Psilocin

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Psilocin
Image:Psilocin chemical structure.png
General
Systematic name	4-Hydroxy-N,N-dimethyl-tryptamine
Other names	3-(2-(Dimethylamino)ethyl)- 1H-indol-4-ol
Molecular formula	C₁₂H₁₆N₂O
SMILES	OC1=CC=CC2=C1C(CCN(C)C)=CN2
Molar mass	204.27 g/mol
CAS number	[520-53-6]
Properties
Melting point	173 - 176 °C (base)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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.<ref>"Green list"</ref>

Psilocin is almost identical to the chemical structure of the chemical of another known hallucinogen bufotenin, the only difference is the hydroxyl (OH-) group is moved one place over on the benzene 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

[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