PMID- 19183967
OWN - NLM
STAT- MEDLINE
DCOM- 20090529
LR  - 20211020
IS  - 1618-2650 (Electronic)
IS  - 1618-2642 (Print)
IS  - 1618-2642 (Linking)
VI  - 393
IP  - 6-7
DP  - 2009 Mar
TI  - Hydrolysis of 3,4-methylenedioxymethamphetamine (MDMA) metabolite conjugates in 
      human, squirrel monkey, and rat plasma.
PG  - 1607-17
LID - 10.1007/s00216-009-2607-1 [doi]
AB  - Characterizing the formation of metabolites of 3,4-methylenedioxymethamphetamine 
      (MDMA, "Ecstasy") in different species (rat, squirrel monkey, and human) may 
      provide insight into mechanisms of MDMA neurotoxicity. Two prominent MDMA 
      metabolites, 3,4-dihydroxymethamphetamine (HHMA) and 
      4-hydroxy-3-methoxymethamphetamine (HMMA), are conjugated with glucuronic or 
      sulfuric acid, but reference standards are not available; therefore, 
      quantification is only possible after conjugate cleavage. Different 
      concentrations of HHMA and HMMA were obtained in human, squirrel monkey, and rat 
      plasma specimens when acid or enzymatic cleavage was performed. Our data document 
      that these differences are due to species-specific influences on conjugate 
      cleavage. Acidic hydrolysis should be used for analyzing free HHMA and HMMA in 
      human or squirrel monkey plasma, while enzymatic hydrolysis with glucuronidase or 
      sulfatase maximizes recovery of free HHMA and HMMA in rat plasma. Optimization of 
      cleavage conditions showed that sulfate conjugates were more readily cleaved by 
      acid hydrolysis and glucuronides by glucuronidase.
FAU - Mueller, Melanie
AU  - Mueller M
AD  - Department of Experimental and Clinical Toxicology, Institute of Experimental and 
      Clinical Pharmacology and Toxicology, Saarland University, 66421, Homburg, 
      (Saar), Germany.
FAU - Kolbrich-Spargo, Erin A
AU  - Kolbrich-Spargo EA
FAU - Peters, Frank T
AU  - Peters FT
FAU - Huestis, Marilyn A
AU  - Huestis MA
FAU - Ricaurte, George A
AU  - Ricaurte GA
FAU - Maurer, Hans H
AU  - Maurer HH
LA  - eng
GR  - F32 DA005707/DA/NIDA NIH HHS/United States
GR  - R01 DA005707/DA/NIDA NIH HHS/United States
GR  - DA017964/DA/NIDA NIH HHS/United States
GR  - DA05707/DA/NIDA NIH HHS/United States
GR  - ZIA DA000468-07/ImNIH/Intramural NIH HHS/United States
GR  - K05 DA017964/DA/NIDA NIH HHS/United States
PT  - Journal Article
PT  - Research Support, N.I.H., Extramural
PT  - Research Support, N.I.H., Intramural
DEP - 20090130
PL  - Germany
TA  - Anal Bioanal Chem
JT  - Analytical and bioanalytical chemistry
JID - 101134327
RN  - 0 (Sulfuric Acids)
RN  - 117652-28-5 (4-hydroxy-3-methoxymethamphetamine)
RN  - 15398-87-5 (alpha-methylepinine)
RN  - 44RAL3456C (Methamphetamine)
RN  - 8A5D83Q4RW (Glucuronic Acid)
RN  - EC 3.1.6.- (Sulfatases)
RN  - EC 3.2.1.31 (Glucuronidase)
RN  - O40UQP6WCF (sulfuric acid)
RN  - R7339QLN1C (Deoxyepinephrine)
SB  - IM
MH  - Animals
MH  - Chromatography, Liquid
MH  - Deoxyepinephrine/*analogs & derivatives/blood/chemistry
MH  - Glucuronic Acid/chemistry
MH  - Glucuronidase/metabolism
MH  - Humans
MH  - Hydrolysis
MH  - Methamphetamine/*analogs & derivatives/blood/chemistry
MH  - Rats
MH  - Rats, Sprague-Dawley
MH  - Saimiri
MH  - Sensitivity and Specificity
MH  - Spectrometry, Mass, Electrospray Ionization
MH  - Sulfatases/metabolism
MH  - Sulfuric Acids/chemistry
PMC - PMC3163102
MID - NIHMS317065
EDAT- 2009/02/03 09:00
MHDA- 2009/05/30 09:00
PMCR- 2011/08/28
CRDT- 2009/02/03 09:00
PHST- 2008/10/20 00:00 [received]
PHST- 2009/01/08 00:00 [accepted]
PHST- 2008/12/19 00:00 [revised]
PHST- 2009/02/03 09:00 [entrez]
PHST- 2009/02/03 09:00 [pubmed]
PHST- 2009/05/30 09:00 [medline]
PHST- 2011/08/28 00:00 [pmc-release]
AID - 10.1007/s00216-009-2607-1 [doi]
PST - ppublish
SO  - Anal Bioanal Chem. 2009 Mar;393(6-7):1607-17. doi: 10.1007/s00216-009-2607-1. 
      Epub 2009 Jan 30.