Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 47, Pages 12166-12171Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202101382
Keywords
bufotenin; chromophores; oxidation; psilocybin; tryptamine
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Funding
- International Leibniz Research School (ILRS) for Microbial Interactions
- Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) [239748522-SFB 1127]
- Usona Institute (Madison, WI)
- Projekt DEAL
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Psilocin is the dephosphorylated and psychotropic metabolite of psilocybin, and the blue color stems from the quinoid 7,7'-coupled dimer of psilocin.
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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