Indolealkylamine and phenalkylamine hallucinogens. Effect of alpha-methyl and N-methyl substituents on behavioral activity.
Richard A Glennon, R Young, John M. Jacyno
Biochemical Pharmacology April 1, 1983 DOI: 10.1016/0006-2952(83)90281-2 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Animal behavioral pharmacology study (drug discrimination) Peer reviewed |
|---|---|
| Population | Rats trained to discriminate DOM from saline |
| Interventions | DOM phenalkylamine derivatives alpha-methyltryptamine (alpha-MeT) |
| Key points | Alpha-methyl analogs were more active than N-methyl or alpha-demethyl counterparts in both the indolealkylamine and phenalkylamine series. The more potent isomer of alpha-methyltryptamine (S) had the opposite absolute configuration of the more potent DOM isomer (R). The authors state these findings are not inconsistent with a common site hypothesis for these agents. |
Abstract
Animals (rats), trained to discriminate the hallucinogenic agent 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) from saline in a two-lever operant procedure, were challenged with various doses of several indolealkylamine and phenalkylamine derivatives. In both series, the alpha-methyl analogs were found to be more active than either their N-methyl or alpha-demethyl counterparts. Furthermore, when the activities of the optical isomers of DOM were compared with the activities of S-(+) and R-(-)-alpha-methyltryptamine (alpha-MeT), it was found that the more potent isomer of alpha-MeT (i.e. S) possessed the opposite absolute configuration of the more potent isomer of DOM (i.e. R). With respect to the mechanism of action of these agents, these findings are not inconsistent with a common site hypothesis.
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- Serotonin Receptor Binding Affinities of Several Hallucinogenic Phenylalkylamine and N,N-Dimethyltryptamine Analogues Journal of Medicinal Chemistry 1978
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