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

Crystal structure of serotonin

Marilyn Naeem  1 , Andrew R Chadeayne  2 , James A Golen  1 , David R Manke  1
Affiliations

Crystal structure of serotonin

Marilyn Naeem et al. Acta Crystallogr E Crystallogr Commun. .

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 [Ca-Ca-Cm-Cm and Ca-Cm-Cm-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.

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Figures

Figure 1
Figure 1
The mol­ecular structure of serotonin free base showing the atomic labeling. Displacement ellipsoids are drawn at the 50% probability level.
Figure 2
Figure 2
The different hydrogen-bonding inter­actions between the serotonin mol­ecules. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity. Symmetry codes: (i) formula image  − x, 1 − y, formula image  + z (ii) 2 − x, − formula image  + y, formula image  − z (iii) 3/2 − x, −y, − formula image  + z.
Figure 3
Figure 3
The crystal packing of serotonin free base viewed along the a-axis. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonds are omitted for clarity.
See this image and copyright information in PMC

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    Naeem M, Le AN, Bauer BE, Chadeayne AR, Golen JA, Manke DR. Naeem M, et al. Acta Crystallogr E Crystallogr Commun. 2023 Jul 25;79(Pt 8):752-756. doi: 10.1107/S2056989023006217. eCollection 2023 Jul 1. Acta Crystallogr E Crystallogr Commun. 2023. PMID: 37601400 Free PMC article.
  • N-Methyl-serotonin hydrogen oxalate.
    Naeem M, Anas NA, Chadeayne AR, Golen JA, Manke DR. Naeem M, et al. IUCrdata. 2023 May 5;8(Pt 5):x230378. doi: 10.1107/S2414314623003784. eCollection 2023 May. IUCrdata. 2023. PMID: 37287863 Free PMC article.

References

    1. Akula, R., Giridhar, P. & Ravishankar, G. A. (2011). Plant Signal. Behav. 6, 800–809. - PMC - PubMed
    1. Amit, A., Mester, L., Klewe, B. & Furberg, S. (1978). Acta Chem. Scand. 32a, 267–270.
    1. Bacqué-Cazenave, J., Bharatiya, R., Barrière, G., Delbecque, J.-P., Bouguiyoud, N., Di Giovanni, G., Cattaert, D. & De Deurwaerdère, P. (2020). Int. J. Mol. Sci. 21, 1649. - PMC - PubMed
    1. Berger, M., Gray, J. A. & Roth, B. L. (2009). Annu. Rev. Med. 60, 355–366. - PMC - PubMed
    1. Bruker (2018). APEX3, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

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