Stereospecific Actions of DOET (2,5-Dimethoxy-4-Ethylamphetamine) in Man
Archives of General Psychiatry July 1, 1974 DOI: 10.1001/archpsyc.1974.01760130079013 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Clinical study Peer reviewed |
|---|---|
| Population | Normal human subjects |
| Intervention | DOET (2 |
| Topics | LSD Mescaline Psilocybin |
| Keywords | Stereochemistry Stereospecificity Hallucinogen Drug Pharmacology |
| Citations | 25 |
| Key points | The (-) "R" isomer of DOET is about four times as potent as the (+) "S" isomer in normal human subjects. |
Abstract
Several different molecular conformations of psychedelic drugs have been proposed to explain the very similar effects of drugs with markedly divergent chemical structures, such as mescaline andd-lysergic acid diethylamide (LSD). In some of these models, the α-carbon of methoxyamphetamine psychedelics approximates the asymmetric carbon No. 5 of LSD predicting that the (-) "R" isomer of the methoxyamphetamines should possess greater psychedelic activity than the ( + ) "S" isomer. The present study reports a comparison of the psychotropic effects of isomers of DOET (2,5-dimethoxy-4-ethylamphetamine) a "psychedelic" methoxyamphetamine, in normal human subjects. The (-) "R" isomer is about four times as potent as the ( + ) "S" isomer, thus specifying the psychoactive conformation of the drug. This clinical study represents a novel approach to determining the molecular conformation of a drug at its receptor site.