| Abstract: | The synthesis of morphine labeled with deuterium in the N-methyl group and at positions 1 and 6 is described. Reduction of N-carboethoxy-1-bromonorcodeinone (IV) with lithium aluminum deuteride in tetrahydrofuran-d5 yielded the codeine-d5. O-Demethylation with sodium propylmercaptide-dimethyl formamide afforded morphine-d5, which could be remethylated with perdeuterioiodomethane to give codeine-d8. The labeled compounds are useful as standards for field ionization mass spectrometric analysis. |
