Demethyl analogues of psychoactive methoxyphenalkylamines: synthesis and serotonin receptor affinities.
Richard A Glennon, Stephen M. Liebowitz, D Leming-Doot, John A. Rosecrans
Journal of Medicinal Chemistry September 1980 DOI: 10.1021/jm00183a006 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Preclinical pharmacology study Peer reviewed |
|---|---|
| Population | Isolated rat fundus preparations and rats trained in a discriminative stimulus paradigm |
| Interventions | DOM 5-methoxy-N N-dimethyltryptamine 5-dimethoxyphenalkylamines |
| Measures | discriminative stimulus paradigm |
| Topics | Serotonin |
| Key points | Mono-O-demethylation of several 2,5-dimethoxyphenalkylamines increased affinity for serotonin receptors in isolated rat fundus, and some demethylated compounds produced non-competitive antagonism. For DOM, the 2-hydroxy analogue, but not the 5-hydroxy analogue, produced interoceptive cues similar to those of 5-methoxy-N,N-dimethyltryptamine in rats. |
Abstract
Mono-O-demethylation of several 2,5-dimethoxyphenalkylamines increases their affinity for the serotonin receptors of the isolated rat fundus preparation. In several instances, demethylation of methoxyphenalkylamines results in compounds which produce an antagonism which is not of a competitive nature. With respect to 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM), demethylation of the 2-methoxy group alters affinity in a manner which parallels that observed upon demethylation of 5-methoxy-N,N-dimethyltryptamine. Using a discriminative stimulus paradigm, behavioral studies with rats reveal that the 2-hydroxy analogue, but not the 5-hydroxy analogue, of DOM produces effects (interoceptive cues) similar to those produced by 5-methoxy-N,N-dimethyltryptamine.
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| 3,4-Methylenedioxymethamphetamine and 3,4-methylenedioxyamphetamine destroy serotonin terminals in rat brain: quantification of neurodegeneration by measurement of [3H]paroxetine-labeled serotonin uptake sites. Rat brain | 1987 | Animal experiment | |
| Comparison of the monoamine transporters from human and mouse in their sensitivities to psychostimulant drugs Human and mouse dopamine, norepinephrine, and serotonin transporters expressed in cells | 2006 | In vitro laboratory study |
Citations in the library
Cited by 6
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- ECSTACY: A Review of MDMA and MDA The International Journal of Psychiatry in Medicine December 1, 1987
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