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Journal of the Chilean Chemical Society

On-line version ISSN 0717-9707

Abstract

TIRAPEGUI, CRISTIAN; TORO-SAZO, MIGUEL A  and  CASSELS, BRUCE K. SYNTHESIS OF N-(HALOGENATED) BENZYL ANALOGS OF SUPERPOTENT SEROTONIN LIGANDS. J. Chil. Chem. Soc. [online]. 2014, vol.59, n.3, pp.2625-2627. ISSN 0717-9707.  http://dx.doi.org/10.4067/S0717-97072014000300022.

In the last four years a group of extremely potent designer drugs, the N-benzylated phenylethylamines known as the NBOMe series, has surfaced on the street and in the news media. Although data documenting their high affinity and preference for 5-HT2 serotonin receptors abound (5-HT2A receptor activation is generally associated with the action of the "classical" hallucinogens), relatively little is known about the molecular basis of their potency and selectivity. In the setting of a project aiming to evaluate the possible involvement of halogen bonds in the binding of monoaminergic ligands to their receptors, we have begun to synthesize halogenated derivatives of known N-benzylated compounds for their pharmacological study. Here we report the synthesis of new phenylethylamine and tryptamine derivatives incorporating bromine atoms in their N-benzyl moiety.

Keywords : designer drugs; N-benzylphenylethylamine; N-benzyltryptamine; synthesis.

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