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1. Precursors of the mammalian synthesis of morphine: (+)-salutaridine and (−)-thebaine from (+)-6-demethylsalutaridine, and (−)-N-13CH3-thebaine from (−)-northebaine

Author

Raymond Dumont, Bogda Wegrzynski, Voldemar Toome, Arnold Brossi, Kenner C. Rice, and Amy Hauck Newman

Subjects
Standard sample, Thebaine, Chemical Phenomena, Stereochemistry, Biophysics, Methylation, Biochemistry, chemistry.chemical_compound, Structural Biology, 13c label, Genetics, medicine, Animals, Molecular Biology, Carbon atom, Morphine, Circular Dichroism, Salutaridine, Cell Biology, Rats, Chemistry, Morphinans, chemistry, Mammalian biosynthesis, medicine.drug
Abstract

Standard samples of pure (+)-salutaridine and (−)-thebaine required to study the mammalian origin of morphine, were prepared from (+)-6-demethylsalutaridine by published procedures and were characterized by CD spectra and physical data. Reductive N-methylation of (−)-northebaine afforded (−)-thebaine, and when 13C-labeled formalin was used, (−)-thebaine with a 13C label on the N-methyl carbon atom resulted. The latter represents a model procedure to prepare ultimately N-14CH3-labeled (−)-thebaine and 14C-labeled congeners.

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