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Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites by gas chromatography/mass spectrometry

AutorPizarro, Nieves; Llebaria, Amadeu; Cano, Silvia; Joglar Tamargo, Jesús; Farré, Magí; Segura, Jordi; Torre, Rafael de la
Palabras clave3,4-Methylenedioxymethamphetamine
Gas chromatography-mass spectrometry
Metabolic reactions
Plasma Analysis
Urine analysis
Fecha de publicación6-ene-2003
CitaciónRapid Communications in Mass Spectrometry 17(4): 330-336 (2003)
Resumen3,4-Methylenedioxymethamphetamine (MDMA, ecstasy) is consumed as the racemate but some metabolic steps are enantioselective. In addition, chiral properties are preserved during MDMA biotransformation. A quantitative analytical methodology using gas chromatography/mass spectrometry (GC/MS) to determine enantioselective disposition in the body of MDMA and its main metabolites including 3,4-methylenedioxyamphetamine (MDA), 4-hydroxy-3-methoxymethamphetamine (HMMA), and 4-hydroxy-3-methoxyamphetamine (HMA) was developed. Plasma and urine samples were collected from a male volunteer. The analysis of MDMA, MDA, and 4-hydroxy-3-methoxy metabolites by GC/MS required a two-step derivatization procedure. The first step consisted of derivatization of the amine with enantiomerically pure Mosher's reagent ((R)-MTPCl). Triethylamine was used as a base to neutralize hydrochloric acid formed during the reaction allowing quantitative derivatization, which resulted in a substantial improvement in the sensitivity of the method compared with other previously described techniques. Further treatment with ammonium hydroxide was required since both amine and hydroxyl groups underwent derivatization in the reaction. Ammonium hydroxide breaks bonds formed with hydroxyl groups without affecting amine derivatives. The second derivatization step using hexamethyldisilazane was needed for metabolites containing phenol residues. This derivatization method permitted the stereochemically specific study of MDMA and its main monohydroxylated metabolites by GC/MS. A detailed study of the chemical reactions involved in the derivatization steps was indispensable to develop a straightforward, sensitive, and reproducible method for the analysis of the parent drug compound and its metabolites.
Descripción7 pages, 3 figures, 3 tables.-- PMID: 12569443 [PubMed].-- Printed version published Feb 28, 2003.
Versión del editorhttp://dx.doi.org/10.1002/rcm.919
ISSN0951-4198 (Print)
1097-0231 (Online)
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