Determination of Tryptamines and β-Carbolines in Ayahuasca Beverage Consumed During Brazilian Religious Ceremonies

Santos, Matheus; Navickiene, Sandro; Gaujac, Alain

doi:10.5740/jaoacint.16-0337

Cited by 13 publications

(18 citation statements)

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“…In this context, the quantification of ayahuasca’s main alkaloids prior to its administration in animal or human studies is essential, as well as the knowledge of the tea’s sample origin, storage, and transportation conditions. Various analytical methods have been reported in the literature for the analysis of ayahuasca’s botanical preparations; these include solid-phase extraction (SPE), solid-phase microextraction (SPME), liquid–liquid extraction (LLE), and dilute-and-shoot for sample preparation prior to liquid chromatography or gas chromatography, both coupled to mass spectrometry and other detector types [ 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 ].…”

Section: Introductionmentioning

confidence: 99%

Stability Evaluation of DMT and Harmala Alkaloids in Ayahuasca Tea Samples

et al. 2020

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Ayahuasca tea is a hallucinogenic beverage used for religious purposes in Brazil and many other countries that has therapeutic potential in the treatment of some mental health disorders. In the context of psychedelic research, quantification of the tea’s main alkaloids prior to its administration in animal or human studies is essential. For this reason, this study aims to provide information regarding the stability of the main ayahuasca alkaloids (dimethyltryptamine, DMT; harmine, HRM; tetrahydroharmine, THH; harmaline, HRL) in three different conditions: (1) A year stored in a refrigerator either in plastic or glass containers, (2) seven days at 37 °C to reproduce usual mail transportation, and (3) after three freeze–thaw cycles. Samples were quantified after a dilute-and-shoot procedure using liquid chromatography tandem mass spectrometry (LC-ESI-MS/MS). There was no significant degradation of DMT concentration over time in all tested conditions. Harmala alkaloids (THH, HRL, and HRM) showed important variations after long-term and high-temperature storages. Although DMT has proven to be stable in all studied conditions, the harmala alkaloids revealed intense degradation and even concentration increment. This may be caused by degradation, alkaloid inter-conversion, and leaching from tea precipitate material. Therefore, ayahuasca quantification before administration in controlled sets is mandatory.

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Section: Introductionmentioning

confidence: 99%

Stability Evaluation of DMT and Harmala Alkaloids in Ayahuasca Tea Samples

et al. 2020

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“…18 The results demonstrated that menthone-thiosemicarbazone or coconut charcoal could be used as the extractant phase for determination of these alkaloids in ayahuasca beverages, since the concentrations were in agreement with those obtained using commercial silica as the adsorbent material (0.3 to 36.7 mg mL -1 ). 13 For these selected alkaloids, some studies have shown concentration range from 0.01 to 46.7 mg mL -1 . 6,9,19 The discrepancy in alkaloid concentration can be explained by the different methods of preparation as well as the amounts and proportions of the source plants.…”

Section: Methods Applicationmentioning

confidence: 99%

“…Ayahuasca samples were prepared from specimens of Banisteriopsis caapi stems and Psychotria viridis leaves by members of a religious group located in the city of Fortaleza, Ceará State, Brazil, according to the method reported by Santos et al 13 Aqueous decoctions of the plants were prepared from harvested material. At the end of the 20-h decoction, the extracts were bottled, frozen, and shipped to the Department of Chemistry at the Federal University of Sergipe.…”

Section: Sample Preparationmentioning

confidence: 99%

“…In an earlier work, 13 our group studied the use of commercial silica as the sorbent material and acidified methanol as the eluting solvent, using an SPE procedure for the recovery of different alkaloids from ayahuasca beverages. Analogously, in the present study, evaluation was made through the use of coconut charcoal and menthonethiosemicarbazone polymer as alternative sorbents for the determination of harmine, harmaline, tetrahydroharmine, harmalol, tryptamine, and DMT in ayahuasca beverage.…”

Section: Optimization Of the Extraction Proceduresmentioning

confidence: 99%

“…While the menthone-thiosemicarbazone was chosen to evaluate its performance relative to commercial silica, which was previously studied. 13…”

