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Nicholse DE, Frescas S.
“Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin”.
Synthesis. 1999;6:935-938.
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Abstract
Abstract: An improved procedure to accomplish the O-phosphorylation of 4-hydroxy-N,N-dimethyltryptamine (psilocin 5) is reported that utilizes reaction between the O-lithium salt of 5 and tetra-Obenzylpyrophosphate. The O-benzyl groups were removed by catalytic hydrogenation over palladium on carbon to afford N,N-dimethyl- 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 catalytic O-debenzylation of 4-benzyloxy-N,N-dimethyltryptamine in the presence of acetic anhydride and sodium acetate.
Key Words: psilocin, psilocybin, tetra-O-benzylpyrophosphate, phosphorylation
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