Synthesis and pharmacology of 8-amino-3-(cyclopropylmethyl)-1,2,3,4,5,6-hexahydro-cis-6,11-dimethyl-2,6-methano-3-benzazocine and related compounds

The little compound 1a has been prepared and was found to be a strong, orally active agonist with narcotic--antagonist properties. 1a was prepared by two independent routes: (1) nitration of volazocine and subsequent reduction and (b) a sequence involving dissolving metal reduction of cyclazocine me...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1980-01, Vol.23 (1), p.71-74
Main Authors: Wentland, Mark P, Albertson, Noel F, Pierson, Anne K
Format: Article
Language:English
Subjects:
Analgesics - chemical synthesis
Animals
Cyclazocine - analogs & derivatives
Dose-Response Relationship, Drug
Mice
Narcotic Antagonists - chemical synthesis
Rats
Reaction Time - drug effects
Structure-Activity Relationship
Time Factors
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Summary:The little compound 1a has been prepared and was found to be a strong, orally active agonist with narcotic--antagonist properties. 1a was prepared by two independent routes: (1) nitration of volazocine and subsequent reduction and (b) a sequence involving dissolving metal reduction of cyclazocine methyl ether, followed by oximination and Semmler--Wolff rearrangement. Several analogues were prepared and tested.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00175a013