Abwandlungsprodukte von Psilocybin und Psilocin. 2. Mitteilung über synthetische Indolverbindungen
Helvetica Chimica Acta – January 01, 1959
Source: OpenAlex
Summary
Understanding the precise chemistry behind psychedelics like psilocybin is crucial for drug development. Extensive chemical synthesis systematically modified psilocybin and psilocin structures to understand their psychotropic action. Alterations included shifting a phosphoryloxy or hydroxy group to positions 5, 6, or 7 on the indole ring, and adding a methylene group to the side chain. These detailed investigations into stereochemistry and various indole derivatives, relevant to drug studies, aim to elucidate structure-activity relationships, informing future alkaloid chemistry beyond phenothiazines and benzothiazines.
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.