Psilocin

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Psilocin
Systematic (IUPAC) name
4-Hydroxy-N,N-dimethyl-tryptamine
Identifiers
CAS number	520-53-6
ATC code	?
PubChem	?
Chemical data
Formula	C₁₂H₁₆N₂O
Mol. mass	204.27 g/mol
SMILES	search in eMolecules, PubChem
Physical data
Melt. point	173–176 °C (343–349 °F)
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Prohibited (S9)(AU) Schedule III(CA) Class A(UK) Schedule I(US)
Routes	?

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.^[1]

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.

1 History
2 Chemistry
3 Pharmacology
4 See also
5 References
6 External links

[edit] History

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

[edit] 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 that are usually more stable upon storage. Psilocin base can be evaporated by heating.

[edit] Pharmacology

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

See psilocybin for more details.

[edit] See also

[edit] References

^ "Green list"

[edit] 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