Identification of ω-N-Methyl-4-hydroxytryptamine (Norpsilocin) as a Psilocybe Natural Product
Journal of Natural Products – September 20, 2017
Source: OpenAlex
Summary
Norpsilocin, a previously unidentified natural product from the hallucinogenic mushroom Psilocybe cubensis, has been isolated and characterized using advanced techniques like NMR spectroscopy and high-resolution mass spectrometry. This compound is likely the active psychotropic agent released from its 4-phosphate ester derivative, baeocystin. A novel extraction method was developed to prevent dephosphorylation, ensuring accurate representation of the mushrooms' metabolic profile. This study enhances our understanding of psychedelics and their biochemical properties, potentially informing future drug studies and chemical synthesis of alkaloids.
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.