14-Hydroxy-7,8-dihydromorphinone

Synonym 14-hydroxy-dihydromorphinone Trade names Numorphan (Endo) Opana (Endo) Indications Pain (moderate to severe)... 

Pasternak GW, Hahn EF (1980) Long-acting opiate agonists and antagonists 14-hydroxy-dihydromorphinone hydrazones. J Med Chem 23 674-676... 

The inifial sfeps in fhe mefabolism of morphine and codeine by Pseudomonas putida MIO involve oxidafion of fhe C-6 hydroxy group and subsequenf reducfion of fhe 7,8-olefinic bond, forming hydromorphone (dihydromorphinone) and hydrocodone (dihydrocodeinone), respectively (Scheme 4) [52], These products have important industrial appUcations hydromorphone is an analgesic some seven times more potent than morphine [53],... 

The synthesis of TAMO is outlined in Scheme 3.11. The 3-hydroxy group of 14/ -amino-7,8-dihydromorphinone (71) [114] was protected with tert-bu-... 

During the total synthesis of ( )3-deoxy-7,8-dihydromorphinone (72), a morphine derivative lacking aromatic ring substitution,<166,167) two novel aromatic ring substituted analogs were isolated as intermediates, 4,5-epoxy-2-hydroxy-N-methylmorphinan-6-one (71, R = H) and a related 1-bromo derivative (70), together with their respective methyl ethers. No biological data on these were reported. 

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