Synthesis and biological evaluation of 14-alkoxymorphinans. 2. (-)-N-(Cyclopropylmethyl)-4,14-dimethoxymorphinan-6-one, a selective .mu. opioid receptor antagonist

(-)-N-(Cyclopropylmethyl)-4,14-dimethoxymorphinan-6-one (2) was synthesized with 4,14-dimethoxy-N-methylmorphinan-6-one (1) as starting material. In vivo and in vitro experiments show 2 (cyprodime) to be a pure opioid receptor antagonist. Some of these tests (opioid receptor binding assays, guinea p...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1989-02, Vol.32 (2), p.418-421
Main Authors: Schmidhammer, Helmut, Burkard, Willy P, Eggstein-Aeppli, Lislott, Smith, Colin F. C
Format: Article
Language:English
Subjects:
Animals
Guinea Pigs
In Vitro Techniques
Male
Mice
Morphinans - chemical synthesis
Morphinans - pharmacology
Narcotic Antagonists - chemical synthesis
Narcotic Antagonists - pharmacology
Rats
Receptors, Opioid - drug effects
Receptors, Opioid, mu
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Summary:(-)-N-(Cyclopropylmethyl)-4,14-dimethoxymorphinan-6-one (2) was synthesized with 4,14-dimethoxy-N-methylmorphinan-6-one (1) as starting material. In vivo and in vitro experiments show 2 (cyprodime) to be a pure opioid receptor antagonist. Some of these tests (opioid receptor binding assays, guinea pig ileal longitudinal muscle preparation, rat and mouse vas deferens preparation, acetic acid writhing antagonism test) indicate that 2 is a selective mu opioid receptor antagonist.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00122a021