PMID- 10388483
OWN - NLM
STAT- MEDLINE
DCOM- 19990716
LR  - 20190722
IS  - 0009-9147 (Print)
IS  - 0009-9147 (Linking)
VI  - 45
IP  - 7
DP  - 1999 Jul
TI  - Stereospecific analysis and enantiomeric disposition of 3, 
      4-methylenedioxymethamphetamine (Ecstasy) in humans.
PG  - 1058-69
AB  - BACKGROUND: Little is known concerning the enantioselective disposition of 
      3,4-methylenedioxymethamphetamine (MDMA; ecstasy) in humans. In addition, the 
      potential of utilizing the stereochemical composition of an analyte in biological 
      media for forensic purposes requires investigation. METHODS: The enantiomers of 
      MDMA and its demethylated metabolite, 3,4-methylenedioxyamphetamine (MDA), 
      present in plasma and urine extracts were derivatized with 
      (-)-(R)-alpha-methoxy-alpha-trifluoromethylphenylacetyl chloride and analyzed by 
      gas chromatography-mass spectrometry and gas chromatography, respectively. The 
      enantioselective disposition of MDMA and MDA was determined following oral 
      administration of racemic MDMA (40 mg) to eight male volunteers. RESULTS: The 
      plasma concentrations of (R)-MDMA exceeded those of the S-enantiomer [ratio R:S 
      of the area under the curve (AUC), 2.4 +/- 0.3], and the plasma half-life of 
      (R)-MDMA (5.8 +/- 2.2 h) was significantly longer than that of the S-enantiomer 
      (3.6 +/- 0.9 h). The majority of the recovered material in urine was excreted 
      within 24 h after dosing, with the recovery of (R)-MDMA (21.4% +/- 11.6%) being 
      significantly greater than that of (S)-MDMA (9.3% +/- 4.9%), and with (S)- and 
      (R)-MDA accounting for 1.4% +/- 0.5% and 1.0% +/- 0.3% of the dose, respectively. 
      Mathematical modeling of plasma enantiomeric composition vs sampling time 
      demonstrated the applicability of using stereochemical data for the prediction of 
      time elapsed after drug administration. CONCLUSIONS: Analytical methods for 
      determining the enantiomeric composition of MDMA and MDA in plasma and urine were 
      developed. The disposition of MDMA in humans is stereoselective, with the more 
      active S-enantiomer having a reduced AUC and shorter half-life than (R)-MDMA. The 
      determination of stereochemical composition may be applicable for forensic 
      purposes.
FAU - Fallon, J K
AU  - Fallon JK
AD  - Drug Control Centre and Department of Pharmacy, King's College London, Manresa 
      Road, London SW3 6LX, UK.
FAU - Kicman, A T
AU  - Kicman AT
FAU - Henry, J A
AU  - Henry JA
FAU - Milligan, P J
AU  - Milligan PJ
FAU - Cowan, D A
AU  - Cowan DA
FAU - Hutt, A J
AU  - Hutt AJ
LA  - eng
PT  - Clinical Trial
PT  - Journal Article
PL  - England
TA  - Clin Chem
JT  - Clinical chemistry
JID - 9421549
RN  - 0 (Hallucinogens)
RN  - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine)
SB  - IM
EIN - Clin Chem 1999 Sep;45(9):1585
MH  - Administration, Oral
MH  - Adult
MH  - Gas Chromatography-Mass Spectrometry
MH  - Hallucinogens/blood/*pharmacokinetics/urine
MH  - Humans
MH  - Male
MH  - N-Methyl-3,4-methylenedioxyamphetamine/blood/*pharmacokinetics/urine
MH  - Regression Analysis
MH  - Reproducibility of Results
MH  - Stereoisomerism
EDAT- 1999/07/01 00:00
MHDA- 1999/07/01 00:01
CRDT- 1999/07/01 00:00
PHST- 1999/07/01 00:00 [pubmed]
PHST- 1999/07/01 00:01 [medline]
PHST- 1999/07/01 00:00 [entrez]
PST - ppublish
SO  - Clin Chem. 1999 Jul;45(7):1058-69.