Dimethylsulfonium analogues of the muscarinic agent McN-A-343: [4-[[N-(3- or 4-halophenyl)carbamoyl]oxy]-2-butynyl] dimethylsulfonium perchlorates.
Some 3- and 4-bromophenyl and dimethylsulfonium analogues of the muscarinic agent [4-[[N-(3-chlorophenyl)-carbamoyl]oxy]-2-butynyl] trimethylammonium chloride (McN-A-343) (1) were synthesized. The new compounds were assayed for effects on arterial blood pressure in the pithed rat (ganglionic muscarinic activity). The dimethylsulfonium salts (13a-d) appeared to be partial agonists in relation to 1. The 4-bromophenyl-substituted trimethylammonium iodide 10d exceeded 1 in potency by 3-fold. The compounds retained the selectivity for ganglionic muscarinic receptors shown by 1 since they had only weak effects on the guinea pig ileum in vitro.
Mellin
C
C
Department of Pharmacology, School of Medicine, University of California, Los Angeles 90024-1735.
Vargas
H M
HM
Ringdahl
B
B
D008455:(4-(m-Chlorophenylcarbamoyloxy)-2-butynyl)trimethylammonium Chloride / Q000138:chemical synthesis / Q000494:pharmacology*; D000818:Animals; D001794:Blood Pressure / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D004305:Dose-Response Relationship, Drug; D005726:Ganglia, Parasympathetic / Q000187:drug effects; D006168:Guinea Pigs; D007082:Ileum / Q000187:drug effects; D066298:In Vitro Techniques; D008745:Methylation; D009132:Muscles / Q000187:drug effects; D000644:Quaternary Ammonium Compounds / Q000494:pharmacology*; D011898:Ranidae; D051381:Rats; D013464:Sulfuric Acids
D000644:Quaternary Ammonium Compounds; D013464:Sulfuric Acids; D008455:(4-(m-Chlorophenylcarbamoyloxy)-2-butynyl)trimethylammonium Chloride