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Structure Elucidation and Spectroscopic Analysis of Chromophores Produced by Oxidative Psilocin Dimerization

Claudius Lenz, Sebastian Dörner, Alexander M. Sherwood, Dirk Hoffmeister

Chemistry - A European Journal June 1, 2021 DOI: 10.1002/chem.202101382 (opens in new tab)

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Study at a glance

AI-extracted from the abstract
Characteristics Experimental study Peer reviewed
Topics Psilocybin
Keywords Bufotenin Psilocybin chemistry psilocybin Molecular structure Unique chemistry 5'-coupled psilocin dimer 7'-coupled quinoid chromophores Chemical oxidation oxidation Oxidized tryptamine derivatives Result of oxidation Chromophore identification chromophores Blue chromophores Vivid blue
Citations 19
Key findings The blue color of bruised psilocybin-producing mushrooms stems from the quinoid 7,7'-coupled dimer of psilocin, not the previously hypothesized 5,5'-coupled quinone dimer.

Abstract

Abstract Psilocin ( 1 ) is the dephosphorylated and psychotropic metabolite of the mushroom natural product psilocybin. Oxidation of the phenolic hydroxy group at the C‐4 position of 1 results in formation of oligomeric indoloquinoid chromophores responsible for the iconic blueing of bruised psilocybin‐producing mushrooms. Based on previous NMR experiments, the hypothesis included that the 5,5’‐coupled quinone dimer of 1 was the primary product responsible for the blue color. To test this hypothesis, ring‐methylated 1 derivatives were synthesized to provide stable analogs of 1 dimers that could be completely characterized. The chemically oxidized derivatives were spectroscopically analyzed and compared to computationally derived absorbance spectra. Experimental evidence did not support the original hypothesis. Rather, the blue color was shown to stem from the quinoid 7,7’‐coupled dimer of 1 .

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Long-term follow-up of psilocybin-assisted psychotherapy for psychiatric and existential distress in patients with life-threatening cancer Participants with cancer-related psychiatric distress who completed a parent randomized... 2020 Long-term within-subjects follow-up analysis n = 15
Enzymatic Synthesis of Psilocybin 2017 Laboratory study

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