PMID- 1981721
OWN - NLM
STAT- MEDLINE
DCOM- 19910425
LR  - 20141120
IS  - 0090-9556 (Print)
IS  - 0090-9556 (Linking)
VI  - 18
IP  - 5
DP  - 1990 Sep-Oct
TI  - Stereochemical differences in the metabolism of 3,4-methylenedioxymethamphetamine 
      in vivo and in vitro: a pharmacokinetic analysis.
PG  - 686-91
AB  - The in vivo N-demethylation of (+) and (-)3,4-methylenedioxymethamphetamine 
      (MDMA) to 3,4-methylenedioxyamphetamine (MDA) was determined and the 
      pharmacokinetic relationship between the two compounds calculated. The levels of 
      MDA formed after iv administration of (+)MDMA to male rats were about 3 times 
      greater than those for (-)MDMA, although the plasma levels of the parent drugs 
      were comparable. Plasma MDA concentrations were lower in phenobarbital-pretreated 
      rats, but SKF 525-A pretreatment, at the dose used, had minimal effects. In liver 
      microsome experiments conducted with microM concentrations of (+)MDMA, 
      3,4-dihydroxymethamphetamine (N-methyl-alpha-methyldopamine) was shown to be the 
      major metabolite. MDA was also formed in vitro, but the enantioselectivity was 
      the opposite of that found in vivo, pointing out the difficulties in 
      extrapolation of in vitro observations to in vivo disposition. The high levels of 
      MDA observed after administration of (+)MDMA to intact animals suggest that this 
      active metabolite could be important in the overall effects of (+)MDMA.
FAU - Cho, A K
AU  - Cho AK
AD  - Department of Pharmacology, School of Medicine, University of California, Los 
      Angeles 90024-1735.
FAU - Hiramatsu, M
AU  - Hiramatsu M
FAU - Distefano, E W
AU  - Distefano EW
FAU - Chang, A S
AU  - Chang AS
FAU - Jenden, D J
AU  - Jenden DJ
LA  - eng
GR  - DA 04206/DA/NIDA NIH HHS/United States
PT  - Journal Article
PT  - Research Support, U.S. Gov't, P.H.S.
PL  - United States
TA  - Drug Metab Dispos
JT  - Drug metabolism and disposition: the biological fate of chemicals
JID - 9421550
RN  - 0 (Pyridines)
RN  - 17286-92-9 (metapyrone)
RN  - 4764-17-4 (3,4-Methylenedioxyamphetamine)
RN  - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine)
RN  - YQE403BP4D (Phenobarbital)
SB  - IM
MH  - 3,4-Methylenedioxyamphetamine/*analogs & derivatives/metabolism/pharmacokinetics
MH  - Animals
MH  - Biotransformation
MH  - Chromatography, High Pressure Liquid
MH  - Dealkylation
MH  - Electrochemistry
MH  - Gas Chromatography-Mass Spectrometry
MH  - In Vitro Techniques
MH  - Male
MH  - Microsomes, Liver/metabolism
MH  - N-Methyl-3,4-methylenedioxyamphetamine
MH  - Phenobarbital/pharmacology
MH  - Pyridines/pharmacology
MH  - Rats
MH  - Rats, Inbred Strains
MH  - Stereoisomerism
EDAT- 1990/09/01 00:00
MHDA- 1990/09/01 00:01
CRDT- 1990/09/01 00:00
PHST- 1990/09/01 00:00 [pubmed]
PHST- 1990/09/01 00:01 [medline]
PHST- 1990/09/01 00:00 [entrez]
PST - ppublish
SO  - Drug Metab Dispos. 1990 Sep-Oct;18(5):686-91.