ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
Structure Elucidation and Spectroscopic Analysis of Chromophores Produced by Oxidative Psilocin Dimerization.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Psilocybin Production With Genetically Modified Aspergillus nidulans Under Pressurized Conditions.Biotechnology and bioengineering · 2026Article
- Review
- Article
- Chemical Composition and Biological Activities ofPharmaceuticals (Basel, Switzerland) · 2025Review
- Comprehensive analysis of 42 psilocybin-producing fungal strains reveals metabolite diversity and species-specific clusters.Scientific reports · 2025Article
- Substrate recognition by the 4-hydroxytryptamine kinase PsiK in psilocybin biosynthesis.FEBS letters · 2025Article
- Cultivation, chemistry, and genome ofJournal of psychedelic studies · 2024Article
- Phylogenomics of the psychoactive mushroom genusProceedings of the National Academy of Sciences of the United States of America · 2024Article
- Indole Alkaloids from Psychoactive Mushrooms: Chemical and Pharmacological Potential as Psychotherapeutic Agents.Biomedicines · 2023Review
- Assessment of Bioactivity-Modulating Pseudo-Ring Formation in Psilocin and Related Tryptamines.Chembiochem : a European journal of chemical biology · 2022Article
- Structure Elucidation and Spectroscopic Analysis of Chromophores Produced by Oxidative Psilocin Dimerization.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
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Authors and funding
4 authors.
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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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