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 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Experimental study Peer reviewed |
|---|---|
| Topics | Mescaline |
| Keywords | Psychotomimetic Pharmacology Hallucinogen |
| Citations | 20 |
| Key findings | 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.
Comparable studies
Other experimental studies on mescaline, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Enzymatic Formation of Psychotomimetic Metabolites from Normally Occurring Compounds Rabbit lung | 1961 | Experimental study | |
| PSYCHOTOMIMETICS, CLINICAL AND THEORETICAL CONSIDERATIONS: HARMINE, WIN-2299 AND NALLINE Schizophrenic patients | 1957 | Experimental study | |
| Phencyclidine, Lysergic Acid Diethylamide, and Mescaline: Cerebral Artery Spasms and Hallucinogenic Activity Isolated basilar and middle cerebral arteries | 1981 | Experimental study | |
| Acquired and Crossed Tolerance to Mescaline, LSD-25, and BOL-148 | 1959 | Experimental study | |
| Effects of Hallucinogenic and Tranquilizing Drugs on Serotonin Evoked Uterine Contractions. Uterus of spayed rat | 1956 | Experimental study |
Citations in the library
Cited by 5
- Structure–activity relationships of serotonin 5‐HT2Aagonists Wiley Interdisciplinary Reviews Membrane Transport and Signalling February 28, 2012
- Synthesis of the 3-(3,4,5-Trimethoxyphenyl)-pyrrolidine: A New Conformationally Constrained Mescaline Analogue Synthetic Communications June 1, 2007
- Receptor interaction profiles of 4-alkoxy-2,6-dimethoxyphenethylamines (Ψ derivatives) and related amphetamines Frontiers in Pharmacology November 20, 2025
- ChemInform Abstract: SULFUR ANALOGUES OF PSYCHOTOMIMETIC AGENTS. MONOTHIO ANALOGS OF MESCALINE AND ISOMESCALINE Chemischer Informationsdienst April 20, 1982
- Studies of the relationship between molecular structure and hallucinogenic activity. Pharmacology, Biochemistry, and Behavior February 1986