PMID- 2569654
OWN - NLM
STAT- MEDLINE
DCOM- 19890914
LR  - 20190701
IS  - 0024-3205 (Print)
IS  - 0024-3205 (Linking)
VI  - 45
IP  - 4
DP  - 1989
TI  - Stereochemistry of the metabolism of MDMA to MDA.
PG  - 295-301
AB  - The chiral derivatizing reagent N-trifluoroacetyl-L-prolyl chloride (LTPC) was 
      used to form diastereomers of 3,4-methylenedioxymethamphetamine (MDMA) and 
      3,4-methylenedioxyamphetamine (MDA) which were resolved on an achiral gas 
      chromatographic column using a mass spectrometer as a detector. Rats were 
      subcutaneously dosed with 40 mg/kg of (+/-) MDMA.HCl and blood was obtained by 
      decapitation four hours after dosing. Plasma was separated and extracted. The 
      extract was derivatized on-column with LTPC. In addition to the two MDMA isomers, 
      the demethylated metabolites, S(+) and R(-)-MDA were identified. In all 
      experimental groups (male rats, food deprived male rats, female rats, post partum 
      female rats, and mice) dosed with racemic MDMA, higher levels of the S(+) isomer 
      of MDA relative to the R(-) MDA isomer were observed. This may be significant 
      since it has been shown that the S(+) isomer of MDMA is the more neurotoxic 
      isomer of the racemic drug of abuse MDMA.
FAU - Fitzgerald, R L
AU  - Fitzgerald RL
AD  - Department of Pharmacology and Toxicology, Medical College of Virginia, Richmond 
      23298.
FAU - Blanke, R V
AU  - Blanke RV
FAU - Rosecrans, J A
AU  - Rosecrans JA
FAU - Glennon, R A
AU  - Glennon RA
LA  - eng
PT  - Journal Article
PL  - Netherlands
TA  - Life Sci
JT  - Life sciences
JID - 0375521
RN  - 0 (Amphetamines)
RN  - 4764-17-4 (3,4-Methylenedioxyamphetamine)
RN  - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine)
SB  - IM
MH  - 3,4-Methylenedioxyamphetamine/analogs & 
      derivatives/blood/*metabolism/pharmacokinetics
MH  - Amphetamines/*metabolism
MH  - Animals
MH  - Biotransformation
MH  - Female
MH  - Gas Chromatography-Mass Spectrometry
MH  - Kinetics
MH  - N-Methyl-3,4-methylenedioxyamphetamine
MH  - Rats
MH  - Rats, Inbred Strains
MH  - Stereoisomerism
EDAT- 1989/01/01 00:00
MHDA- 1989/01/01 00:01
CRDT- 1989/01/01 00:00
PHST- 1989/01/01 00:00 [pubmed]
PHST- 1989/01/01 00:01 [medline]
PHST- 1989/01/01 00:00 [entrez]
AID - 0024-3205(89)90138-0 [pii]
AID - 10.1016/0024-3205(89)90138-0 [doi]
PST - ppublish
SO  - Life Sci. 1989;45(4):295-301. doi: 10.1016/0024-3205(89)90138-0.