Development of enantioselective high-performance liquid chromatography-tandem mass spectrometry method for the quantitative determination of 3,4-methylenedioxy-methamphetamine (MDMA) and its phase-1 metabolites in human biological fluids
In the present study enantioselective high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS) methods were developed for the quantitative determination of 3,4-methylenedioxy-methamphetamine (MDMA) and its major phase-1 metabolites 4-hydroxy-3-methoxyamphetamine (HMA), 4-hydroxy-3-...
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| Published in | Journal of pharmaceutical and biomedical analysis Vol. 238; p. 115768 |
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| Main Authors | , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier B.V
20.01.2024
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| Abstract | In the present study enantioselective high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS) methods were developed for the quantitative determination of 3,4-methylenedioxy-methamphetamine (MDMA) and its major phase-1 metabolites 4-hydroxy-3-methoxyamphetamine (HMA), 4-hydroxy-3-methoxymethamphetamine (HMMA) and 3,4-methylenedioxyamphetamine (MDA) in human plasma, sweat, oral fluid (OF) and urine. The simultaneous separation of all these compounds and their respective enantioseparation was accomplished on two polysaccharide-based chiral columns. The Lux AMP column with a proprietary chiral selector enabled baseline separation of the enantiomers of MDMA, HMA and HMMA while MDA enantiomers could not be separated with this column under the experimental conditions used in this study. The Lux i-Amylose-3 column based on amylose tris(5-chloro-3-methylphenylcarbamate) as chiral selector baseline-separated the enantiomers of MDMA, HMMA and MDA while the enantiomers of HMA could not be separated. Thus, the various samples were analyzed by using both columns alternatively in combinations with acetonitrile containing 25% (v/v) 5 mM ammonium bicarbonate buffer at pH 11.0 as mobile phase. Analysis time was less than 4 min with the Lux AMP column and less than 6 min with the Lux i-Amylose-3 column. Both methods were validated and applied to the enantioselective determination of MDMA and its phase-I metabolites in human biological fluids, and enantioselective metabolism of MDMA was confirmed.
•An enantioselective method for quantitative determination of MDMA and some of its metabolites in human biological fluids.•The method is simple and fast, allowing high-throughput analyses.•The method was applied for the enantioselectivity in metabolism and pharmacokinetic of the parent compound and metabolites. |
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| AbstractList | In the present study enantioselective high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS) methods were developed for the quantitative determination of 3,4-methylenedioxy-methamphetamine (MDMA) and its major phase-1 metabolites 4-hydroxy-3-methoxyamphetamine (HMA), 4-hydroxy-3-methoxymethamphetamine (HMMA) and 3,4-methylenedioxyamphetamine (MDA) in human plasma, sweat, oral fluid (OF) and urine. The simultaneous separation of all these compounds and their respective enantioseparation was accomplished on two polysaccharide-based chiral columns. The Lux AMP column with a proprietary chiral selector enabled baseline separation of the enantiomers of MDMA, HMA and HMMA while MDA enantiomers could not be separated with this column under the experimental conditions used in this study. The Lux i-Amylose-3 column based on amylose tris(5-chloro-3-methylphenylcarbamate) as chiral selector baseline-separated the enantiomers of MDMA, HMMA and MDA while the enantiomers of HMA could not be separated. Thus, the various samples were analyzed by using both columns alternatively in combinations with acetonitrile containing 25% (v/v) 5 mM ammonium bicarbonate buffer at pH 11.0 as mobile phase. Analysis time was less than 4 min with the Lux AMP column and less than 6 min with the Lux i-Amylose-3 column. Both methods were validated and applied to the enantioselective determination of MDMA and its phase-I metabolites in human biological fluids, and enantioselective metabolism of MDMA was confirmed.
•An enantioselective method for quantitative determination of MDMA and some of its metabolites in human biological fluids.•The method is simple and fast, allowing high-throughput analyses.•The method was applied for the enantioselectivity in metabolism and pharmacokinetic of the parent compound and metabolites. In the present study enantioselective high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS) methods were developed for the quantitative determination of 3,4-methylenedioxy-methamphetamine (MDMA) and its major phase-1 metabolites 4-hydroxy-3-methoxyamphetamine (HMA), 4-hydroxy-3-methoxymethamphetamine (HMMA) and 3,4-methylenedioxyamphetamine (MDA) in human plasma, sweat, oral fluid (OF) and urine. The simultaneous separation of all these compounds and their respective enantioseparation was accomplished on two polysaccharide-based chiral columns. The Lux AMP column with a proprietary chiral selector enabled baseline separation of the enantiomers of MDMA, HMA and HMMA while MDA enantiomers could not be separated with this column under the experimental conditions used in this study. The Lux i-Amylose-3 column based on amylose tris(5-chloro-3-methylphenylcarbamate) as chiral selector baseline-separated the enantiomers of MDMA, HMMA and MDA while the enantiomers of HMA could not be separated. Thus, the various samples were analyzed by using both columns alternatively in combinations with acetonitrile containing 25% (v/v) 5 mM ammonium bicarbonate buffer at pH 11.0 as mobile phase. Analysis time was less than 4 min with the Lux AMP column and less than 6 min with the Lux i-Amylose-3 column. Both methods were validated and applied to the enantioselective determination of MDMA and its phase-I metabolites in human biological fluids, and enantioselective metabolism of MDMA was confirmed.In the present study enantioselective high-performance liquid chromatography-tandem mass spectrometry (LC-MS/MS) methods were developed for the quantitative determination of 3,4-methylenedioxy-methamphetamine (MDMA) and its major phase-1 metabolites 4-hydroxy-3-methoxyamphetamine (HMA), 4-hydroxy-3-methoxymethamphetamine (HMMA) and 3,4-methylenedioxyamphetamine (MDA) in human plasma, sweat, oral fluid (OF) and urine. The simultaneous separation of all these compounds and their respective enantioseparation was accomplished on two polysaccharide-based chiral columns. The Lux AMP column with a proprietary chiral selector enabled baseline separation of the enantiomers of MDMA, HMA and HMMA while MDA enantiomers could not be separated with this column under the experimental conditions used in this study. The Lux i-Amylose-3 column based on amylose tris(5-chloro-3-methylphenylcarbamate) as chiral selector baseline-separated the enantiomers of MDMA, HMMA and MDA while the enantiomers of HMA could not be separated. Thus, the various samples were analyzed by using both columns alternatively in combinations with acetonitrile containing 25% (v/v) 5 mM ammonium bicarbonate buffer at pH 11.0 as mobile phase. Analysis time was less than 4 min with the Lux AMP column and less than 6 min with the Lux i-Amylose-3 column. Both methods were validated and applied to the enantioselective determination of MDMA and its phase-I metabolites in human biological fluids, and enantioselective metabolism of MDMA was confirmed. |
| ArticleNumber | 115768 |
| Author | Poyatos, Lourdes Sprega, Giorgia Farkas, Tivadar Lo Faro, Alfredo Fabrizio Berretta, Paolo Tini, Anstasio Takaishvili, Nino Chankvetadze, Bezhan Papaseit, Esther Farre, Magì Beradinelli, Diletta Di Giorgi, Alessandro Busardò, Francesco Paolo |
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| Keywords | Chiral HPLC Enantioselective metabolism Enantioseparation, MDMA and metabolites |
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