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

Andrew R Chadeayne; Duyen N K Pham; Brian G Reid; James A Golen; David R Manke

doi:10.1021/acsomega.0c02208

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

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

Authors

Andrew R Chadeayne¹, Duyen N K Pham², Brian G Reid³, James A Golen², David R Manke²

Affiliations

¹ CaaMTech, Inc., 58 East Sunset Way, Suite 209, Issaquah, Washington 98027, United States.
² Department of Chemistry & Biochemistry, University of Massachusetts Dartmouth, North Dartmouth, Massachusetts 02747, United States.
³ Canopy Growth USA, 35715 US Hwy 40, Suite D-102, Evergreen, Colorado 80439, United States.

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-HT_1A, 5-HT_2A, and 5-HT_2B, though it does not bind at the 5-HT₃ receptor, where activity was previously predicted.