ArticleChembiochem : a European journal of chemical biology2022
Assessment of Bioactivity-Modulating Pseudo-Ring Formation in Psilocin and Related Tryptamines.
Article in Chembiochem : a European journal of chemical biology, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 23 citations in OpenAlex.
- Serotonergic psychedelics induce distinct patterns of metabolic activity and covariance within biologically informed rat brain networks.Nature communications · 2026Article
- The Role of Hydrogen Bond Donors and Intramolecular Hydrogen Bonding in Modulating Blood-Brain Barrier Permeability: Implications for CNS Drug Design.Molecules (Basel, Switzerland) · 2026Review
- Naturally Derived Psilocybin for Therapeutic Use: A Six-Criterion Framework for Evidence, Safety, and Benefit-Risk Considerations in Policy and Clinical Development.Biomolecules · 2026Review
- Short- and Long-Acting Psychedelics: Structure-Activity Relationships, Pharmacology, and Implications for Neuropsychiatric Therapeutics.ACS chemical neuroscience · 2026Review
- Dissimilar Reactions and Enzymes for Psilocybin Biosynthesis in Inocybe and Psilocybe Mushrooms.Angewandte Chemie (International ed. in English) · 2025Article
- Efficient Acyloxymethylation of Psilocin and Other Tryptamines Yielding ACOM Prodrugs for Psychedelic-Assisted Therapy.Archiv der Pharmazie · 2025Article
- Pseudo-Ring Methodology to Control the Conformations of Macrocyclic Peptides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Substrate recognition by the 4-hydroxytryptamine kinase PsiK in psilocybin biosynthesis.FEBS letters · 2025Article
- High-resolution tracking of unconfined zebrafish behavior reveals stimulatory and anxiolytic effects of psilocybin.Molecular psychiatry · 2024Article
- Methyl transfer in psilocybin biosynthesis.Nature communications · 2024Article
- Novel Psilocin Prodrugs with Altered Pharmacological Properties as Candidate Therapies for Treatment-Resistant Anxiety Disorders.Journal of medicinal chemistry · 2024Article
- Psychedelic-like Activity of Norpsilocin Analogues.ACS chemical neuroscience · 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
Corrections and comments
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Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Psilocybin (1) is the major alkaloid found in psychedelic mushrooms and acts as a prodrug to psilocin (2, 4-hydroxy-N,N-dimethyltryptamine), a potent psychedelic that exerts remarkable alteration of human consciousness. In contrast, the positional isomer bufotenin (7, 5-hydroxy-N,N-dimethyltryptamine) differs significantly in its reported pharmacology. A series of experiments was designed to explore chemical differences between 2 and 7 and specifically to test the hypothesis that the C-4 hydroxy group of 2 significantly influences the observed physical and chemical properties through pseudo-ring formation via an intramolecular hydrogen bond (IMHB). NMR spectroscopy, accompanied by quantum chemical calculations, was employed to compare hydrogen bond behavior in 4- and 5-hydroxylated tryptamines. The results provide evidence for a pseudo-ring in 2 and that sidechain/hydroxyl interactions in 4-hydroxytryptamines influence their oxidation kinetics. We conclude that the propensity to form IMHBs leads to a higher number of uncharged species that easily cross the blood-brain barrier, compared to 7 and other 5-hydroxytryptamines, which cannot form IMHBs. Our work helps understand a fundamental aspect of the pharmacology of 2 and should support efforts to introduce it (via the prodrug 1) as an urgently needed therapeutic against major depressive disorder.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.