Stability Evaluation of DMT and Harmala Alkaloids in Ayahuasca Tea Samples

Silveira, Geraldo; Santos, Rafael G. dos; Lourenço, Felipe Rebello; Rossi, Giordano Novak; Hallak, Jaime Eduardo Cecílio; Yonamine, Maurı́cio

doi:10.3390/molecules25092072

Cited by 20 publications

(24 citation statements)

References 33 publications

(51 reference statements)

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“…These differences in the ayahuasca preparation may indeed impact the β-carboline ratios, although a clear pattern could not be seen in the seven Daime honey samples analyzed in this study ( Table S2 ). A recent study showed that THH is stable in ayahuasca samples for about 9 days at 37 °C, simulating an extreme transport and storage situation, while harmine and harmaline concentrations vary under the same conditions [ 51 ].…”

Section: Discussionmentioning

confidence: 99%

Biodiversity of β-Carboline Profile of Banisteriopsis caapi and Ayahuasca, a Plant and a Brew with Neuropharmacological Potential

Santos

Oliveira

Sonsin‐Oliveira

et al. 2020

Plants

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Ayahuasca is a psychoactive infusion with a large pharmacological application normally prepared with Banisteriopsis caapi, which contains the monoamine oxidase inhibitors β-carbolines, and Psichotria virids, which contains the serotonin receptor agonist N,N dimethyltryptamine (DMT). The objectives of this study were to investigate the chemical profile of B. caapi and of ayahuasca collected in various Brazilian regions. In total, 176 plant lianas, of which 159 B. caapi and 33 ayahuasca samples were analyzed. Dried liana samples were powdered, extracted with methanol, diluted, and analyzed by LC-MS/MS. Ayahuasca samples were diluted and analyzed. Mean concentrations in B. caapi were 4.79 mg/g harmine, 0.451 mg/g harmaline, and 2.18 mg/g tetrahydroharmine (THH), with a high variability among the samples (RSD from 78.9 to 170%). Native B. caapi samples showed significantly higher harmine concentrations than cultivated ones, and samples from the Federal District/Goiás had higher THH content than those collected in the State of Acre. The other Malpighiaceae samples did not contain β-carbolines, except for one D. pubipetala sample. Concentrations in ayahuasca samples ranged from 0.109 to 7.11 mg/mL harmine, 0.012 to 0.945 mg/mL harmaline, 0.09 to 3.05 mg/mL THH, and 0.10 to 3.12 mg/mL DMT. The analysis of paired ayahuasca/B. caapi confirmed that harmine is reduced to harmaline and to THH during the brew preparation. This is the largest study conducted with Malpighiaceae samples and showed a large variability in the main β-carbolines present in B. caapi. This biodiversity is a challenge for standardization of the material used in ethnopharmacological studies of B. caapi and ayahuasca.

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Section: Discussionmentioning

confidence: 99%

Biodiversity of β-Carboline Profile of Banisteriopsis caapi and Ayahuasca, a Plant and a Brew with Neuropharmacological Potential

Santos

Oliveira

Sonsin‐Oliveira

et al. 2020

Plants

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“…Growing the plants in the country where the session is to take place and the plant materials being fresh is likely to be important in ensuring quality (de Oliveira Silveira et al, 2020). However, freezedried ayahuasca can be safely administered with the desired effects (dos .…”

