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 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Chemical identification and method development Peer reviewed |
|---|---|
| Population | Psilocybe cubensis carpophores (fruiting bodies) |
| Topics | Psilocybin |
| Keywords | Natural product Stereochemistry Mushroom Dephosphorylation Mass spectrometry Derivative finance Biochemistry Chromatography Pharmacology Hallucinogen Phosphatase Food science Enzyme Alkaloids |
| Citations | 62 |
| Key points | 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.
Citations in the library
Cited by 39
- Structure–Activity Relationships for Psilocybin, Baeocystin, Aeruginascin, and Related Analogues to Produce Pharmacological Effects in Mice ACS Pharmacology & Translational Science November 2, 2022
- Simultaneous Production of Psilocybin and a Cocktail of β‐Carboline Monoamine Oxidase Inhibitors in “Magic” Mushrooms Chemistry - A European Journal November 14, 2019
- Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin Journal of Natural Products February 20, 2020
- Stability of psilocybin and its four analogs in the biomass of the psychotropic mushroom Psilocybe cubensis Drug Testing and Analysis October 29, 2020
- In vitro and in vivo metabolism of psilocybin’s active metabolite psilocin Frontiers in Pharmacology April 29, 2024
and 34 more in the library
Cites 11
- Psilocybin with psychological support for treatment-resistant depression: an open-label feasibility study. The Lancet Psychiatry May 17, 2016
- Pilot Study of Psilocybin Treatment for Anxiety in Patients With Advanced-Stage Cancer Archives of General Psychiatry September 7, 2010
- Acute psychological and physiological effects of psilocybin in healthy humans: a double-blind, placebo-controlled dose?effect study Psychopharmacology March 1, 2004
- Psilocybin und Psilocin, zwei psychotrope Wirkstoffe aus mexikanischen Rauschpilzen Helvetica Chimica Acta 1959
- Enzymatic Synthesis of Psilocybin Angewandte Chemie International Edition August 1, 2017
and 6 more in the library