Norpsilocin: freebase and fumarate salt

Abstract

The solid-state structures of the naturally occurring psychoactive tryptamine norpsilocin {4-hydroxy- N -methyltryptamine (4-HO-NMT); systematic name: 3-[2-(methylamino)ethyl]-1 H -indol-4-ol}, C 11 H 14 N 2 O, and its fumarate salt (4-hydroxy- N -methyltryptammonium fumarate; systematic name: bis{[2-(4-hydroxy-1 H -indol-3-yl)ethyl]methylazanium} but-2-enedioate), C 11 H 15 N 2 O + ·0.5C 4 H 2 O 4 2− , are reported. The freebase of 4-HO-NMT has a single molecule in the asymmetric unit joined together by N—H...O and O—H...O hydrogen bonds in a two-dimensional network parallel to the (100) plane. The ethylamine arm of the tryptamine is modeled as a two-component disorder with a 0.895 (3) to 0.105 (3) occupancy ratio. The fumarate salt of 4-HO-NMT crystallizes with a tryptammonium cation and one half of a fumarate dianion in the asymmetric unit. The ions are joined together by N—H...O and O—H...O hydrogen bonds to form a three-dimensional framework, as well as π–π stacking between the six-membered rings of inversion-related indoles (symmetry operation: 2 − x , 1 − y , 2 – z ).