3,4-Methylenedioxymethamphetamine (MDMA): stereoselective interactions at brain 5-HT1 and 5-HT2 receptors.
R A Lyon, Richard A Glennon, M Titeler
Psychopharmacology 1986 DOI: 10.1007/bf00178519 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | In vitro receptor binding study Peer reviewed |
|---|---|
| Topics | MDMA Serotonin |
| Key points | R(-)-MDA and R(-)-MDMA bound 5-HT2 sites with moderate affinity (Ki 3425 and 3310 nM), while their S(+)-enantiomers bound more weakly (Ki 13,000 and 15,800 nM); D2 binding was very low (Ki above 25,000 nM). The authors suggest that MDMA, unlike MDA and other hallucinogenic phenylisopropylamines, does not work primarily through direct interaction at 5-HT sites. |
Abstract
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 greater than 25,000 nM in each case). The (-) greater than (+) 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.
Comparable studies
Other preclinical and animal studies on MDMA, most cited first.
Citations in the library
Cited by 57
- Differences Between the Mechanism of Action of MDMA, MBDB, and the Classic Hallucinogens. Identification of a New Therapeutic Class: Entactogens Journal of Psychoactive Drugs October 1, 1986
- Psilocybin Biases Facial Recognition, Goal-Directed Behavior, and Mood State Toward Positive Relative to Negative Emotions Through Different Serotonergic Subreceptors Biological Psychiatry May 9, 2012
- 3,4‐Methylenedioxymethamphetamine (MDMA, “Ecstasy”): pharmacology and toxicology in animals and humans Addiction May 1, 1994
- 3,4-Methylenedioxymethamphetamine (MDMA) neurotoxicity in rats: a reappraisal of past and present findings Psychopharmacology March 15, 2006
- The Background and Chemistry of MDMA Journal of Psychoactive Drugs October 1, 1986
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