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(−)‐ N ‐[(Cyclopropyl) methyl]‐3,4‐dimethoxy‐5‐methylmorphinan‐6‐one, an opioid agonist with preference for kappa opioid receptors
Author(s) -
Schmidhammer Helmut,
Fritsch Florian,
Burkard Willy P.,
EggsteinAeppli Lislott,
Hefti Fridolin,
Holck Mark I.
Publication year - 1988
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.19880710318
Subject(s) - chemistry , κ opioid receptor , opioid , kappa , agonist , stereochemistry , receptor , preference , pharmacology , biochemistry , medicine , linguistics , philosophy , economics , microeconomics
N ‐Allyl‐ and N ‐[(Cyclopropyl)methyl]‐3,4‐dimethoxy‐5‐methylmorphinan‐6‐one ( 9 and 10, resp.) were synthesized from 5‐methyldih drothebainone ( 1 ). This essential intermediate was prepared from the baine via 5‐methylthebaine (5) employing a novel route. The Pharmacological studies showed 9 and 10 to be potent opioid agonists. Compound 10 was found to have preference for kappa rather than mu opioid receptors.