Active Metabolite of Aeruginascin (4-Hydroxy-N,N,N-trimethyltryptamine): Synthesis, Structure, and Serotonergic Binding Affinity
A.r. Chadeayne, Duyen N. K. Pham, Brian G. Reid, James A. Golen, David R. Manke
ACS Omega July 2, 2020 DOI: 10.1021/acsomega.0c02208 via OpenAlex
Summary
AI-generated from the abstractAeruginascin, a naturally occurring tryptamine found in magic mushrooms, is thought to produce its effects through an active metabolite. This metabolite was synthesized and its structure confirmed. Competitive radioligand binding assays showed it binds with high affinity to human serotonin receptors 5-HT1A, 5-HT2A, and 5-HT2B, but does not bind to the 5-HT3 receptor, contrary to earlier predictions.
Study at a glance
| Characteristics | Laboratory study Peer reviewed |
|---|---|
| Topics | Serotonin |
| Keywords | Tryptamine Stereochemistry 5-HT Receptor |
| Citations | 31 |
| Key finding | The putative active metabolite of aeruginascin has high affinity at 5-HT1A, 5-HT2A, and 5-HT2B receptors but does not bind at the 5-HT3 receptor. |
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.