBDB malonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 18.1°2 ⁇ , 20.4°2 ⁇ , and 22.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB malonate is crystalline MBDB malonate characterized by XRPD signals at 18.1°2 ⁇ , 20.4°2 ⁇ , and 22.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB malonate is crystalline MBDB malonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.2°2 ⁇ , 18.1°2 ⁇ , 20.4°2 ⁇ , 22.7°2 ⁇ , and 27.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB malonate is MBDB malonate characterized by XRPD signals at 14.2°2 ⁇ , 18.1°2 ⁇ , 20.4°2 ⁇ , 22.7°2 ⁇ , and 27.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB malonate is crystalline MBDB malonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 10.2°2 ⁇ , 14.2°2 ⁇ , and 16.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB malonate is crystalline MBDB malonate characterized by XRPD signals at 10.2°2 ⁇ , 14.2°2 ⁇ , and 16.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB malonate is crystalline MBDB malonate characterized by two or more, or three or more XRPD signals selected from the group consisting of 10.2°2 ⁇ , 14.2°2 ⁇ , 16.5°2 ⁇ , 18.1°2 ⁇ , and 22.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB malonate is MBDB malonate characterized by XRPD signals at 10.2°2 ⁇ , 14.2°2 ⁇ , 16.5°2 ⁇ , 18.1°2 ⁇ , and 22.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB malonate 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 34.
  • the present disclosure provides solid forms of MBDB succinate Form 2, e.g., crystalline forms of MBDB succinate Form 2.
  • the MBDB succinate Form 2 XRPD profile is substantially similar to that shown in FIG. 36 .
  • the MBDB succinate Form 2 1 H NMR spectrum is substantially similar to that shown in FIG. 79 .
  • the MBDB succinate Form 2 TGA profile is substantially similar to that shown in FIG. 80 .
  • the MBDB succinate Form 2 DSC profile is substantially similar to that shown in FIG. 80 .
  • the solid form of MBDB succinate Form 2 is crystalline MBDB succinate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.0°2 ⁇ , 20.3°2 ⁇ , and 21.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB succinate Form 2 is crystalline MBDB succinate Form 2 characterized by XRPD signals at 13.0°2 ⁇ , 20.3°2 ⁇ , and 21.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB succinate Form 2 is crystalline MBDB succinate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.6°2 ⁇ , 13.0°2 ⁇ , 20.3°2 ⁇ , 20.7°2 ⁇ , and 21.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB succinate Form 2 is MBDB succinate Form 2 characterized by XRPD signals at 11.6°2 ⁇ , 13.0°2 ⁇ , 20.3°2 ⁇ , 20.7°2 ⁇ , and 21.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB succinate Form 2 is crystalline MBDB succinate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.6°2 ⁇ , 13.0°2 ⁇ , and 21.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB succinate Form 2 is crystalline MBDB succinate Form 2 characterized by XRPD signals at 11.6°2 ⁇ , 13.0°2 ⁇ , and 21.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB succinate Form 2 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 35.
  • the present disclosure provides solid forms of MBDB tosylate, e.g., crystalline forms of MBDB tosylate.
  • the MBDB tosylate XRPD profile is substantially similar to FIG. 37 .
  • the MBDB tosylate 1 H NMR spectrum is substantially similar to that shown in FIG. 82 .
  • the MBDB tosylate TGA profile is substantially similar to that shown in FIG. 83 .
  • the MBDB tosylate DSC profile is substantially similar to that shown in FIG. 83 .
  • the solid form of MBDB tosylate is crystalline MBDB tosylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.1°2 ⁇ , 18.1°2 ⁇ , and 19.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB tosylate is crystalline MBDB tosylate characterized by XRPD signals at 13.1°2 ⁇ , 18.1°2 ⁇ , and 19.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB tosylate is crystalline MBDB tosylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.1°2 ⁇ , 13.1°2 ⁇ , 18.1°2 ⁇ , 19.1°2 ⁇ , and 23.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB tosylate is MBDB tosylate characterized by XRPD signals at 6.1°2 ⁇ , 13.1°2 ⁇ , 18.1°2 ⁇ , 19.1°2 ⁇ , and 23.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB tosylate is crystalline MBDB tosylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.1°2 ⁇ , 11.3°2 ⁇ , and 13.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB tosylate is crystalline MBDB tosylate characterized by XRPD signals at 6.1°2 ⁇ , 11.3°2 ⁇ , and 13.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB tosylate is crystalline MBDB tosylate characterized by two or more, or three or more XRPD signals selected from the group consisting of 6.1°2 ⁇ , 10.0°2 ⁇ , 11.3°2 ⁇ , 12.1°2 ⁇ , and 13.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB tosylate is MBDB tosylate characterized by XRPD signals at 6.1°2 ⁇ , 10.0°2 ⁇ , 11.3°2 ⁇ , 12.1°2 ⁇ , and 13.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB 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, 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
  • the present disclosure provides solid forms of MBDB HCl Form A, e.g., crystalline forms of MBDB HCl Form A.
  • the MBDB HCl Form A XRPD profile is substantially similar to that shown in any one of FIG. 38 or 86 .
  • the MBDB HCl Form A 1 H NMR spectrum is substantially similar to that shown in FIG. 90 .
  • the MBDB HCl Form A TGA profile is substantially similar to that shown in FIG. 91 .
  • the MBDB HCl Form A DSC profile is substantially similar to that shown in FIG. 91 .
  • the solid form of MBDB HCl Form A is crystalline MBDB HCl Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.3°2 ⁇ , 14.9°2 ⁇ , and 25.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form A is crystalline MBDB HCl Form A characterized by XRPD signals at 14.3°2 ⁇ , 14.9°2 ⁇ , and 25.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form A is crystalline MBDB HCl Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.1°2 ⁇ , 14.3°2 ⁇ , 14.9°2 ⁇ , 25.4°2 ⁇ , and 26.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form A is MBDB HCl Form A characterized by XRPD signals at 7.1°2 ⁇ , 14.3°2 ⁇ , 14.9°2 ⁇ , 25.4°2 ⁇ , and 26.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form A is crystalline MBDB HCl Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.1°2 ⁇ , 12.3°2 ⁇ , and 14.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form A is crystalline MBDB HCl Form A characterized by XRPD signals at 7.1°2 ⁇ , 12.3°2 ⁇ , and 14.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form A is crystalline MBDB HCl Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.1°2 ⁇ , 12.3°2 ⁇ , 14.3°2 ⁇ , 14.9°2 ⁇ , and 16.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form A is MBDB HCl Form A characterized by XRPD signals at 7.1°2 ⁇ , 12.3°2 ⁇ , 14.3°2 ⁇ , 14.9°2 ⁇ , and 16.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB HCl 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, or thirty XRPD signals selected from those set forth in Table 37.
  • the solid form of MBDB HCl Form A is crystalline MBDB HCl Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.4°2 ⁇ , 15.0°2 ⁇ , and 25.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form A is crystalline MBDB HCl Form A characterized by XRPD signals at 14.4°2 ⁇ , 15.0°2 ⁇ , and 25.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form A is crystalline MBDB HCl Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.4°2 ⁇ , 15.0°2 ⁇ , 16.2°2 ⁇ , 21.6°2 ⁇ , and 25.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form A is MBDB HCl Form A characterized by XRPD signals at 14.4°2 ⁇ , 15.0°2 ⁇ , 16.2°2 ⁇ , 21.6°2 ⁇ , and 25.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form A is crystalline MBDB HCl Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.2°2 ⁇ , 12.4°2 ⁇ , and 14.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form A is crystalline MBDB HCl Form A characterized by XRPD signals at 7.2°2 ⁇ , 12.4°2 ⁇ , and 14.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form A is crystalline MBDB HCl Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.2°2 ⁇ , 12.4°2 ⁇ , 14.4°2 ⁇ , 15.0°2 ⁇ , and 16.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form A is MBDB HCl Form A characterized by XRPD signals at 7.2°2 ⁇ , 12.4°2 ⁇ , 14.4°2 ⁇ , 15.0°2 ⁇ , and 16.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB HCl 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, or forty XRPD signals selected from those set forth in Table 38.
  • the present disclosure provides solid forms of MBDB HCl Form B, e.g., crystalline forms of MBDB HCl Form B.
  • the MBDB HCl Form B XRPD profile is substantially similar to that shown in any one of FIG. 39 or 87 .
  • the MBDB HCl Form B 1 H NMR spectrum is substantially similar to that shown in FIG. 93 .
  • the MBDB HCl Form B TGA profile is substantially similar to that shown in FIG. 94 .
  • the MBDB HCl Form B DSC profile is substantially similar to that shown in FIG. 94 .
  • the solid form of MBDB HCl Form B is crystalline MBDB HCl Form B characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.7°2 ⁇ , 25.0°2 ⁇ , and 30.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form B is crystalline MBDB HCl Form B characterized by XRPD signals at 19.7°2 ⁇ , 25.0°2 ⁇ , and 30.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form B is crystalline MBDB HCl Form B characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.6°2 ⁇ , 18.5°2 ⁇ , 19.7°2 ⁇ , 25.0°2 ⁇ , and 30.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form B is MBDB HCl Form B characterized by XRPD signals at 7.6°2 ⁇ , 18.5°2 ⁇ , 19.7°2 ⁇ , 25.0°2 ⁇ , and 30.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form B is crystalline MBDB HCl Form B characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.6°2 ⁇ , 13.3°2 ⁇ , and 14.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form B is crystalline MBDB HCl Form B characterized by XRPD signals at 7.6°2 ⁇ , 13.3°2 ⁇ , and 14.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form B is crystalline MBDB HCl Form B characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.6°2 ⁇ , 13.3°2 ⁇ , 14.2°2 ⁇ , 18.5°2 ⁇ , and 19.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form B is MBDB HCl Form B characterized by XRPD signals at 7.6°2 ⁇ , 13.3°2 ⁇ , 14.2°2 ⁇ , 18.5°2 ⁇ , and 19.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB HCl 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, or twenty-four XRPD signals selected from those set forth in Table 39.
