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Structure-Activity Relationship of Oxygenated Morphinans. V. Narcotic agonist and antagonist activity in the 14-hydroxymorphinan series. Preliminary communication

✍ Scribed by Helmut Schmidhammer; Arthur E. Jacobson; Louise Atwell; Arnold Brossi

Book ID
102251737
Publisher
John Wiley and Sons
Year
1981
Tongue
German
Weight
244 KB
Volume
64
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The synthesis of several 14‐hydroxymorphinans, using oxymorphone (= 3, 14‐dihydroxy‐4,5‐epoxy‐N‐methylmorphinan‐6‐one, 1) as starting material, is described. The antinociceptive potency of the N‐methyl substituted 14‐hydroxy‐morphinans was determined. Thus, in order of antinociceptive potency, 14‐hydroxy‐4‐methoxy‐N‐methylmorphinan‐6‐one (5) >4,5‐epoxy‐14‐hydroxy‐N‐methyl‐morphinan‐6‐one (3)>4, 14‐dihydroxy‐N‐methylmorphinan‐6‐one (4)>14‐hydroxy‐4‐methoxy‐N‐methylmorphinan (11) ≈4, 14‐dihydroxy‐N‐methylmorphinan (12). The most potent compound in this series, 14‐hydroxy‐4‐methoxy‐N‐methyl‐morphinan‐6‐one (5), was found to have about six times the potency of morphine; it was equipotent with levorphanol.

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Structure-Activity Relationship of Oxyge
Structure-Activity Relationship of Oxygenated Morphinans. VII. 5-Methylated and 14-Hydroxy-substituted Agonists and Antagonists of the 4-Hydroxy- and 3, 4-Dioxygenated 6-Morphinanone Series
✍ Arnold Brossi; Louise Atwell; Arthur E. Jacobson; Maria D. Rozwadowska; Helmut S 📂 Article 📅 1982 🏛 John Wiley and Sons 🌐 German ⚖ 716 KB

## Abstract Several morphinanone agonists differently substituted at C(3), C(4), C(5) and C (14) and antagonists of the 4‐hydroxy and 3, 4‐dimethoxy series were prepared by conventional chemistry. It was demonstrated that the oxygenation pattern in the bay‐area, encompassing C(3) and C(4), is impor