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Enantioselective Quantitation of the Ecstasy Compound (R)- And (S)-N-ethyl-3,4-methylenedioxyamphetamine and Its Major Metabolites in Human Plasma and Urine

Enantioselective Quantitation of the Ecstasy Compound (R)- And (S)-N-ethyl-3,4-methylenedioxyamphetamine and Its Major Metabolites in Human Plasma and Urine

Jochen Buechler, Matthias Schwab, Gerd Mikus, Beate Fischer, Leo Hermle, Claudia Marx, Georg Grön, Manfred Spitzer, Karl Artur Kovar

J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Aug 15;793(2):207-22.

PMID: 12906896

Abstract:

An enantioselective HPLC method has been developed and validated for the stereospecific analysis of N-ethyl-3,4-methylenedioxyamphetamine (MDE) and its major metabolites N-ethyl-4-hydroxy-3-methoxyamphetamine (HME) and 3,4-methylenedioxyamphetamine (MDA). These compounds have been analyzed both from human plasma and urine after administration of 70 mg pure MDE-hydrochloride enantiomers to four subjects. The samples were prepared by hydrolysis of the o-glucuronate and sulfate conjugates using beta-glucuronidase/arylsulfatase and solid-phase extraction with a cation-exchange phase. A chiral stationary protein phase (chiral-CBH) was used for the stereoselective determination of MDE, HME and MDA in a single HPLC run using sodium dihydrogenphosphate, ethylendiaminetetraacetic acid disodium salt and isopropanol as the mobile phase (pH 6.44) and fluorimetric detection (lambda(ex) 286 nm, lambda(em) 322 nm). Moreover, a suitable internal standard (N-ethyl-3,4-methylenedioxybenzylamine) was synthesized and qualified for quantitation purposes. The method showed high recovery rates (>95%) and limits of quantitation for MDE and MDA of 5 ng/ml and for HME of 10 ng/ml. The RSDs for all working ranges of MDE, MDA and HME in plasma and urine, respectively, were less than 1.5%. After validation of the analytical methods in plasma and urine samples pharmacokinetic parameters were calculated. The plasma concentrations of (R)-MDE exceeded those of the S-enantiomer (ratio R:S of the area under the curve, 3.1) and the plasma half time of (R)-MDE was longer than that of (S)-MDE (7.9 vs. 4.0 h). In contrast, the stereochemical disposition of the MDE metabolites HME and MDA was reversed. Concentrations of the (S)-metabolites in plasma of volunteers were much higher than those of the (R)-enantiomers.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP6292917	(±)-3,4-Methylenedioxyamphetamine hydrochloride		6292-91-7	Price

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