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

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.