Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin
Journal of Natural Products – February 20, 2020
Source: OpenAlex
Summary
A compelling finding reveals not all tryptamines in psilocybin-producing mushrooms are hallucinogens. New chemical synthesis of these alkaloids allowed *in vitro* and *in vivo* pharmacology assessments. Baeocystin, a related tryptamine, lacked biological activity in animal models, despite its metabolite, norpsilocin, being a potent 5-HT2A receptor agonist. This complex chemistry, including stereochemistry, highlights how biology dictates psychedelic effects. Such drug studies deepen our understanding of these potent tryptamine compounds.
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.