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 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Experimental synthesis and pharmacological evaluation Peer reviewed |
|---|---|
| Population | Humans |
| Interventions | di- and triethoxy homologues of mescaline |
| Topics | Mescaline |
| Keywords | Psychotomimetic Citation Social media Icon Library science Information retrieval |
| Citations | 14 |
| Key findings | 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.
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 4
- MDMA (3,4-Methylenedioxymethamphetamine) Analogues as Tools to Characterize MDMA-Like Effects: An Approach to Understand Entactogen Pharmacology Current Neuropharmacology August 1, 2013
- Identification and characterization of 2,5-dimethoxy-3,4-dimethyl-β-phenethylamine (2C-G)--a new designer drug. Drug Testing and Analysis July 1, 2013
- Receptor interaction profiles of 4-alkoxy-2,6-dimethoxyphenethylamines (Ψ derivatives) and related amphetamines Frontiers in Pharmacology November 20, 2025
- ChemInform Abstract: SULFUR ANALOGS OF PSYCHOTOMIMETIC AGENTS. 30. ETHYL HOMOLOGS OF MESCALINE AND D THEIR MONOTHIOANALOGS Chemischer Informationsdienst November 27, 1984