See discussions, stats, and author profiles for this publication at: https://www.researchgate.net/publication/224940266 Analytical techniques for the determination of tryptamines and β-carbolines in plant matrices and in psychoactive beverages consumed during religious ceremonies and neo-shamanic ur... Article in Drug Testing and Analysis · July 2012 DOI: 10.1002/dta.1343 · Source: PubMed CITATIONS READS 18 301 5 authors, including: Sandro Navickiene Simon D. Brandt Universidade Federal de Sergipe Liverpool John Moores University 69 PUBLICATIONS 837 CITATIONS 121 PUBLICATIONS 2,306 CITATIONS SEE PROFILE SEE PROFILE Some of the authors of this publication are also working on these related projects: Detection of synthetic cannabinoids in human urine and hair samples View project Photoantimicrobial discovery View project All content following this page was uploaded by Alain Gaujac on 26 March 2018. The user has requested enhancement of the downloaded file. Drug Testing Review and Analysis Received: 18 November 2011 Revised: 23 February 2012 Accepted: 23 February 2012 Published online in Wiley Online Library (wileyonlinelibrary.com) DOI 10.1002/dta.1343 Analytical techniques for the determination of tryptamines and b-carbolines in plant matrices and in psychoactive beverages consumed during religious ceremonies and neo-shamanic urban practices Alain Gaujac,a,e,f Sandro Navickiene,c Mark I. Collins,d Simon D. Brandte and Jailson Bittencourt de Andradea,b* The consumption of ayahuasca, a hallucinogenic beverage used by indigenous communities in the Amazon, is increasing worldwide due to the expansion of syncretic religions founded in the north of Brazil in the first half of the twentieth century, such as Santo Daime and União do Vegetal. Another example is the jurema wine, a drink that originated from indigenous cultures of the northeast of Brazil. It is currently used for several religious practices throughout Brazil involving urban neo-shamanic rituals and syncretic Brazilian religions, such as Catimbó and Umbanda. Both plant products contain N,N-dimethyltryptamine which requires co-administration of naturally occurring monoamine oxidase inhibitors, for example b-carboline derivatives, in order to induce its psychoactive effects in humans. This review explores the cultural use of tryptamines and b-carbolines and focuses on the analytical techniques that have been recently applied to the determination of these compounds in ayahuasca, its analogues, and the plants used during the preparation of these beverages. Copyright © 2012 John Wiley & Sons, Ltd. Keywords: ayahuasca; jurema wine; plants; tryptamines; b-carbolines; detection; hallucinogens Introduction represent simple indole alkaloids that are commonly present in the biota. Since the emergence of civilizations, the consumption of psycho- Ayahuasca is most commonly produced as a decoction using active plants has been used to induce altered states of cons- leaves of chacrona (Psychotria viridis) and sections of the stem ciousness. In pre-Columbian societies, the use of these plants of the yage vine (Banisteriopsis caapi). Important key components was normally associated with mystical-religious rituals and of the vine are b-carboline derivatives that act as inhibitors of preparation for war. Colonization of the Americas resulted in monoamine oxidase (MAO). The leaves of P. viridis contain the European explorers coming into contact with a variety of psychoactive/hallucinogenic N,N-dimethyltryptamine (DMT) and psychoactive plants, including tobacco (Nicotiana spp.), maracujá or passion fruit (Passiflora spp.), guaraná (Paulinia cupana) and yopo (Anadenanthera peregrina).[1–4] Four centuries after the * Correspondence to: Jailson Bittencourt de Andrade, Universidade Federal global spread of tobacco, consumption of the plant-derived da Bahia (UFBA). Rua Barão de Jeremoabo, s/n. Ondina. CEP 40170–115. beverage ayahuasca, which originated in indigenous Amazon Salvador-Ba, Brazil. E-mail: [email protected] cultures, is attracting devotees throughout the world as a result of the creation of syncretic religious groups in Brazil during the a Universidade Federal da Bahia (UFBA), Ondina, Salvador-Ba, Brazil twentieth century.[5] Two of these religions, Santo Daime and b Instituto Nacional de Ciência e Tecnologia, Centro Interdisciplinar de Energia e União do Vegetal (UDV), are represented in various countries Ambiente, Campus Universitário de Ondina, Salvador-Ba, Brazil around the world including Australia, the United States, and Europe. In some countries, a number of legal disputes have c Universidade Federal de Sergipe (UFS), Campus São Cristóvão, São Cristóvão- been described concerning the legalization of ayahuasca and Se, Brazil [6–9] ‘ consumption during religious rituals. In addition, ayahuasca d Universidade Estadual do Ceará (UECE), Campus do Itaperi, Fortaleza- tourism’ is becoming increasingly common in those equatorial Ce, Brazil South American countries that share areas of the Amazon rainforest.