PMID- 21983032
OWN - NLM
STAT- MEDLINE
DCOM- 20120120
LR  - 20211020
IS  - 1873-2968 (Electronic)
IS  - 0006-2952 (Print)
IS  - 0006-2952 (Linking)
VI  - 83
IP  - 1
DP  - 2012 Jan 1
TI  - Stereoselective urinary MDMA (ecstasy) and metabolites excretion kinetics 
      following controlled MDMA administration to humans.
PG  - 131-8
LID - 10.1016/j.bcp.2011.09.023 [doi]
AB  - The R- and S-enantiomers of racemic 3,4-methylenedioxymethamphetamine (MDMA) 
      exhibit different dose-concentration curves. In plasma, S-MDMA was eliminated at 
      a higher rate, most likely due to stereoselective metabolism. Similar data were 
      shown in various in vitro experiments. The aim of the present study was the in 
      vivo investigation of stereoselective elimination of MDMA's phase I and phase II 
      metabolites in human urine following controlled oral MDMA administration. Urine 
      samples from 10 participants receiving 1.0 and 1.6 mg/kg MDMA separated by at 
      least one week were analyzed blind by liquid chromatography-high resolution-mass 
      spectrometry and gas chromatography-mass spectrometry after chiral derivatization 
      with S-heptafluorobutyrylprolyl chloride. R/S ratios at C(max) were comparable 
      after low and high doses with ratios >1 for MDMA, free DHMA, and HMMA sulfate, 
      and with ratios <1 for MDA, free HMMA, DHMA sulfate and HMMA glucuronide. In the 
      five days after the high MDMA dose, a median of 21% of all evaluated compounds 
      were excreted as R-stereoisomers and 17% as S-stereoisomers. Significantly 
      greater MDMA, DHMA, and HMMA sulfate R-enantiomers and HMMA and HMMA glucuronide 
      S-stereoisomers were excreted. No significant differences were observed for MDA 
      and DHMA sulfate stereoisomers. Changes in R/S ratios could be observed over time 
      for all analytes, with steady increases in the first 48 h. R/S ratios could help 
      to roughly estimate time of MDMA ingestion and therefore, improve interpretation 
      of MDMA and metabolite urinary concentrations in clinical and forensic 
      toxicology.
CI  - Copyright (c) 2011 Elsevier Inc. All rights reserved.
FAU - Schwaninger, Andrea E
AU  - Schwaninger AE
AD  - Department of Experimental and Clinical Toxicology, Institute of Experimental and 
      Clinical Pharmacology and Toxicology, Saarland University, Homburg, Saar, 
      Germany.
FAU - Meyer, Markus R
AU  - Meyer MR
FAU - Barnes, Allan J
AU  - Barnes AJ
FAU - Kolbrich-Spargo, Erin A
AU  - Kolbrich-Spargo EA
FAU - Gorelick, David A
AU  - Gorelick DA
FAU - Goodwin, Robert S
AU  - Goodwin RS
FAU - Huestis, Marilyn A
AU  - Huestis MA
FAU - Maurer, Hans H
AU  - Maurer HH
LA  - eng
GR  - ZIA DA000468-08/Intramural NIH HHS/United States
PT  - Comparative Study
PT  - Journal Article
PT  - Randomized Controlled Trial
PT  - Research Support, Non-U.S. Gov't
DEP - 20110929
PL  - England
TA  - Biochem Pharmacol
JT  - Biochemical pharmacology
JID - 0101032
RN  - 0 (Biomarkers)
RN  - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine)
SB  - IM
MH  - Biomarkers/urine
MH  - Double-Blind Method
MH  - Humans
MH  - N-Methyl-3,4-methylenedioxyamphetamine/administration & dosage/*chemistry/*urine
MH  - Stereoisomerism
PMC - PMC3225738
MID - NIHMS334743
EDAT- 2011/10/11 06:00
MHDA- 2012/01/21 06:00
PMCR- 2013/01/01
CRDT- 2011/10/11 06:00
PHST- 2011/08/11 00:00 [received]
PHST- 2011/09/22 00:00 [revised]
PHST- 2011/09/23 00:00 [accepted]
PHST- 2011/10/11 06:00 [entrez]
PHST- 2011/10/11 06:00 [pubmed]
PHST- 2012/01/21 06:00 [medline]
PHST- 2013/01/01 00:00 [pmc-release]
AID - S0006-2952(11)00703-9 [pii]
AID - 10.1016/j.bcp.2011.09.023 [doi]
PST - ppublish
SO  - Biochem Pharmacol. 2012 Jan 1;83(1):131-8. doi: 10.1016/j.bcp.2011.09.023. Epub 
      2011 Sep 29.