Sulfur analogues of psychotomimetic agents. Monothio analogs of mescaline and isomescaline
Peyton Jacob, Alexander T. Shulgin
Journal of Medicinal Chemistry November 1, 1981 DOI: 10.1021/jm00143a017 via OpenAlex
Summary
AI-generated from the abstractTwo sulfur-containing analogues of mescaline, 3-thiomescaline and 4-thiomescaline, were synthesized and found to be psychotomimetic in humans, with 4-thiomescaline being 12 times more potent and 3-thiomescaline 6 times more potent than mescaline itself. Three additional analogues of isomescaline were also synthesized but were not psychotomimetic. All five compounds were broken down by bovine plasma monoamine oxidase in the lab, but the rate of this enzymatic degradation did not correlate with their potency as hallucinogens in people.
Study at a glance
| Characteristics | Experimental study Peer reviewed |
|---|---|
| Topics | Mescaline |
| Keywords | Chemistry Psychotomimetic Pharmacology Hallucinogen |
| Citations | 20 |
| Key finding | 3-thiomescaline and 4-thiomescaline are psychotomimetic in humans, with 4-thiomescaline being 12 times more potent than mescaline, and no correlation exists between their potency and their degradation by monoamine oxidase. |
Abstract
Two monothio analogues of mescaline and three monothio analogues of 2,3,4-trimethoxyphenethylamine (isomescaline) have been synthesized and characterized. Only the two mescaline analogues (3-and 4-thiomescaline) were found to be psychotomimetics in man, being 6 and 12 times more potent than mescaline, respectively. All five compounds can serve as substrates for bovine plasma monoamine oxidase in vitro, but no positive correlation is apparent between the extent of enzymatic degradation and human psychotomimetic potency.