Crystal structures of the Teonanácatl hallucinogens. Part II. Psilocin, C12H15N2O

Psilocin, the minor hallucinogenic component of the sacred Mexican mushroom Teonanácatl, crystallizes in the monoclinic space group P21/c with unit-cell dimensions a = 1060(3), b = 853(2), c = 1251(3) pm and β = 91.25(30)°. The structure, solved by direct methods and refined to R = 0.047, shows intermolecular hydrogen bonds between the ethylamino-nitrogen and the indole hydroxy-group. Disorder of the proton in this hydrogen bond indicates the crystal contains a statistical mixture of zwitterions and uncharged species. The molecular conformation of psilocin differs from that found in psilocybin.

Study at a glance

Abstract

The crystal structure of Psilocin, the minor hallucinogenic component of Teonanácatl, the sacred mushroom of Mexico, has been determined. Crystals are monoclinic, space group P21/c, a= 1060(3), b= 853(2), c= 1251(3) pm, β= 91·25(30)°. Data were collected on a linear diffractometer employing graphite monochromatised Mo-Kα radiation. The structure was solved by direct methods and refined by block diagonal least-squares to R 0·047 over 1132 significant data. There are intermolecular hydrogen bonds between the ethylamino-nitrogen and the indole hydroxy-group, and disorder of the proton in this hydrogen bond suggests that the crystal is composed of a statistical mixture of zwitterions and uncharged species. The molecular conformation is different from that found in psilocybin.