WO2023225186A1 - Extraction de psilocybine et de psilocine - Google Patents

Extraction de psilocybine et de psilocine Download PDF

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Publication number
WO2023225186A1
WO2023225186A1 PCT/US2023/022720 US2023022720W WO2023225186A1 WO 2023225186 A1 WO2023225186 A1 WO 2023225186A1 US 2023022720 W US2023022720 W US 2023022720W WO 2023225186 A1 WO2023225186 A1 WO 2023225186A1
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WO
WIPO (PCT)
Prior art keywords
psilocybin
extraction
psilocin
solvent
mixture
Prior art date
Application number
PCT/US2023/022720
Other languages
English (en)
Inventor
William Lanier
Shane Jacob Hamill BENJAMIN
Original Assignee
Chemtor, Lp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chemtor, Lp filed Critical Chemtor, Lp
Priority to US18/327,946 priority Critical patent/US20230374561A1/en
Publication of WO2023225186A1 publication Critical patent/WO2023225186A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/06—Fungi, e.g. yeasts
    • A61K36/07—Basidiomycota, e.g. Cryptococcus
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/028—Flow sheets
    • B01D11/0284—Multistage extraction
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0288—Applications, solvents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/04—Solvent extraction of solutions which are liquid
    • B01D11/0492—Applications, solvents used
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
    • B01D15/12—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to the preparation of the feed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C07D209/16—Tryptamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings
    • C07F9/5728—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0215—Solid material in other stationary receptacles
    • B01D11/0253—Fluidised bed of solid materials
    • B01D11/0257—Fluidised bed of solid materials using mixing mechanisms, e.g. stirrers, jets

