Investigations into the polymorphic properties of N,N-dimethyltryptamine by X-ray diffraction and differential scanning calorimetry
Alain Gaujac, James L. Ford, Nicola M. Dempster, Jaílson B. de Andrade, Simon D. Brandt
Microchemical Journal March 20, 2013 DOI: 10.1016/j.microc.2013.03.009 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Experimental study Peer reviewed |
|---|---|
| Topics | 5-MeO-DMT DMT |
| Keywords | Differential scanning calorimetry Acetonitrile Recrystallization geology Melting point Powder diffraction Polymorphism computer science Crystallography Solvent Analytical chemistry journal Organic chemistry Optics |
| Citations | 10 |
| Key findings | DMT free base exists in at least two polymorphic forms with distinct melting points (Form I: 57–58 °C, Form II: 45–46 °C), and Form II converts to Form I under standard DSC conditions. |
Abstract
The powerful psychoactive features of N,N-dimethyltryptamine (DMT) have sparked the imagination of many research disciplines for several decades. One of the key chemical features associated with compound identity is the determination of melting points. The descriptions of both melting points and morphology associated with DMT free base have long been a source of interest and discussion, especially when considering that these values encountered in the scientific literature range dramatically between 38–40 °C and 73–74 °C, respectively. Such variations in reported melting points suggest that DMT may exist in two or more polymorphic forms and it was the aim of this study to examine the potential polymorphism of DMT via X-ray powder diffraction (XRPD) and differential scanning calorimetry (DSC), including fast scan DSC. DMT samples were prepared following extraction from Mimosa tenuiflora inner barks or by laboratory synthesis and then its crystals were recrystallized from solutions of the alkaloid using either hexane or acetonitrile. Irrespective of source, crystals originating from synthesis were predominantly white crystals obtained using crystallization from hexane, whereas yellow samples following recrystallization with acetonitrile. Irrespective of source or solvent, two polymorphs appeared to exist with melting points, determined by DSC, of 57 °C to 58 °C for Form I and 45 °C to 46 °C for Form II. Estimates for their enthalpies were 91.9 ± 2.4 J g− 1 for Form I and 98.3 ± 2.8 J g− 1 for Form II. Form II converted to Form I during DSC; conversion was thus prevented by fast scanning rates of 100 °C min− 1. A transition temperature (Tg) in the range − 21 °C (2 °C min− 1) to − 13 °C (100 °C min− 1) was determined depending on DSC scanning rate. Its closeness to the melting point indicates a tendency of Form II to convert to Form I on storage, a phenomenon that was also facilitated by grinding. This study indicates that the presence of differently colored DMT free base crystals obtained from recrystallization might also point towards the existence of polymorphs rather than just the presence of impurities.
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
Cited by 6
- Synthesis and characterization of high‐purity N,N‐dimethyltryptamine hemifumarate for human clinical trials Drug Testing and Analysis July 1, 2020
- On the advances in machine learning and complex network measures to an EEG dataset from DMT experiments Journal of Physics: Complexity January 22, 2024
- Application of microarray patches for the transdermal administration of psychedelic drugs in micro-doses. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V February 1, 2025
- Yagé: Crisis de occidente y trabajo espiritual Universidad y Salud August 2, 2019
- Extraction of N, N-dimethyltryptamine (DMT) from Mimosa tenuiflora, syn. Mimosa hostilis (Tepescohuite) using supercritical CO 2 and study of its surface activity Natural Product Research December 6, 2025
and 1 more in the library
Cites 12
- The Hallucinogen N,N -Dimethyltryptamine (DMT) Is an Endogenous Sigma-1 Receptor Regulator Science February 13, 2009
- Clinical investigations of the therapeutic potential of ayahuasca: rationale and regulatory challenges. Pharmacology & Therapeutics May 1, 2004
- Human psychopharmacology of N,N-dimethyltryptamine Behavioural Brain Research December 1, 1995
- Increased frontal and paralimbic activation following ayahuasca, the pan-amazonian inebriant Psychopharmacology March 30, 2006
- Dimethyltryptamine and other hallucinogenic tryptamines exhibit substrate behavior at the serotonin uptake transporter and the vesicle monoamine transporter. Journal of Neural Transmission September 12, 2009
and 7 more in the library