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The high frequency  1 H and  13 C NMR spectra (at 500 and 75.47 MHz, respectively) of N-allyl- N-normetazocine (NAM) hydrochloride in  2 H 2 O solution were run and fully analyzed with the aid of both homonuclear  1 H - 1 H and heteronuclear 13C -  1 H chemical shift correlation experiments. Selective broadening of the signals of the protons in 3-, 4-, 8-, 9-, 12-positions was observed at temperatures &lt;350 K. This was found to be consistent with an inversion process occurring between the N-equatorial and N-axial configurational isomers of NAM whose rate of exchange is of the same order of magnitude of the chemical shifts differences at 500 MHz. The increase of temperature at 350 K is thus adequate to make “fast” the process in the NM R time scale and then to resolve the spectral portions.

zeitschrift für naturforschung b

Molecular Determinants for Drug Receptor Interactions, 9  1 H and  13 C NMR Spectra of the Narcotic Antagonist N-Allyl-N-normetazocine by Two-Dimensional Chemical Shift Correlation Spectroscopy