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

Abstract

The solid-state structures of N-cyclo-hexyl-tryptamine (I) {systematic name: N-[2-(1H-indol-3-yl)eth-yl]cyclo-hexa-namine}, C₁₆H₂₂N₂, 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}, C₁₆H₂₃N₂ ⁺·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), 2C₁₆H₂₃N₂ ⁺·C₄H₂O₄ ^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.

Keywords: crystal structure; hydrogen bonds; indoles; tryptamines.