Active Metabolite of Aeruginascin (4-Hydroxy‑N,N,N‑trimethyltryptamine): Synthesis, Structure, and Serotonergic Binding Affinity

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.