  • the solid form of MBDB HCl Form B is crystalline MBDB HCl Form B characterized by two or more, or three or more XRPD signals selected from the group consisting of 18.5°2 ⁇ , 19.6°2 ⁇ , and 24.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form B is crystalline MBDB HCl Form B characterized by XRPD signals at 18.5°2 ⁇ , 19.6°2 ⁇ , and 24.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form B is crystalline MBDB HCl Form B characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.8°2 ⁇ , 18.5°2 ⁇ , 19.6°2 ⁇ , 24.9°2 ⁇ , and 27.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form B is MBDB HCl Form B characterized by XRPD signals at 16.8°2 ⁇ , 18.5°2 ⁇ , 19.6°2 ⁇ , 24.9°2 ⁇ , and 27.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form B is crystalline MBDB HCl Form B characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.4°2 ⁇ , 14.2°2 ⁇ , and 16.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form B is crystalline MBDB HCl Form B characterized by XRPD signals at 13.4°2 ⁇ , 14.2°2 ⁇ , and 16.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form B is crystalline MBDB HCl Form B characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.4°2 ⁇ , 14.2°2 ⁇ , 16.8°2 ⁇ , 18.5°2 ⁇ , and 19.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form B is MBDB HCl Form B characterized by XRPD signals at 13.4°2 ⁇ , 14.2°2 ⁇ , 16.8°2 ⁇ , 18.5°2 ⁇ , and 19.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB HCl 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, or twenty-nine XRPD signals selected from those set forth in Table 40.
  • the present disclosure provides solid forms of MEAI HCl, e.g., crystalline forms of MEAI HCl.
  • the MEAI HCl XRPD profile is substantially similar to that shown in FIG. 40 .
  • the solid form of MEAI HCl is crystalline MEAI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 21.6°2 ⁇ , 21.7°2 ⁇ , and 32.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MEAI HCl is crystalline MEAI HCl characterized by XRPD signals at 21.6°2 ⁇ , 21.7°2 ⁇ , and 32.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MEAI HCl is crystalline MEAI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 21.6°2 ⁇ , 21.7°2 ⁇ , 24.5°2 ⁇ , 32.7°2 ⁇ , and 32.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MEAI HCl is MEAI HCl characterized by XRPD signals at 21.6°2 ⁇ , 21.7°2 ⁇ , 24.5°2 ⁇ , 32.7°2 ⁇ , and 32.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MEAI HCl is crystalline MEAI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.9°2 ⁇ , 18.2°2 ⁇ , and 24.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MEAI HCl is crystalline MEAI HCl characterized by XRPD signals at 14.9°2 ⁇ , 18.2°2 ⁇ , and 24.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MEAI HCl is crystalline MEAI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.9°2 ⁇ , 18.2°2 ⁇ , 24.0°2 ⁇ , 24.5°2 ⁇ , and 25.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MEAI HCl is MEAI HCl characterized by XRPD signals at 21.6°2 ⁇ , 21.7°2 ⁇ , 24.5°2 ⁇ , 32.7°2 ⁇ , and 32.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MEAI HCl 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 41.
  • the present disclosure provides solid forms of 5,6-dimethoxy-2-aminoindane HCl, e.g., crystalline forms of 5,6-dimethoxy-2-aminoindane HCl.
  • the 5,6-dimethoxy-2-aminoindane HCl XRPD profile is substantially similar to that shown in FIG. 42 .
  • the solid form of 5,6-dimethoxy-2-aminoindane HCl is crystalline 5,6-dimethoxy-2-aminoindane HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.7°2 ⁇ , 18.2°2 ⁇ , and 18.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 5,6-dimethoxy-2-aminoindane HCl is crystalline 5,6-dimethoxy-2-aminoindane HCl characterized by XRPD signals at 11.7°2 ⁇ , 18.2°2 ⁇ , and 18.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 5,6-dimethoxy-2-aminoindane HCl is crystalline 5,6-dimethoxy-2-aminoindane HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.7°2 ⁇ , 18.2°2 ⁇ , 18.9°2 ⁇ , 23.0°2 ⁇ , and 23.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 5,6-dimethoxy-2-aminoindane HCl is 5,6-dimethoxy-2-aminoindane HCl characterized by XRPD signals at 11.7°2 ⁇ , 18.2°2 ⁇ , 18.9°2 ⁇ , 23.0°2 ⁇ , and 23.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 5,6-dimethoxy-2-aminoindane HCl is crystalline 5,6-dimethoxy-2-aminoindane HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 11.7°2 ⁇ , 27.3°2 ⁇ , and 27.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 5,6-dimethoxy-2-aminoindane HCl is crystalline 5,6-dimethoxy-2-aminoindane HCl characterized by XRPD signals at 11.7°2 ⁇ , 27.3°2 ⁇ , and 27.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 5,6-dimethoxy-2-aminoindane HCl is crystalline 5,6-dimethoxy-2-aminoindane HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.0°2 ⁇ , 9.1°2 ⁇ , 11.7°2 ⁇ , 27.3°2 ⁇ , and 27.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of 5,6-dimethoxy-2-aminoindane HCl is 5,6-dimethoxy-2-aminoindane HCl characterized by XRPD signals at 9.0°2 ⁇ , 9.1°2 ⁇ , 11.7°2 ⁇ , 27.3°2 ⁇ , and 27.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline 5,6-dimethoxy-2-aminoindane HCl 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 42.
  • the present disclosure provides solid forms of MBDB maleate Form 2, e.g., crystalline forms of MBDB maleate Form 2.
  • the MBDB maleate Form 2 XRPD profile is substantially similar to that shown in FIG. 96 .
  • the MBDB maleate Form 2 1 H NMR spectrum is substantially similar to that shown in FIG. 98 .
  • the MBDB maleate Form 2 TGA profile is substantially similar to that shown in FIG. 100 .
  • the MBDB maleate Form 2 DSC profile is substantially similar to that shown in FIG. 100 .
  • the solid form of MBDB maleate Form 2 is crystalline MBDB maleate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 19.3°2 ⁇ , 23.7°2 ⁇ , and 24.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 2 is MBDB maleate Form 2 characterized by XRPD signals at 19.3°2 ⁇ , 23.7°2 ⁇ , and 24.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 2 is crystalline MBDB maleate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.5°2 ⁇ , 15.3°2 ⁇ , 19.3°2 ⁇ , 23.7°2 ⁇ , and 24.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 2 is MBDB maleate Form 2 characterized by XRPD signals at 14.5°2 ⁇ , 15.3°2 ⁇ , 19.3°2 ⁇ , 23.7°2 ⁇ , and 24.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 2 is crystalline MBDB maleate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.7°2 ⁇ , 11.8°2 ⁇ , and 14.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 2 is MBDB maleate Form 2 characterized by XRPD signals at 9.7°2 ⁇ , 11.8°2 ⁇ , and 14.5°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 2 is crystalline MBDB maleate Form 2 characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.7°2 ⁇ , 11.8°2 ⁇ , 14.5°2 ⁇ , 15.3°2 ⁇ , and 19.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 2 is MBDB maleate Form 2 characterized by XRPD signals at 9.7°2 ⁇ , 11.8°2 ⁇ , 14.5°2 ⁇ , 15.3°2 ⁇ , and 19.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB 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, or thirty-two XRPD signals selected from those set forth in Table 42A.
  • the present disclosure provides solid forms of MBDB maleate Form 3, e.g., crystalline forms of MBDB maleate Form 3.
  • the MBDB maleate Form 3 XRPD profile is substantially similar to that shown in FIG. 97 .
  • the MBDB maleate Form 3 1 H NMR spectrum is substantially similar to that shown in FIG. 99 .
  • the MBDB maleate Form 3 TGA profile is substantially similar to that shown in FIG. 101 .
  • the MBDB maleate Form 3 DSC profile is substantially similar to that shown in FIG. 101 .
  • the solid form of MBDB maleate Form 3 is crystalline MBDB maleate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 17.0°2 ⁇ , 22.8°2 ⁇ , and 28.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 3 is MBDB maleate Form 3 characterized by XRPD signals at 17.0°2 ⁇ , 22.8°2 ⁇ , and 28.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 3 is crystalline MBDB maleate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.7 20, 10.9°2 ⁇ , 17.0°2 ⁇ , 22.8°2 ⁇ , and 28.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 3 is MBDB maleate Form 3 characterized by XRPD signals at 9.7 20, 10.9°2 ⁇ , 17.0°2 ⁇ , 22.8°2 ⁇ , and 28.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 3 is crystalline MBDB maleate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.3°2 ⁇ , 9.7°2 ⁇ , and 10.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 3 is MBDB maleate Form 3 characterized by XRPD signals at 9.3°2 ⁇ , 9.7°2 ⁇ , and 10.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 3 is crystalline MBDB maleate Form 3 characterized by two or more, or three or more XRPD signals selected from the group consisting of 9.3°2 ⁇ , 9.7°2 ⁇ , 10.9°2 ⁇ , 14.7°2 ⁇ , and 17.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB maleate Form 3 is MBDB maleate Form 3 characterized by XRPD signals at 9.3°2 ⁇ , 9.7°2 ⁇ , 10.9°2 ⁇ , 14.7°2 ⁇ , and 17.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB maleate 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, or thirty-five XRPD signals selected from those set forth in Table 42B.
  • the present disclosure provides solid forms of (R)-MDE HCl, e.g., crystalline forms of (R)-MDE HCl.
  • the (R)-MDE HCl XRPD profile is substantially similar to that shown in FIG. 102 .
