Molecular requirements of the active sites of the cholinergic receptors. XII - 3-Methyl-2-oxo-1-dimethylaminomethylcyclopentane methiodide as a new selective agonist for the nicotinic receptor.
To investigate further the nature of the active sites of cholinergic receptors, the carbocyclic analogs of isomuscarone and isomuscarine [(IV) and (V a-d)] were synthesized and tested for their cholinergic activity. Like isomuscarines, such compounds are completely devoid of muscarinic activity which further support the hypothesis that the receptor site, corresponding to position 2 of the ring, cannot accept groups larger than and/or with a dipole having a different direction from that of an ether oxygen. On the other hand nicotinic activity is quite good. In this respect compound (IV) is particulary interesting, being as active as ACh and pratically devoid of muscarinic activity.
D000009:Abdominal Muscles / Q000187:drug effects; D000818:Animals; D001001:Anura; D055598:Chemical Phenomena; D002621:Chemistry; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000494:pharmacology; D006168:Guinea Pigs; D007082:Ileum / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D011950:Receptors, Cholinergic; D011976:Receptors, Muscarinic; D013055:Spectrophotometry, Infrared
C028087:3-methyl-2-oxo-1-dimethylaminomethylcyclopentane methiodide; D003517:Cyclopentanes; D011950:Receptors, Cholinergic; D011976:Receptors, Muscarinic