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Analysis of a Verapamil Microsomal Incubation using Metabolite ID and Mass FrontierTM

e considered. The Spectra Manager and Fragments & Mechanisms modules work together to automatically highlight those peaks in the experimental MS2 spectrum explained by the predicted fragmentation. In the case of verapamil, Mass Frontier was able to make structural assignments for the MS2 peaks at m/zs 165, 260, and 303.

The next step is to look for the three corresponding fragments in the experimental MS2 spectrum of the demethylated metabolite. The MS2 spectra of verapamil and its demethylated metabolite can be simultaneously viewed in the Spectra Manager window by selecting the Compare Spectra option (See Figure 8). An inspection of the spectra in this window indicates that the mass 165 and 260 peaks in the MS2 spectrum of verapamil are unshifted in the MS2 spectrum of the demethylated metabolite while the mass 303 peak has been shifted downwards by 14 daltons to mass 289.

Table 5 lists the three fragments along with the structures predicted by Mass Frontier. The structure of verapamil with its five possible sites of demethylation is shown in Figure 9. Sites 4 and 5 can be eliminated as possible sites of demethylated by the observation that the mass 165 MS2 fragment of verapamil is unshifted in the demethylated metabolite. The same logic applied to the mass 260 MS2 fragment eliminates sites 1 and 2. This leaves site 3 as the only possible site of demethylation and is confirmed by the mass 303 MS2 fragment which is shifted lower by 14 daltons to mass 289. This Ndemethylated metabolite is called norverapamil and has been previously described in the literature as the major demethylation metabolite of verapamil.

Using the same approach as above, the sites of demethylation in the two N-dealkylated/demethylated metabolites at 14.79 and 15.82 (both with MH+:277) minutes can also be determined. However,
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