PMID- 21656610
OWN - NLM
STAT- MEDLINE
DCOM- 20110907
LR  - 20211020
IS  - 1096-9888 (Electronic)
IS  - 1076-5174 (Print)
IS  - 1076-5174 (Linking)
VI  - 46
IP  - 7
DP  - 2011 Jul
TI  - Development and validation of LC-HRMS and GC-NICI-MS methods for stereoselective 
      determination of MDMA and its phase I and II metabolites in human urine.
PG  - 603-14
LID - 10.1002/jms.1929 [doi]
AB  - 3,4-Methylenedioxymethamphetamine (MDMA) is a racemic drug of abuse and its R- 
      and S-enantiomers are known to differ in their dose-response curve. The 
      S-enantiomer was shown to be eliminated at a higher rate than the R-enantiomer 
      most likely explained by stereoselective metabolism that was observed in various 
      in vitro experiments. The aim of this work was the development and validation of 
      methods for evaluating the stereoselective elimination of phase I and 
      particularly phase II metabolites of MDMA in human urine. Urine samples were 
      divided into three different methods. Method A allowed stereoselective 
      determination of the 4-hydroxy-3-methoxymethamphetamine (HMMA) glucuronides and 
      only achiral determination of the intact sulfate conjugates of HMMA and 
      3,4-dihydroxymethamphetamine (DHMA) after C18 solid-phase extraction by liquid 
      chromatography-high-resolution mass spectrometry with electrospray ionization. 
      Method B allowed the determination of the enantiomer ratios of DHMA and HMMA 
      sulfate conjugates after selective enzymatic cleavage and chiral analysis of the 
      corresponding deconjugated metabolites after chiral derivatization with 
      S-heptafluorobutyrylprolyl chloride using gas chromatography-mass spectrometry 
      with negative-ion chemical ionization. Method C allowed the chiral determination 
      of MDMA and its unconjugated metabolites using method B without sulfate cleavage. 
      The validation process including specificity, recovery, matrix effects, process 
      efficiency, accuracy and precision, stabilities and limits of quantification and 
      detection showed that all methods were selective, sensitive, accurate and precise 
      for all tested analytes.
CI  - Copyright (c) 2011 John Wiley & Sons, Ltd.
FAU - Schwaninger, Andrea E
AU  - Schwaninger AE
AD  - Department of Experimental and Clinical Toxicology, Institute of Experimental and 
      Clinical Pharmacology and Toxicology, Saarland University, D-66421 Homburg 
      (Saar), Germany.
FAU - Meyer, Markus R
AU  - Meyer MR
FAU - Huestis, Marilyn A
AU  - Huestis MA
FAU - Maurer, Hans H
AU  - Maurer HH
LA  - eng
GR  - ZIA DA000468-07/Intramural NIH HHS/United States
GR  - ZIA DA000468-08/Intramural NIH HHS/United States
GR  - ZIA DA000468-09/Intramural NIH HHS/United States
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - England
TA  - J Mass Spectrom
JT  - Journal of mass spectrometry : JMS
JID - 9504818
RN  - 0 (Glucuronides)
RN  - 0 (Sulfates)
RN  - 117652-28-5 (4-hydroxy-3-methoxymethamphetamine)
RN  - 15398-87-5 (alpha-methylepinine)
RN  - 44RAL3456C (Methamphetamine)
RN  - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine)
RN  - R7339QLN1C (Deoxyepinephrine)
SB  - IM
MH  - Chromatography, Liquid
MH  - Deoxyepinephrine/*analogs & derivatives/chemistry/urine
MH  - Drug Stability
MH  - Gas Chromatography-Mass Spectrometry
MH  - Glucuronides/chemistry/urine
MH  - Humans
MH  - Least-Squares Analysis
MH  - Mass Spectrometry/*methods
MH  - Methamphetamine/*analogs & derivatives/chemistry/urine
MH  - N-Methyl-3,4-methylenedioxyamphetamine/*analogs & derivatives/chemistry/*urine
MH  - Reproducibility of Results
MH  - Sensitivity and Specificity
MH  - Stereoisomerism
MH  - Sulfates/chemistry/urine
PMC - PMC3874414
MID - NIHMS487014
EDAT- 2011/06/10 06:00
MHDA- 2011/09/08 06:00
PMCR- 2013/12/29
CRDT- 2011/06/10 06:00
PHST- 2011/06/10 06:00 [entrez]
PHST- 2011/06/10 06:00 [pubmed]
PHST- 2011/09/08 06:00 [medline]
PHST- 2013/12/29 00:00 [pmc-release]
AID - 10.1002/jms.1929 [doi]
PST - ppublish
SO  - J Mass Spectrom. 2011 Jul;46(7):603-14. doi: 10.1002/jms.1929.