Sulfur analogs of psychotomimetic agents. 2. Analogs of (2,5-dimethoxy-4-methylphenyl)- and of (2,5-dimethoxy-4-ethylphenyl)isopropylamine
Peyton Jacob, Alexander T. Shulgin
Journal of Medicinal Chemistry May 1, 1983 DOI: 10.1021/jm00359a021 (opens in new tab) via OpenAlex
Summary
AI-generated from the abstractTwo thio analogues of the psychotomimetic drugs DOM and DOET were synthesized and tested in humans. The 5-thio isomers are more potent than the 2-thio isomers but are about ten times less potent than the original sulfur-free drugs. The dithio analogue of DOM showed no central activity at a dose roughly 50 times the effective dose of DOM.
Study at a glance
| Characteristics | Pharmacological evaluation in man Peer reviewed |
|---|---|
| Population | Humans |
| Keywords | Isopropylamine Psychotomimetic Thio- Tetrahydrothiophene Potency |
| Citations | 18 |
| Key finding | The 5-thio isomers of DOM and DOET are more potent psychotomimetic agents than the 2-thio isomers but are an order of magnitude less potent than the sulfur-free counterparts, and the dithio analogue of DOM lacks central activity at high doses. |
Abstract
The two thio analogues of each of the well-known psychotomimetic drugs DOM [(2,5-dimethoxy-4-methylphenyl)isopropylamine] and DOET [(2,5-dimethoxy-4-ethylphenyl)isopropylamine] have been synthesized and pharmacologically evaluated in man. The 5-thio isomers are more potent as psychotomimetic agents than the 2-thio isomers but still represent a drop of an order of magnitude in potency from the sulfur-free counterparts. The dithio analogue of DOM was synthesized and found to be without central activity at a dosage of approximately 50 times the mean effective dose of DOM.