Sulfur analogs of psychotomimetic agents. 30. Ethyl homologs of mescaline and their monothioanalogs
Peyton Jacob, Alexander T. Shulgin
Journal of Medicinal Chemistry July 1, 1984 DOI: 10.1021/jm00373a013 via OpenAlex
Summary
AI-generated from the abstractAll possible monothio analogues of mono-, di-, and triethoxy homologues of mescaline were synthesized and tested in humans. Modifications at the ring position para to the ethylamine chain, using a sulfur atom, a longer alkyl chain, or both, produce compounds with high central nervous system activity. The 4-n-propoxy and 4-n-butoxy homologues and their corresponding 4-thio analogues were also made and tested. Propyl homologues retain high potency, but a butyl group, with or without sulfur, reduces activity. Meta-ethyl or meta-thio analogues retain some central action, while diethoxy and especially triethoxy homologues are relatively inactive as psychotomimetic drugs.
Study at a glance
| Characteristics | Experimental synthesis and pharmacological evaluation Peer reviewed |
|---|---|
| Population | Humans |
| Topics | Mescaline |
| Keywords | Psychotomimetic Citation Social media Icon |
| Citations | 14 |
| Key finding | Modifications at the para ring position with sulfur or longer alkyl chains yield compounds with high central nervous system activity, but butyl groups reduce activity and triethoxy homologues are relatively inactive as psychotomimetic drugs. |
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.