Quimica

Research Article
Received: 6 March 2008, Revised: 6 October 2008, Accepted: 21 October 2008 Published online 12 January 2009 in Wiley Interscience

(www.interscience.wiley.com) DOI 10.1002/pca.1110

Gas Chromatographic Analysis of Dimethyltryptamine and b-Carboline Alkaloids in Ayahuasca, an Amazonian Psychoactive Plant Beverage
John Wiley & Sons, Ltd.

Ana Paula Salum Pires, CarolinaDizioli Rodrigues De Oliveira, Sidnei Moura, Felipe Augusto Dörr, Wagner Abreu E. Silva and Mauricio Yonamine*
ABSTRACT: Introduction – Ayahuasca is obtained by infusing the pounded stems of Banisteriopsis caapi in combination with the leaves of Psychotria viridis. P. viridis is rich in the psychedelic indole N,N-dimethyltryptamine, whereas B. caapi contains substantial amounts of b-carbolinealkaloids, mainly harmine, harmaline and tetrahydroharmine, which are monoamine-oxidase inhibitors. Because of differences in composition in ayahuasca preparations, a method to measure their main active constituents is needed. Objective – To develop a gas chromatographic method for the simultaneous determination of dimethyltryptamine and the main b-carbolines found in ayahuasca preparations. Methodology– The alkaloids were extracted by means of solid phase extraction (C18) and detected by gas chromatography with nitrogen/phosphorous detector. Results – The lower limit of quantification (LLOQ) was 0.02 mg/mL for all analytes. The calibration curves were linear over a concentration range of 0.02–4.0 mg/mL (r2 > 0.99). The method was also precise (RSD < 10%). Conclusion – A simple gaschromatographic method to determine the main alkaloids found in ayahuasca was developed and validated. The method can be useful to estimate administered doses in animals and humans for further pharmacological and toxicological investigations of ayahuasca. Copyright © 2009 John Wiley & Sons, Ltd.
A method was developed and validated for the simultaneous determination of dimethyltryptamine and β-carfbolinesalkaloids (harmine, harmaline and tetrahydroharmine) in ayahuasca preparations. The alkaloids were extracted by menas of solid phase extraction (C18) and detected by gas

Keywords: Dimethyltryptamine; β-carbolines; ayahuasca; gas chromatography

Introduction
Ayahuasca, also known by the names Hoasca, Daime, Yajé, Natema and Vegetal, is a psychoactive plant tea originally used by shamansthroughout the Amazon Basin in magico-religious practices and folk medicine of indigenous people (Riba et al., 2003). This beverage is obtained by infusing the pounded stems of Banisteriopsis caapi in combination with the leaves of Psychotria viridis. P. viridis contains the psychedelic agent N,N-dimethyltryptamine (Fig. 1), whereas B. caapi contains βcarbolines such as harmine, harmaline andtetrahydroharmine (Fig. 1), which are potent monoamine oxidase (MAO) inhibitors. Dimethyltryptamine is not orally active itself because it is inactivated by peripheral MAO (present in liver and gut). However, the inhibition of MAO by β-carbolines allows the oral activity of dimethyltryptamine, enabling it to reach its site of action in the central nervous system. The synergistic interaction of thesealkaloids is the basis of the psychotropic action of ayahuasca (McKenna, 2004). In Brazil, ayahuasca has been incorporated in rituals of modern syncretic religious groups, mainly the Santo Daime and the União do Vegetal (UDV), where the beverage is reported to be used to facilitate self-knowledge and introspection. In 2004, the use of ayahuasca within religious context was officially recognised andFigure 1. Chemical structures of the main ayahuasca alkaloids: (A) dimethyltryptamine, (B) harmine, (C) harmaline and (D) tetrahydroharmine.

* Correspondence to: M. Yonamine, Department of Clinical and Toxicological Analysis, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Prof. Lineu Prestes, 580 B13B, 05508-900, São Paulo, SP, Brazil. E-mail: yonamine@usp.br Department of...