Studies on several 7-substituted N,N-dimethyltryptamines
Richard A Glennon, E. Schubert, John M. Jacyno, John A. Rosecrans
Journal of Medicinal Chemistry November 1, 1980 DOI: 10.1021/jm00185a014 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Experimental study Peer reviewed |
|---|---|
| Population | Rats |
| Interventions | 7-Me-DMT 5-OMe-7-Me-DMT 5 7-(OMe)2-DMT 7-Br-DMT 6-Me-DMT |
| Topics | 5-MeO-DMT DMT |
| Keywords | Stereochemistry |
| Citations | 33 |
| Key findings | 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.
Comparable studies
Other preclinical and animal studies on 5-MeO-DMT, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Psychedelic N,N-dimethyltryptamine and 5-methoxy-N,N-dimethyltryptamine modulate innate and adaptive inflammatory responses through the sigma-1 receptor of human monocyte-derived dendritic cells. Human primary monocyte-derived dendritic cells | 2014 | In vitro study | |
| Effects of N,N-Dimethyltryptamine on Rat Behaviors Relevant to Anxiety and Depression Adult male Sprague-Dawley rats | 2018 | Experimental study | |
| Hallucinogen-like actions of 5-methoxy-N,N-diisopropyltryptamine in mice and rats. Mice and rats | 2006 | Preclinical study | |
| Agonist Properties of N,N-Dimethyltryptamine at Serotonin 5-HT2A and 5-HT2C Receptors Rats and transfected fibroblasts | 1998 | Experimental study | |
| Subtypes of the 5-HT receptor mediating the behavioural responses to 5-methoxy-N,N-dimethyltryptamine in the rat Intact rats and rats depleted of monoamines with reserpine | 1985 | Experimental study |
Citations in the library
Cited by 5
- Receptor binding profiles and behavioral pharmacology of ring-substituted N,N-diallyltryptamine analogs. Neuropharmacology November 1, 2018
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- “Biosynthesis of psilocybin and its nonnatural derivatives by a promiscuous psilocybin synthesis pathway in Escherichia coli” Biotechnology and Bioengineering June 20, 2023
- Synthesis and characterization of high‐purity N,N‐dimethyltryptamine hemifumarate for human clinical trials Drug Testing and Analysis July 1, 2020
- Synthesis and Biological Evaluation of 4-Bromo- N,N- dimethyltryptamine (4-Br-DMT): A Synthetic Building Block for Future Analog Development ACS Omega June 23, 2026