Active Metabolite of Aeruginascin (4-Hydroxy-N,N,N-trimethyltryptamine): Synthesis, Structure, and Serotonergic Binding Affinity
ACS Omega – July 02, 2020
Source: OpenAlex
Summary
A key active metabolite from "magic mushrooms" has been synthesized, revealing its potent serotonergic chemistry and stereochemistry. This tryptamine, an alkaloid, shows high affinity for human 5-HT receptors 5-HT<sub>1A</sub>, 5-HT<sub>2A</sub>, and 5-HT<sub>2B</sub>, as demonstrated by competitive radioligand assays. This biochemistry is crucial for understanding its effects. Interestingly, it does not bind to the 5-HT<sub>3</sub> receptor, contrary to prior predictions. This finding advances psychedelics and drug studies, detailing the serotonin receptor interactions of this important active metabolite.
Abstract
The putative active metabolite of aeruginascin, a naturally occurring tryptamine of "magic mushrooms," has been synthesized and structurally characterized. Competitive radioligand binding assays demonstrate that it has a high affinity at human serotonin receptors 5-HT1A, 5-HT2A, and 5-HT2B, though it does not bind at the 5-HT3 receptor, where activity was previously predicted.