Synthesis and pharmacology of the putative novel muscarinic agonist (S)- 4-F-MePyMcN [(S)-4-(pyrrolidino)-1-methyl-2-butynyl-N-(4-fluorophenyl) carbamate oxalate]

Saleh Athmani, Karen N. Bradley, Alan L. Harvey, Edgar Kornisiuk, Diana Jerusalinsky

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(S)-4-F-MePyMcN [(S)-4-(pyrrolidino)-1-methyl-2-butynyl-N-(4- fluorophenyl) carbamate oxalate] has been suggested to be a selective agonist at the M1 subtype of muscarinic receptor [Lambrecht G. et al., Life Sci. 56 (1995) 815-822]. We synthesized the compound and tested its selectivity for different muscarinic receptors with binding experiments using rat cerebral cortex synaptosomal membranes and cloned human ml to m5 receptors and by functional experiments on rabbit vas deferens preparations. There was little difference in affinity for the compound at the different cloned muscarinic receptors (IC50s for displacement of 3H-N-methylscopolamine were 0.7-1.0 μM). On rabbit vas deferens preparations, (S)-4-F-MePyMcN did reduce twitch responses to electrical stimulation like the known M1 agonist McN-A-343, but unlike McN-A-343 the compound reduced postsynaptic sensitivity to noradrenaline, ATP and KCl. Because of these additional actions, (S)-4-F- MePyMcN may not be suitable as a tool to study M1 muscarinic receptors selectively.

Original languageEnglish
Pages (from-to)935-941
Number of pages7
JournalEuropean Journal of Medicinal Chemistry
Issue number12
Publication statusPublished - 31 Dec 1998


  • ligand binding
  • McN-A-343
  • muscarinic receptors
  • N- methylscopolamine
  • selective agonists


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