Psilocin

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Psilocin chemical structure Psilocin
4-Hydroxy-N,N-dimethyl-tryptamine IUPAC name
CAS number 520-53-6	ATC code [[ATC_code_|]][1]
PubChem [2]	DrugBank {{{DrugBank}}}
Chemical formula	{{{chemical_formula}}}
Molecular weight	204.27 g/mol
Bioavailability
Metabolism
Elimination half-life
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Psilocin, sometimes called psilocine or psilotsin, is a psychedelic (hallucinogenic) mushroom alkaloid. It is found in most psychedelic mushrooms together with its close congener psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances.

Psilocin is almost identical to the chemical structure of the chemical of another known hallucinogen, bufotenin. The only difference is the position of the hydroxyl (OH-) group on the benzene ring - in psilocin, the hydroxyl group is at the 4-position in the indole ring, and in bufotenin, the hydroxyl group is at the 5-position on the indole ring.

History

The Swiss chemist Albert Hofmann and the laboratory assistant Hans Tscherter from Sandoz Laboratories isolated psilocin and its phosphate ester psilocybin from Psilocybe mushrooms in 1959 guided by self-administration.

Chemistry

Psilocin can be obtained by dephosphorylation of natural psilocybin under strongly acidic or under alkaline conditions (hydrolysis). One synthetic route uses the Speeter-Anthony tryptamine synthesis starting from 4-hydroxyindole.

Psilocin is relatively unstable in solution due to its phenolic OH group. Under alkaline conditions in the presence of oxygen it immediately forms bluish and dark black degradation products. Similar products are also formed under acidic conditions in the presence of oxygen and Fe³⁺ ions (Keller's reagent, FeCl₃ / MeOH / HCl). Psilocin is an amine and forms salts with acids [citation needed] that are usually more stable upon storage. Psilocin base can be evaporated by heating.

Pharmacology

Psilocin is the pharmacologically active agent in the body after ingestion of psilocybin or psychedelic mushrooms.

See psilocybin for more details.

See also

• Psychedelic mushrooms
• Psilocybin
• Tryptamine
• Indole
• Psychedelic drug
• Psychoactive drug
• Manna
• Teonanactl
• Ayahuasca
• Soma

External links

• The Ones That Stain Blue Studies in ethnomycology including the contributions of Maria Sabina, Dr. Albert Hofmann and Dr. Gaston Guzman.
• The Shroomery Detailed information about Psilocybin mushrooms including identification, cultivation and spores, psychedelic images, trip reports, a dosage calculator and an active community.
• 4-HO-DMT entry in TiHKAL

• Link page to external chemical sources.

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