Investigations into the polymorphic properties of N,N-dimethyltryptamine by X-ray diffraction and differential scanning calorimetry

Gaujac, Alain; Ford, James L.; Dempster, Nicola M.; Andrade, Jaílson Bittencourt de; Brandt, Simon D.

doi:10.1016/j.microc.2013.03.009

Cited by 9 publications

(5 citation statements)

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“…Literature melting point values for DMT free base vary widely, ranging between 38°C and 73°C, with most data falling within the 45°C–68°C range 74 . The different melting points are due to variable amounts of polymorphic Forms I and II 74 . GC: free base DMT eluted as a single peak with a GC retention time of 13.157 min (Supporting Information Figure S2A).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of high‐purity N,N‐dimethyltryptamine hemifumarate for human clinical trials

Cozzi

Daley²

2020

Drug Testing and Analysis

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Since 2006, there has been a resurgent interest in the pharmacology and therapeutics of psychedelic drugs. Psilocybin, the 4-phosphoryl ester of N,Ndimethyltryptamine (DMT), has been studied most often, but DMT itself is also appealing because of its brief but profound psychological effects and its presence as an endogenous substance in mammalian brain. Although there have been a few studies of ayahuasca, a DMT-containing water infusion, only one human study with pure DMT has been reported since the early 2000s. Newly planned clinical trials to assess the safety and efficacy of DMT in humans with major depressive disorders require high-purity water-soluble DMT for intravenous administration. Accordingly, we synthesized and characterized DMT hemifumarate for these upcoming studies. The synthetic approach of Speeter and Anthony was slightly modified to gain some efficiency in time. In particular, this is the first known report to use aluminum hydride, generated in situ from lithium aluminum hydride, to reduce the intermediate 2-(1Hindol-3-yl)-N,N-dimethyl-2-oxoacetamide to DMT. A quench protocol was developed to produce a good yield of exceptionally pure free base DMT upon workup, which was then converted to the hemifumarate salt. Analysis of the final product included differential scanning calorimetry, thermogravimetric analysis, gas chromatographymass spectrometry (GC-MS), 1 H and 13 C nuclear magnetic resonance spectroscopy, high-performance liquid chromatography, residual solvent analysis by GC headspace sampling, X-ray powder diffraction analysis, and residual lithium analysis by inductively coupled plasma-mass spectrometry. The DMT hemifumarate was minimally 99.9% pure, with no significant impurities or residual solvents, thus meeting regulatory standards for administration to humans.

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Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of high‐purity N,N‐dimethyltryptamine hemifumarate for human clinical trials

Cozzi

Daley²

2020

Drug Testing and Analysis

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“…En este orden de ideas, la investigación sobre el yagé está en un momento inicial, existen postulados sobre sus posibles usos para determinadas enfermedades y trastornos, pero las evidencias en la investigación biomédica no son concluyentes por el momento. En este sentido, la investigación biomédica se ha acercado al abordaje del problema (38) . El estado de emergencia de la metodología bioquímica está haciendo posible conocer de modo científico las pretendidas propiedades curativas del yagé (39) produciendo un efecto de apropiación al quedar avaladas por la ciencia médica (14) .…”

Section: Discusión La Metonimia Del Yagé Y El Trabajo Espiritualunclassified

Yagé: Crisis de occidente y trabajo espiritual

2019

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Introducción: Ante la crisis epistemológica y sistémica que se encuentra en la civilización occidental, el yagé emerge como alternativa que invita a una reponderación axiológica profunda. Asimismo, el ritual del yagé evidencia los límites del conocimiento médico moderno, dando pauta al abordaje transdisciplinario. Por otro lado, se presentan consecuencias de inserción en el libre mercado, implicando problemas de lucro a costa de tradiciones originarias. En este contexto, se explora el concepto «trabajo espiritual» como práctica que busca descolocarse del colonialismo mercantil al tiempo que se aleja del modelo médico moderno. Objetivo: Reflexionar la incorporación del ritual de yagé en Occidente y sus posibilidades como alternativa epistemológica y médica. Materiales y Métodos: Revisión de artículos de la base de datos especializados Web of Science, con la palabra clave: “ayahuasca”. Resultados: Se estructuró la información teniendo en cuenta los aspectos relacionados con: (a) el contexto de incorporación del yagé al occidente, (b) los límites del conocimiento médico moderno y (c) los problemas de inserción al libre mercado. Conclusiones: Se apoya el diagnóstico de la ruptura epistemológica con occidente, pero reconociendo el estado inicial de las investigaciones y la falta de evidencias documentadas para entrar en una etapa más fructífera para el debate.

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“…The substance was first synthesized in 1931 [8], while its psychoactive effects were described for the first time many years later in 1956 by [9]. When administered externally in large quantities, DMT can cause altered states of consciousness [10], hallucinations [11][12][13] and spiritual experiences such as communication with 'presences' or 'entities' , plus reflections on death [14]. Exogenous ingestion can be done by smoking or injecting.…”

Section: Introductionmentioning

confidence: 99%

On the advances in machine learning and complex network measures to an EEG dataset from DMT experiments

Alves,

Ciba,

de O. Toutain

et al. 2024

J. Phys. Complex.

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There is a growing interest in the medical use of psychedelic substances, as preliminary studies using them for psychiatric disorders have shown positive results. In particular, one of these substances is N, N-dimethyltryptamine (DMT), an agonist serotonergic psychedelic that can induce profound alterations in the state of consciousness. In this work, we use an exploratory tool to reveal DMT-induced changes in brain activity using EEG data and provide new insights into the mechanisms of action of this psychedelic substance. We used a two-class classification based on (A) the connectivity matrix or (B) complex network measures derived from it as input to a support vector machine.We found that both approaches could detect changes in the brain's automatic activity, with case (B) showing the highest AUC (89%), indicating that complex network measurements best capture the brain changes that occur due to DMT use. In the second step, we ranked the features that contributed the most to this result. For case (A), we found that differences in the high alpha, low beta, and delta frequency bands were most important in distinguishing between the state before and after DMT inhalation, which is consistent with the results described in the literature. Further, the connection between the temporal (TP8) and central cortex (C3) and between the precentral gyrus (FC5) and the lateral occipital cortex (P8) contributed most to the classification result. The connection between regions TP8 and C3 has been found in the literature associated with finger movements that might have occurred during DMT consumption. However, the connection between cortical areas FC5 and P8 has not been found in the literature and is presumably related to the volunteers' emotional, visual, sensory, perceptual, and mystical experiences during DMT consumption.For case (B), closeness centrality was the most crucial complex network measure. Furthermore, we discovered larger communities and longer average path lengths when DMT was used and the converse when not, showing that the balance between functional segregation and integration had been disrupted. These findings supportthe idea that cortical brain activity becomes more entropic under psychedelics.Overall, a robust computational workflow has been developed here with interpretability of how DMT (or other psychedelics) modify brain networks and insights into their mechanism of action. Finally, the same methodology applied here may help interpret EEG time series from patients who consumed other psychedelic drugs.

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Investigations into the polymorphic properties of N,N-dimethyltryptamine by X-ray diffraction and differential scanning calorimetry

Cited by 9 publications

References 50 publications

Synthesis and characterization of high‐purity N,N‐dimethyltryptamine hemifumarate for human clinical trials

Synthesis and characterization of high‐purity N,N‐dimethyltryptamine hemifumarate for human clinical trials

Yagé: Crisis de occidente y trabajo espiritual

On the advances in machine learning and complex network measures to an EEG dataset from DMT experiments

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