, Volume 88, Issue 4, pp 525–526 | Cite as

3,4-Methylenedioxymethamphetamine (MDMA): Stereoselective interactions at brain 5-HT1 and 5-HT2 receptors

  • Robert A. Lyon
  • Richard A. Glennon
  • Milt Titeler
Rapid Communications


3,4-Methylenedioxymethamphetamine (MDMA), 3,4-methylenedioxy-amphetamine (MDA), and their optical isomers, were assayed for their affinities at radiolabeled brain serotonin (5-HT1, 5-HT2) and dopamine (D2) binding sites. (R(−)-MDA and R(−)-MDMA) displayed moderate affinities for 3H-ketanserin-labeled 5-HT2 sites (Ki=3425 and 3310 nM, respectively) whereas the affinities for their S(+)-enantiomers were lower (Ki=13,000 and 15,800 nM, respectively). Similar absolute and relative affinities were obtained at 3H-serotonin-labeled 5-HT1 sites; binding at D2 sites was very low (Ki>25,000 nM in each case). The (−)>(+) order of potency at 5-HT2 sites is consistent with the observation that R(−)-MDA is a more potent psychoactive agent than its S(+)-enantiomer, but contrasts with the reported finding that S(+)-MDMA is more potent than R(−)-MDMA in humans. These results suggest that MDMA, unlike MDA and other hallucinogenic phenylisopropylamines, does not work primarily through a direct interaction at 5-HT sites.

Key words

3,4-methylenedioxymethamphetamine 3,4-methylenedioxyamphetamine 5-HT receptors dopamine receptors 


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Copyright information

© Springer-Verlag 1986

Authors and Affiliations

  • Robert A. Lyon
    • 1
  • Richard A. Glennon
    • 2
  • Milt Titeler
    • 1
  1. 1.Department of Pharmacology and ToxicologyAlbany Medical CollegeAlbanyUSA
  2. 2.Department of Medicinal Chemistry, School of Pharmacy, Medical College of VirginiaVirginia Commonwealth UniversityRichmondUSA

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