Marine Inspired 2-(5-Halo-1H-indol-3-yl)-N,N-dimethylethanamines as Modulators of Serotonin Receptors: An Example Illustrating the Power of Bromine as Part of the Uniquely Marine Chemical Space
Marine Drugs October 26, 2018 Mohamed A. Ibrahim, Abir T. El-Alfy, Kelly Ezel et al. 22 citations
Several halogen-substituted tryptamine compounds were synthesized and tested for antidepressant and sedative effects in mice. Six compounds—1a, 1d, 2a, 2c, 2d, and 2e—showed significant antidepressant-like action in the forced swim test, while three (2c, 2d, 2e) also exhibited potent sedative activity in the locomotor activity test. Compounds 2a, 2c, 2d, and 2e bound to serotonin receptors 5-HT1A and 5-HT7 with nanomolar affinities. The in vitro data suggests that the antidepressant effects are mediated, at least in part, through interaction with serotonin receptors. Bromine substitutions were highlighted as valuable for creating novel chemical interactions.