Studies on several 7-substituted N,N-dimethyltryptamines
R. A. Glennon, E. Schubert, John M. Jacyno, John A. Rosecrans
Journal of Medicinal Chemistry November 1, 1980 DOI: 10.1021/jm00185a014 via OpenAlex
Summary
AI-generated from the abstractSeveral 7-substituted derivatives of N,N-dimethyltryptamine (DMT) were synthesized and tested. 7-Me- and 5-OMe-7-Me-DMT showed higher serotonin receptor affinity (pA2) than DMT itself, while 5,7-(OMe)2-DMT showed lower affinity. All three produced behavioral effects in rats similar to the hallucinogen 5-OMe-DMT. 7-ET- and 7-Br-DMT had higher receptor affinity than DMT but did not produce hallucinogen-like behavioral effects. 6-Me-DMT and its 5-OMe derivative did not interact competitively with serotonin receptors and were inactive in the behavioral assay.
Study at a glance
| Characteristics | Experimental study Peer reviewed |
|---|---|
| Population | Rats |
| Keywords | Stereochemistry |
| Citations | 33 |
| Key finding | 7-Me- and 5-OMe-7-Me-DMT have higher serotonin receptor affinity than DMT and produce hallucinogen-like behavioral effects, whereas 7-ET- and 7-Br-DMT have higher affinity but lack such behavioral effects. |
Abstract
Several 7-substituted derivatives of N,N-dimethyltryptamine (DMT) were prepared and evaluated in the rat fundus serotonin receptor assay and in a behavioral (discriminative stimulus) assay in rats. Both 7-Me- and 5-OMe-7-Me-DMT possess a higher pA2, and 5,7-(OMe)2-DMT a lower pA2, than that of DMT itself. Like DMT, all three of these compounds produce behavioral effects in rats which are similar to those of the hallucinogen 5-OMe-DMT. Although 7-ET- and 7-Br-DMT possess a higher serotonin receptor affinity than DMT, neither produce behavioral effects which parallel those of 5-OMe-DMT. In contrast, 6-Me-DMT and its 5-OMe derivative do not interact with the serotonin receptors in a competitive manner and are inactive in the discriminative stimulus assay.