Section: Introductionmentioning

confidence: 99%

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Use of Coconut Charcoal and Menthone-Thiosemicarbazone Polymer as Solid Phase Materials for the Determination of N,N-Dimethyltryptamine, Harmine, Harmaline, Harmalol, and Tetrahydroharmine in Ayahuasca Beverage by Liquid Chromatography-Tandem Mass Spectrometry

Navickiene¹,

Santos²,

Santos³

et al. 2018

J. Braz. Chem. Soc.

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An extraction method based on solid-phase extraction was developed to determine the major alkaloid components, N,N-dimethyltryptamine, harmine, harmaline, harmalol, and tetrahydroharmine, in ayahuasca using ultra-performance liquid chromatography-tandem mass spectrometry. Coconut charcoal and menthone-thiosemicarbazone polymer were tested as new adsorbent materials. Experiments carried out at levels of 1, 5, 10, 50, 100, and 250 μg mL-1 resulted in recoveries in the ranges 45.3-115.7% for menthone-thiosemicarbazone and 40.6-116.2% for coconut charcoal. The detection and quantification limits ranged from 0.003 to 0.016 μg mL-1 and from 0.009 to 0.043 μg mL-1 , respectively. The method developed was linear over the tested range (0.05-1.0 μg mL-1), with correlation coefficients ranging from 0.9969 to 0.9998. The technique was applied for analysis of the compounds in an ayahuasca sample collected from a religious group located in the city of Fortaleza, obtaining concentrations in the range from 0.3 to 19.3 mg mL-1 .

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Comparative study of sample preparation procedures to determine the main compounds in ayahuasca beverages by QuEChERS and high‐performance liquid chromatography analysis

Gonçalves,

Rosado,

Barroso

et al. 2024

Phytochemical Analysis

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IntroductionAyahuasca is a psychoactive drink originally consumed by indigenous people of the Amazon. The lack of regulation of this drink leads to uncontrolled consumption, and it is often consumed in religious contexts.ObjectiveThe aim of this work is to compare three miniaturised extraction techniques for extracting the main ayahuasca compounds from beverages.MethodologyThree sample pretreatment techniques were evaluated (dispersive liquid–liquid microextraction [DLLME], microextraction by packed sorbent [MEPS] and QuEChERS [Quick, Easy, Cheap, Effective, Rugged and Safe]) for the simultaneous extraction of N,N‐dimethyltryptamine (DMT), tetrahydroharmine (THH), harmine, harmaline, harmol and harmalol from ayahuasca beverage samples. Then, the most promising technique (QuEChERS) was chosen to pre‐concentrate the analytes, subsequently detected by high‐performance liquid chromatography coupled to a diode array detector (HPLC‐DAD).ResultsThe procedure was optimised, with the final conditions being 500 μL of extractor solvent, 85 mg of primary secondary amine (PSA) and 4 s of vortexing. The analytical method was validated, showing to be linear between 0.16 and 10 μg/mL for β‐carbolines and between 0.016 and 1 μg/mL for DMT, with coefficients of determination (R2) between 0.9968 and 0.9993. The limit of detection (LOD) and lower limit of quantification (LLOQ) were 0.16 μg/mL for all compounds, except for DMT (0.016 μg/mL) and extraction efficiencies varied between 60.2% and 88.0%.ConclusionThe analytical methodology proved to be accurate and precise, with good linearity, LODs and LLOQs. This method has been fully validated and successfully applied to ayahuasca beverage samples.

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Determination of Tryptamines and β-Carbolines in Ayahuasca Beverage Consumed During Brazilian Religious Ceremonies

Cited by 13 publications

References 8 publications

Stability Evaluation of DMT and Harmala Alkaloids in Ayahuasca Tea Samples

Stability Evaluation of DMT and Harmala Alkaloids in Ayahuasca Tea Samples

Use of Coconut Charcoal and Menthone-Thiosemicarbazone Polymer as Solid Phase Materials for the Determination of N,N-Dimethyltryptamine, Harmine, Harmaline, Harmalol, and Tetrahydroharmine in Ayahuasca Beverage by Liquid Chromatography-Tandem Mass Spectrometry

Comparative study of sample preparation procedures to determine the main compounds in ayahuasca beverages by QuEChERS and high‐performance liquid chromatography analysis

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