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2-Bromomelatonin: Synthesis and characterization of a potent melatonin agonist

Authors
Journal
Life Sciences
0024-3205
Publisher
Elsevier
Publication Date
Volume
51
Issue
7
Identifiers
DOI: 10.1016/0024-3205(92)90024-j
Disciplines
  • Biology

Abstract

Abstract A practical synthesis of N-[2-(bromo-5-methoxy-1 H-indol-3-yl ethyl]-acetamide (2-bromomelatonin) was achieved by direct bromination of melatonin with N-bromosuccinimide (NBS) in anhydrous acetic acid at room temperature under nitrogen, followed by flash-chromatography. 1H-NMR and mass spectra showed the bromine to be incorporated at the C-2 position of the indole moiety. Tests performed in vitro with isolated melatonin receptors from rabbit parietal cortex demonstrated that the relative binding affinity of 2-bromomelatonin was about ten times higher than that of melatonin and close to that of 2-iodomelatonin. 2-Bromomelatonin behaved as a potent agonist in the physiological studies. It showed enhanced activity in inhibiting the spontaneous firing activity of cortical neurons and similarly to melatonin and 2-iodomelatonin potentiated significantly the inhibitory effect of GABA. 2-Bromomelatonin was also an extremely effective agonist in the tests performed in vivo in the Syrian hamster gonadal regression model.

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