PMID- 22342062
OWN - NLM
STAT- MEDLINE
DCOM- 20130507
LR  - 20191210
IS  - 1873-264X (Electronic)
IS  - 0731-7085 (Linking)
VI  - 73
DP  - 2013 Jan 25
TI  - Chiral separation of 3,4-methylenedioxymethamphetamine (MDMA) enantiomers using 
      batch chromatography with peak shaving recycling and its effects on oxidative 
      stress status in rat liver.
PG  - 13-7
LID - S0731-7085(12)00045-3 [pii]
LID - 10.1016/j.jpba.2012.01.025 [doi]
AB  - This work reports the multimiligram separation of 
      3,4-methylenedioxy-methamphetamine (MDMA) enantiomers using batch chromatography 
      with peak shaving recycling. The effect of both enantiomers compared to the 
      racemic mixture was examined on the oxidative stress status of rat liver. The 
      enantiomeric purification was performed using a based cyclodextrin chiral 
      selector and methanol:ammonium acetate buffer (pH 6.0, 100mM) (30:70, v/v) as 
      mobile phase. The average mass rate obtained was 40.0mg/day, providing 45.0mg of 
      the (R)-(-)-MDMA (e.r. 99.0%) and 75.0mg (e.r. 96.0%) of (S)-(+)-MDMA. Racemic 
      MDMA and both enantiomers were administered per orally to Wistar rats and 
      oxidative stress status parameters, as liver total glutathione levels and 
      malondialdehyde (MDA) production in liver were evaluated. There was a significant 
      decrease in hepatic glutathione content in the racemic MDMA and the 
      (R)-(-)-MDMA-treated rats when compared to the control and to (S)-(+)-MDMA. These 
      results demonstrate that the R-enantiomer is the enantiomer that contributes to 
      the depletion of hepatic glutathione induced by the racemic mixture. The high 
      reactivity of the R-enantiomer of MDMA in the liver can also be observed in 
      animals treated with (R)-(-)-MDMA. The production of malondialdehyde (MDA) by 
      (R)-(-)-MDMA was significantly higher when compared to the other treated groups 
      and control.
CI  - Copyright (c) 2012 Elsevier B.V. All rights reserved.
FAU - Lourenco, Tiago C
AU  - Lourenco TC
AD  - Departamento de Quimica, Universidade Federal de Sao Carlos, Sao Carlos - SP, 
      Brazil.
FAU - Bosio, Graziela C
AU  - Bosio GC
FAU - Cassiano, Neila M
AU  - Cassiano NM
FAU - Cass, Quezia B
AU  - Cass QB
FAU - Moreau, Regina L M
AU  - Moreau RL
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20120130
PL  - England
TA  - J Pharm Biomed Anal
JT  - Journal of pharmaceutical and biomedical analysis
JID - 8309336
RN  - 0 (Illicit Drugs)
RN  - 4Y8F71G49Q (Malondialdehyde)
RN  - GAN16C9B8O (Glutathione)
RN  - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine)
SB  - IM
MH  - Animals
MH  - Chromatography, High Pressure Liquid/*methods
MH  - Glutathione/metabolism
MH  - High-Throughput Screening Assays
MH  - Illicit Drugs/chemistry/*isolation & purification/toxicity
MH  - Lipid Peroxidation/drug effects
MH  - Liver/*drug effects/metabolism
MH  - Male
MH  - Malondialdehyde/metabolism
MH  - N-Methyl-3,4-methylenedioxyamphetamine/chemistry/*isolation & 
      purification/toxicity
MH  - Oxidative Stress/*drug effects
MH  - Rats
MH  - Rats, Wistar
MH  - Stereoisomerism
EDAT- 2012/02/22 06:00
MHDA- 2013/05/08 06:00
CRDT- 2012/02/21 06:00
PHST- 2011/12/07 00:00 [received]
PHST- 2012/01/19 00:00 [revised]
PHST- 2012/01/21 00:00 [accepted]
PHST- 2012/02/21 06:00 [entrez]
PHST- 2012/02/22 06:00 [pubmed]
PHST- 2013/05/08 06:00 [medline]
AID - S0731-7085(12)00045-3 [pii]
AID - 10.1016/j.jpba.2012.01.025 [doi]
PST - ppublish
SO  - J Pharm Biomed Anal. 2013 Jan 25;73:13-7. doi: 10.1016/j.jpba.2012.01.025. Epub 
      2012 Jan 30.