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Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin

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    Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin
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    • Alexander M. Sherwood*
      Alexander M. Sherwood
      Usona Institute, 2780 Woods Hollow Road, Madison, Wisconsin 53711, United States
      *E-mail: [email protected]
      More by Alexander M. Sherwood
      Orcidhttp://orcid.org/0000-0003-0895-0791
    • Adam L. Halberstadt
      Adam L. Halberstadt
      Department of Psychiatry, University of California San Diego, La Jolla, California 92093, United States
      Research Service, VA San Diego Healthcare System, San Diego, California 92161, United States
      More by Adam L. Halberstadt
    • Adam K. Klein
      Adam K. Klein
      Department of Psychiatry, University of California San Diego, La Jolla, California 92093, United States
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    • John D. McCorvy
      John D. McCorvy
      Department of Cell Biology, Neurobiology, and Anatomy, Medical College of Wisconsin, Milwaukee, Wisconsin 53226, United States
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    • Kristi W. Kaylo
      Kristi W. Kaylo
      Usona Institute, 2780 Woods Hollow Road, Madison, Wisconsin 53711, United States
      More by Kristi W. Kaylo
    • Robert B. Kargbo
      Robert B. Kargbo
      Usona Institute, 2780 Woods Hollow Road, Madison, Wisconsin 53711, United States
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    • Poncho Meisenheimer
      Poncho Meisenheimer
      Usona Institute, 2780 Woods Hollow Road, Madison, Wisconsin 53711, United States
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    Journal of Natural Products

    Cite this: J. Nat. Prod. 2020, 83, 2, 461–467
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    https://doi.org/10.1021/acs.jnatprod.9b01061
    Published February 20, 2020
    Copyright © 2020 American Chemical Society and American Society of Pharmacognosy
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    A general synthetic method was developed to access known tryptamine natural products present in psilocybin-producing mushrooms. In vitro and in vivo experiments were then conducted to inform speculations on the psychoactive properties, or lack thereof, of the natural products. In animal models, psychedelic activity by baeocystin alone was not evident using the mouse head twitch response assay, despite its putative dephosphorylated metabolite, norpsilocin, possessing potent agonist activity at the 5-HT2A receptor.

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    • 1H and 13C NMR spectra for all final products and intermediates; UPLC chromatograms and low/high collision energy HRMS spectra for 4–7 (PDF)

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    This article is cited by 52 publications.

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    Journal of Natural Products

    Cite this: J. Nat. Prod. 2020, 83, 2, 461–467
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jnatprod.9b01061
    Published February 20, 2020
    Copyright © 2020 American Chemical Society and American Society of Pharmacognosy
    Request reuse permissions

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