Crystal structure of serotonin

Marilyn Naeem; Andrew R Chadeayne; James A Golen; David R Manke

doi:10.1107/S2056989022002559

Crystal structure of serotonin

Acta Crystallogr E Crystallogr Commun. 2022 Mar 10;78(Pt 4):365-368. doi: 10.1107/S2056989022002559. eCollection 2022 Apr 1.

Authors

Marilyn Naeem¹, Andrew R Chadeayne², James A Golen¹, David R Manke¹

Affiliations

¹ University of Massachusetts Dartmouth, 285 Old Westport Road, North Dartmouth, MA 02747, USA.
² CaaMTech, Inc., 58 East Sunset Way, Suite 209, Issaquah, WA 98027, USA.

Abstract

The title compound, serotonin or 5-hy-droxy-tryptamine (5-HT) [systematic name: 3-(2-amino-eth-yl)-1H-indol-5-ol], C₁₀H₁₂N₂O, has one mol-ecule in the asymmetric unit. The conformation of the ethyl-amino side chain is gauche-gauche [C_a-C_a-C_m-C_m and C_a-C_m-C_m-N (a = aromatic, m = methyl-ene) torsion angles = -64.2 (3) and -61.9 (2)°, respectively]. In the crystal, the mol-ecules are linked into a three-dimensional network by N-H⋯O and O-H⋯N hydrogen bonds.

Keywords: crystal structure; free base; indole; serotonin; tryptamine.

Grants and funding

This work was funded by National Science Foundation, Directorate for Mathematical and Physical Sciences grant CHE-1429086.