N-Cyclo­hexyl­tryptamine: freebase, bromide and fumarate

The solid-state structures of N-cyclo­hexyl­tryptamine (I) {systematic name: N-[2-(1H-indol-3-yl)eth­yl]cyclo­hexa­namine}, C(16)H(22)N(2), and two of its salts, N-cyclo­hexyl­tryptammonium bromide (II) {systematic name: N-[2-(1H-indol-3-yl)eth­yl]cyclo­hexa­naminium bromide}, C(16)H(23)N(2) (+)·Br(−), and N-cyclo­hexyl­tryptammonium fumarate (III) (systematic name: bis­{N-[2-(1H-indol-3-yl)eth­yl]cyclo­hexa­naminium} (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 inter­actions in two-dimensional sheets along (001). The fumarate salt is held together in infinite three-dimensional frameworks by N—H⋯O hydrogen bonds.