  • the solid form of (R)-MDE HCl is crystalline (R)-MDE HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.5°2 ⁇ , 17.0°2 ⁇ , and 22.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MDE HCl is crystalline (R)-MDE HCl characterized by XRPD signals at 14.5°2 ⁇ , 17.0°2 ⁇ , and 22.2°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MDE HCl is crystalline (R)-MDE HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.5°2 ⁇ , 17.0°2 ⁇ , 22.2°2 ⁇ , 22.6°2 ⁇ , and 23.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MDE HCl is (R)-MDE HCl characterized by XRPD signals at 14.5°2 ⁇ , 17.0°2 ⁇ , 22.2°2 ⁇ , 22.6°2 ⁇ , and 23.4°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MDE HCl is crystalline (R)-MDE HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.5°2 ⁇ , 23.4°2 ⁇ , and 24.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MDE HCl is crystalline (R)-MDE HCl characterized by XRPD signals at 14.5°2 ⁇ , 23.4°2 ⁇ , and 24.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MDE HCl is crystalline (R)-MDE HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.5°2 ⁇ , 23.4°2 ⁇ , 24.8°2 ⁇ , 27.4°2 ⁇ , and 27.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MDE HCl is (R)-MDE HCl characterized by XRPD signals at 14.5°2 ⁇ , 23.4°2 ⁇ , 24.8°2 ⁇ , 27.4°2 ⁇ , and 27.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline (R)-MDE 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 58.
  • the present disclosure provides solid forms of (S)-MDE HCl, e.g., crystalline forms of (S)-MDE HCl.
  • the (S)-MDE HCl XRPD profile is substantially similar to that shown in FIG. 103 .
  • the solid form of (S)-MDE HCl is crystalline (S)-MDE HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.5°2 ⁇ , 23.4°2 ⁇ , and 25.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MDE HCl is crystalline (S)-MDE HCl characterized by XRPD signals at 14.5°2 ⁇ , 23.4°2 ⁇ , and 25.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MDE HCl is crystalline (S)-MDE HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.5°2 ⁇ , 27.6°2 ⁇ , and 31.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MDE HCl is crystalline (S)-MDE HCl characterized by XRPD signals at 14.5°2 ⁇ , 27.6°2 ⁇ , and 31.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MDE HCl is crystalline (S)-MDE HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.5°2 ⁇ , 23.4°2 ⁇ , 25.0°2 ⁇ , 27.6°2 ⁇ , and 31.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MDE HCl is (S)-MDE HCl characterized by XRPD signals at 14.5°2 ⁇ , 23.4°2 ⁇ , 25.0°2 ⁇ , 27.6°2 ⁇ , and 31.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline (S)-MDE HCl is characterized by one, two, three, four, or five XRPD signals selected from those set forth in Table 59.
  • the present disclosure provides solid forms of (R)-MBDB HCl, e.g., crystalline forms of (R)-MBDB HCl.
  • the (R)-MBDB HCl XRPD profile is substantially similar to that shown in FIG. 104 .
  • the solid form of (R)-MBDB HCl is crystalline (R)-MBDB HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.2°2 ⁇ , 14.1°2 ⁇ , and 16.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MBDB HCl is crystalline (R)-MBDB HCl characterized by XRPD signals at 13.2°2 ⁇ , 14.1°2 ⁇ , and 16.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MBDB HCl is crystalline (R)-MBDB HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.2°2 ⁇ , 14.1°2 ⁇ , 16.7°2 ⁇ , 19.6°2 ⁇ , and 24.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MBDB HCl is (R)-MBDB HCl characterized by XRPD signals at 13.2°2 ⁇ , 14.1°2 ⁇ , 16.7°2 ⁇ , 19.6°2 ⁇ , and 24.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MBDB HCl is crystalline (R)-MBDB HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 18.4°2 ⁇ , 19.6°2 ⁇ , and 24.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MBDB HCl is crystalline (R)-MBDB HCl characterized by XRPD signals at 18.4°2 ⁇ , 19.6°2 ⁇ , and 24.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MBDB HCl is crystalline (R)-MBDB HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.7°2 ⁇ , 18.4°2 ⁇ , 19.6°2 ⁇ , 24.9°2 ⁇ , and 27.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MBDB HCl is (R)-MBDB HCl characterized by XRPD signals at 16.7°2 ⁇ , 18.4°2 ⁇ , 19.6°2 ⁇ , 24.9°2 ⁇ , and 27.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; 10 ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline (R)-MBDB HCl is characterized by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, or thirteen XRPD signals selected from those set forth in Table 60.
  • the present disclosure provides solid forms of (S)-MBDB HCl, e.g., crystalline forms of (S)-MBDB HCl.
  • the (S)-MBDB HCl XRPD profile is substantially similar to that shown in FIG. 105 .
  • the solid form of (S)-MBDB HCl is crystalline (S)-MBDB HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.3°2 ⁇ , 16.7°2 ⁇ , and 19.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MBDB HCl is crystalline (S)-MBDB HCl characterized by XRPD signals at 13.3°2 ⁇ , 16.7°2 ⁇ , and 19.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MBDB HCl is crystalline (S)-MBDB HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 13.3°2 ⁇ , 16.7°2 ⁇ , 19.6°2 ⁇ , 22.2°2 ⁇ , and 24.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MBDB HCl is (S)-MBDB HCl characterized by XRPD signals at 13.3°2 ⁇ , 16.7°2 ⁇ , 19.6°2 ⁇ , 22.2°2 ⁇ , and 24.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MBDB HCl is crystalline (S)-MBDB HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 18.4°2 ⁇ , 19.6°2 ⁇ , and 24.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MBDB HCl is crystalline (S)-MBDB HCl characterized by XRPD signals at 18.4°2 ⁇ , 19.6°2 ⁇ , and 24.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MBDB HCl is crystalline (S)-MBDB HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.7°2 ⁇ , 18.4°2 ⁇ , 19.6°2 ⁇ , 24.6°2 ⁇ , and 24.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MBDB HCl is (S)-MBDB HCl characterized by XRPD signals at 16.7°2 ⁇ , 18.4°2 ⁇ , 19.6°2 ⁇ , 24.6°2 ⁇ , and 24.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline (S)-MBDB HCl 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 61.
  • the present disclosure provides solid forms of MBDB HCl Form A, e.g., crystalline forms of MBDB HCl Form A.
  • the MBDB HCl Form A XRPD profile is substantially similar to that shown in FIG. 106 .
  • the solid form of MBDB HCl Form A is crystalline MBDB HCl Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.2°2 ⁇ , 14.8°2 ⁇ , and 16.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form A is crystalline MBDB HCl Form A characterized by XRPD signals at 14.2°2 ⁇ , 14.8°2 ⁇ , and 16.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form A is crystalline MBDB HCl Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 14.2°2 ⁇ , 14.8°2 ⁇ , and 16.1°2 ⁇ , 16.8°2 ⁇ , and 17.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MBDB HCl Form A is MBDB HCl Form A characterized by XRPD signals at 14.2°2 ⁇ , 14.8°2 ⁇ , and 16.1°2 ⁇ , 16.8°2 ⁇ , and 17.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MBDB HCl Form A 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 62.
  • the present disclosure provides solid forms of MDAI HCl, e.g., crystalline forms of MDAI HCl.
  • the MDAI HCl XRPD profile is substantially similar to that shown in FIG. 107 .
  • the solid form of MDAI HCl is crystalline MDAI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.2°2 ⁇ , 15.5°2 ⁇ , and 24.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is crystalline MDAI HCl characterized by XRPD signals at 15.2°2 ⁇ , 15.5°2 ⁇ , and 24.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is crystalline MDAI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.2°2 ⁇ , 15.5°2 ⁇ , 24.1°2 ⁇ , 26.2°2 ⁇ , and 27.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is MDAI HCl characterized by XRPD signals at 15.2°2 ⁇ , 15.5°2 ⁇ , 24.1°2 ⁇ , 26.2°2 ⁇ , and 27.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is crystalline MDAI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 23.5°2 ⁇ , 24.1°2 ⁇ , and 27.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is crystalline MDAI HCl characterized by XRPD signals at 23.5°2 ⁇ , 24.1°2 ⁇ , and 27.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is crystalline MDAI HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.2°2 ⁇ , 23.2°2 ⁇ , 23.5°2 ⁇ , 24.1°2 ⁇ , and 27.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDAI HCl is MDAI HCl characterized by XRPD signals at 15.2°2 ⁇ , 23.2°2 ⁇ , 23.5°2 ⁇ , 24.1°2 ⁇ , and 27.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDAI HCl is characterized by one, two, three, four, five, six, seven, eight, or nine XRPD signals selected from those set forth in Table 63.
  • the present disclosure provides solid forms of MDMA hemifumarate Form A, e.g., crystalline forms of MDMA hemifumarate Form A.
  • the MDMA hemifumarate Form A XRPD profile is substantially similar to that shown in FIG. 116 .
  • the solid form of MDMA hemifumarate Form A is crystalline MDMA hemifumarate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 18.2°2 ⁇ , 18.6°2 ⁇ , 21.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA hemifumarate Form A is crystalline MDMA hemifumarate Form A characterized by XRPD signals at 18.2°2 ⁇ , 18.6°2 ⁇ , 21.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA hemifumarate Form A is crystalline MDMA hemifumarate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.7°2 ⁇ , 18.2°2 ⁇ , 18.6°2 ⁇ , 19.1°2 ⁇ , 21.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA hemifumarate Form A is MDMA hemifumarate Form A characterized by XRPD signals at 16.7°2 ⁇ , 18.2°2 ⁇ , 18.6°2 ⁇ , 19.1°2 ⁇ , 21.8°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA hemifumarate Form A is crystalline MDMA hemifumarate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.3°2 ⁇ , 10.9°2 ⁇ , and 13.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA hemifumarate Form A is crystalline MDMA hemifumarate Form A characterized by XRPD signals at 8.3°2 ⁇ , 10.9°2 ⁇ , and 13.0°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA hemifumarate Form A is crystalline MDMA hemifumarate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.3°2 ⁇ , 10.9°2 ⁇ , 13.0°2 ⁇ , 16.7°2 ⁇ , and 17.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA hemifumarate Form A is MDMA hemifumarate Form A characterized by XRPD signals at 8.3°2 ⁇ , 10.9°2 ⁇ , 13.0°2 ⁇ , 16.7°2 ⁇ , and 17.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDMA hemifumarate 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 64.
  • the present disclosure provides solid forms of MDMA hemifumarate Form A, e.g., crystalline forms of MDMA hemifumarate Form A.
  • the MDMA hemifumarate Form A XRPD profile is substantially similar to that shown in FIG. 115 .
