Reaction of N,N‑Dimethyltryptamine with Dichloromethane Under Common Experimental Conditions
ACS Omega May 7, 2018 DOI: 10.1021/acsomega.8b00507 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Experimental study Peer reviewed |
|---|---|
| Duration | Contact times <30 min |
| Topics | 5-MeO-DMT DMT |
| Citations | 15 |
| Key findings | The quaternary ammonium salt byproduct forms slowly and is removed by aqueous extraction, so DMT can be safely exposed to DCM for short periods (<30 min) without significant degradation. |
Abstract
-dimethyltryptamine (DMT) structural core. Previous reports have described the reaction of this motif with dichloromethane (DCM), a common laboratory solvent used during extraction and purification, leading to the formation of an undesired quaternary ammonium salt byproduct. However, the kinetics of this reaction under various conditions have not been thoroughly described. Here, we report a series of experiments designed to simulate the exposure of DMT to DCM that would take place during extraction from plant material, biphasic aqueous work-up, or column chromatography purification. We find that the quaternary ammonium salt byproduct forms at an exceedingly slow rate, only accumulates to a significant extent upon prolonged exposure of DMT to DCM, and is readily extracted into water. Our results suggest that DMT can be exposed to DCM under conditions where contact times are limited (<30 min) with minimal risk of degradation and that this byproduct is not observed following aqueous extraction. However, alternative solvents should be considered when the experimental conditions require longer contact times. Our work has important implications for preparing a wide-range of pharmaceuticals bearing the DMT structural motif in high yields and purities.
Comparable studies
Other experimental studies on 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 | |
| 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 |
| Metabolism and disposition of N,N‐dimethyltryptamine and harmala alkaloids after oral administration of ayahuasca Healthy male volunteers | 2012 | Observational pharmacokinetic study | n = 10 |
| 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
Cited by 8
- Chronic, Intermittent Microdoses of the Psychedelic N , N -Dimethyltryptamine (DMT) Produce Positive Effects on Mood and Anxiety in Rodents ACS Chemical Neuroscience March 4, 2019
- Dark Classics in Chemical Neuroscience:N,N-Dimethyltryptamine (DMT) ACS Chemical Neuroscience July 23, 2018
- Synthesis and Characterization of 5-MeO-DMT Succinate for Clinical Use ACS Omega December 2, 2020
- New Insights into the Chemical Composition of Ayahuasca ACS Omega April 1, 2022
- Synthesis and characterization of high‐purity N,N‐dimethyltryptamine hemifumarate for human clinical trials Drug Testing and Analysis July 1, 2020
and 3 more in the library
Cites 10
- Antidepressant effects of a single dose of ayahuasca in patients with recurrent depression: a preliminary report Brazilian Journal of Psychiatry March 1, 2015
- Antidepressive, anxiolytic, and antiaddictive effects of ayahuasca, psilocybin and lysergic acid diethylamide (LSD): a systematic review of clinical trials published in the last 25 years Therapeutic Advances in Psychopharmacology March 18, 2016
- Clinical investigations of the therapeutic potential of ayahuasca: rationale and regulatory challenges. Pharmacology & Therapeutics May 1, 2004
- Ayahuasca: Pharmacology, neuroscience and therapeutic potential Brain Research Bulletin March 11, 2016
- Effects of N,N-Dimethyltryptamine on Rat Behaviors Relevant to Anxiety and Depression ACS Chemical Neuroscience April 17, 2018
and 5 more in the library