title: [Structure- and conformation-activity relationship of heterocyclic acetylcholine analogs. 13. Cholinergic properties of tertiary and quaternary 4-acetoxyquinuclidines].
abstract: In the course of investigations of structure and conformation-activity relationships of heterocyclic acetylcholine analogues, the cholinergic properties of the tertiary (7) and quaternary (8) 4-acetoxyquinuclidine were studied. Both esters have no affinity when tested at the nicotinic receptor, and they are not hydrolyzed by acetylcholinesterase. In the guinea-pig ileum and atrium assay, the heterocyclic analogues 7 and 8 demonstrate agonistic properties, but their potency is three to four orders of magnitude lower than that of acetylcholine. Stereochemical restrictions seem to be responsible for the weak muscarinic potency of both quinuclidine analogues.
mesh_terms: D000818:Animals; D002800:Cholinesterase Inhibitors; D006168:Guinea Pigs; D066298:In Vitro Techniques; D008968:Molecular Conformation; D009119:Muscle Contraction / Q000187:drug effects; D009130:Muscle, Smooth / Q000187:drug effects; D009538:Nicotine / Q000494:pharmacology; D010277:Parasympathomimetics; D011812:Quinuclidines / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D002800:Cholinesterase Inhibitors; D010277:Parasympathomimetics; D011812:Quinuclidines; D009538:Nicotine
vernacular_title: Struktur- und Konformations-Wirkungs-Beziehungen heterozyklischer Acetylcholin-Analoga. 13. Mitteilung: Cholinerge Eigenschaften des tertiären und quartären 4-Acetoxychinuclidin.