title: Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothio analogues.
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.
mesh_terms: D000328:Adult; D006213:Hallucinogens / Q000138:chemical synthesis*; D006801:Humans; D008635:Mescaline / Q000031:analogs & derivatives* / Q000494:pharmacology; D011680:Pupil / Q000187:drug effects; D013329:Structure-Activity Relationship; D013455:Sulfur
chemical_list: D006213:Hallucinogens; D013455:Sulfur; D008635:Mescaline