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Communication | Regular issue | Vol 16, No. 11, 1981, pp.1859-1862
Published online, 1st January, 1970
DOI: 10.3987/R-1981-11-1859
Structure-activity Relationships of Oxygenated Morphinas. II. Synthesis and Biological Properties of 4-Methoxymorphinan-6-ones with Narcotic Antagonist Side-chains on Nitrogen

Helmut Schmidhammer, Arthur E. Jacobson, Louise Atwell, and Arnold Brossi*

*Laboratoryof Chemistry, Medical Chemistry Section, National Arthritis Institute, National Institute of Health, Behesda, Maryland 20892, U.S.A.


The synthesis of narcotic antagonists from the 4-methoxymorphinan-6-one series is described. The synthesis started from optically active 4-hydroxy-6-keto-N-formylmorphinan prepared from morphine, by employing conventional procedures. The compounds have pentazocine-like agonist activity and N-cyclopropylmethyl-4-methoxymorphinan-6-one is somewhat more potent than nalorphine as a narcotic antagonist.