Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogs
David E. Nichols, Donald C. Dyer
Journal of Medicinal Chemistry February 1, 1977 DOI: 10.1021/jm00212a022 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Experimental study Peer reviewed |
|---|---|
| Population | Sheep umbilical artery preparation |
| Topics | Mescaline Serotonin |
| Keywords | Lipophilicity Stereochemistry Serotonin agonist Pharmacology 5-HT Receptor |
| Citations | 23 |
| Key findings | Replacing the 4-methoxy of mescaline with higher alkyl homologues or bromine increases serotonin receptor activity, which correlates with lipophilicity, but activity drops when the 4-substituent is about five atoms long. |
Abstract
Replacement of the 4-methoxy of mescaline with higher alkyl homologues or with bromine led to increased activity at serotonin receptors in a sheep umbilical artery preparation. This activity appears correlated with lipophilicity, as measured by 1-octanol-water partition coefficients, but drops off when the 4-substituent is about five atoms in length. It is suggested that 3,4,5-trisubhe 2,4,5-substitution pattern.
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 8
- Structure–activity relationships of serotonin 5‐HT2Aagonists Wiley Interdisciplinary Reviews Membrane Transport and Signalling February 28, 2012
- Structure-Activity Assessment and In-Depth Analysis of Biased Agonism in a Set of Phenylalkylamine 5-HT2A Receptor Agonists. ACS Chemical Neuroscience August 2, 2023
- Comparison of the behavioral effects of mescaline analogs using the head twitch response in mice Journal of Psychopharmacology February 21, 2019
- Chemistry/structural biology of psychedelic drugs and their receptor(s). British Journal of Pharmacology October 2, 2024
- Synthesis of the 3-(3,4,5-Trimethoxyphenyl)-pyrrolidine: A New Conformationally Constrained Mescaline Analogue Synthetic Communications June 1, 2007
and 3 more in the library