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- Title
Structure-Activity Relationships of Oxygenated Morphinans. I. 4-Mono- and 3,4-dimethoxy- N-methylmorphinans and - N-methyl-morphinan-6-ones with unusually high antinociceptive potency. Preliminary communication.
- Authors
Jacobson, Arthur E.; Hsu, Fu-Lian; Rozwadowska, Maria D.; Schmidhammer, Helmut; Atwell, Louise; Brossi, Arnold; Medzihradsky, Fedor
- Abstract
The antinociceptive potency and receptor affinity of several optically active aromatic mono- and di-oxygenated N-methylmorphinans and N-methylmorphinan-6-ones, prepared from natural morphine, were determined. Thus, in order of antinociceptive potency, 4-methoxy- N-methylmorphinan-6-one ≈ 3,4-dimethoxy- N-methylmorphinan-6-one ≈ 3,4-dimethoxy- N-methylmorphinan > 4-methoxy- N-methylmorphinan ≈ 4-acetoxy- N-methylmorphinan-6-one > 4-acetoxy- N-methylmorphinan ≈ 4-hydroxy- N-methylmorphinan-6-one ≈ 4-hydroxy- N-methylmorphinan. The 4-hydroxy compounds were slightly less potent than morphine, and the 4-methoxy and 3,4-dimethoxy compounds were found to have three times the potency of morphine. 4-Methoxy- N-methylmorphinan-6-one showed an opiate receptor affinity one-third that of morphine; this is a remarkably high affinity for a non-phenolic compound.
- Publication
Helvetica Chimica Acta, 1981, Vol 64, Issue 5, p1298
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19810640506