Chiral Analysis of Amphetamine and Methamphetamine in Urine by Liquid Chromatography-Tandem Mass Spectrometry Applying M
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ORIGINAL
Chiral Analysis of Amphetamine and Methamphetamine in Urine by Liquid Chromatography‑Tandem Mass Spectrometry Applying Mosher Derivatization Carina de Souza Anselmo1 · Christiane Martins de Vasconcellos Silveira1 · Vinicius Figueiredo Sardela1 · Henrique Marcelo Gualberto Pereira1 Received: 17 July 2020 / Revised: 20 October 2020 / Accepted: 26 October 2020 © Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract Methamphetamine (MA) and amphetamine (AM) are central nervous system doping agents, listed in the WADA Prohibited List, which in the past years showed the highest prevalence among all stimulants. Specifically, concerning these stimulants, it is essential to distinguish between d and l-isomers of AM and MA due to their distinction in illicit or legal nonprescription use. The main separation methods used for the urinary determination of MA and AM enantiomers are based on chromatographic procedures, such as gas chromatography after chiral derivatization or liquid chromatography (LC) applying chiral columns, followed by the mass spectrometer (MS) detection. The use of the optically pure reagent R-(-)-α-methoxyα-(trifluoromethyl) phenylacetic acid chloride (R-MTPA-Cl – Mosher’s Reagent) allows the isomeric separation by both chromatographic procedures while preserving the isomeric composition of the substances. Therefore, in the present work, an LC-MS2 approach has been developed for AM and MA detection in urine after Mosher derivatization. The method was validated and can be used for the enantioselective confirmation of AM and MA for doping control purposes and forensic analysis in general, being useful for the distinction between the medicinal and illicit use of both stimulants. Keywords Doping control · Chiral analysis · Stimulants · R-(-)-α-methoxy-α-(trifluoromethyl) phenylacetic acid chloride (R-MTPA-cl) · Liquid chromatography · Mass spectrometry
Introduction Stimulants are among the most misused substances in sport as doping agents, behind only anabolics and diuretics [1]. Methamphetamine (MA) and amphetamine (AM) (Fig. 1) are central nervous system doping agents [2], listed in the World Anti-Doping Agency (WADA) Prohibited List [3], which in the past years showed the highest prevalence among all stimulants [1]. Several therapeutic and illicit drugs contain or are metabolized to MA and AM and are excreted in the urine [2]. Furthermore, MA can also be metabolized to AM, preserving its isomeric structural composition [4]. Thus, the detection of these prohibited substances * Carina de Souza Anselmo [email protected] 1
Federal University of Rio de Janeiro, Institute of Chemistry, LBCD – LADETEC, Av. Horácio Macedo, 1281, Bloco C ‑ Cidade Universitária, Rio de Janeiro, Brazil
in biological specimens is a central issue in toxicological analysis for doping control [5, 6]. Concerning MA and AM, it is essential to distinguish between d- and l-isomers due to the distinction between illicit or legal non-prescription use [2, 7]. In fact, illegal AM is available mainly as a mi
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