SYNTHESIS OF N-(HALOGENATED) BENZYL ANALOGS OF SUPERPOTENT SEROTONIN LIGANDS
Cristián Tirapegui, Miguel A Toro-Sazo, Bruce K. Cassels
Journal of the Chilean Chemical Society September 1, 2014 DOI: 10.4067/s0717-97072014000300022 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Chemical synthesis and pharmacological study Peer reviewed |
|---|---|
| Topics | Serotonin |
| Keywords | Moiety Monoaminergic Tryptamine Stereochemistry Hallucinogen Combinatorial chemistry Serotonin antagonists 5-HT Receptor |
| Citations | 1 |
| Key points | New phenylethylamine and tryptamine derivatives incorporating bromine atoms in their N-benzyl moiety were synthesized for pharmacological study. |
Abstract
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.