7925. Psilocin

Nomenclature

CAS number: 520-53-6
3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol; 4-hydroxy-N,N-dimethyltryptamine; psilocyn.
C12H16N2O; mol wt 204.27.
C 70.56%, H 7.89%, N 13.71%, O 7.83%.

Description and references

The minor hallucinogenic component of Teonanácatl, the sacred mushroom of Mexico. Isolated in trace amounts from the fruiting bodies of Psilocybe mexicana Heim, Agaricaceae: Hofmann et al., Experientia 14, 107 (1958); Heim et al., Helv. Chim. Acta 42, 1557 (1959). Prepn: Heim et al., DE 1087321 (1960 to Sandoz). Synthetic precursor of psilocybin: Hofmann, Troxler, US 3075992 (1963 to Sandoz). Psilocin, the 4-hydroxy analog of psilocybin, is formed by metabolic dephosphorylation of psilocybin and is the active species in the central nervous system: Horita, Weber, Toxicol. Appl. Pharmacol. 4, 730 (1962). Crystal structure: T. J. Petcher, H. P. Weber, J. Chem. Soc. Perkin Trans. 2 1974, 946. Review: Hofmann, Bull. Narc. 23, 3 (1971).

Chemical structure

Properties

Plates from methanol, mp 173-176°. Amphoteric substance. Unstable in soln, esp. akaline soln. Very slightly sol in water. uv max: 222, 260, 267, 283, 293 nm (log ε 4.6, 3.7, 3.8, 3.7, 3.6).

Note

This is a controlled substance (hallucinogen): 21 CFR, 1308.11.