Trans-2-Acetoxycyclobutyltrimethylammonium iodide, a cyclobutane analog of "trans-ACTM".
The (+/-) title compound was prepared to evaluate prior observations that certain acetylcholine congeners derived from cyclobutane are devoid of muscarinic effects. It was prepared by a multistep sequence from trans-2-carbomethoxycyclobutyl methyl ketone. In a guinea pig ileum assay, it was 0.02 times as active as AcCh, and in a dog blood pressure assay, it was 0.09 times as active. In these assays, its (+/-)-cyclopropane congener and AcCh were equally active. This is the first cyclobutane-derived AcCh congener possessing significant muscarinic effect.
D000818:Animals; D001794:Blood Pressure / Q000187:drug effects; D003503:Cyclobutanes / Q000138:chemical synthesis / Q000494:pharmacology; D003521:Cyclopropanes / Q000494:pharmacology; D004285:Dogs; D006168:Guinea Pigs; D007082:Ileum / Q000187:drug effects; D066298:In Vitro Techniques; D009119:Muscle Contraction / Q000187:drug effects; D009130:Muscle, Smooth / Q000187:drug effects; D010277:Parasympathomimetics / Q000138:chemical synthesis* / Q000494:pharmacology; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000494:pharmacology
D003503:Cyclobutanes; D003521:Cyclopropanes; D010277:Parasympathomimetics; D000644:Quaternary Ammonium Compounds