Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin
Synthesis – June 01, 1999
Source: OpenAlex
Summary
An improved organic chemistry method now allows for more efficient chemical synthesis of psilocybin, a potent hallucinogen. This advance, crucial for Psychedelics and Drug Studies, involves using a lithium salt of psilocin and specific reagents to create the psychedelic alkaloid. The process also yields an alternative, 4-acetoxy-N,N-dimethyltryptamine, synthesized with acetic anhydride. This compound could be valuable for pharmacological studies exploring neurotransmitter receptor influence on behavior, offering new avenues for understanding these powerful substances.
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.