Section: Ayahuascamentioning

confidence: 99%

N,N‐dimethyltryptamine and Amazonian ayahuasca plant medicine

James

Keppler

Robertshaw

et al. 2022

Human Psychopharmacology

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Objective Reports have indicated possible uses of ayahuasca for the treatment of conditions including depression, addictions, post‐traumatic stress disorder, anxiety and specific psychoneuroendocrine immune system pathologies. The article assesses potential ayahuasca and N,N‐dimethyltryptamine (DMT) integration with contemporary healthcare. The review also seeks to provide a summary of selected literature regarding the mechanisms of action of DMT and ayahuasca; and assess to what extent the state of research can explain reports of unusual phenomenology. Design A narrative review. Results Compounds in ayahuasca have been found to bind to serotonergic receptors, glutaminergic receptors, sigma‐1 receptors, trace amine‐associated receptors, and modulate BDNF expression and the dopaminergic system. Subjective effects are associated with increased delta and theta oscillations in amygdala and hippocampal regions, decreased alpha wave activity in the default mode network, and stimulations of vision‐related brain regions particularly in the visual association cortex. Both biological processes and field of consciousness models have been proposed to explain subjective effects of DMT and ayahuasca, however, the evidence supporting the proposed models is not sufficient to make confident conclusions. Ayahuasca plant medicine and DMT represent potentially novel treatment modalities. Conclusions Further research is required to clarify the mechanisms of action and develop treatments which can be made available to the general public. Integration between healthcare research institutions and reputable practitioners in the Amazon is recommended.

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“…The UPLC-MS/MS analysis, which has previously proven to be suitable for the analysis of ayahuasca tea samples (de Oliveira Silveira et al, 2020 ), has shown to be similarly adequate for the identification and quantification of all analytes in urine specimens using an 8-min chromatographic run as shown in Figure 1 . Although chromatographic separation is not mandatory when using MRM, special attention was given to HRL and HRM separation since initial experimentation has demonstrated possible ion suppression for HRL when overlapped with HRM.…”

Section: Resultsmentioning

confidence: 98%

Fast Hollow Fiber Liquid-Phase Microextraction as a Greener Alternative for the Determination of N,N-Dimethyltryptamine and Harmala Alkaloids in Human Urine

et al. 2020

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Ayahuasca tea is an entheogen hallucinogenic beverage used for shamanic and spiritual purposes, prepared by the decoction of different Amazonian plants containing N,N-dimethyltryptamine (DMT) and harmala alkaloids. Since the therapeutic potential of this tea has been broadly studied in recent years, mainly for the treatment of psychiatric disorders, the determination of the ayahuasca tea components in human and animal matrices is of utmost importance. In order to avoid the use of large amounts of toxic solvents, typically employed in traditional sample preparation methods, hollow fiber liquid-phase microextraction (HF-LPME) presents a greener and time-saving alternative. The present study aims to fully develop and apply an HF-LPME method for the determination of DMT, harmine (HRM), harmaline (HRL), and tetrahydroharmine (THH) in human urine samples using liquid chromatography-tandem mass spectrometry (LC-MS/MS). Fractional factorial and Box–Behnken designs were used to identify and optimize significant method variables. Once optimized, validation has shown a limit of detection (LoD) of 1.0 ng/ml for DMT and 2.0 ng/ml for the harmala alkaloid. The limit of quantification (LoQ) was of 5.0 ng/ml for all analytes. The method has shown to be linear over a concentration range of 5–200 ng/ml ( r 2 ≥ 0.99). Intra/inter-day precision and accuracy met the acceptance criteria at the three quality control (QC) levels studied (15.0, 90.0, and 170.0 ng/ml, n = 6, each). Matrix effect evaluation showed predominant ion enhancement and recovery values were above 80%. Dilution factors of 10- and 20-fold have shown acceptable values of accuracy. Selectivity studies showed no interferences. Analysis of eight authentic samples collected from four subjects proved method feasibility. A simple, time-saving and green alternative for the analysis of DMT and harmala alkaloids in human urine samples was developed, optimized using design of experiments, fully validated and applied to authentic samples.

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Stability Evaluation of DMT and Harmala Alkaloids in Ayahuasca Tea Samples

Cited by 20 publications

References 33 publications

Biodiversity of β-Carboline Profile of Banisteriopsis caapi and Ayahuasca, a Plant and a Brew with Neuropharmacological Potential

Biodiversity of β-Carboline Profile of Banisteriopsis caapi and Ayahuasca, a Plant and a Brew with Neuropharmacological Potential

N,N‐dimethyltryptamine and Amazonian ayahuasca plant medicine

Fast Hollow Fiber Liquid-Phase Microextraction as a Greener Alternative for the Determination of N,N-Dimethyltryptamine and Harmala Alkaloids in Human Urine

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