Racemic and optically active 2, 9-dimethyl-5-(m-hydroxyphenyl) morphans and pharmacological comparison with the 9-demethyl homologs

…, MD Aceto, H Merz, ME Rogers, LS Harris

Index: Awaya, Hiroyoshi; May, Everette L.; Aceto, Mario D.; Merz, Herbert; Rogers, Michael E.; Harris, Louis S. Journal of Medicinal Chemistry, 1984 , vol. 27, # 4 p. 536 - 539

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Citation Number: 31

Abstract

2, 9a-Dimethyl-5-(m-hydroxyphenyl) morphan (3a) has been synthesized from 5-(m- methoxyphenyl)-2-methyl-9-oxomorphan (4) and resolved into its enantiomers (+)-3a and (-)- 3a. The assigned a-orientation of the 9-methyl group was derived from studies of induced NMR shifts using E~(fod)~-d,~. Compound (+)-3a has inappreciable agonist (antinociceptive) activity in mice, and (-)-3a shows codeine-like potency in the hot-plate ...