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

The solid-state structures of N -cyclo-hexyl-tryptamine ( I ) {systematic name: N -[2-(1 H -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-(1 H -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-(1 H -indol-3-yl)eth-yl]cyclo-hexa-naminium} (2 E )-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.