Definitions

  • the present disclosure is related to purification and extraction of psilocybin and psilocin.
  • Psilocybin mushrooms Most or nearly all fungi of the genus Psilocybe contain psychedelic compounds psilocybin, psilocin, and baeocystin (“psilocybin mushrooms”).
  • Psilocybin is a phosphorylated counterpart of psilocin, which is a pharmacologically active agent that acts on serotonin receptors in the brain, and psilocybin is rapidly dephosphorylated in the body to psilocin.
  • Psilocybin (3-[2-(dimethylamino)ethyl]-l//-indol-4-yl dihydrogen phosphate) has the following chemical formula:
  • Psilocybin is of pharmacological importance with known uses in treating drug dependence, anxiety, and mood and mental health disorders, such as post-traumatic stress disorder (PTSD) and depression. There is also evidence that psilocybin can induce neural regeneration and/or increase neuroplasticity.
  • PTSD post-traumatic stress disorder
  • Psilocybin can be synthetically produced, but methods for producing synthetic psilocybin are expensive. As such, there is a demand for psilocybin extracts from natural sources. Psilocybin and psilocin may be extracted and isolated from caps, stems, and/or spores of psilocybin mushrooms. However, current extraction methods, such as maceration and Soxhlet extraction, have very low efficiency, often 15% or less, and may be highly time-consuming and/or labor-intensive.
  • FIGURES illustrate embodiments of the subject matter disclosed herein.
  • the claimed subject matter may be understood by reference to the following description taken in conjunction with the accompanying FIGURES, in which:
  • FIG. l is a diagram of an extraction system according to embodiments of the present disclosure.
  • FIG. 2 is a schematic of an extraction process according to embodiments of the present disclosure.
  • fungi a system 100 for extraction and isolation of psilocybin and psilocin from psilocybin mushrooms (referred to herein as “fungi”) is shown.
  • the system 100 includes fungi supply 10 configured to supply fungi to an extraction vessel 16.
  • the fungi supply 10 may include one or more species of fungi.
  • the fungi include one or more species from the genus Psilocybe such as Psilocybe cubensis (Stropharia cubensis), Psilocybe cyanescens, Psilocybe semilanceata, and/or Psilocybe azurescens.
  • the fungi in the fungi supply 10 may be powdered or ground.
  • the fungi supply 10 includes a grinder.
  • Chitin is a component of the cell walls of fungi, such as psilocybin mushrooms. Chitin is a stable molecule, resistant to degradation, and insoluble in typical solvents such as water, organic solvents, and mild acidic or basic solutions. The presence of chitin therefore may negatively affect extraction efficiency of psilocybin. In order to overcome this issue, chitin is digested in the present extraction system 100.
  • Chitinases are hydrolytic enzymes that break down glycosidic bonds in chitin. Chitinases are naturally found in organisms that either need to reshape their own chitin or dissolve and digest the chitin of fungi or animals. For example, fungi may produce their own chitinases to, for example, modify or remodel cell walls or aid in cell division. Naturally derived and synthetic chitinases are commercially available. As such, it is believed that enzymes derived from members of the Psilocybe genus and/or those taxa that naturally defend against these fungi in the wild, will likely prove to be the most effective in terms of breaking down classes of chitin specific to these fungi. An example of a suitable chitinase is that derived from Aspergillus niger.
  • the system 100 includes an enzyme supply 12 configured to supply chitinase to the extraction vessel 16.
  • the enzyme supply 12 may include one or more chitinases.
  • the chitinase may be specified based on the fungi present in fungi supply 10.
  • the enzyme supply 12 may include an agitator, such as a stir bar.
  • the system 100 further includes an extractant supply 14 configured to supply an extraction solution to the extraction vessel 16.
  • the extraction solution is water.
  • the extraction solution is pH adjusted to pH 5-8.
  • the temperature is adjusted to 30-40 °C.
  • the extraction solution includes one or more salts dissolved therein.
  • the extraction solution is ethanol or a mixture of water and ethanol.
  • the extraction solution may include acetone, chloroform, ether (e.g., dimethyl ether or diethyl ether), hexane, methanol, water, or combinations thereof.
  • the extraction solution includes more than one of the foregoing due to the different solubilities of psilocybin and psilocin. That is, psilocybin is soluble in water, slightly soluble in acetone, ether, and methanol, and insoluble in chloroform and hexane. Conversely, psilocin is soluble in acetone, chloroform, ether, hexane, and methanol, and slightly soluble in water.
  • the extraction vessel 16 is configured to receive ground fungi from the fungi supply 10, the extraction solution from extractant supply 14, and the chitinase from the enzyme supply 12.
  • the extraction vessel 16 may receive the fungi, extraction solution, and chitinase in a weight ratio of at least 0.1 g, 1 to 100 g, 5 to 80 g, 10 to 60 g, or 20 to 40 g of chitinase per g of fungi digested per each hour. Increasing the number of units of chitinase per gram will result in shorter digestion times.
  • a weight ratio of chitinase to fungi is 0.1 to 10, 0.1 to 1, 0.1 to 2, 0.2 to 5, 0.3 to 2, about 0.5, about 1, or about 2:3.
  • the extraction vessel 16 may include an agitator, such as a stir bar or air agitator to enhance extraction efficiency.
  • the extraction vessel 16 first receives the fungi and extraction solution, mixes the fungi and extraction solution, and then the chitinase is supplied 1 minute, 5 minutes, or 15 minutes thereafter.
  • the components may be supplied simultaneously.
  • the extraction solution and the chitinase may be first mixed in the extraction vessel and then the fungi may be supplied immediately thereafter.
  • the extraction vessel 16 includes a heater, wherein the extraction vessel may be maintained at an elevated temperature to facilitate digestion of chitin in the fungi by the chitinase.
  • the extraction vessel 16 is configured to be maintained at a temperature of from 25 to 75 °C with higher temperatures being feasible if chitinase from extremophiles are utilized.
  • the extraction mixture (fungi, extraction solution, and chitinase) has a set residence time in the extraction vessel 16.
  • the extraction mixture may be continuously mixed, intermittently mixed, or not mixed.