  • the solid form of MDMA hemifumarate Form A is crystalline MDMA hemifumarate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.7°2 ⁇ , 18.6°2 ⁇ , and 21.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA hemifumarate Form A is crystalline MDMA hemifumarate Form A characterized by XRPD signals at 16.7°2 ⁇ , 18.6°2 ⁇ , and 21.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA hemifumarate Form A is crystalline MDMA hemifumarate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 16.7°2 ⁇ , 17.3°2 ⁇ , 18.2°2 ⁇ , 18.6°2 ⁇ , 21.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA hemifumarate Form A is MDMA hemifumarate Form A characterized by XRPD signals at 16.7°2 ⁇ , 17.3°2 ⁇ , 18.2°2 ⁇ , 18.6°2 ⁇ , 21.9°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA hemifumarate Form A is crystalline MDMA hemifumarate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.4°2 ⁇ , 10.9°2 ⁇ , and 13.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA hemifumarate Form A is crystalline MDMA hemifumarate Form A characterized by XRPD signals at 8.4°2 ⁇ , 10.9°2 ⁇ , and 13.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA hemifumarate Form A is crystalline MDMA hemifumarate Form A characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.4°2 ⁇ , 10.9°2 ⁇ , 13.1°2 ⁇ , 16.7°2 ⁇ , and 17.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA hemifumarate Form A is MDMA hemifumarate Form A characterized by XRPD signals at 8.4°2 ⁇ , 10.9°2 ⁇ , 13.1°20, 16.7°2 ⁇ , and 17.3°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDMA hemifumarate 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, or forty-four XRPD signals selected from those set forth in Table 65.
  • the present disclosure provides solid forms of MDMA freebase, e.g., crystalline forms of MDMA freebase.
  • the MDMA freebase XRPD profile is substantially similar to that shown in FIG. 3 .
  • the solid form of MDMA freebase is crystalline MDMA freebase characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.1°2 ⁇ , 19.8°2 ⁇ , and 17.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA freebase is crystalline MDMA freebase characterized by XRPD signals at 15.1°2 ⁇ , 19.8°2 ⁇ , and 17.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA freebase is crystalline MDMA freebase characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.1°2 ⁇ , 19.8°2 ⁇ , 17.6, 27.3°2 ⁇ , and 21.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA freebase is MDMA freebase characterized by XRPD signals at 15.1°2 ⁇ , 19.8°2 ⁇ , 17.6, 27.3°2 ⁇ , and 21.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA freebase is crystalline MDMA freebase characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.3°2 ⁇ , 11.4°2 ⁇ , and 15.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA freebase is crystalline MDMA freebase characterized by XRPD signals at 8.3°2 ⁇ , 11.4°2 ⁇ , and 15.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA freebase is crystalline MDMA freebase characterized by two or more, or three or more XRPD signals selected from the group consisting of 8.3°2 ⁇ , 11.4°2 ⁇ , 15.1°2 ⁇ , 16.7°2 ⁇ , 17.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of MDMA freebase is MDMA freebase characterized by XRPD signals at 8.3°2 ⁇ , 11.4°2 ⁇ , 15.1°2 ⁇ , 16.7°2 ⁇ , 17.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline MDMA freebase 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 66.
  • the present disclosure provides solid forms of (S)-MDMA HCl, e.g., crystalline forms of (S)-MDMA HCl.
  • the (S)-MDMA HCl profile is substantially similar to that shown in FIGS. 13 and 14 .
  • the solid form of (S)-MDMA HCl is crystalline (S)-MDMA HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.7°2 ⁇ , 17.4°2 ⁇ , and 20.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MDMA HCl is crystalline (S)-MDMA HCl characterized by XRPD signals at 15.7°2 ⁇ , 17.4°2 ⁇ , and 20.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MDMA HCl is crystalline (S)-MDMA HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.7°2 ⁇ , 17.4°2 ⁇ , 20.6°2 ⁇ , 24.7°2 ⁇ , and 29.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MDMA HCl is (S)-MDMA HCl characterized by XRPD signals at 15.7°2 ⁇ , 17.4°2 ⁇ , 20.6°2 ⁇ , 24.7°2 ⁇ , and 29.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MDMA HCl is crystalline (S)-MDMA HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.9°2 ⁇ , 14.0°2 ⁇ , and 15.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MDMA HCl is crystalline (S)-MDMA HCl characterized by XRPD signals at 7.9°2 ⁇ , 14.0°2 ⁇ , and 15.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MDMA HCl is crystalline (S)-MDMA HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.9°2 ⁇ , 14.0°2 ⁇ , 15.7°2 ⁇ , 19.6°2 ⁇ , and 20.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (S)-MDMA HCl is (S)-MDMA HCl characterized by XRPD signals at 7.9°2 ⁇ , 14.0°2 ⁇ , 15.7°2 ⁇ , 19.6°2 ⁇ , and 20.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline (S)-MDMA HCl 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 67A.
  • the present disclosure provides solid forms of (R)-MDMA HCl, e.g., crystalline forms of (R)-MDMA HCl.
  • the (R)-MDMA HCl profile is substantially similar to that shown in FIGS. 15 and/or 16 .
  • the solid form of (R)-MDMA HCl is crystalline (R)-MDMA HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.7°2 ⁇ , 17.4°2 ⁇ , and 20.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MDMA HCl is crystalline (R)-MDMA HCl characterized by XRPD signals at 15.7°2 ⁇ , 17.4°2 ⁇ , and 20.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MDMA HCl is crystalline (R)-MDMA HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 15.7°2 ⁇ , 17.4°2 ⁇ , 20.6°2 ⁇ , 24.7°2 ⁇ , and 29.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MDMA HCl is (R)-MDMA HCl characterized by XRPD signals at 15.7°2 ⁇ , 17.4°2 ⁇ , 20.6°2 ⁇ , 24.7°2 ⁇ , and 29.1°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MDMA HCl is crystalline (R)-MDMA HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.9°2 ⁇ , 14.0°2 ⁇ , and 15.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MDMA HCl is crystalline (R)-MDMA HCl characterized by XRPD signals at 7.9°2 ⁇ , 14.0°2 ⁇ , and 15.7°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MDMA HCl is crystalline (R)-MDMA HCl characterized by two or more, or three or more XRPD signals selected from the group consisting of 7.9°2 ⁇ , 14.0°2 ⁇ , 15.7°2 ⁇ , 19.6°2 ⁇ , and 20.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the solid form of (R)-MDMA HCl is (R)-MDMA HCl characterized by XRPD signals at 7.9°2 ⁇ , 14.0°2 ⁇ , 15.7°2 ⁇ , 19.6°2 ⁇ , and 20.6°2 ⁇ ( ⁇ 0.2°2 ⁇ ; ⁇ 0.1°2 ⁇ ; or ⁇ 0.0°2 ⁇ ; Cu K ⁇ 1 radiation).
  • the crystalline (R)-MDMA HCl 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 67B.
  • the present disclosure provides a pharmaceutical composition
  • a pharmaceutical composition comprising one or more of the disclosed solid forms of MDMA, (R)-MDMA, (S)-MDMA, MDE, MDAI, MBDB, MEAI, 5,6-Dimethoxy-2-aminoindane, or salts thereof, 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, such as intravenous, 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 as solutions, orally or parenterally, such as 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 the present 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 the compounds 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 corn, 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 compounds of the present disclosure are dispersed homogeneously therein, as by stirring.
  • the molten homogeneous mixture is then poured into convenient sized molds, allowed to cool, and thereby to solidify.
  • Liquid form preparations include solutions and 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 a coloring agent
  • flavoring agents such as aqueous suspension
  • 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.
  • liquid forms include suspensions.
  • These preparations may contain, in addition to the active component, colorants, flavors, stabilizers, buffers, artificial and natural sweeteners, dispersants, thickeners, solubilizing agents, and the like.
  • 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 present 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. Such formulations can also contain a demulcent, a preservative, or a coloring agent.
  • 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). Both transdermal and intradermal routes afford constant delivery for weeks or months.
  • 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.
  • compositions of the present disclosure 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.
  • Al-Muhammed J. Microencapsul. 13:293-306, 1996; Chonn, Curr. Opin. Biotechnol. 6:698-708, 1995; Ostro, Am. J. Hosp. Pharm. 46:1576-1587, 1989).
  • 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 preferably in unit dosage 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.
  • 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 (R)-MDMA or (S)-MDMA forms administered herein typically are administered to provide between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the MDMA forms administered herein typically are administered to provide between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • Suitable dosage ranges for the N-ethyl-3,4-methylenedioxyamphetamine hydrochloride forms disclosed herein are administered in about 10 mg to about 300 mg or about 100 mg to about 180 mg or about 120 mg or about 150 mg or about 160 mg.
  • Suitable dosages for the N-ethyl-3,4-methylenedioxyamphetamine hydrochloride forms disclosed herein include about 1 mg, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 200, 300, or 400 mg.
  • Suitable dosage ranges for the MDAI HCl forms disclosed herein include from about 10 mg to about 500 mg or about 60 mg to about 180 mg or about 160 mg to about 300 mg. Suitable dosages for the MDAI HCl forms disclosed herein include about 5 mg, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 300, 400, or 500 mg.
  • Suitable dosage ranges for the N-methyl-1,3-benzodioxolylbutanamine hydrochloride forms disclosed herein are administered in about 10 mg to about 500 mg or about 150 mg to about 250 mg or about 180 mg or about 210 mg or about 250 mg.
  • Suitable dosages ranges for the MBDB salt and solid forms disclosed herein are administered in about 10 mg to about 500 mg or from about 150 mg to about 250 mg or about 180 mg or about 210 mg or about 250 mg.
  • Suitable dosage ranges for the (S)—N-ethyl-3,4-methylenedioxyamphetamine salts and solid forms disclosed herein are administered in about 10 mg to about 300 mg or about 100 mg to about 180 mg or about 120 mg or about 150 mg or about 160 mg.
  • Suitable dosages for the (S)—N-ethyl-3,4-methylenedioxyamphetamine salts and solid forms disclosed herein include about 1 mg, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 200, 300, 400, 500, 600, 700, 800, 900 or 1000 mg.
