Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin
Synthesis June 1, 1999 DOI: 10.1055/s-1999-3490 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Methodological paper Peer reviewed |
|---|---|
| Topics | Psilocybin |
| Keywords | Lithium medication Acetic anhydride Formylation Organic chemistry Nuclear chemistry Hallucinogen |
| Citations | 68 |
| Key points | An improved synthesis of psilocybin via O-lithium salt and tetra-O-benzylpyrophosphate is described, and 4-acetoxy-N,N-dimethyltryptamine is proposed as a practical alternative for pharmacological research. |
Abstract
An improved procedure to accomplish the O-phosphor- ylation of 4-hydroxy-N,N-dimethyltryptamine (psilocin 5) is report- ed that utilizes reaction between the O-lithium salt of 5 and tetra-O- benzylpyrophosphate. The O-benzyl groups were removed by cata- lytic hydrogenation over palladium on carbon to afford N,N-dime- thyl-4-phosphoryloxytryptamine (psilocybin, 1). In view of difficulties encountered in the preparation of 1, it is suggested that 4-acetoxy-N,N-dimethyltryptamine (2) may be a useful alternative for pharmacological studies. The latter was obtained following cat- alytic O-debenzylation of 4-benzyloxy-N,N-dimethyltryptamine in the presence of acetic anhydride and sodium acetate.
Citations in the library
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- The Therapeutic Potential of Psilocybin Molecules May 15, 2021
- Psilocybin: from ancient magic to modern medicine The Journal of Antibiotics May 12, 2020
- Persisting Reductions in Cannabis, Opioid, and Stimulant Misuse After Naturalistic Psychedelic Use: An Online Survey Frontiers in Psychiatry January 22, 2020
- DARK Classics in Chemical Neuroscience: Psilocybin ACS Chemical Neuroscience June 29, 2018
- Metabolic engineering of Saccharomyces cerevisiae for the de novo production of psilocybin and related tryptamine derivatives Metabolic Engineering March 26, 2020
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