  • the extraction mixture may be maintained at a single temperature or the temperature may vary.
  • the residence time is at least 1 hour, at least 6 hours, at least 12 hours, at least 24 hours, about 12 hours, or about 24 hours relative to the ratio of fungi present to units of chitinase added.
  • the extraction mixture is transferred from the extraction vessel 16 to a purification process 18.
  • the purification process 18 is configured to isolate the psilocybin from remaining components in the extraction mixture.
  • the purification process 18 may include a filter as an initial component, wherein the filter may remove any remaining solids from the extraction mixture prior to purification.
  • the extraction mixture is separated from solids using a centrifuge.
  • the extraction mixture does not include any solid matter (i.e., the extraction may fully digest the fungi).
  • the purification process 18 includes a conduit reactor, such as those described in patent U.S. Patent No. 11,198,107, which is hereby incorporated by reference in its entirety.
  • the purification process 18 includes contacting the extraction mixture with a solvent in the conduit reactor.
  • the solvent is immiscible (or only slightly miscible) with water and psilocybin and/or psilocin is more soluble in the solvent than in the extraction solution of the extraction mixture.
  • the solvent is ethyl acetate. Ethyl acetate is a polar-nonpolar solvent that is slightly miscible with water.
  • the contact between the aqueous extraction mixture and the solvent transfers psilocybin from the extraction mixture into the solvent while leaving one or more unwanted components in the extraction mixture.
  • an additive may be added to the solvent and/or extraction mixture to aid in transferring the psilocybin into the solvent.
  • a phase transfer catalyst may be used.
  • the contacting may be facilitated by simultaneously introducing the extraction mixture, solvent, and, optionally, the additive(s) into a first end of the conduit reactor, wherein the reaction products may then be received in separator opposite the first end.
  • the reaction products include a heavier aqueous phase comprising the extraction solution and a light organic phase comprising the solvent and psilocybin.
  • the two phases may then be separately removed from the separator.
  • the organic phase (a psilocybin/psilocin isolate) may be further refined to remove additional unwanted components or may constitute a final product.
  • the aqueous phase may be discarded, remediated, or further processed to extract desirable compounds therefrom (e.g., residual psilocybin/psilocin).
  • the contacting may involve mixing the extraction mixture, solvent, and, optionally, the additive(s) in a vessel and then introducing this mixture into the first end of the conduit reactor.
  • the purification process 18 utilizes a salting out technique to isolate the psilocybin and/or psilocin from the extraction mixture.
  • a buffered solution of phosphate salt such as sodium phosphate
  • phosphate-containing compounds such as psilocybin fall out of solution in solid form.
  • the solid psilocybin and/or psilocin may then be isolated using, e.g., filtration or dialysis to yield a psilocybin isolate which may be further purified through, e.g., recrystallization.
  • the purification process 18 utilizes a chromatography column to isolate the psilocybin and/or psilocin from the extraction mixture.
  • suitable solvents may include water, acetone, DMSO, methanol, ethanol, and/or a mixture thereof.
  • the resulting psilocybin and/or psilocin isolate may be transferred to an isolate tank 20.
  • a method 200 of extracting and isolating psilocybin and/or psilocin from fungi is depicted.
  • the fungi is ground into a powder.
  • the grinding step 210 may be conducted prior to introducing the fungi into the fungi supply 10 or may be conducted in the fungi supply 10.
  • the fungi, extraction solution, and chitinase are supplied to the extraction vessel 18 from the fungi supply 10, extractant supply 14, and enzyme supply 12, respectively, and mixed. The mixing may be facilitated by an agitator disposed in the extraction vessel 18.
  • the chitinase digests the chitin of the fungi.
  • Step 230 may begin during step 220 or may entirely coincide with step 220.
  • steps 220 and/or 230 involve heating the mixture as described above.
  • the method 200 includes a step 240 of filtering solids from the mixture to yield an extract.
  • steps 220 and 230 yield the extract. That is, in some embodiments, steps 220 and 230 may entirely liquify the mixture such that the filtering step 240 is not required.
  • the method 200 includes a step 250 of purifying the extract. Step 250 may utilize the extraction process 18 described above. Step 250 yields a psilocybin and/or psilocin isolate.
  • extraction efficiency of psilocybin and/or psilocin from psilocybin mushrooms may be greatly improved. This is due at least in part to the digestion of chitin using one or more chitinases, which allows for more effective extraction of psilocybin into the extraction solution.
  • sample sets were prepared, each containing 15 grams of Psilocybe cubensis biomass.
  • the extraction solvents used across these samples were water, ethanol, or a combination of both; with or without the addition of chitinase.
  • the specific compositions of the sample sets were as follows:
  • Comparative Sample #1 used 250 grams of ethanol as the solvent
  • Sample #2 employed 10 grams of chitinase and 250 grams of ethanol;
  • Sample #3 contained 10 grams of chitinase, 125 grams of water, and 125 grams of ethanol;
  • Sample #4 utilized 10 grams of chitinase and 250 grams of water;
  • Reference Sample #5 was 15 grams of Psilocybe cubensis used as a reference.
  • each sample underwent extraction in the above-referenced extractant solvents for 24 hours before undergoing sonication at 250 watts and 50% amplitude for 3 minutes. Immediately following sonication, each sample was subjected to gravity fdtration for 10 minutes using a 20 micrometer fdter paper and a gravity filtration system. Each extractant was collected and tested using gas chromatography and mass spectroscopy (GCMS). Table 1 below summarizes the results.
  • GCMS gas chromatography and mass spectroscopy
  • Comparative Sample #1 was only able to recover 30.7% of psilocin and 3.6% of psilocybin, wherein Sample #2, using the same solvent with the addition of chitinase, was able to include the recovery amounts to 55.0% and 4.2%, respectively.

