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

• Published in: Acta crystallographica. Section E, Crystallographic communications Vol. 79; no. Pt 8; pp. 752 - 756
• Main Authors: Naeem, Marilyn, Le, Alexander N, Bauer, Barbara E, Chadeayne, Andrew R, Golen, James A, Manke, David R
• Format: Journal Article
• Language: English
• Published: International Union of Crystallography 25.07.2023
• Subjects: Research Communications
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989023006217

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