Psilocin

Psilocin
Clinical data


Routes of administration	Oral, IV
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited) CA: Schedule III DE: Anlage I (Controlled) NZ: Class A UK: Class A US: Schedule I
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	1-3 hours
Excretion	Urine
Identifiers
IUPAC name 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol
Synonyms	4-hydroxy-N,N-dimethyltryptamine
CAS Number	520-53-6^N
PubChem (CID)	4980
ChemSpider	4807^Y
KEGG	C08312^Y
ChEBI	CHEBI:8613^Y
ChEMBL	CHEMBL65547^Y
ECHA InfoCard	100.007.543
Chemical and physical data
Formula	C₁₂H₁₆N₂O
Molar mass	204.27 g/mol
3D model (Jmol)	Interactive image
Melting point	173 to 176 °C (343 to 349 °F)
SMILES Oc1cccc2c1c(cn2)CCN(C)C
InChI InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3^Y Key:SPCIYGNTAMCTRO-UHFFFAOYSA-N^Y
^NY (what is this?)

Psilocin (also known as 4-HO-DMT, psilocine, psilocyn, or psilotsin) is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. The mind-altering effects of psilocin are highly variable and subjective and resemble those of LSD and DMT.

Psilocin and its phosphorylated cousin, psilocybin, were first isolated and named in 1958 by Swiss chemist Albert Hofmann. Hofmann obtained the chemicals from laboratory-grown specimens of the entheogenic mushroom Psilocybe mexicana. Hofmann also succeeded in finding the synthetic routes to these chemicals.

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

Psilocin is relatively unstable in solution due to its phenolic hydroxy (-OH) group. In the presence of oxygen it readily 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).

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