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  • Life Sciences & Earth Sciences (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
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  • Engineering & Computer Science (AREA)
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  • Food Science & Technology (AREA)
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Abstract

Un procédé d'extraction et d'isolement de psilocybine et/ou de psilocine à partir de champignons à psilocybine comprend la formation d'un mélange des champignons, d'une solution d'extraction et d'une chitinase capable de digérer la chitine présente dans les champignons. Les solides peuvent être filtrés du mélange pour produire un extrait comprenant de la psilocybine et/ou de la psilocine. L'extrait peut être purifié pour isoler la psilocybine et/ou la psilocine.
PCT/US2023/022720 2022-05-18 2023-05-18 Extraction de psilocybine et de psilocine WO2023225186A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US18/327,946 US20230374561A1 (en) 2022-05-18 2023-06-02 Extraction of psilocybin and psilocin

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US202263364927P 2022-05-18 2022-05-18
US63/364,927 2022-05-18

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011236183A (ja) * 2010-05-13 2011-11-24 Unitika Ltd きのこ類由来エルゴステロールペルオキシドの抽出方法
US10954259B1 (en) * 2017-10-09 2021-03-23 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
WO2021159213A1 (fr) * 2020-02-12 2021-08-19 Neonmind Biosciences Inc. Procédé de production d'un extrait de champignon et extrait de champignon fabriqué grâce à ce procédé
US11198107B2 (en) * 2019-09-05 2021-12-14 Visionary Fiber Technologies, Inc. Conduit contactor and method of using the same
US11331357B2 (en) * 2020-06-17 2022-05-17 Psilo Scientific Ltd. Methods and compositions comprising psychoactive compounds from psychoactive organisms

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011236183A (ja) * 2010-05-13 2011-11-24 Unitika Ltd きのこ類由来エルゴステロールペルオキシドの抽出方法
US10954259B1 (en) * 2017-10-09 2021-03-23 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11198107B2 (en) * 2019-09-05 2021-12-14 Visionary Fiber Technologies, Inc. Conduit contactor and method of using the same
WO2021159213A1 (fr) * 2020-02-12 2021-08-19 Neonmind Biosciences Inc. Procédé de production d'un extrait de champignon et extrait de champignon fabriqué grâce à ce procédé
US11331357B2 (en) * 2020-06-17 2022-05-17 Psilo Scientific Ltd. Methods and compositions comprising psychoactive compounds from psychoactive organisms

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BERGSTRÖM ALEXANDER: "Enzymatic pre-treatment of shiitake mushroom", 1 January 2006 (2006-01-01), XP093114308, Retrieved from the Internet <URL:https://www.diva-portal.org/smash/get/diva2:1024106/FULLTEXT01.pdf> [retrieved on 20231220] *
HATEET RASHID RAHIM: "GC-MS Analysis of extract for Endophytic fungus Acremonium coenophialum and its Antimicrobial and Antidiabetic", RESEARCH JOURNAL OF PHARMACY AND TECHNOLOGY, A & V PUBLICATIONS, INDIA, vol. 13, no. 1, India , pages 119, XP093114305, ISSN: 0974-3618, DOI: 10.5958/0974-360X.2020.00024.4 *
SHABA REHAM: "Development of an improved psilocybin synthesis", UPPSALA UNIVERSITY, 1 June 2020 (2020-06-01), XP093114306, Retrieved from the Internet <URL:https://www.diva-portal.org/smash/get/diva2:1470170/FULLTEXT01.pdf> [retrieved on 20231220] *

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