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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Analgesic, antimuscarinic activity and enantioselectivity of the four isomers of 3-quinuclidinyl tropate as compared with the enantiomers of hyoscyamine.

The four stereoisomers of 3-quinuclidinyl tropate (2) were synthesized and their absolute configuration established. The analgesic activity of the four isomers on the hot-plate test and their muscarinic antagonism on rabbit vas deferens (M1), guinea-pig heart (Force, M2) and ileum (M3) and on the muscarinic receptors present in immature guinea-pig uterus were evaluated. The results were compared with those of the enantiomers of hyoscyamine (1). No apparent correlation was found between the analgesic activity and antimuscarinic activity on M1, M2 and M3 receptors, whereas striking differences exist between the affinity values of the analgesic enantiomer of hyoscyamine (R-(+)-1) and those of the inactive isomers of 2 on the muscarinic receptor present in immature guinea pig uterus. Molecular Modelling studies have shown that the only difference between 1 and 2 lies in the volumes occupied by the basic part of the molecules.[1]

References

  1. Analgesic, antimuscarinic activity and enantioselectivity of the four isomers of 3-quinuclidinyl tropate as compared with the enantiomers of hyoscyamine. Dei, S., Bellucci, C., Gualtieri, F., Romanelli, M.N., Scapecchi, S., Teodori, E., Bartolini, A., Ghelardini, C. Farmaco (1995) [Pubmed]
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