Homochiral (R)- and (S)-3,4-methylenedioxymethamphetamine (MDMA) were prepared in six steps (each) from the chiral pool precursors d- l-alanine, respectively. The key step, copper-catalysed regioselective ring-opening of an N-tosylaziridine with aryl Grignard reagent, proceeded high yield complete regioselectivity. Elaboration was achieved preservation configurational integrity, affording R- S-...

The cardiovascular and neuroendocrine effects and pharmacokinetics of 3,4-methylenedioxymethamphetamine (MDMA, "ecstasy") were assessed in a double-blind, randomized, crossover, and controlled (placebo and amphetamine) clinical trial. Eight men with experience in the recreational use of MDMA participated in four 10-h experimental sessions with a 1-week washout period. Single oral doses of 125 m...

BACKGROUND: 3, 4-methylenedioxymethamphetamine (MDMA, also known as "ecstasy") has been shown to exhibit neurotoxic effects on the hippocampus. However, exposure to sub-lethal insults of MDMA has been reported to result in neuroprotection. OBJECTIVE: To investigate the effects of MDMA on hippocampal neuronal viability, caspase-3 activity, and mRNA expression of the N-methyl-D-aspartate (NMDA) r...

A comparison of the use of aqueous and nonaqueous buffers in association with beta-CD for the chiral separation of (R)- and (S)-3,4-methylenedioxymethamphetamine and related compounds is described. The (R)- and (S)-isomers of 3,4-methylenedioxymethamphetamine (MDMA) and its major metabolite 3,4-methylenedioxyamphetamine (MDA) were prepared. Under aqueous and nonaqueous buffer conditions and bas...

Ecstasy is a widely used recreational drug that usually consists primarily of 3,4-methylenedioxymethamphetamine (MDMA). Most ecstasy users consume other substances as well, which complicates the interpretation of research in this field. The positively rated effects of MDMA consumption include euphoria, arousal, enhanced mood, increased sociability, and heightened perceptions; some common advers...

BACKGROUND Little is known concerning the enantioselective disposition of 3,4-methylenedioxymethamphetamine (MDMA; ecstasy) in humans. In addition, the potential of utilizing the stereochemical composition of an analyte in biological media for forensic purposes requires investigation. METHODS The enantiomers of MDMA and its demethylated metabolite, 3,4-methylenedioxyamphetamine (MDA), present...