Sulfur analogs of psychotomimetic agents. 30. Ethyl homologs of mescaline and their monothioanalogs
Journal of Medicinal Chemistry – July 01, 1984
Source: OpenAlex
Summary
Modifications to mescaline's structure can significantly impact its potency as a psychotomimetic drug. In a study involving various synthesized analogues, 4-n-propoxy and 4-n-butoxy compounds were found to retain high central nervous system activity, while the addition of a butyl group diminished effectiveness. Specifically, the propyl homologues maintained strong potency, whereas diethoxy and triethoxy variants showed limited activity. This synthesis and evaluation provide valuable insights into the coordination chemistry of sulfur-containing compounds and their potential applications in pharmacology.
Abstract
All possible monothio analogues of the mono-, di-, and triethoxy homologues of mescaline have been synthesized and pharmacologically evaluated in man. Modifications at the ring position para to the ethylamine chain, either with a sulfur atom, a longer alkyl chain, or both, lead to compounds of high central nervous system activity. The 4-n-propoxy and 4-n-butoxy homologues and their corresponding 4-thio analogues were also synthesized and pharmacologically evaluated. The propyl homologues retain high potency, but a butyl group (either with or without a sulfur atom) leads to a decrease in activity. The m-ethyl or m-thio analogues retain some central action but the diethoxy and especially the triethoxy homologues are relatively inactive as psychotomimetic drugs.