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Psilocin

 

Psilocin

Psilocin
Chemical name4-hydroxy-N,N-dimethyl-tryptamine or
3-(2-(dimethylamino)ethyl)-1H-indol-4-ol
Chemical formulaC12H16N2O
Molecular mass204.27 g/mol
Melting point173 - 176 °C
CAS number520-53-6
SMILESOC1=CC=CC2=C1C(CCN(C)C)=CN2

Psilocin is a mushroom alkaloid and derivative of the psychedelic hallucinogenic drug psilocybin. It is found in most magic mushrooms together with psilocybin. It is a psychedelic hallucinogenic drug.

History

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

Chemistry

Psilocin is obtained by dephosphorylation of psilocybin under strongly acidic or alkaline conditions. Psilocin is relatively unstable 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 a basic amine and forms salts with acids that are usually more stable upon storage. Psilocin base can be evaporated by heating.

Pharmacology

Please read under psilocybin for more details.

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

See also


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