  • Suitable dosage ranges for the 5-methoxy-2-aminoindane hydrochloride forms disclosed herein and the 5,6-dimethoxy-2-aminoindane hydrochloride forms disclosed herein include from about 10 mg to about 500 mg. Suitable dosages include those from about 1 mg per kg to about 5 mg per kg, such as from about 1.6 mg per kg to about 4.8 mg per kg or about 99.2 mg to about 297.6 mg. In one embodiment suitable dosages range from about 60 mg to about 180 mg or from about 160 mg to about 300 mg.
  • Suitable dosages for the 5-methoxy-2-aminoindane hydrochloride forms disclosed herein and the 5,6-dimethoxy-2-aminoindane hydrochloride forms disclosed herein include about 1 mg, 5, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 300, 400, or 500 mg.
  • the compounds disclosed herein can be administered at any suitable frequency, interval and duration.
  • the compounds can be administered once an hour, or two, three or more times an hour, once a day, or two, three, or more times per day, or once every 2, 3, 4, 5, 6, or 7 days, so as to provide the preferred dosage level.
  • representative intervals include 5, 10, 15, 20, 30, 45 and 60 minutes, as well as 1, 2, 4, 6, 8, 10, 12, 16, 20, and 24 hours.
  • the compound of the present invention can be administered once, twice, or three or more times, for an hour, for 1 to 6 hours, for 1 to 12 hours, for 1 to 24 hours, for 6 to 12 hours, for 12 to 24 hours, for a single day, for 1 to 7 days, for a single week, for 1 to 4 weeks, for a month, for 1 to 12 months, for a year or more, or even indefinitely.
  • composition can also contain other compatible therapeutic agents.
  • the compounds described herein can be used in combination with one another, with other active agents known to be useful in modulating a glucocorticoid receptor, or with adjunctive agents that may not be effective alone, but may contribute to the efficacy of the active agent.
  • the compounds of the present invention can be co-administered with a second active agent.
  • Co-administration includes administering the compound of the present invention and active agent within 0.5, 1, 2, 4, 6, 8, 10, 12, 16, 20, or 24 hours of each other.
  • Co-administration also includes administering the compound of the present invention and active agent simultaneously, approximately simultaneously (e.g., within about 1, 5, 10, 15, 20, or 30 minutes of each other), or sequentially in any order.
  • the compound of the present disclosure and the active agent can each be administered once a day, or two, three, or more times per day so as to provide the preferred dosage level per day.
  • 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.
  • the compound of the present disclosure and the second active agent can be formulated separately.
  • the disclosed compounds and the second active agent can be present in the compositions of the present disclosure in any suitable weight ratio, such as from about 1:100 to about 100:1 (w/w), or about 1:50 to about 50:1, or about 1:25 to about 25:1, or about 1:10 to about 10:1, or about 1:5 to about 5:1 (w/w).
  • the compound of the present disclosure and the second active agent can be present in any suitable weight ratio, such as about 1:100 (w/w), 1:50, 1:25, 1:10, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 10:1, 25:1, 50:1 or 100:1 (w/w).
  • Other dosages and dosage ratios of the compound of the present disclosure and the active agent are suitable in the compositions and methods disclosed herein.
  • the solid forms 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 solid forms of the present disclosure can also be used for increasing at least one of translation, transcription or secretion of neurotrophic factors.
  • a compound of the present disclosure is used to treat neurological diseases.
  • 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 compounds have, for example, anti-addictive properties, antidepressant properties, anxiolytic properties, or a combination thereof.
  • the compositions provided herein have, for example, anti-addictive properties, antidepressant properties, anxiolytic properties, or a combination thereof.
  • the neurological disease is a neuropsychiatric disease.
  • 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, disorder, or neurological disease is a neurodegenerative disorder, Alzheimer's disease or Parkinson's disease.
  • the neurological disease is a psychological disorder.
  • 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 comprises treatment resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, stroke, traumatic brain injury or substance use disorder and/or anxiety.
  • 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 selected from 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).
  • the neuropsychiatric disease or neurological disease is depression.
  • the neuropsychiatric disease or neurological disease is anxiety.
  • the neuropsychiatric disease or neurological disease is post-traumatic stress disorder (PTSD).
  • the neurological disease is stroke or traumatic brain injury.
  • the neuropsychiatric disease or neurological disease is schizophrenia.
  • 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. In some embodiments, the compounds described herein are used for treating a brain disorder. In some embodiments, 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 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 is post-traumatic stress disorder.
  • the disease or disorder is fibromyalgia.
  • 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 solid form described herein.
  • 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 solid forms of the present disclosure have activity as 5-HT 2A modulators.
  • the compounds of the present disclosure elicit a biological response by activating the 5-HT 2A receptor (by way of example, through allosteric modulation or modulation of a biological target that activates the 5-HT 2A receptor).
  • 5-HT 2A 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, LSD, and DOI.
  • the compounds of the present disclosure function as 5-HT 2A 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 are non-hallucinogenic or are administered at a dose that is non-hallucinogenic.
  • non-hallucinogenic 5-HT 2A modulators e.g., 5-HT 2A agonists
  • the hallucinogenic potential of the compounds described herein is assessed in vitro.
  • the hallucinogenic potential assessed in vitro of the compounds and combinations of 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.
  • the presently disclosed compound forms function as serotonin receptor modulators, such as modulators of serotonin receptor 2A (5-HT 2A modulators, e.g., 5-HT 2A agonists), and 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. In such cases the second therapeutic agent can be an agonist or an antagonist.
  • the second therapeutic agent is a serotonin receptor modulator.
  • Serotonin receptor modulators including 5-HT 2A antagonists, 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
  • 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), pruvanserin, 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
  • 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 three hours prior to the administration or release of a compound disclosed herein. In some embodiments, the serotonin receptor modulator is administered at about one or about three hours prior to the administration or release of a presently disclosed compound. In some embodiments, the serotonin receptor modulator is administered at most about one hour prior to the administration or release presently disclosed compound. Thus, in some embodiments of combination therapy with the presently disclosed compounds, the second therapeutic agent is a serotonin receptor modulator.
  • the second therapeutic agent serotonin receptor modulator is provided at a dose of from about 10 mg to about 350 mg. In some embodiments, the serotonin receptor modulator is provided at a dose of from about 20 mg to about 200 mg. In some embodiments, the serotonin receptor modulator is provided at a dose of from about 10 mg to about 100 mg. In certain such embodiments, the compound of the present disclosure is provided at a dose of from about 10 mg to about 100 mg, or from about 20 to about 200 mg, or from about 15 to about 300 mg, and the serotonin receptor modulator is provided at a dose of about 10 mg to about 100 mg.
  • non-hallucinogenic 5-HT 2A modulators are used to treat neurological diseases.
  • the solid forms of the present disclosure act as non-hallucinogenic 5-HT 2A modulators (e.g., 5-HT 2A agonists) that are used to treat neurological diseases.
  • 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.
  • the solid forms of this disclosure act as non-hallucinogenic 5-HT 2A modulators (e.g., 5-HT 2A agonists) that are used for increasing neuronal plasticity. In some embodiments, the solid forms of this disclosure act as non-hallucinogenic 5-HT 2A modulators (e.g., 5-HT 2A agonists) that are used for treating a brain disorder. In some embodiments, the solid forms of this disclosure act as non-hallucinogenic 5-HT 2A modulators (e.g., 5-HT 2A agonists) that are used for increasing at least one of translation, transcription, or secretion of neurotrophic factors.
  • the present forms are used as 5-HT 2A modulators (e.g., 5-HT 2A agonists) for increasing neuronal plasticity. In some embodiments, the present forms are used as 5-HT 2A modulators (e.g., 5-HT 2A agonists) to treat a brain disorder. In some embodiments, the compound forms are used as 5-HT 2A modulators (e.g., 5-HT 2A agonists) to increase at least one of translation, transcription, or secretion of neurotrophic factors.
  • the presently disclosed compounds are given to patients in a low dose that is lower than would produce noticeable psychedelic effects but high enough to provide a therapeutic benefit.
  • This dose range is predicted to be between 200 ug (micrograms) and 2 mg.
  • 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. In some embodiments, 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 compounds 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. In some embodiments, increasing neuronal plasticity improves a brain disorder described herein.
  • a compound of the present disclosure is used to increase neuronal plasticity.
  • the compounds 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-HT 2A agonist assay, a 5-HT 2A antagonist assay, a 5-HT 2A 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.
  • the present disclosure provides a method of treating a disease, including administering to a subject in need thereof, a therapeutically effective amount of a solid form of the present disclosure.
  • the disease is a brain disorder.
  • brain disorders include, for example, migraines, addiction (e.g., substance use disorder), depression, and anxiety. Such disorders also may be considered neuropsychiatric disorders or neurological disorders.
  • neurological disorders that can be treated relate to other disease conditions.
  • the disease is a musculoskeletal pain disorder including fibromyalgia, muscle pain, joint stiffness, osteoarthritis, rheumatoid arthritis, 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
  • post-partum depression and menopause.
  • 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. In some embodiments, 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-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.
  • 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), N-ethyl-3,4-methylenedioxyamphetamine (MDE; MDEA), solid forms and analogs thereof.
  • MDMA 3,4-methylene-dioxymethamphetamine
  • MDE N-ethyl-3,4-methylenedioxyamphetamine
  • solid forms and analogs thereof solid forms and analogs thereof.
  • Other suitable empathogenic agents for use in combination with the presently disclosed solid forms include, without limitation,
  • 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.
  • Neurotrophic factors refers 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-HT 2A modulators e.g., 5-HT 2A 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.
  • the experiment or assay used to determine increase secretion of neurotrophic factors includes ELISA, western blot, immunofluorescence assays, proteomic experiments, and mass spectrometry.
  • 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 is used as described herein.
  • a form of MDMA, S-MDMA, R-MDMA, MDAI, MDE, R-MDE, S-MDE, MBDB, R-MBDB, S-MBDB, 5, methoxy-2-aminoindane, or 5,6-dimethoxy-2-aminoindane described herein is administered in combination with a serotonin receptor modulator.
