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GB911946A - Psilocybin and psilocin and processes for their preparation - Google Patents

Psilocybin and psilocin and processes for their preparation

Info

Publication number
GB911946A
GB911946A GB4841/59A GB484159A GB911946A GB 911946 A GB911946 A GB 911946A GB 4841/59 A GB4841/59 A GB 4841/59A GB 484159 A GB484159 A GB 484159A GB 911946 A GB911946 A GB 911946A
Authority
GB
United Kingdom
Prior art keywords
heim
active compounds
extraction
stropharia
degreasing
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB4841/59A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sandoz AG
Original Assignee
Sandoz AG
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
Priority claimed from CH5614358A external-priority patent/CH393637A/en
Priority claimed from CH6239358A external-priority patent/CH377482A/en
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB911946A publication Critical patent/GB911946A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • A61K36/078—Psilocybe
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • 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
    • B01D9/00—Crystallisation
    • B01D9/005—Selection of auxiliary, e.g. for control of crystallisation nuclei, of crystal growth, of adherence to walls; Arrangements for introduction thereof
    • B01D9/0054—Use of anti-solvent
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/10—Nitrogen as only ring hetero atom

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Mycology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Microbiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Biotechnology (AREA)
  • Public Health (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Medical Informatics (AREA)
  • Botany (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

The invention comprises the psychotropically active compounds Psilocybin of the formula: <FORM:0911946/IV (b)/1> and Psilocin of the formula: <FORM:0911946/IV (b)/2> and a process for their extraction from fungal material of the genera Psilocybe, Stropharia and Panaeolus or biological variants or mutants thereof, by treatment with water or a water-miscible organic solvent, degreasing the product, isolating the active material by chromatography and removing any halogen material present. Examples detail the extraction of the active compounds from Psilocybe mexicana Heim, P. caerulescens Murill var. Mazatecorum Heim, P. Zapotecorum Heim, P. semperviva Heim and Cailleux, P. Aztecorum Heim, Stropharia cubensis Earle preferably by cultivation on a synthetic medium, extraction of the dried fruit bodies with methanol or aqueous methanol, degreasing the extract with petroleum ether and chloroform, chromatographing the product on cellulose, eluting with aqueous butanol (detection of active compounds is effected with the Keller reagent), removing halogen by treatment with silver carbonate and purifying the active compounds by crystallisation. The compounds may be formulated into psychotherapeutic compositions with inert carriers suitable for sub-cutaneous injection or oral administration.
GB4841/59A 1958-02-21 1959-02-11 Psilocybin and psilocin and processes for their preparation Expired GB911946A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH5614358A CH393637A (en) 1958-02-21 1958-02-21 Process for preparing psilocybin and psilocin
CH6239358A CH377482A (en) 1958-07-30 1958-07-30 Process for obtaining psilocybin and psilocin

Publications (1)

Publication Number Publication Date
GB911946A true GB911946A (en) 1962-12-05

Family

ID=25737584

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4841/59A Expired GB911946A (en) 1958-02-21 1959-02-11 Psilocybin and psilocin and processes for their preparation

Country Status (1)

