Abwandlungsprodukte von Psilocybin und Psilocin. 2. Mitteilung über synthetische Indolverbindungen

Modifications to the molecular structure of the natural psychedelic compounds psilocybin and psilocin were systematically explored to clarify how structure relates to psychotropic activity. The synthesis and properties of several derivatives are described, including position isomers with a phosphoryloxy or hydroxy group at positions 5, 6, or 7, the four isomeric hydroxygramines, and psilocin variants altered at the ω-nitrogen, indole nitrogen, or side-chain (e.g., additional methylene, methyl substitution, or hydroxylation). Also reported are phosphoric acid esters of some derivatives, esters with organic carbonic and sulfonic acids, methylcarbaminic and sulfuric acid esters, and position isomers with the dimethylaminoethyl side-chain at position 1 or 2.

Study at a glance

Abstract

Abstract Various modifications were made in the molecular structure of the natural psychotropic substances psilocybin (I) and psilocin (11) to obtain an insight into the relationship between structure and psychotropic action of this group of substances. A description is given of the synthesis and properties of the position isomers of I and II with a phosphoryloxy or hydroxy group in position 5, 6 or 7, of the four isomeric hydroxygramines, and of a series of further derivatives of 4‐hydroxy‐indole in which the structure of II was systematically modified, i.e. psilocin derivatives with other substitution at the ω‐nitrogen; derivatives of II substituted at the indole nitrogen; psilocin derivatives with one additional methylene group in the side‐chain or with a methyl‐substituted or hydroxylated side‐chain; phosphoric acid esters of some derivatives of II; esters of II with organic carbonic and sulfonic acids, with methylcarbaminic and with sulfuric acid; position isomers of psilocin with the dimethylaminoethyl side‐chain in position 1 or 2.