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Synthesis and Biological Evaluation of 14‐Alkoxymorphinans. Part 9 . 14‐ O ‐ethyl‐5‐methylnaltrexone, and opioid antagonist with unusual selectivity
Author(s) -
Schmidhammer Helmut,
Schratz Andrea,
Schmidt Charlotte,
Patel Dinesh,
Traynor John R.
Publication year - 1993
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.19930760131
Subject(s) - chemistry , naltrexone , antagonism , antagonist , opioid , selectivity , sufentanil , pharmacology , opioid receptor , morphine , μ opioid receptor , fentanyl , in vivo , stereochemistry , receptor , organic chemistry , biochemistry , catalysis , medicine , microbiology and biotechnology , biology
14 O ‐Ethyl‐5m‐ethylnaloxone ( 7 ) and 14 O ‐ethyl‐5‐methylnaltrexone ( 8 ) have been prepared starting from 14 O ‐ethyl‐5‐methyloxycodone ( 9 ) in several steps. Both, 7 and 8 , were found to be opioid antagonists in vitro and in vivo . Compound 7 exhibited some selectivity for μ opioid receptors, whereas compound 8 did not show selectivity for any of the receptor types. In the AcOH‐writhing antagonism test, 8 was not able to antagonize morphine‐induced antinociception, but antagonized fentanyl‐ and sufentanil‐induced antinociception.