Cation-π interaction of N, N-Dimethyltryptamine in hydrochloric acid solution characteristic to gastric acid
A. Vidak, I. M. Šapić, V. Dananić
June 20, 2016 DOI: 10.15761/imm.1000166 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Theoretical or experimental chemistry study |
|---|---|
| Measures | FTIR, Raman spectroscopy, DFT-B3LYP vibrational frequency calculations |
| Topics | 5-MeO-DMT DMT |
| Key findings | The authors report that N,N-DMT in 0.1 M hydrochloric acid shows a vibrational frequency shift, confirmed by DFT-B3LYP calculations. They propose that this shift arises from a cation-pi bond between N,N-DMT and HCl near the benzene ring. |
Abstract
N,N-DMT molecule is known in many cultures as endogenous hallucinogen and most research has been directed towards the psychological effects or structural definition while molecular interactions in conditions of the human body are poorly understood. We have complemented past structural research of N,N-DMT and investigated molecular interactions of N,N-DMT in the environment of 0.1 M hydrochloric acid which is characteristic to gastric fluid. Experimentally we have measured spectra of N,N-DMT with IR and Raman techniques and computed individual vibrational frequencies at DFT–B3LYP level of theory. Furthermore we put N,N-DMT in solution similar to gastric fluid environment and experimentally detected shift in vibrational frequency which is confirmed in our calculation. Our theoretical model shows that the cause of this shift is cationπ bond between N,N-DMT and HCl in the vicinity of the benzene ring. Abbreviations: N,N-DMT: N,N-dimethyltryptamine; HCl: Hydrocloric acid, FTIR: Fourier transform infrared; IR: Infrared
Comparable studies
Other experimental studies on 5-MeO-DMT, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Short term changes in the proteome of human cerebral organoids induced by 5-MeO-DMT. Human cerebral organoids | 2017 | Experimental study | |
| Bufo alvarius: a potent hallucinogen of animal origin. Bufo alvarius toad venom | 1994 | Experimental study | |
| Prospective examination of synthetic 5-methoxy-N,N-dimethyltryptamine inhalation: effects on salivary IL-6, cortisol levels, affect, and non-judgment Volunteers | 2019 | Within-subjects experimental study | n = 11 |
| Unmasking of a neonatal somatovesical reflex in adult cats by the serotonin autoreceptor agonist 5-methoxy-N,N-dimethyltryptamine. Adult cats | 1990 | Experimental study | n = 10 |
| Studies on the Mechanism of Action of Monoamine Oxidase: Metabolism of N,N-Dimethyltryptamine and N,N-Dimethyltryptamine-N-Oxide | 1962 | Experimental study |
Citations in the library
Cites 4
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- Enzymatic Formation of Psychotomimetic Metabolites from Normally Occurring Compounds Science August 4, 1961
- Potentially hallucinogenic 5-hydroxytryptamine receptor ligands bufotenine and dimethyltryptamine in blood and tissues. Scandinavian Journal of Clinical and Laboratory Investigation 2005
- Application of analytical methods for the structural characterization and purity assessment of N,N-dimethyltryptamine, a potent psychedelic agent isolated from Mimosa tenuiflora inner barks Microchemical Journal April 5, 2012