PMID- 15319342
OWN - NLM
STAT- MEDLINE
DCOM- 20050623
LR  - 20131121
IS  - 0090-9556 (Print)
IS  - 0090-9556 (Linking)
VI  - 32
IP  - 9
DP  - 2004 Sep
TI  - Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main 
      metabolites in human samples including the catechol-type metabolite 
      (3,4-dihydroxymethamphetamine).
PG  - 1001-7
AB  - 3,4-Methylenedioxymethamphetamine (MDMA; "ecstasy") is a designer drug commonly 
      misused in large segments of young populations. MDMA is usually formulated in 
      tablets of its racemate (1:1 mixture of its enantiomers) in doses ranging from 50 
      to 200 mg. MDMA has an enantioselective metabolism, the (S)-enantiomer being 
      metabolized faster than the (R)-enantiomer. Different pharmacologic properties 
      have been attributed to each enantiomer. The carbon responsible for MDMA 
      chirality is preserved along its metabolic disposition. An analytical method has 
      been developed to determine MDMA enantiomers and those from its major 
      metabolites, 3,4-methylenedioxyamphetamine (MDA), 3,4-dihydroxymeth-amphetamine 
      (HHMA), and 4-hydroxy-3-methoxymethamphet-amine (HMMA). It has been applied to 
      the analysis of plasma and urine samples from healthy recreational users of MDMA 
      who participated voluntarily in a clinical trial and received 100 mg (R,S)-MDMA. 
      HCl orally. (R)/(S) ratios both in plasma (0-48 h) and urine (0-72 h) for MDMA 
      and MDA were >1 and <1, respectively. Ratios corresponding to HHMA and HMMA, 
      close to unity, deviate from theoretical expectations and are most likely 
      explained by the ability of MDMA to autoinhibit its own metabolism. The short 
      elimination half-life of (S)-MDMA (4.8 h) is consistent with the subjective 
      effects and psychomotor performance reported in subjects exposed to MDMA, whereas 
      the much longer half-life of the (R)-enantiomer (14.8 h) correlates with mood and 
      cognitive effects experienced on the next days after MDMA use.
FAU - Pizarro, Nieves
AU  - Pizarro N
AD  - Pharmacology Research Unit, Institut Municipal d'Investigacio Medica (IMIM), 
      Universitat Autonoma de Barcelona, Spain.
FAU - Farre, Magi
AU  - Farre M
FAU - Pujadas, Mitona
AU  - Pujadas M
FAU - Peiro, Ana Ma
AU  - Peiro AM
FAU - Roset, Pere N
AU  - Roset PN
FAU - Joglar, Jesus
AU  - Joglar J
FAU - de la Torre, Rafael
AU  - de la Torre R
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - United States
TA  - Drug Metab Dispos
JT  - Drug metabolism and disposition: the biological fate of chemicals
JID - 9421550
RN  - 117652-28-5 (4-hydroxy-3-methoxymethamphetamine)
RN  - 15398-87-5 (alpha-methylepinine)
RN  - 44RAL3456C (Methamphetamine)
RN  - 4764-17-4 (3,4-Methylenedioxyamphetamine)
RN  - EC 1.14.14.1 (Cytochrome P-450 CYP2D6)
RN  - EC 2.1.1.6 (Catechol O-Methyltransferase)
RN  - R7339QLN1C (Deoxyepinephrine)
SB  - IM
MH  - 3,4-Methylenedioxyamphetamine/*chemistry/*metabolism/pharmacology
MH  - Administration, Oral
MH  - Area Under Curve
MH  - Catechol O-Methyltransferase/metabolism
MH  - Cytochrome P-450 CYP2D6/genetics/metabolism
MH  - Deoxyepinephrine/*analogs & derivatives/chemistry/*metabolism/pharmacokinetics
MH  - Half-Life
MH  - Humans
MH  - Male
MH  - Methamphetamine/*analogs & derivatives/chemistry/metabolism/pharmacokinetics
MH  - Methods
MH  - Phenotype
MH  - Polymorphism, Genetic/genetics
MH  - *Stereoisomerism
EDAT- 2004/08/21 05:00
MHDA- 2005/06/24 09:00
CRDT- 2004/08/21 05:00
PHST- 2004/08/21 05:00 [pubmed]
PHST- 2005/06/24 09:00 [medline]
PHST- 2004/08/21 05:00 [entrez]
AID - 32/9/1001 [pii]
PST - ppublish
SO  - Drug Metab Dispos. 2004 Sep;32(9):1001-7.