Identification of ω-N-Methyl-4-hydroxytryptamine (Norpsilocin) as a Psilocybe Natural Product
Claudius Lenz, Jonas Wick, Dirk Hoffmeister
Journal of Natural Products September 20, 2017 DOI: 10.1021/acs.jnatprod.7b00407 via OpenAlex
Summary
AI-generated from the abstractA previously unreported natural compound, ω-N-methyl-4-hydroxytryptamine (norpsilocin), was identified in the fruiting bodies of the hallucinogenic mushroom Psilocybe cubensis. Its structure was determined using NMR spectroscopy and high-resolution mass spectrometry. Norpsilocin is likely the actual psychoactive agent released from its phosphate ester derivative, the known natural product baeocystin. The authors also developed a simple extraction method that avoids dephosphorylation, thereby preserving the natural metabolic profile of Psilocybe mushrooms for analysis.
Study at a glance
| Characteristics | Chemical identification and method development Peer reviewed |
|---|---|
| Population | Psilocybe cubensis carpophores (fruiting bodies) |
| Topics | Psilocybin |
| Keywords | Natural product Stereochemistry Mushroom Dephosphorylation |
| Citations | 62 |
| Key finding | Norpsilocin, a new natural product from Psilocybe cubensis, is likely the active psychotropic agent derived from baeocystin. |
Abstract
We report the identification of ω-N-methyl-4-hydroxytryptamine (norpsilocin, 1) from the carpophores of the hallucinogenic mushroom Psilocybe cubensis. The structure was elucidated by 1D and 2D NMR spectroscopy and high-resolution mass spectrometry. Norpsilocin has not previously been reported as a natural product. It likely represents the actual psychotropic agent liberated from its 4-phosphate ester derivative, the known natural product baeocystin. We further present a simple and artifact-free extraction method that prevents dephosphorylation and therefore helps reflect the naturally occurring metabolic profile of Psilocybe mushrooms in subsequent analyses.