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Brunnenberg M, Kovar KA. 
“Stereospecific analysis of ecstasy-like N-ethyl-3,4-methylenedioxyamphetamine and its metabolites in humans”. 
J Chromatogr B Biomed Sci Appl. 2001 Feb 05;751(1):9-18.
A chiral HPLC method has been developed for the ecstasy analogue R,S-N-ethyl-3,4-methylenedioxyamphetamine MDE and its metabolites o-glucuronyl-R,S-N-ethyl-4-hydroxy-3-methoxyamphetamine HME and R,S-3,4-methylenedioxyamphetamine MDA in human plasma. The chiral discrimination of the compounds was carried out with an enantioselective HPLC method using beta-cyclodextrin in the mobile phase for MDE and MDA and a chiral protein phase chiral-CBH for HME. MDE and MDA were detected fluorimetrically at 322 nm, while the major metabolite HME was selectively determined by electrochemical detection at +600 mV. After hydrolysis of the conjugates using beta-glucuronidase/arylsulfatase and solid-phase extraction with a cation-exchange phase for sample preparation high recovery rates of more than 95 were yielded. The limit of quantitation for the enantiomers of MDE and its metabolites in plasma were between 1.2 MDA and 16 ng/ml HME and the relative method standard deviations VxO, Table 1 were less than 3. The methods described have been used successfully in the enantioselective quantitation of the compounds in plasma samples obtained from six healthy volunteers in a clinical study after oral administration of 140 mg racemic MDE hydrochloride. Significant differences were found in the plasma concentrations of the examined stereoisomers. Whereas the R-enantiomer of the parent substance, MDE, was predominant in the plasma samples investigated, higher plasma concentrations of the S-enantiomers of the metabolites MDA and HME were measured.
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