title: Stereochemical analogs of a muscarinic, ganglionic stimulant. 3. 2,3-Substituted bicyclo(2.2.1)hept-5-enes and -heptanes related to 4-(N-(3-chlorophenyl)carbamoyloxy)-2-butynyltrimethylammonium chloride (McN-A-343).
abstract: Preparation of analogs of 4-[N-(3-chlorophenyl)carbamoyloxy]-2-butynyltrimethylammonium chloride (1, McN-A-343), the isomeric 2-trimethylammoniomethyl-3-[N-(4-chlorophenyl)carbamoyloxymethyl]bicyclo [2.2.1]hept-5-ene iodides (10-13), and the corresponding -bicyclo[2.2.1]heptane iodides (14-17) are reported. None of the compounds demonstrated ganglion-stimulating activity similar to 1 or antagonized the effects of 1.
mesh_terms: D008455:(4-(m-Chlorophenylcarbamoyloxy)-2-butynyl)trimethylammonium Chloride / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D001794:Blood Pressure / Q000187:drug effects; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D002415:Cats; D003508:Cycloheptanes / Q000138:chemical synthesis / Q000494:pharmacology; D005731:Ganglionic Stimulants / Q000138:chemical synthesis*; D010277:Parasympathomimetics / Q000138:chemical synthesis*; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis*
chemical_list: D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds; D003508:Cycloheptanes; D005731:Ganglionic Stimulants; D010277:Parasympathomimetics; D000644:Quaternary Ammonium Compounds; D008455:(4-(m-Chlorophenylcarbamoyloxy)-2-butynyl)trimethylammonium Chloride