Thebaine composition

Thebenine, CjgHjgOgN. This secondary amine, which differs by CHj in empirical composition from thebaine, is formed by the action of hot dilute hydrochloric acid on thebaine or codeinone, but not -codeinone, which does, however, yield triacetylthebenine and ethanolmethylamine... 

Neodihydrothebaine (7), which was known as a synthetic derivative of the-baine (45), has been found in Papaver bracteatum, from which it was extracted as an inseparable mixture with bractazonine (8). The composition of the mixture was determined by GC-MS analysis and 1H-NMR studies and was further confirmed by comparison with an artificial mixture of synthetic neodihydrothebaine (7) and bractazonine (8) (24). Both alkaloids are considered to be biogenetically derived from thebaine (45) or its immediate precursor salutaridinol (103). 

In 1935 an alkaloid named oripavine having the composition Ci8H2i03N was isolated from Papaver orientale [124] and subsequently from Papaver bracteatum [125], It was shown to contain one —OMe, one —NMo, and one phenolic —OH group [124], and was eventually converted to thebaine [v] by methylation with diazomethane [126] and is in fact 3-0-desmethylthebaine [xxxvn] it bears the same relationship to morphine as thebaine does to codeine. On boiling with... 

Morphothebaine was first believed to be simply a demethylated thebaine and to have the composition C17H15OH(OH)2 [3], but later was correctly shown to have the formula C18H1903N, and to contain one methoxyl group [7]. It contains two phenolic hydroxyl groups and cannot be converted back to thebaine [7]. 

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