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

ACS Omega
Andrew R ChadeayneDavid R Manke

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.

References

Sep 8, 2010·Archives of General Psychiatry·Charles S GrobGeorge R Greer
Jul 14, 2011·British Journal of Pharmacology·Ethan B Russo
Sep 13, 2014·Journal of Psychopharmacology·Matthew W JohnsonRoland R Griffiths
Jan 15, 2015·Journal of Psychopharmacology·Michael P BogenschutzRick J Strassman
Apr 14, 2016·The Lancet. Psychiatry·Michael C MithoeferTimothy D Brewerton
Jan 12, 2017·Drug Metabolism Reviews·Ricardo Jorge Dinis-Oliveira
Sep 21, 2017·Journal of Natural Products·Claudius LenzDirk Hoffmeister

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Citations

Nov 26, 2020·ChemPlusChem·Claudius LenzDirk Hoffmeister
Feb 23, 2021·Acta Crystallographica. Section E, Crystallographic Communications·Duyen N K PhamDavid R Manke
Feb 23, 2021·Acta Crystallographica. Section E, Crystallographic Communications·Duyen N K PhamDavid R Manke
Jun 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Henry LoweLorenzo Gordon

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Methods Mentioned

BETA
single-crystal diffraction

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