Country Link
GB (1) GB911946A (en)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1474126A4 (en) * 2002-01-18 2007-08-08 Massachusetts Inst Technology TREATMENTS OF NEUROTOXICITY IN ALZHEIMER'S DISEASE
US10519175B2 (en) 2017-10-09 2019-12-31 Compass Pathways Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11331357B2 (en) 2020-06-17 2022-05-17 Psilo Scientific Ltd. Methods and compositions comprising psychoactive compounds from psychoactive organisms
WO2022140851A1 (en) * 2020-12-28 2022-07-07 Psilo Scientific Ltd Injectable psychoactive alkaloid composition and preparation thereof
US11382942B2 (en) 2020-06-17 2022-07-12 Psilo Scientific Ltd. Extraction of psychoactive compounds from psilocybin fungus
US11510952B2 (en) 2020-06-17 2022-11-29 Psilo Scientific Ltd. Ethanol extraction of psychoactive compounds from psilocybin fungus
US11564935B2 (en) 2019-04-17 2023-01-31 Compass Pathfinder Limited Method for treating anxiety disorders, headache disorders, and eating disorders with psilocybin
US11724985B2 (en) 2020-05-19 2023-08-15 Cybin Irl Limited Deuterated tryptamine derivatives and methods of use
EP4161547A4 (en) * 2020-06-17 2023-11-01 Psilo Scientific Ltd METHANOL-BASED EXTRACTION OF PSYCHOACTIVE COMPOUNDS FROM MUSHROOMS
EP4339200A3 (en) * 2020-06-17 2024-03-27 Psilo Scientific Ltd Ethanol extraction of psychoactive compounds from psilocybin fungus
US12060328B2 (en) 2022-03-04 2024-08-13 Reset Pharmaceuticals, Inc. Co-crystals or salts of psilocybin and methods of treatment therewith
EP4387616A4 (en) * 2021-10-18 2024-11-13 Psilo Scientific Ltd EXTRACTION OF PURIFIED PSYCHOACTIVE ALKALOID USING ACIDIFIED ACETONE
US12233355B2 (en) 2020-06-17 2025-02-25 Psilo Scientific Ltd. Methanol-based extraction of psychoactive alkaloids from fungus
US12331020B2 (en) 2020-12-31 2025-06-17 1280225 B.C. Ltd. Method of synthesizing indole compounds
US12459965B2 (en) 2017-10-09 2025-11-04 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use