  • 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, 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), pruvanserin, nelotanserin, lorcaserin, flibanserin, roluperiodone or a pharmaceutically acceptable salt, solvate, metabolite, deuterated analog, derivative, prodrug, or combinations thereof.
  • glemanserin MDL-11,939
  • eplivanserin SR
  • combination therapy is used as described herein.
  • a form of any one of the compounds as described herein is administered in combination with a serotonin receptor modulator.
  • 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, 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), pruvanserin, nelotanserin, lorcaserin, flibanserin, roluperiodone or a pharmaceutically
  • the serotonin receptor modulator comprises 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, ICI-169369, methiothepin, methysergide, t
  • 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, and risperidone.
  • the serotonin receptor modulator for use with the psychedelic MDMA is eplivanserin and, wherein the eplivanserin is administered in about 1 mg to about 40 mg, or about 5 mg to about 10 mg, and the MDMA is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered in about 1 mg to about 60 mg, or about 5 mg to about 20 mg, and the MDMA is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the psychedelic MDMA is ketanserin, wherein the ketanserin is administered in about 10 mg to about 80 mg, about 30 mg to about 50 mg, or about 40 mg and the MDMA is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the psychedelic MDMA is ritanserin, wherein the ritanserin is administered in about 1 mg to about 40 mg, or about 2.5 mg to about 10 mg, and the MDMA is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered in about 1 mg to about 60 mg, or about 17 mg to about 34 mg, and the MDMA is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the psychedelic MDMA is nelotanserin, wherein the nelotanserin is administered in about 1 mg to about 80 mg, or about 40 mg to about 80 mg, and the MDMA is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the psychedelic MDMA is pruvanserin, wherein the pruvanserin is administered in about 1 mg to about 40 mg, or about 3 mg to about 10 mg, and the MDMA is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the psychedelic MDMA is flibanserin, wherein the flibanserin is administered in about 10 mg to about 200 mg, or about 80 mg to about 120 mg, or about 100 mg and the MDMA is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA salts and solid forms disclosed herein, including those described in Table Ex3, is eplivanserin, wherein the eplivanserin is administered in about 1 mg to about 40 mg, or about 5 mg to about 10 mg, and the MDMA salts and solid forms disclosed herein, including those described in Table Ex3, are administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA salts and solid forms disclosed herein, including those described in Table Ex3, is volinanserin, wherein the volinanserin is administered in about 1 mg to about 60 mg, or about 5 mg to about 20 mg, and the MDMA salts and solid forms disclosed herein, including those described in Table Ex3, are administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA salts and solid forms disclosed herein, including those described in Table Ex3 is ketanserin, wherein the ketanserin is administered in about 10 mg to about 80 mg, about 30 mg to about 50 mg, or about 40 mg and the MDMA salts and solid forms disclosed herein, including those described in Table Ex3 are administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA salts and solid forms disclosed herein, including those described in Table Ex3 is ritanserin, wherein the ritanserin is administered in about 1 mg to about 40 mg, or about 2.5 mg to about 10 mg, and the MDMA salts and solid forms disclosed herein, including those described in Table Ex3 are administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator is pimavanserin and the MDMA salts and solid forms disclosed herein, including those described in Table Ex3, wherein the pimavanserin is administered in about 1 mg to about 60 mg, or about 17 mg to about 34 mg, and the MDMA salts and solid forms disclosed herein, including those described in Table Ex3 are administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA salts and solid forms disclosed herein, including those described in Table Ex3 is nelotanserin, wherein the nelotanserin is administered in about 1 mg to about 80 mg, or about 40 mg to about 80 mg, and the MDMA salts and solid forms disclosed herein, including those described in Table Ex3 are administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA salts and solid forms disclosed herein, including those described in Table Ex3 is pruvanserin, wherein the pruvanserin is administered in about 1 mg to about 40 mg, or about 3 mg to about 10 mg, and the MDMA salts and solid forms disclosed herein, including those described in Table Ex3 are administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA salts and solid forms disclosed herein, including those described in Table Ex3 is flibanserin, wherein the flibanserin is administered in about 10 mg to about 200 mg, or about 80 mg to about 120 mg, or about 100 mg and the MDMA salts and solid forms disclosed herein, including those described in Table Ex3 are administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA salts and solid forms disclosed herein, including those described in Table Ex3 is olanzapine, wherein the olanzapine is administered 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 MDMA salts and solid forms disclosed herein, including those described in Table Ex3 are administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA salts and solid forms disclosed herein, including those described in Table Ex3 is an extended-release of olanzapine such as ZYPREXA RELPREVV, wherein the extended release olanzapine is administered 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 MDMA salts and solid forms disclosed herein, including those described in Table Ex3 are administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • olanzapine such as ZYPREXA RELPREVV
  • the serotonin receptor modulator for use with the MDMA salts and solid forms disclosed herein, including those described in Table Ex3 is quetiapine, wherein the quetiapine is administered 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 MDMA salts and solid forms disclosed herein, including those described in Table Ex3 are administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA salts and solid forms disclosed herein, including those described in Table Ex3 is an extended-release of quetiapine, wherein the extended-release of quetiapine is administered 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 MDMA salts and solid forms disclosed herein, including those described in Table Ex3 are administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA salts and solid forms disclosed herein, including those described in Table Ex3 is risperidone, wherein the risperidone is administered in about 0.5 mg to about 20 mg or about 0.5 mg, or about 1 mg, 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 MDMA salts and solid forms disclosed herein, including those described in Table Ex3 are administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA salts and solid forms disclosed herein, including those described in Table Ex3 is an extended-release of risperidone including (RISPERDAL CONSTA), wherein the extended-release of risperidone is administered in about 12.5 mg, or about 25 mg, or about 37.5 mg, or about 50 mg, and the MDMA salts and solid forms disclosed herein, including those described in Table Ex3 are administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • RISPERDAL CONSTA RISPERDAL CONSTA
  • the serotonin receptor modulator for use with the MDMA hemifumarate Form A is eplivanserin, wherein the eplivanserin is administered in about 1 mg to about 40 mg, or about 5 mg to about 10 mg, and the MDMA hemifumarate Form A is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA hemifumarate Form A is volinanserin, wherein the volinanserin is administered in about 1 mg to about 60 mg, or about 5 mg to about 20 mg, and the MDMA hemifumarate Form A is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA hemifumarate Form A is ketanserin, wherein the ketanserin is administered in about 10 mg to about 80 mg, about 30 mg to about 50 mg, or about 40 mg and the MDMA hemifumarate Form A is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA hemifumarate Form A is ritanserin, wherein the ritanserin is administered in about 1 mg to about 40 mg, or about 2.5 mg to about 10 mg, and the MDMA hemifumarate Form A is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator is pimavanserin and the MDMA hemifumarate Form A wherein the pimavanserin is administered in about 1 mg to about 60 mg, or about 17 mg to about 34 mg, and the MDMA hemifumarate Form A is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA hemifumarate Form A is nelotanserin, wherein the nelotanserin is administered in about 1 mg to about 80 mg, or about 40 mg to about 80 mg, and the MDMA hemifumarate Form A is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA hemifumarate Form A is pruvanserin, wherein the pruvanserin is administered in about 1 mg to about 40 mg, or about 3 mg to about 10 mg, and the MDMA hemifumarate Form A is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA hemifumarate Form A is flibanserin, wherein the flibanserin is administered in about 10 mg to about 200 mg, or about 80 mg to about 120 mg, or about 100 mg and the MDMA hemifumarate Form A is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA hemifumarate Form A is olanzapine, wherein the olanzapine is administered 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 MDMA hemifumarate Form A is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA hemifumarate Form A is an extended-release of olanzapine such as ZYPREXA RELPREVV, wherein the extended release olanzapine is administered 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 MDMA hemifumarate Form A is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • olanzapine such as ZYPREXA RELPREVV
  • the serotonin receptor modulator for use with the MDMA hemifumarate Form A is quetiapine, wherein the quetiapine is administered 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 MDMA hemifumarate Form A is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA hemifumarate Form A is an extended-release of quetiapine, wherein the extended-release of quetiapine is administered 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 MDMA hemifumarate Form A is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA hemifumarate Form A is risperidone, wherein the risperidone is administered in about 0.5 mg to about 20 mg or about 0.5 mg, or about 1 mg, 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 MDMA hemifumarate Form A is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • the serotonin receptor modulator for use with the MDMA hemifumarate Form A is an extended-release of risperidone including (RISPERDAL CONSTA), wherein the extended-release of risperidone is administered in about 12.5 mg, or about 25 mg, or about 37.5 mg, or about 50 mg, and the MDMA hemifumarate Form A is administered between about 50 mg and about 200 mg, or between about 80 mg and 120 mg.
  • RISPERDAL CONSTA RISPERDAL CONSTA
  • a MDMA form disclosed herein, including those described in Table Ex3 is co-administered with a serotonin receptor modulator in the same or in separate compositions.
  • the serotonin receptor modulator is administered prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the MDMA form disclosed herein, including those described in Table Ex3 is administered in a modified release formulation such that the subject is effectively pretreated with serotonin receptor modulator prior to release of an effective amount of the MDMA.
  • the serotonin receptor modulator is part of a single fixed dose formulation that releases serotonin receptor modulator first followed by the MDMA on two different release profiles.
  • the serotonin receptor modulator is administered first as a single dosage and after a length of time, the MDMA form disclosed herein, including those described in Table Ex3 is administered as a second dosage separate from the first dosage.
