Chemoenzymatic Synthesis of 5-Methylpsilocybin: A Tryptamine with Potential Psychedelic Activity
| Autor: | Janis Fricke, Adam L. Halberstadt, Alexander M. Sherwood, Robert B. Kargbo, Dirk Hoffmeister |
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| Rok vydání: | 2021 |
| Předmět: |
Tryptamine
Psilocybe cubensis Pharmaceutical Science Dimethyltryptamine 01 natural sciences Article Analytical Chemistry Psilocybin Mice chemistry.chemical_compound Drug Discovery medicine Animals Bioassay Pharmacology chemistry.chemical_classification Chromatography Molecular Structure biology 010405 organic chemistry Chemistry Kinase Organic Chemistry biology.organism_classification Tryptamines 0104 chemical sciences 010404 medicinal & biomolecular chemistry Enzyme Complementary and alternative medicine Hallucinogens Molecular Medicine Psilocybe medicine.drug |
| Zdroj: | J Nat Prod |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/acs.jnatprod.1c00087 |
| Popis: | A novel analogue of psilocybin was produced by hybrid chemoenzymatic synthesis in sufficient quantity to enable bioassay. Utilizing purified 4-hydroxytryptamine kinase from Psilocybe cubensis, chemically synthesized 5-methylpsilocin (2) was enzymatically phosphorylated to provide 5-methylpsilocybin (1). The zwitterionic product was isolated from the enzymatic step with high purity utilizing a solvent–antisolvent precipitation approach. Subsequently, 1 was tested for psychedelic-like activity using the mouse head-twitch response assay, which indicated activity that was more potent than the psychedelic dimethyltryptamine, but less potent than that of psilocybin. |
| Databáze: | OpenAIRE |
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