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. 2013 Sep;69(Pt 9):1055-61.
doi: 10.1107/S0108270113019823. Epub 2013 Aug 7.

A new structure of a serotonin salt: comparison and conformational analysis of all known serotonin complexes

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A new structure of a serotonin salt: comparison and conformational analysis of all known serotonin complexes

Denis Rychkov et al. Acta Crystallogr C. 2013 Sep.

Abstract

Four serotonin salt structures (serotonin adipate, C10H13N2O(+)·C6H9O4(-), is a previously unknown structure) were analysed to understand the influence of the anion on serotonin conformation. Hydrogen bonding alone favours a flat conformation, whereas additional stacking interactions between ions may possibly account for the nonplanar conformation. Since molecular conformation, stability and biological activity are interrelated, one can consider influencing the chemical and biological properties of serotonin by selecting an appropriate counter-ion for salt formation.

Keywords: Hirshfeld surfaces; conformation; crystal structure; hydrogen bonding; serotonin adipate; stacking interactions.

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