  • the serotonin receptor modulator is administered or released from a composition provided herein prior to the administration and/or release of the psychedelic. This allows pretreatment to attenuate activation of the serotonin receptor by the psychedelic.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 15 minutes prior to the administration of MDMA. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat between at least 30 minutes prior and 360 minutes prior to the release or administration of the MDMA. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat between at least 60 minutes prior and 360 minutes prior to the release or administration the MDMA.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at between least 90 minutes and 240 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 120 minutes prior to the MDMA.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 150 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 180 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 210 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 240 minutes prior to the MDMA.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 270 minutes prior to MDMA. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 300 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 330 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 360 minutes prior to the MDMA.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein eplivanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of MDMA.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat a subject between at least 15 minutes and 360 minutes prior to the administration or release of MDMA.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat between at least 30 minutes and 360 minutes prior to the administration or release of MDMA.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of MDMA.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 90 minutes prior to MDMA. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 120 minutes prior to the MDMA.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 150 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 180 minutes prior to the MDMA.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 210 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 240 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 270 minutes prior to the MDMA.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 300 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 330 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 360 minutes prior to the MDMA. In some preferred embodiments, the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein volinanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of MDMA.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 15 minutes prior to the administration of MDMA. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat between at least 30 minutes and 360 minutes prior to the administration or release MDMA. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of MDMA.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 90 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 120 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 150 minutes prior to the MDMA.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 180 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 210 minutes prior to the MDMA.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 240 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 270 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 300 minutes prior to the MDMA.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 330 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 360 minutes prior to the MDMA. In some preferred embodiments, the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein ketanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of MDMA.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 15 minutes prior to the administration of MDMA. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 30 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of MDMA.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 90 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 120 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 150 minutes prior to the MDMA.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 180 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 210 minutes prior to the MDMA.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 240 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 270 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 300 minutes prior to the MDMA.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 330 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 360 minutes prior to the MDMA. In some preferred embodiments, the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein ritanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of MDMA.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 15 minutes prior to the administration of MDMA. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 30 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of MDMA.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 90 minutes prior to the MDMA.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 120 minutes prior to the MDMA.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 150 minutes prior to the MDMA.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 180 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 210 minutes prior to the MDMA.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 240 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 270 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 300 minutes prior to the MDMA.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 330 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 360 minutes prior to the MDMA. In some preferred embodiments, the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein pimavanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of MDMA.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 15 minutes prior to the administration of MDMA. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 30 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of MDMA.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 90 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 120 minutes prior to the MDMA.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 150 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 180 minutes prior to the MDMA.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 210 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 240 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 270 minutes prior to the MDMA.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 300 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 330 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 360 minutes prior to the MDMA. In some preferred embodiments, the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein nelotanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of MDMA.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 15 minutes prior to the administration of MDMA. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 30 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of MDMA.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 90 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 120 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 150 minutes prior to the MDMA.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 180 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 210 minutes prior to the MDMA.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 240 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 270 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 300 minutes prior to the MDMA.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 330 minutes prior to the MDMA. In some embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 360 minutes prior to the MDMA. In some preferred embodiments, the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein pruvanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of MDMA.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 15 minutes prior to the administration of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat between at least 30 minutes prior and 360 minutes prior to the release or administration of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat between at least 60 minutes prior and 360 minutes prior to the release or administration the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at between least 90 minutes and 240 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 120 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 150 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 180 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 210 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 240 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 270 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 300 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 330 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein the eplivanserin is administered to pretreat at least 360 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is eplivanserin and the psychedelic is MDMA, wherein eplivanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat a subject between at least 15 minutes and 360 minutes prior to the administration or release of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat between at least 30 minutes and 360 minutes prior to the administration or release of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 90 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 120 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 150 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 180 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 210 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 240 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 270 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 300 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 330 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein the volinanserin is administered to pretreat at least 360 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is volinanserin and the psychedelic is MDMA, wherein volinanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 15 minutes prior to the administration of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat between at least 30 minutes and 360 minutes prior to the administration or release the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 90 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 120 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 150 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 180 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 210 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 240 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 270 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 300 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 330 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein the ketanserin is administered to pretreat at least 360 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ketanserin and the psychedelic is MDMA, wherein ketanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 15 minutes prior to the administration of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 30 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 90 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 120 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 150 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 180 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 210 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 240 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 270 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 300 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 330 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein the ritanserin is administered to pretreat at least 360 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is ritanserin and the psychedelic is MDMA, wherein ritanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 15 minutes prior to the administration of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 30 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 90 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 120 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 150 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 180 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 210 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 240 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 270 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 300 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 330 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein the pimavanserin is administered to pretreat at least 360 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pimavanserin and the psychedelic is MDMA, wherein pimavanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 15 minutes prior to the administration of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 30 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 90 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 120 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 150 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 180 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 210 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 240 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 270 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 300 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 330 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein the nelotanserin is administered to pretreat at least 360 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is nelotanserin and the psychedelic is MDMA, wherein nelotanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 15 minutes prior to the administration of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 30 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 90 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 120 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 150 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 180 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 210 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 240 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 270 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 300 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 330 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein the pruvanserin is administered to pretreat at least 360 minutes prior to the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is pruvanserin and the psychedelic is MDMA, wherein pruvanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the MDMA form disclosed herein, including those described in Table Ex3.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (R)-MDMA, wherein the flibanserin is administered to pretreat at least 15 minutes prior to the administration of the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (R)-MDMA, wherein the flibanserin is administered to pretreat at least 30 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (R)-MDMA, wherein the flibanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (R)-MDMA, wherein the flibanserin is administered to pretreat at least 90 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (R)-MDMA, wherein the flibanserin is administered to pretreat at least 120 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (R)-MDMA, wherein the flibanserin is administered to pretreat at least 150 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (R)-MDMA, wherein the flibanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (R)-MDMA, wherein the flibanserin is administered to pretreat at least 180 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (R)-MDMA, wherein the flibanserin is administered to pretreat at least 210 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (R)-MDMA, wherein the flibanserin is administered to pretreat at least 240 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (R)-MDMA, wherein the flibanserin is administered to pretreat at least 270 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (R)-MDMA, wherein the flibanserin is administered to pretreat at least 300 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (R)-MDMA, wherein the flibanserin is administered to pretreat at least 330 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (R)-MDMA, wherein the flibanserin is administered to pretreat at least 360 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (R)-MDMA, wherein flibanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (R)-MDMA, wherein the olanzapine is administered to pretreat at least 15 minutes prior to the administration of the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (R)-MDMA, wherein the olanzapine is administered to pretreat at least 30 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (R)-MDMA, wherein the olanzapine is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (R)-MDMA, wherein the olanzapine is administered to pretreat at least 90 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (R)-MDMA, wherein the olanzapine is administered to pretreat at least 120 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (R)-MDMA, wherein the olanzapine is administered to pretreat at least 150 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (R)-MDMA, wherein the olanzapine is administered to pretreat between about 15 minutes and about 150 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (R)-MDMA, wherein the olanzapine is administered to pretreat at least 180 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (R)-MDMA, wherein the olanzapine is administered to pretreat at least 210 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (R)-MDMA, wherein the olanzapine is administered to pretreat at least 240 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (R)-MDMA, wherein the olanzapine is administered to pretreat at least 270 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (R)-MDMA, wherein the olanzapine is administered to pretreat at least 300 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (R)-MDMA, wherein the olanzapine is administered to pretreat at least 330 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (R)-MDMA, wherein the olanzapine is administered to pretreat at least 360 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (R)-MDMA, wherein olanzapine is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (R)-MDMA, wherein the quetiapine is administered to pretreat at least 15 minutes prior to the administration of the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (R)-MDMA, wherein the quetiapine is administered to pretreat at least 30 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (R)-MDMA, wherein