Abstract
The (R)-( + )- and (S)-( – )-enantiomers of the anticholinergic compound, oxyphencyclimine, were synthesized from (R)-( – )- and (S)-( + )-2-cyclohexyl-2-hydroxy-2-phenylethanoic acid, respectively. The potencies of the enantiomers were compared using a cholinergic receptor binding assay. The (R)-( + )-enantiomer inhibited binding 29 times more potently than the (S)-( – )-enantiomer.
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REFERENCES
A. Osol, G. D. Chase, A. R. Genmaro, M. R. Gibson, C. B. Granberg, S. C. Harvey, R. E. King, A. N. Martin, E. A. Swinyard, and G. L. Zink. Remington's Pharmaceutical Sciences, 16th. ed., Mack, Easton, Pa., 1980.
R. B. Barlow, F. M. Franks, and J. D. M. Pearson. J. Med. Chem. 16:439–446 (1973).
R. W. Brimblecombe, D. M. Green, T. D. Inch, and P. B. J. Thompson. J. Pharm. Pharmacol. 23:745–757 (1971).
R. W. Brimblecombe, T. D. Inch, J. Wetherell, and N. Williams. J. Pharm. Pharmacol. 23:649–661 (1971).
B. W. J. Ellenbroek, R. J. F. Nivard, J. M. van Rossum, and E. J. Ariëns. J. Pharm. Pharmacol. 17:393–404 (1965).
R. Tacke, H. Linoh, D. Schomburg, L. Ernst, U. Moser, E. Mutschler, and G. Lambrecht. Justus Liebigs Ann. Chem. 242–250 (1986).
R. B. Barlow. J. Pharm. Pharmacol. 23:90–97 (1971).
L. Schjelderup, O. Harbitz, P. Groth, and A. J. Aasen. Acta Chem. Scand. B 41:356–361 (1987).
L. Schjelderup and A. J. Aasen. Acta Chem. Scand. B40:601–603 (1986).
S. G. Kuznetsov and Z. I. Bobysheva. Zh. Obshch. Khim. 32:3779–3783 (1962) (Engl., p. 3707).
W. H. Pirkle, D. L. Sikkenga, and M. S. Pavlin. J. Org. Chem. 43:384–387 (1977).
W. H. Pirkle and C. W. Boeder. J. Org. Chem. 42:3697–3700 (1977).
G. R. Luthin and B. B. Wolfe. Mol. Pharmacol. 26:164–169 (1984).
H. I. Yamamura and S. H. Snyder. Proc. Natl. Acad. Sci. USA 71:1725–1729 (1974).
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Schjelderup, L., Kozlowski, M.R., Weissman, A. et al. Antimuscarinic Effects of (R)- and (S)-Oxyphencyclimine Hydrochloride. Pharm Res 5, 236–237 (1988). https://doi.org/10.1023/A:1015945830309
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DOI: https://doi.org/10.1023/A:1015945830309