Portal de Periódicos da CAPES

Metabolism of Drugs. LX. The Synthesis of Codeine and Morphine Glucuronides

1968; Pharmaceutical Society of Japan; Volume: 16; Issue: 11 Linguagem: Inglês

10.1248/cpb.16.2114

1347-5223

Hidetoshi Yoshimura, Kazuta Oguri, Hisao Tsukamoto,

Analytical Methods in Pharmaceuticals

The first synthesis of three glucuronides of narcotics was reported. Codeine glucuronide (Va) was prepared by the condensation of codeine (Ia) with acetobromo sugar derivative (II) in the presence of silver carbonate and the following removal of the protecting groups by solvolysis and hydrolysis with sodium methoxide and aq. barium hydroxide, respectively. Morphine-6-glucuronide (Vb) was synthesized similarly to Va utilizing 3-acetyl-morphine (Ib) as the starting material. Morphine-3-glucuronide (VIII) was prepared by the condensation of morphine (VI) with II in sodium hydroxide-acetone. In this reaction, the intermediate derivative (VII) was not obtained but hydrolyzed to the free glucuronide (VIII).