Abwandlungsprodukte von Psilocybin und Psilocin. 2. Mitteilung über synthetische Indolverbindungen
Helvetica Chimica Acta January 1, 1959 F. Troxler, Frauke Seemann, A. Hofmann 69 citations
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.