SYNTHESIS OF N-(HALOGENATED) BENZYL ANALOGS OF SUPERPOTENT SEROTONIN LIGANDS
Journal of the Chilean Chemical Society – September 01, 2014
Source: OpenAlex
Summary
The emergence of the NBOMe series, potent designer drugs, is noteworthy due to their high affinity for 5-HT2 serotonin receptors, crucial for hallucinogenic effects. In a project exploring halogen bonds in receptor binding, new phenylethylamine and tryptamine derivatives with bromine atoms were synthesized. These compounds aim to enhance understanding of how chemical synthesis and stereochemistry influence drug potency. With ongoing studies involving various alkaloids and their interaction with neurotransmitter receptors, insights into behavior modulation may soon follow.
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.