Synthesis, Structure Elucidation, and Pharmacological Evaluation of 5‐Methyl‐oxymorphone (= 4,5α‐epoxy‐3,14‐dihydroxy‐5,17‐dimethylmorphinan‐6‐one)
1988; Wiley; Volume: 71; Issue: 7 Linguagem: Inglês
10.1002/hlca.19880710721
ISSN1522-2675
AutoresHelmut Schmidhammer, Jack B. Deeter, Noel D. Jones, J. David Leander, Darryle D. Schoepp, J. K. SWARTZENDRUBER,
Tópico(s)Alkaloids: synthesis and pharmacology
ResumoAbstract Synthesis of 5‐methyl‐oxymorphone ( 3 ) was accomplished by oxidation of 5‐methylthebaine ( 4 ) with performic acid, followed by catalytic hydrogenation and cleavage of the 3‐MeO group. X‐Ray analysis confirmed that the 14‐OH group has, like the one in oxymorphone ( 1 ), β‐orientation. Pharmacological studies in vivo and in vitro showed 3 to possess slightly less opioid agonistic properties than 1 .
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