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Synthesis and Biological Evaluation of 14‐Alkoxymorphinans. Part 10 . 14‐ O ‐Methyl derivatives of 5‐methylnaltrexone and 5‐methylnaloxone
Author(s) -
Schmidhammer Helmut,
Nussbaumer Christine,
Patel Dinesh,
Traynor John R.
Publication year - 1994
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.19940770614
Subject(s) - chemistry , in vivo , antagonism , vas deferens , in vitro , agonist , ileum , stereochemistry , pharmacology , guinea pig , receptor , biochemistry , endocrinology , medicine , microbiology and biotechnology , biology
Abstract In several steps, 5, 14‐ O ‐dimethylnaltrexone ( 3 ) and 5, 14‐ O ‐dimethylnaloxone ( 4 ) were prepared starting from 5, 14‐ O ‐dimethyloxycodone ( 5 ). Compound 3 exhibited opioid agonism in vitro (guinea‐pig ileum and mouse vas deferens preparations) and antagonism in vivo (AcOH‐writhing test in mice), while compound 4 was found to be an agonist in vitro and in vivo .