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. 2020 Jul 2;5(27):16940-16943.
doi: 10.1021/acsomega.0c02208. eCollection 2020 Jul 14.

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

Andrew R Chadeayne  1 , Duyen N K Pham  2 , Brian G Reid  3 , James A Golen  2 , David R Manke  2
Affiliations

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

Andrew R Chadeayne et al. ACS Omega. .

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.

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Conflict of interest statement

The authors declare the following competing financial interest(s): Andrew R. Chadeayne and Brian G. Reid report ownership interests in CaaMTech, Inc., which owns U.S. and worldwide patent applications, covering new tryptamine compounds, compositions, formulations, novel crystalline forms, and methods of making and using the same.

Figures

Figure 1
Figure 1
Analogy of psilocybin and aeruginascin derivatives.
Scheme 1
Scheme 1. Synthesis of the Active Metabolite of Aeruginascin Where (a) MeI/MeOH and (b) AcOH/H2O
Figure 2
Figure 2
Crystal structures of the iodide salts of 4-AcO-TMT (top) and 4-HO-TMT (bottom) with thermal ellipsoids shown at the 50% probability level.
See this image and copyright information in PMC

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