Molecular Requirements of the Active Site of CholinergicReceptors XV: Synthesis and Biological Activity of2, 3 -Dehydrodeoxamuscarone and 2,3 -Dehydrodeoxamuscarines

To elucidate the molecular requirements of the activesites of cholinergic receptors, 3-methyl-4-oxo- 1-(N,N-dimethylaminomethyl)cyclopent-2-ene methiodide (2,3-dehydrodeoxamuscarone) andcis- and trons- 3-methyl-4-hydroxy-1-(N,N-dimethylaminomethyl)cyclopent-2-ene methiodides (cis- and trons-dehydrodeoxamuscarines)were synthesized and tested. The results, compared with those of thecorresponding oxygenated compounds, seem to indicate that 2,3-dehydrodeoxamuscarinesand muscarine bind at the same site while 2,3-dehydrodeoxamuscarone interacts with the site normally occupied bymuscarone. Furthermore, the previously suggested hypothesis that theunpolar site might somehow incorporate that of muscarone was considered.