Identification of ω-N-Methyl-4-hydroxytryptamine (Norpsilocin) as a Psilocybe Natural Product
| Autor: | Jonas Wick, Claudius Lenz, Dirk Hoffmeister |
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| Rok vydání: | 2017 |
| Předmět: |
Serotonin
Indoles Stereochemistry Psilocybe cubensis Pharmaceutical Science 010402 general chemistry Mass spectrometry 01 natural sciences Analytical Chemistry chemistry.chemical_compound Alkaloids Drug Discovery Organic chemistry Pharmacology Biological Products Mushroom Psilocybe Natural product Molecular Structure biology 010405 organic chemistry Organic Chemistry biology.organism_classification Organophosphates 0104 chemical sciences Baeocystin Complementary and alternative medicine chemistry Hallucinogens Molecular Medicine Agaricales Two-dimensional nuclear magnetic resonance spectroscopy Derivative (chemistry) |
| Zdroj: | Journal of Natural Products. 80:2835-2838 |
| ISSN: | 1520-6025 0163-3864 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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