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Identification of ω-N-Methyl-4-hydroxytryptamine (Norpsilocin) as a Psilocybe Natural Product

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    Identification of ω-N-Methyl-4-hydroxytryptamine (Norpsilocin) as a Psilocybe Natural Product
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    Department of Pharmaceutical Microbiology at the Hans-Knöll-Institute, Friedrich-Schiller-Universität Jena, Winzerlaer Strasse 2, 07745 Jena, Germany
    *Phone: +49 3641 949850. Fax: +49 3641 949852. E-mail: [email protected]
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    Journal of Natural Products

    Cite this: J. Nat. Prod. 2017, 80, 10, 2835–2838
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    https://doi.org/10.1021/acs.jnatprod.7b00407
    Published September 20, 2017
    Copyright © 2017 The American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    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.

    Copyright © 2017 The American Chemical Society and American Society of Pharmacognosy

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    Cite this: J. Nat. Prod. 2017, 80, 10, 2835–2838
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jnatprod.7b00407
    Published September 20, 2017
    Copyright © 2017 The American Chemical Society and American Society of Pharmacognosy
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