Distribution of 3,4-methylenedioxymethamphetamine (MDMA) and 3,4-methylenedioxyamphetamine (MDA) stereoisomers in a fatal poisoning

Questions and Hypotheses

“…For example, after 125 mg MDMA, total clearance for MDMA was 51.1 ± 14.1 per hr, while renal clearance was 13.0 ± 5.4 per hr (de la Torre et al 2000a). The findings of the Spanish researchers are consistent with other investigations using limited doses (Fallon et al 1999;Hensley and Cody 1999) or illicit users (Crifasi and Long 1996;Moore et al 1996;Ramcharan et al 1998). …”

“…For example, Fallon et al (1999) reported that the area under the curve (AUC) of plasma concentrations was two to four times higher for the R-enantiomer than the S-enantiomer after 40 mg, p.o., in human volunteers. Moore et al (1996) found greater levels of R-(-)-MDMA in blood, liver, vitreous and bile samples from an individual who died shortly after illicit MDMA use. Stereoselective analysis of biosamples in both an MDMA overdose and a traffic fatality had similar findings (Ramcharan et al, 1998;Crifasi and Long, 1996).…”

“…The stereoselective pharmacokinetics of MDMA are reflected in formation of MDA and DHMA enantiomers (Fallon et al 1999;Pizarro et al 2004;Pizarro et al 2003). In the first 24 hours after MDMA administration, greater plasma and urine concentrations of S-(+)-MDA than its R-enantiomer occur (Fallon et al 1999;Moore et al 1996). By contrast, R/S ratios of HMMA are more similar to those for MDA (greater amounts of R-(-)-HMMA than S-(+)-HMMA during the first 24 hours), or there is no difference between concentrations of the two enantiomers of HMMA (Pizarro et al 2003;Pizarro et al 2004).…”

Evaluation of drug incorporation into hair segments and nails by enantiomeric analysis following controlled single MDMA intakes

“…MDMA is used for its entactogenic effects and stimulation of the central nervous system [28] which are mainly attributed to the S-MDMA enantiomer [29]. The R-enantiomer was reported to be more abundant in human tissues and fluids representing its enantioselective metabolism most likely because of the elimination of the S-enantiomer from plasma at a higher rate [30][31][32][33]. MDMA is primarily metabolized to 3,4-dihydroxymethamphetamine (DHMA) by the cytochrome P450 isoenzyme CYP2D6 [29], which is polymorphic [34].…”

Comparison of the use of aqueous and nonaqueous buffers in association with cyclodextrin for the chiral separation of 3,4-methylenedioxymethamphetamine and related compounds

“…Because of the difference in the pharmacological activity of these enantiomers [2,3], it is necessary to determine the distribution of these enantiomers in clandestine tablets and in suspect urine samples. It is especially noteworthy that (2)-methamphetamine can also be extracted from a Vicks Inhaler [4] and that (2)-methamphetamine is used in certain prescription drugs [5].…”