PMID- 9373962
OWN - NLM
STAT- MEDLINE
DCOM- 19980107
LR  - 20131121
IS  - 1076-5174 (Print)
IS  - 1076-5174 (Linking)
VI  - 32
IP  - 11
DP  - 1997 Nov
TI  - Gas chromatographic/mass spectrometric assay for profiling the enantiomers of 
      3,4-methylenedioxymethamphetamine and its chiral metabolites using positive 
      chemical ionization ion trap mass spectrometry.
PG  - 1236-46
AB  - A qualitative GC/MS profile was obtained and its mass spectrometric features 
      characterized for the analysis of the enantiomers of 
      (RS)-3,4-methylenedioxymethamphetamine (MDMA) and its metabolites 
      (RS)-3,4-methylenedioxyamphetamine (MDA), (RS)-4-hydroxy-3-methoxymethamphetamine 
      (HMMA) and (RS)-4-hydroxy-3-methoxyamphetamine (HMA). A chiral derivatization 
      method was selected to obtain the diastereomers required for the separation of 
      the respective enantiomers with a non-chiral GC stationary phase. The selected 
      derivatization consisted of a reaction with N-heptafluorobutyryl-(S)-prolyl 
      chloride combined with a consecutive reaction with 
      N-methyl-N-trimethylsilyltrifluoroacetamide, resulting in 
      N-[heptafluorobutyryl-(S)-prolyl]-O-trimethylsilyl derivatives. Detection was 
      carried out with electron ionization and positive chemical ionization (PCI) ion 
      trap mass spectrometry. Mass spectra of the derivatives of reference standards of 
      the compounds of interest obtained with PCI demonstrated that this method 
      simultaneously induces proton and charge-transfer reactions in the ion trap. The 
      advantage is that high mass information is provided while some fragmentation 
      remains to elucidate structural details. Subsequently, in three urine samples 
      obtained from different and unrelated MDMA intoxications, the enantiomers of MDMA 
      and MDA were identified. In some urine samples also HMMA and/or HMA were found. 
      In addition to these compounds, an unexpected compound and/or additional chiral 
      metabolite, N-hydroxy-(RS)-3,4-methylenedioxyamphetamine, was identified in two 
      out of three urine samples. Preliminary results also indicated an 
      enantioselective metabolism in the N-demethylation pathway for MDMA in humans.
FAU - de Boer, D
AU  - de Boer D
AD  - Department of Human Toxicology, Utrecht Institute for Pharmaceutical Sciences, 
      University of Utrecht, The Netherlands. D.de Boer@far.ruu.nl
FAU - Tan, L P
AU  - Tan LP
FAU - Gorter, P
AU  - Gorter P
FAU - van de Wal, R M
AU  - van de Wal RM
FAU - Kettenes-van den Bosch, J J
AU  - Kettenes-van den Bosch JJ
FAU - de Bruijn, E A
AU  - de Bruijn EA
FAU - Maes, R A
AU  - Maes RA
LA  - eng
PT  - Journal Article
PL  - England
TA  - J Mass Spectrom
JT  - Journal of mass spectrometry : JMS
JID - 9504818
RN  - 0 (Hallucinogens)
RN  - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine)
SB  - IM
MH  - Biotransformation
MH  - Gas Chromatography-Mass Spectrometry
MH  - Hallucinogens/*pharmacokinetics/*urine
MH  - Humans
MH  - Isomerism
MH  - N-Methyl-3,4-methylenedioxyamphetamine/*pharmacokinetics/*urine
MH  - Reference Standards
EDAT- 1997/11/28 02:44
MHDA- 2000/06/22 10:00
CRDT- 1997/11/28 02:44
PHST- 1997/11/28 02:44 [pubmed]
PHST- 2000/06/22 10:00 [medline]
PHST- 1997/11/28 02:44 [entrez]
AID - 10.1002/(SICI)1096-9888(199711)32:11<1236::AID-JMS584>3.0.CO;2-K [pii]
AID - 10.1002/(SICI)1096-9888(199711)32:11<1236::AID-JMS584>3.0.CO;2-K [doi]
PST - ppublish
SO  - J Mass Spectrom. 1997 Nov;32(11):1236-46. doi: 
      10.1002/(SICI)1096-9888(199711)32:11<1236::AID-JMS584>3.0.CO;2-K.