Cited By (49)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1474126A4 (en) * 2002-01-18 2007-08-08 Massachusetts Inst Technology TREATMENTS OF NEUROTOXICITY IN ALZHEIMER'S DISEASE
US12459965B2 (en) 2017-10-09 2025-11-04 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US12312375B2 (en) 2017-10-09 2025-05-27 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US10954259B1 (en) 2017-10-09 2021-03-23 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11149044B2 (en) 2017-10-09 2021-10-19 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11180517B2 (en) 2017-10-09 2021-11-23 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11939346B2 (en) 2017-10-09 2024-03-26 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US10519175B2 (en) 2017-10-09 2019-12-31 Compass Pathways Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11851451B2 (en) 2017-10-09 2023-12-26 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11447510B2 (en) 2017-10-09 2022-09-20 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11629159B2 (en) 2017-10-09 2023-04-18 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US10947257B2 (en) 2017-10-09 2021-03-16 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US11505564B2 (en) 2017-10-09 2022-11-22 Compass Pathfinder Limited Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use
US12447164B2 (en) 2019-04-17 2025-10-21 Compass Pathfinder Limited Method for treating anxiety disorders, headache disorders, and eating disorders with psilocybin
US12377112B2 (en) 2019-04-17 2025-08-05 Compass Pathfinder Limited Methods of treating neurocognitive disorders, chronic pain and reducing inflammation
US11564935B2 (en) 2019-04-17 2023-01-31 Compass Pathfinder Limited Method for treating anxiety disorders, headache disorders, and eating disorders with psilocybin
US11738035B2 (en) 2019-04-17 2023-08-29 Compass Pathfinder Limited Method for treating anxiety disorders, headache disorders, and eating disorders with psilocybin
US12433904B2 (en) 2019-04-17 2025-10-07 Compass Pathfinder Limited Methods for treating anxiety disorders, headache disorders, and eating disorders with psilocybin
US11724985B2 (en) 2020-05-19 2023-08-15 Cybin Irl Limited Deuterated tryptamine derivatives and methods of use
US12291499B2 (en) 2020-05-19 2025-05-06 Cybin Irl Limited Deuterated tryptamine derivatives and methods of use
US11746088B2 (en) 2020-05-19 2023-09-05 Cybin Irl Limited Deuterated tryptamine derivatives and methods of use
US12240813B2 (en) 2020-05-19 2025-03-04 Cybin Irl Limited Deuterated tryptamine derivatives and methods of use
US12110272B2 (en) 2020-05-19 2024-10-08 Cybin Irl Limited Deuterated tryptamine derivatives and methods of use
US11834410B2 (en) 2020-05-19 2023-12-05 Cybin Irl Limited Deuterated tryptamine derivatives and methods of use
US11958807B2 (en) 2020-05-19 2024-04-16 Cybin Irl Limited Deuterated tryptamine derivatives and methods of use
US11510952B2 (en) 2020-06-17 2022-11-29 Psilo Scientific Ltd. Ethanol extraction of psychoactive compounds from psilocybin fungus
US12233355B2 (en) 2020-06-17 2025-02-25 Psilo Scientific Ltd. Methanol-based extraction of psychoactive alkaloids from fungus
US11382942B2 (en) 2020-06-17 2022-07-12 Psilo Scientific Ltd. Extraction of psychoactive compounds from psilocybin fungus
EP4161548A4 (en) * 2020-06-17 2024-04-24 Psilo Scientific Ltd EXTRACTION OF PSYCHOACTIVE COMPOUNDS FROM PSYCHEDELIC MUSHROOMS
IL298561B2 (en) * 2020-06-17 2025-10-01 Psilo Scientific Ltd Methanol-based extraction of psychoactive compounds from fungus
EP4372094A3 (en) * 2020-06-17 2024-08-07 Psilo Scientific Ltd Aqueous extraction of psychoactive compounds from psilocybin fungus
US11331357B2 (en) 2020-06-17 2022-05-17 Psilo Scientific Ltd. Methods and compositions comprising psychoactive compounds from psychoactive organisms
IL299448B1 (en) * 2020-06-17 2025-07-01 Psilo Scientific Ltd Process for obtaining a purified psychoactive alkaloid solution
EP4161547A4 (en) * 2020-06-17 2023-11-01 Psilo Scientific Ltd METHANOL-BASED EXTRACTION OF PSYCHOACTIVE COMPOUNDS FROM MUSHROOMS
EP4161546A4 (en) * 2020-06-17 2024-10-09 Psilo Scientific Ltd COMPOSITIONS WITH PSYCHOACTIVE COMPOUNDS FROM PSYCHOACTIVE ORGANISMS
IL299448B2 (en) * 2020-06-17 2025-11-01 Psilo Scientific Ltd Process for obtaining a purified psychoactive alkaloid solution
EP4339200A3 (en) * 2020-06-17 2024-03-27 Psilo Scientific Ltd Ethanol extraction of psychoactive compounds from psilocybin fungus
IL298561B1 (en) * 2020-06-17 2025-06-01 Psilo Scientific Ltd Methanol-based extraction of psychoactive compounds from mushrooms
US11642385B2 (en) 2020-06-17 2023-05-09 Psilo Scientific Ltd. Basic extraction of psychoactive compounds from psychoactive organisms
US11571450B2 (en) 2020-06-17 2023-02-07 Psilo Scientific Ltd Aqueous extraction of psychoactive compounds from psilocybin fungus
US11786506B2 (en) 2020-12-28 2023-10-17 Psilo Scientific Ltd Transmucosal psychoactive alkaloid composition and preparation thereof
WO2022140851A1 (en) * 2020-12-28 2022-07-07 Psilo Scientific Ltd Injectable psychoactive alkaloid composition and preparation thereof
US12070446B2 (en) 2020-12-28 2024-08-27 Psilo Scientific, Ltd. Standardized psychoactive alkaloid extract composition
US11491138B2 (en) 2020-12-28 2022-11-08 Psilo Scientific Ltd. Injectable psychoactive alkaloid composition and preparation thereof
US11992476B2 (en) 2020-12-28 2024-05-28 Psilo Scientific Ltd Transdermal psychoactive alkaloid composition and preparation thereof
US11957659B2 (en) 2020-12-28 2024-04-16 Psilo Scientific Ltd. Transmucosal dephosphorylated psychoactive alkaloid composition and preparation thereof
US12331020B2 (en) 2020-12-31 2025-06-17 1280225 B.C. Ltd. Method of synthesizing indole compounds
EP4387616A4 (en) * 2021-10-18 2024-11-13 Psilo Scientific Ltd EXTRACTION OF PURIFIED PSYCHOACTIVE ALKALOID USING ACIDIFIED ACETONE
US12060328B2 (en) 2022-03-04 2024-08-13 Reset Pharmaceuticals, Inc. Co-crystals or salts of psilocybin and methods of treatment therewith

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