Correlation of psychotomimetic activity of phenethylamines and amphetamines with 1-octanol-water partition coefficients
Charles F. Barfknecht, David E. Nichols, William J. Dunn
Journal of Medicinal Chemistry February 1, 1975 DOI: 10.1021/jm00236a023 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Theoretical or philosophical paper Peer reviewed |
|---|---|
| Topics | Mescaline |
| Keywords | Phenethylamines Partition coefficient Psychotomimetic Hallucinogen Stereochemistry Organic chemistry Pharmacology Biochemistry |
| Citations | 42 |
| Key points | Lipophilicity, as measured by log P, may be a significant determinant of hallucinogenic potency in humans, with an ideal log P range for psychotomimetic activity suggested to be from 2.89 to 3.72. |
Abstract
In an attempt to relate the hallucinogenic potencies in man of some biologically important amphetamines and phenethylamines, the 1-octanol-water partition coefficients for 11 amphetamines were determined. Using these values and published Hansch pi constants, the log P for 17 additional amines was estimated. It was found that lipophilicity, as measured by the log of the partition coefficient, may be a significant determinant of the level of hallucinogenic potency. The study also suggests that an ideal log P value for psychotomimetric activity in man may be from 2.89 to 3.72.
Comparable studies
Other theoretical and historical papers on mescaline, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Schizophrenia: A New Approach. II. Result of a Year's Research | 1954 | Theoretical or philosophical paper | |
| Thought insertion as a self-disturbance: An integration of predictive coding and phenomenological approaches | 2016 | Theoretical or philosophical paper | |
| Entactogens: How the Name for a Novel Class of Psychoactive Agents Originated | 2022 | Theoretical or philosophical paper | |
| Steric and Electronic Relationships among Some Hallucinogenic Compounds | 1970 | Theoretical or philosophical paper | |
| EFFECT OF DRUGS One individual | 1952 | Theoretical or philosophical paper | n = 1 |
Citations in the library
Cited by 13
- The neural basis of psychedelic action. Nature Neuroscience October 24, 2022
- Structure–activity relationships of serotonin 5‐HT2Aagonists Wiley Interdisciplinary Reviews Membrane Transport and Signalling February 28, 2012
- Bufotenine: toward an understanding of possible psychoactive mechanisms. Journal of Psychoactive Drugs 2000
- Fluorine in psychedelic phenethylamines Drug Testing and Analysis February 28, 2012
- Comparison of the behavioral effects of mescaline analogs using the head twitch response in mice Journal of Psychopharmacology February 21, 2019
and 8 more in the library