N-Cyclohexyltryptamine: freebase, bromide and fumarate

Abstract

The solid-state structures of N-cyclohexyltryptamine (I) {systematic name: N-[2-(1H-indol-3-yl)ethyl]cyclohexanamine}, C16H22N2, and two of its salts, N-cyclohexyltryptammonium bromide (II) {systematic name: N-[2-(1H-indol-3-yl)ethyl]cyclohexanaminium bromide}, C16H23N2+·Br−, and N-cyclohexyltryptammonium fumarate (III) (systematic name: bis{N-[2-(1H-indol-3-yl)ethyl]cyclohexanaminium} (2E)-but-2-enedioate), 2C16H23N2+·C4H2O42−, were determined by single-crystal X-ray diffraction. The freebase compound forms infinite chains along [010] through N—H...N hydrogen bonds. The bromide salt is held together by N—H...Br interactions in two-dimensional sheets along (001). The fumarate salt is held together in infinite three-dimensional frameworks by N—H...O hydrogen bonds.

Keywords

• crystal structure
• tryptamines
• indoles
• hydrogen bonds