Abstract
Abstract 1H and 13C NMR chemical shift assignments were obtained for the local anesthetics etidocaine (1) and etidocaine hydrochloride (2) in CDCl3 solution, as well as for 2 in D2O solution. The COSY experiment was employed for proton-proton correlation, while onebond and long-range 2D heteronuclear techniques allowed the assignments of all 13C chemical shifts in each molecule. Etidocaine has a chiral carbon; etidocaine hydrochloride has, in addition to the natural chiral center, an acid-induced chirality at the protonated amine nitrogen, resulting in solvent-dependent diastereomers. Ten of the fourteen magnetically nonequivalent 13C nuclei of 2 exhibit doubled 13C resonance peaks (50.3 MHz, 20°C, CDCl3 solution) due to the presence of the two diastereomers.
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