Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin
Alexander M. Sherwood, Adam L. Halberstadt, Adam K. Klein, John D. Mccorvy, Kristi W. Kaylo, Robert B. Kargbo, Poncho Meisenheimer
Journal of Natural Products February 20, 2020 DOI: 10.1021/acs.jnatprod.9b01061 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Experimental study Peer reviewed |
|---|---|
| Population | Mice |
| Interventions | baeocystin norpsilocin |
| Topics | Psilocybin |
| Keywords | Tryptamines Hallucinogen Metabolite Pharmacology Agonist Harmine In vivo Biological activity In vitro Stereochemistry Biochemistry Receptor Biotechnology Alkaloids |
| Citations | 79 |
| Key findings | Baeocystin alone did not show psychedelic activity in the mouse head twitch response assay, whereas its metabolite norpsilocin is a potent 5-HT2A receptor agonist. |
Abstract
A general synthetic method was developed to access known tryptamine natural products present in psilocybin-producing mushrooms. In vitro and in vivo experiments were then conducted to inform speculations on the psychoactive properties, or lack thereof, of the natural products. In animal models, psychedelic activity by baeocystin alone was not evident using the mouse head twitch response assay, despite its putative dephosphorylated metabolite, norpsilocin, possessing potent agonist activity at the 5-HT2A receptor.