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Studies on the psychoative N,N-dimethyltryptamine (DMT) in Mimosa tenuiflora (Willd.) Poiret and in drinks consumed in a religious context.


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Abstract

N,N-dimethyltryptamine (DMT) is a potent psychoactive found in beverages consumed in religion rituals and neo-shamanic practices over the world. Two of these religions, named “Santo Daime” and “União do Vegetal (UDV)”, are represented in countries including Australia, the USA and several European nations. In some of them, there have been legal disputes concerning the legalization of ayahuasca consumption during religious rituals, a beverage rich in DMT. It is a substance banned in most countries, which makes its acquisition difficult. In Brazil, is a controlled drug, enforced by the Brazilian National Health Surveillance Agency (Agência Nacional de Vigilância Sanitária). Nevertheless, in this country, even children and pregnant women are legally authorized to consume ayahuasca in a religious context. The present study describes a simple and fast method to obtain N,N-dimethyltryptamine (DMT) from inner barks of Mimosa tenuiflora for the purpose of using it as a chromatographic analytical standard. Fourier transform infrared spectroscopy (FTIR), single and tandem stage mass spectrometry (MS), nuclear magnetic resonance spectroscopy (1H and 13C NMR) and melting point measurements were performed for the structural characterization of N,Ndimethyltryptamine. The results obtained were in agreement with previous literature reports. The purity of the compound (>95%) was determined using ultraviolet (UV) absorption spectrometry with a tryptamine analytical standard. Observations suggest that DMT may exist in two or more polymorphic forms. A combination of experimental techniques, in this case X-ray diffraction and differential scanning calorimetry (DSC), was done and proved that, in fact, DMT presents at least two polymorphic forms. A new simple and low-cost method based on matrix solid-phase dispersion (MSPD) and gas chromatography with mass spectrometric detection (GC-MS) has been optimized for the determination of N,N-dimethyltryptamine in M. tenuiflora inner bark. The experimental variables that affect the MSPD method, such as the amounts of solid-phase and herbal sample, solvent nature, eluate volume and NaOH concentration were optimized using an experimental design. The method showed good linearity (r = 0.9962) and repeatability (RSD < 7.4%) for DMT compound, with detection limit of 0.12 mg g-1. The proposed method was used to analyze 24 samples obtained locally. The results showed that concentrations of the target compound in M. tenuiflora barks, ranged from 1.26 to 9.35 mg g-1 for these samples. Also, a novel analytical approach combining solid-phase microextraction in headspace mode (HS-SPME) / gas chromatography ion trap mass spectrometry (GC-IT-MS) was developed for the detection and quantification N,Ndimethyltryptamine in ayahuasca and vinho da jurema real samples. The method was performed with a polydimethylsiloxane/divinylbenzene (PDMS/DVB) fiber in headspace mode (70 min at 60 ºC) which resulted in good precision (RSD < 8.6%) and accuracy values (71–109%). Detection and quantification limits obtained for DMT were 0.78 and 9.5 mg L-1, respectively and good linearity (1.56–300 mg L-1, r2 = 0.9975) was also observed. In addition, the proposed method showed good robustness and allowed for the minimization of sample manipulation. Five jurema beverage samples were prepared in the laboratory in order to study the impact of temperature, pH and ethanol on the ability to extract DMT into solution. The developed method was then applied to the analysis of twelve real ayahuasca and vinho da jurema samples, obtained from Brazilian religious groups, which revealed DMT concentration levels between 0.10 and 1.81 g L-1. All liquid samples were diluted by a factor of 10 or 25. Keywords: N,N-Dimethyltryptamine, ayahuasca, vinho da jurema, Mimosa tenuiflora, SPME, MSPD, GC-MS.