N-Oxidation of Drugs: Biochemistry, pharmacology, toxicology by P. Hlavica (ed.), L. A. Damani (ed.)

By P. Hlavica (ed.), L. A. Damani (ed.)

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The administered compound and metabolites were isolated by collection of eluates from HPLC and their identities confirmed with the aid of MS. The advantage of this procedure was that it was able to isolate and identify the intact N-oxide compounds from biological matrices. A sample chromatogram is shown in Fig. 2. (b) Mass spectrometry Electron impact (EI) mass spectra generally provide insufficient evidence for identification of most aliphatic tertiary amine N-oxides because of their labile nature.

5. In the cases of N-monosubstituted and N,N-disubstituted N-hydroxyguanidines, rapid isomerization takes place at room temperature, whereas E/Z-isomers of N,N'-disubstituted derivatives can be detected at room temperature. N,N-unsubstituted and N-monosubstituted amidoximes exist exclusively in the Z-configuration, whereas in the case of N,N-disubstituted amidoximes the E-isomers are thermodynamically more stable. 1 INTRODUCTION With regard to their magnetic moments, both nitrogen isotopes, 14N and lSN, would appear to be suitable for nuclear magnetic resonance spectroscopy (NMR).

Although the magnitudes of the lSN chemical shifts of the doubly bonded nitrogen atoms in amidoximes are larger than those of the N'-hydroxyguanidines, they are still markedly smaller than those of oximes. This can also be explained in terms of the resonance structure III' (Fig. 8). 3) in the amidoximes are again indicative of the Sp2 hybridization of the nitrogen atoms which, in turn, makes electron delocalization possible. Since, as a result of the absence of a nitrogen atom, delocalization is smaller than that in N'-hydroxyguanidines the magnitudes of the chemical shifts of the double-bonded nitrogens are between those for N'-hydroxyguanidines and those for oximes.

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