the quetiapine is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (R)-MDMA, wherein the quetiapine is administered to pretreat at least 90 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (R)-MDMA, wherein the quetiapine is administered to pretreat at least 120 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (R)-MDMA, wherein the quetiapine is administered to pretreat at least 150 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (R)-MDMA, wherein the quetiapine is administered to pretreat between about 15 minutes and about 150 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (R)-MDMA, wherein the quetiapine is administered to pretreat at least 180 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (R)-MDMA, wherein the quetiapine is administered to pretreat at least 210 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (R)-MDMA, wherein the quetiapine is administered to pretreat at least 240 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (R)-MDMA, wherein the quetiapine is administered to pretreat at least 270 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (R)-MDMA, wherein the quetiapine is administered to pretreat at least 300 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (R)-MDMA, wherein the quetiapine is administered to pretreat at least 330 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (R)-MDMA, wherein the quetiapine is administered to pretreat at least 360 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (R)-MDMA, wherein quetiapine is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is risperidone and the psychedelic is (R)-MDMA, wherein the risperidone is administered to pretreat at least 15 minutes prior to the administration of the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is risperidone and the psychedelic is (R)-MDMA, wherein the risperidone is administered to pretreat at least 30 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is risperidone and the psychedelic is (R)-MDMA, wherein the risperidone is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is risperidone and the psychedelic is (R)-MDMA, wherein the risperidone is administered to pretreat at least 90 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is risperidone and the psychedelic is (R)-MDMA, wherein the risperidone is administered to pretreat at least 120 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is risperidone and the psychedelic is (R)-MDMA, wherein the risperidone is administered to pretreat at least 150 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is risperidone and the psychedelic is (R)-MDMA, wherein the risperidone is administered to pretreat between about 15 minutes and about 150 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is risperidone and the psychedelic is (R)-MDMA, wherein the risperidone is administered to pretreat at least 180 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is risperidone and the psychedelic is (R)-MDMA, wherein the risperidone is administered to pretreat at least 210 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is risperidone and the psychedelic is (R)-MDMA, wherein the risperidone is administered to pretreat at least 240 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is risperidone and the psychedelic is (R)-MDMA, wherein the risperidone is administered to pretreat at least 270 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is risperidone and the psychedelic is (R)-MDMA, wherein the risperidone is administered to pretreat at least 300 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is risperidone and the psychedelic is (R)-MDMA, wherein the risperidone is administered to pretreat at least 330 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is risperidone and the psychedelic is (R)-MDMA, wherein the risperidone is administered to pretreat at least 360 minutes prior to the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is risperidone and the psychedelic is (R)-MDMA, wherein risperidone is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the (R)-MDMA form disclosed herein, including those described in Table Ex9.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (S)-MDMA, wherein the flibanserin is administered to pretreat at least 15 minutes prior to the administration of the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (S)-MDMA, wherein the flibanserin is administered to pretreat at least 30 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (S)-MDMA, wherein the flibanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (S)-MDMA, wherein the flibanserin is administered to pretreat at least 90 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (S)-MDMA, wherein the flibanserin is administered to pretreat at least 120 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (S)-MDMA, wherein the flibanserin is administered to pretreat at least 150 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (S)-MDMA, wherein the flibanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (S)-MDMA, wherein the flibanserin is administered to pretreat at least 180 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (S)-MDMA, wherein the flibanserin is administered to pretreat at least 210 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (S)-MDMA, wherein the flibanserin is administered to pretreat at least 240 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (S)-MDMA, wherein the flibanserin is administered to pretreat at least 270 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (S)-MDMA, wherein the flibanserin is administered to pretreat at least 300 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (S)-MDMA, wherein the flibanserin is administered to pretreat at least 330 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (S)-MDMA, wherein the flibanserin is administered to pretreat at least 360 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is flibanserin and the psychedelic is (S)-MDMA, wherein flibanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (S)-MDMA, wherein the olanzapine is administered to pretreat at least 15 minutes prior to the administration of the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (S)-MDMA, wherein the olanzapine is administered to pretreat at least 30 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (S)-MDMA, wherein the olanzapine is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (S)-MDMA, wherein the olanzapine is administered to pretreat at least 90 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (S)-MDMA, wherein the olanzapine is administered to pretreat at least 120 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (S)-MDMA, wherein the olanzapine is administered to pretreat at least 150 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (S)-MDMA, wherein the olanzapine is administered to pretreat between about 15 minutes and about 150 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (S)-MDMA, wherein the olanzapine is administered to pretreat at least 180 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (S)-MDMA, wherein the olanzapine is administered to pretreat at least 210 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (S)-MDMA, wherein the olanzapine is administered to pretreat at least 240 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (S)-MDMA, wherein the olanzapine is administered to pretreat at least 270 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (S)-MDMA, wherein the olanzapine is administered to pretreat at least 300 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (S)-MDMA, wherein the olanzapine is administered to pretreat at least 330 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (S)-MDMA, wherein the olanzapine is administered to pretreat at least 360 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is olanzapine and the psychedelic is (S)-MDMA, wherein olanzapine is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (S)-MDMA, wherein the quetiapine is administered to pretreat at least 15 minutes prior to the administration of the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (S)-MDMA, wherein the quetiapine is administered to pretreat at least 30 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (S)-MDMA, wherein the quetiapine is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (S)-MDMA, wherein the quetiapine is administered to pretreat at least 90 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (S)-MDMA, wherein the quetiapine is administered to pretreat at least 120 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (S)-MDMA, wherein the quetiapine is administered to pretreat at least 150 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (S)-MDMA, wherein the quetiapine is administered to pretreat between about 15 minutes and about 150 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (S)-MDMA, wherein the quetiapine is administered to pretreat at least 180 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (S)-MDMA, wherein the quetiapine is administered to pretreat at least 210 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (S)-MDMA, wherein the quetiapine is administered to pretreat at least 240 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (S)-MDMA, wherein the quetiapine is administered to pretreat at least 270 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (S)-MDMA, wherein the quetiapine is administered to pretreat at least 300 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (S)-MDMA, wherein the quetiapine is administered to pretreat at least 330 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (S)-MDMA, wherein the quetiapine is administered to pretreat at least 360 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is quetiapine and the psychedelic is (S)-MDMA, wherein quetiapine is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is risperidone and the psychedelic is (S)-MDMA, wherein the risperidone is administered to pretreat at least 15 minutes prior to the administration of the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is risperidone and the psychedelic is (S)-MDMA, wherein the risperidone is administered to pretreat at least 30 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is risperidone and the psychedelic is (S)-MDMA, wherein the risperidone is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is risperidone and the psychedelic is (S)-MDMA, wherein the risperidone is administered to pretreat at least 90 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is risperidone and the psychedelic is (S)-MDMA, wherein the risperidone is administered to pretreat at least 120 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is risperidone and the psychedelic is (S)-MDMA, wherein the risperidone is administered to pretreat at least 150 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is risperidone and the psychedelic is (S)-MDMA, wherein the risperidone is administered to pretreat between about 15 minutes and about 150 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is risperidone and the psychedelic is (S)-MDMA, wherein the risperidone is administered to pretreat at least 180 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is risperidone and the psychedelic is (S)-MDMA, wherein the risperidone is administered to pretreat at least 210 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is risperidone and the psychedelic is (S)-MDMA, wherein the risperidone is administered to pretreat at least 240 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is risperidone and the psychedelic is (S)-MDMA, wherein the risperidone is administered to pretreat at least 270 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is risperidone and the psychedelic is (S)-MDMA, wherein the risperidone is administered to pretreat at least 300 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is risperidone and the psychedelic is (S)-MDMA, wherein the risperidone is administered to pretreat at least 330 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is risperidone and the psychedelic is (S)-MDMA, wherein the risperidone is administered to pretreat at least 360 minutes prior to the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is risperidone and the psychedelic is (S)-MDMA, wherein risperidone is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the (S)-MDMA form disclosed herein, including those described in Table Ex8.
  • the serotonin receptor modulator is flibanserin and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the flibanserin is administered to pretreat at least 15 minutes prior to the administration of the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is flibanserin and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the flibanserin is administered to pretreat at least 30 minutes prior to the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is flibanserin and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the flibanserin is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is flibanserin and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the flibanserin is administered to pretreat at least 90 minutes prior to the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is flibanserin and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the flibanserin is administered to pretreat at least 120 minutes prior to the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is flibanserin and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the flibanserin is administered to pretreat at least 150 minutes prior to the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is flibanserin and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the flibanserin is administered to pretreat between about 15 minutes and about 150 minutes prior to the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is flibanserin and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the flibanserin is administered to pretreat at least 180 minutes prior to the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is flibanserin and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the flibanserin is administered to pretreat at least 210 minutes prior to the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is flibanserin and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the flibanserin is administered to pretreat at least 240 minutes prior to the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is flibanserin and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the flibanserin is administered to pretreat at least 270 minutes prior to the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is flibanserin and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the flibanserin is administered to pretreat at least 300 minutes prior to the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is flibanserin and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the flibanserin is administered to pretreat at least 330 minutes prior to the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is flibanserin and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the flibanserin is administered to pretreat at least 360 minutes prior to the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is flibanserin and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein flibanserin is administered to pretreat between about 60 minutes and about 180 minutes prior to the administration of the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is olanzapine and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the olanzapine is administered to pretreat at least 15 minutes prior to the administration of the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is olanzapine and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the olanzapine is administered to pretreat at least 30 minutes prior to the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is olanzapine and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the olanzapine is administered to pretreat between at least 60 minutes and 240 minutes prior to the administration or release of the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is olanzapine and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the olanzapine is administered to pretreat at least 90 minutes prior to the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.
  • the serotonin receptor modulator is olanzapine and the psychedelic is N-ethyl-3,4-methylenedioxyamphetamine, wherein the olanzapine is administered to pretreat at least 120 minutes prior to the N-ethyl-3,4-methylenedioxyamphetamine ⁇ HCl forms disclosed herein, including those described in Table Ex10.

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Cited By (1)

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Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6221335B1 (en) 1994-03-25 2001-04-24 Isotechnika, Inc. Method of using deuterated calcium channel blockers
AU6104196A (en) 1995-06-06 1996-12-24 Neurobiological Technologies, Inc. Novel n-substituted-2-amino-3',4'-methylene-dioxypropiopheno nes
PT1104760E (pt) 1999-12-03 2003-06-30 Pfizer Prod Inc Compostos de sulfamoil-heteroarilpirazole como agentes analgesicos e anti-inflamatorios
TW200413273A (en) 2002-11-15 2004-08-01 Wako Pure Chem Ind Ltd Heavy hydrogenation method of heterocyclic rings
CA2624179A1 (fr) 2005-10-06 2007-04-12 Auspex Pharmaceuticals, Inc. Inhibiteurs deuteries d'atpase h+,k+ gastrique ayant des proprietes therapeutiques renforcees
US7750168B2 (en) 2006-02-10 2010-07-06 Sigma-Aldrich Co. Stabilized deuteroborane-tetrahydrofuran complex
CN107406369B (zh) 2014-12-09 2021-01-15 以西结·戈兰 放纵行为调节剂
WO2022232949A1 (fr) * 2021-05-06 2022-11-10 Pharmala Biotech Inc. Procédés de préparation des énantiomères de la 3,4-méthylènedioxyméthamphétamine (mdma) et de la n-méthyl-1,3-benzodioxolylbutanamine (mbdb)
WO2023283386A2 (fr) * 2021-07-07 2023-01-12 Arcadia Medicine, Inc. Compositions psychoactives plus fiables
AU2021106190A4 (en) * 2021-08-20 2021-10-28 Mind Medicine Australia Limited Improved method of synthesis of 1-(3’,4’-methylene dioxyphenyl)-2-(methylamino) propane (mdma)
WO2023028091A1 (fr) 2021-08-23 2023-03-02 Alexander Shulgin Research Institute Empathogènes deutérés
WO2023081897A1 (fr) 2021-11-05 2023-05-11 Terran Biosciences, Inc. 3,4-méthylènedioxy-n-éthylamphétamine (mde) à enrichissement isotopique et stéréo-isomères associés
WO2023081895A1 (fr) 2021-11-05 2023-05-11 Terran Biosciences, Inc. Analogues enrichis isotopiquement de 5,6-méthylènedioxy-2-aminoindane (mdai)
US20230150965A1 (en) 2021-11-05 2023-05-18 Terran Biosciences, Inc. Isotopically enriched n-methyl-1,3-benzodioxolylbutanamine (mbdb) and stereoisomers thereof
WO2023092044A2 (fr) 2021-11-17 2023-05-25 Terran Biosciences, Inc. Sels de composés de phénéthylamine, formes polymorphes et leurs méthodes d'utilisation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11958821B2 (en) 2021-11-17 2024-04-16 Terran Biosciences Inc. Phenethylamine compounds salts, polymorphic forms and methods of use thereof

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