Enantioselective metabolism of the designer drugs 3,4-methylenedioxymethamphetamine ('ecstasy') and 3,4-methylenedioxyethylamphetamine ('eve') isomers in rat brain and blood

Neurosci Lett. 2002 Sep 20;330(2):193-7. doi: 10.1016/s0304-3940(02)00776-0.


The metabolism of MDA (3,4-methylenedioxyamphetamine), HMMA (3-hydroxy-4-methoxymethylamphetamine) and HME (3-hydroxy-4-methoxyethylamphetamin) of the popular designer drugs MDMA ('ecstasy', 3,4-methylenedioxymethamphetamine) and MDE ('eve', 3,4-methylenedioxyethylamphetamine) was determined in rat serum, whole blood and urine, as well as in whole brain structures (cortex and striatum) after subcutaneous administration of 20 mg/kg MDMA and MDE, respectively. MDMA and MDE were extracted from serum and homogenized brain structures using a solid-phase extraction procedure. The extracts were examined by a validated high-performance liquid chromatography procedure coupled with fluorimetric detection. Our results demonstrate that MDMA is metabolized to a higher degree than MDE, resulting in a higher concentration of neurotoxic dihydroxymetabolites and (S)-MDA. There was no difference between the metabolism of MDMA and MDE and its respective isomers. Different concentrations of the respective isomers of MDMA and MDE let us suggest an enantioselective metabolism for both MDMA and MDE.

MeSH terms

  • Analysis of Variance
  • Animals
  • Brain / metabolism*
  • Brain Chemistry / drug effects
  • Cerebral Cortex / chemistry
  • Cerebral Cortex / drug effects
  • Cerebral Cortex / metabolism
  • Chromatography, High Pressure Liquid / methods
  • Corpus Striatum / chemistry
  • Corpus Striatum / drug effects
  • Corpus Striatum / metabolism
  • Designer Drugs
  • Gas Chromatography-Mass Spectrometry
  • Hallucinogens / blood*
  • Hallucinogens / metabolism
  • Hallucinogens / pharmacokinetics
  • Injections, Subcutaneous
  • Isomerism
  • N-Methyl-3,4-methylenedioxyamphetamine / blood*
  • N-Methyl-3,4-methylenedioxyamphetamine / metabolism
  • N-Methyl-3,4-methylenedioxyamphetamine / pharmacokinetics
  • Rats
  • Rats, Sprague-Dawley
  • Serotonin Agents / blood
  • Serotonin Agents / metabolism
  • Serotonin Agents / pharmacokinetics


  • Designer Drugs
  • Hallucinogens
  • Serotonin Agents
  • N-Methyl-3,4-methylenedioxyamphetamine