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 via OpenAlex
Summary
AI-generated from the abstractThe hallucinogenic potency of certain amphetamines and phenethylamines in humans may be related to their lipophilicity, as measured by the 1-octanol-water partition coefficient. For 11 amphetamines, these coefficients were measured directly, and for 17 additional amines they were estimated using published Hansch pi constants. The analysis suggests that an ideal log P value for psychotomimetic activity in humans may fall between 2.89 and 3.72.
Study at a glance
| Characteristics | Theoretical or philosophical paper Peer reviewed |
|---|---|
| Topics | Mescaline |
| Keywords | Phenethylamines Partition coefficient Psychotomimetic Hallucinogen |
| Citations | 42 |
| Key finding | Lipophilicity, as measured by the log of the partition coefficient, may be a significant determinant of the level of hallucinogenic potency, with an ideal log P range for psychotomimetic activity 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.