Determination of MDMA and its metabolites in blood and urine by gas chromatography-mass spectrometry and analysis of enantiomers by capillary electrophoresis.
A gas chromatography-mass spectrometry (GC-MS) method was used for the simultaneous quantitation of 3,4-methylenedioxymethamphetamine (MDMA) and the 3,4-methylenedioxyamphetamine (MDA), 4-hydroxy-3-methoxymethamphetamine (HMMA), and 4-hydroxy-3-methoxyamphetamine (HMA) metabolites in plasma and urine samples after the administration of 100 mg MDMA to healthy volunteers. Samples were hydrolyzed prior to a solid-phase extraction with Bond Elut Certify columns. Analytes were eluted with ethyl acetate (2% ammonium hydroxide) and analyzed as their trifluoroacyl derivatives. Linear calibration curves were obtained at plasma and urine concentration ranges of 25-400 ng/mL and 250-2000 ng/mL for MDMA and HMMA, and of 2.5-40 ng/mL and 100-1000 ng/mL for MDA and HMA. Following the same urine preparation procedure but without the derivatization step, a capillary electrophoresis (CE) method for enantiomerical resolution of compounds was developed using (2-hydroxy)propyl-beta-cyclodextrin at two different concentrations (10 and 50mM in 50mM H3PO4, pH 2.5) as chiral selector. Calibration curves for the CE method were prepared with the corresponding racemic mixture and were linear between 125 and 2000 ng/mL, 50 and 1000 ng/mL, and 125 and 1500 ng/mL for each enantiomer of MDMA, MDA, and HMMA, respectively. Stereoselective disposition of MDMA and MDA was confirmed. HMMA disposition seems to be in apparent contradiction with MDMA findings as the enantiomer ratio is close to 1 and constant over the time.
Pizarro
Nieves
N
Pharmacology Research Unit, Institut Municipal d'Investigació Mèdica (IMIM), Barcelona, Spain.
Ortuño
Jordi
J
Farré
Magí
M
Hernández-López
Cándido
C
Pujadas
Mitona
M
Llebaria
Amadeu
A
Joglar
Jesús
J
Roset
Pere N
PN
Mas
Marta
M
Segura
Jordi
J
Camí
Jordi
J
de la Torre
Rafael
R
D015104:3,4-Methylenedioxyamphetamine / Q000097:blood / Q000652:urine; D003846:Deoxyepinephrine / Q000031:analogs & derivatives* / Q000097:blood / Q000652:urine; D019075:Electrophoresis, Capillary / Q000379:methods; D008401:Gas Chromatography-Mass Spectrometry; D006213:Hallucinogens / Q000097:blood* / Q000378:metabolism / Q000652:urine*; D006801:Humans; D008297:Male; D008694:Methamphetamine / Q000031:analogs & derivatives* / Q000097:blood / Q000652:urine; D018817:N-Methyl-3,4-methylenedioxyamphetamine / Q000097:blood* / Q000378:metabolism / Q000652:urine*; D015203:Reproducibility of Results; D012680:Sensitivity and Specificity; D013237:Stereoisomerism; D015813:Substance Abuse Detection / Q000379:methods*
D006213:Hallucinogens; C079646:4-hydroxy-3-methoxymethamphetamine; C069512:alpha-methylepinine; D008694:Methamphetamine; D015104:3,4-Methylenedioxyamphetamine; D018817:N-Methyl-3,4-methylenedioxyamphetamine; D003846:Deoxyepinephrine