N-Cyclo-hexyl-tryptamine: freebase, bromide and fumarate.

The solid-state structures of N-cyclo-hexyl-tryptamine (I) {systematic name: N-[2-(1H-indol-3-yl)eth-yl]cyclo-hexa-namine}, C(16)H(22)N(2), and two of its salts, N-cyclo-hexyl-tryptammonium bromide (II) {systematic name: N-[2-(1H-indol-3-yl)eth-yl]cyclo-hexa-naminium bromide}, C(16)H(23)N(2) (+)·Br(-), and N-cyclo-hexyl-tryptammonium fumarate (III) (systematic name: bis-{N-[2-(1H-indol-3-yl)eth-yl]cyclo-hexa-naminium} (2E)-but-2-enedioate), 2C(16)H(23)N(2) (+)·C(4)H(2)O(4) (2-), 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 inter-actions in two-dimensional sheets along (001). The fumarate salt is held together in infinite three-dimensional frameworks by N-H⋯O hydrogen bonds.