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A Simple and Efficient Method for the Preparation of Binaltrorphimine and Derivatives and determination of their K opioid antagonist selectivity
Author(s) -
Schmidhammer Helmut,
Smith Colin F. C.
Publication year - 1989
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19890720408
Subject(s) - chemistry , selectivity , (+) naloxone , antagonist , naltrexone , potency , opioid antagonist , opioid , methylhydrazine , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , receptor , biochemistry , in vitro , catalysis , phenylhydrazine
The bimorphinans 1 (binaltrorphimine), 3 , and 7 have been prepared by treatment of the parent morphinan‐6‐ones naltrexone ( 5 ), naloxone ( 4 ), and dihydrocodeinone ( 6 ), respectively, with N ‐methylhydrazine sulfate in AcOH at room temperature. Compound 3 showed opioid antagonist potency and selectivity for K receptors which were somewhat lower in comparison to 1 .