Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin

J Nat Prod. 2020 Feb 28;83(2):461-467. doi: 10.1021/acs.jnatprod.9b01061. Epub 2020 Feb 20.

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Agaricales
  • Alkaloids / chemistry*
  • Animals
  • Hallucinogens / chemistry*
  • Indoles / chemistry*
  • Mice
  • Molecular Structure
  • Organophosphates / chemistry*
  • Organophosphorus Compounds / chemistry*
  • Psilocybin / chemistry*
  • Tryptamines / chemistry*

Substances

  • Alkaloids
  • Hallucinogens
  • Indoles
  • N, N, N-trimethyl-4-phosphoryloxytryptamine
  • Organophosphates
  • Organophosphorus Compounds
  • Tryptamines
  • baeocystin
  • Psilocybin
  • tryptamine