[6,10] Moreover, the Internet also offers a great variety e Liverpool John Moores University, School of Pharmacy and Biomolecular of opportunities to purchase psychoactive plant materials.[11–13] Sciences, Liverpool UK Among the many compounds found in some of these f Instituto Federal de Educação, Ciência e Tecnologia de Sergipe (IFS), Campus plants, the tryptamine and b-carboline derivatives (Figure 1) São Cristóvão, São Cristóvão-Se, Brazil Drug Test. Analysis (2012) Copyright © 2012 John Wiley & Sons, Ltd. Drug Testing and Analysis A. Gaujac et al. Tryptamine Derivatives expansion in their use for religious, recreational, and clinical research purposes. The need for an in-depth approach towards R4 R1 analytical characterization becomes obvious in cases of untoward R3 N R2 effects or even fatal intoxications which can, for example, arise from ill-informed combinations of plant products with other N – H psychoactive substances.[23 26] At the same time, consideration needs to be given to the promising therapeutic potential that was Tryptamine – reported for constituents present in these plant materials.[27 33] In R1,R2 ,R 3,R 4 = H addition, a wide variation of concentration levels of ayahuasca 5-Hydroxytryptamine (serotonin) R ,R ,R = H R = OH components that differ not only from church to church, but also 1 2 4 ; 3 [34] N-Methyltryptamine (NMT) between different batches of the same church, were also reported. Occasionally, an extremely concentrated form called ‘ayahuasca R1= H;R2 = CH3,R3,R4 = H ’ N,N-Dimethyltryptamine (DMT) honey can also be encountered which derives its name from high R12,R = CH3; R3,R4 = H viscosity similar to honey syrup. Detailed studies on the identity 5-Methoxy-N,N-dimethyltryptamine (5-MeO-DMT) and levels of psychoactive substances found in these preparations fi R12,R = CH3;R3= OCH3;R4 = H and appropriately de ned criteria for their determination are required. This might be of particular interest in cases where there is the concomitant use of other additives such as Cannabis,[35,36] β-Carboline Derivatives P. harmala,tobacco,andjuremawine,whereprecautionsorquality control might be lacking. The objective of this review is to present some cultural and chemical features of DMT-containing plant products. An account is provided of recent developments in R N O N analytical approaches towards the determination of tryptamines, H b b CH3 -carbolines and tetrahydro- -carbolines detected in tissues of M. tenuiflora, P. viridis, P. aquatica, B. caapi and P. harmala, as well Harmol Harmine as in ayahuasca samples. R = H R = CH3 R N O N Psychoactive beverages used for ritual purposes: H CH3 ayahuasca and jurema wine Harmalol Harmaline Ayahuasca R = H R = CH3 Ayahuasca (aya = soul, spirit; huasca = vine), a word belonging to the Quechua dialect still spoken in some regions of South R NH O N America, is a drink that is mostly prepared using a decoction H R of two plants: the leaves of the DMT-containing chacrona (Psychotria viridis) and sections of the stem of the jagube vine Tetrhydronorharmine (Banisteriopsis caapi) that provides three major MAOI compo- R = H nents such as harmine, harmaline and tetrahydroharmine (THH) Tetrahydroharmine (Figure 1). The chemical composition of ayahuasca can differ R = CH 3 between indigenous tribes due to the use of different plant [1,14,15,37] Figure 1. General chemical structure of the tryptamine and b-carboline species although the same psychoactive constituents – derivatives. are present in all preparations.[38 41] Ayahuasca is known by various indigenous names, including yajé, natema and caapi, and was first described by Villavicencio in 1858. Seven years the combination with reversible MAO inhibitors (MAOIs) renders earlier, the English explorer Richard Spruce made contact with the DMT orally active.[14–17] the Tukanoan Indians, in Rio Uaupés (Brazilian Amazonia), but In an analogous fashion, the jurema wine, originally consumed his findings concerning the use of a liana called caapi were only by pre-colonial indigenous tribes in the northeast of Brazil, has not published before 1908 when the plant was identified as become a part of the liturgy of the Catimbó and Afro-Brazilian Banisteria caapi.[37] Clinical research on the physiological and psy- religious groups since colonization. The wine is predominantly chological effects of ayahuasca in humans re-emerged in the produced using the root bark of the jurema tree (Mimosa spp.), which early 1990s which offered important insights into psychopharma- also contains DMT.[18–21] In large urban