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  3. Synthetic studies and pharmacological evaluations on the MDMA ('Ecstasy') antagonist nantenine

Synthetic studies and pharmacological evaluations on the MDMA ('Ecstasy') antagonist nantenine

  • Bioorg Med Chem Lett. 2010 Jan 15;20(2):628-31. doi: 10.1016/j.bmcl.2009.11.053.
Onica Legendre 1,  Stevan Pecic,  Sandeep Chaudhary,  Sarah M Zimmerman,  William E Fantegrossi,  Wayne W Harding
Affiliations

Affiliation

  • 1 Department of Chemistry, Hunter College and the Graduate Center of the City University of New York, 695 Park Avenue, New York, NY 10065, USA.
PMID: 19963380 DOI: 10.1016/j.bmcl.2009.11.053
Abstract

The naturally occurring aporphine alkaloid nantenine, has been shown to antagonize behavioral and physiological effects of MDMA in mice. We have synthesized (+/-)-nantenine via an oxidative cyclization reaction with PIFA and evaluated its binding profile against a panel of CNS targets. To begin to understand the importance of the chiral center of nantenine with regards to its capacity to antagonize the effects of MDMA in vivo, (R)- and (S)-nantenine were prepared and evaluated in a food-reinforced operant task in rats. Pretreatment with either nantenine enantiomer (0.3mg/kg IP) completely blocked the behavioral suppression induced upon administration of 3.0mg/kg MDMA. (+/-)-Nantenine displayed high affinity and selectivity for the alpha(1A) Adrenergic Receptor among several Other receptors suggesting that this alpha(1) subtype may be significantly involved in the anti-MDMA effects of the enantiomers.

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