Conformational study on ketamine by circular dichroism and ultraviolet spectroscopy

TitleConformational study on ketamine by circular dichroism and ultraviolet spectroscopy
Publication TypeJournal Article
Year of Publication1999
AuthorsZsila, F, Gergely, A, Szász, G
JournalChirality
Volume11
Issue4
Pagination280 - 285
Date Published1999
KeywordsCd and Uv spectra, Conformational equilibrium, Enantiomers, Intramolecular H-bond, Ketamine, Octant rule
Abstract

Since the enantiomers of the N-methyl-D-aspartate (NMDA) receptors antagonist ketamine have different pharmacological profiles, CD and UV spectroscopy were applied for the study of conformer equilibrium and ph dependence in ketamine solutions. The assignment of the configurations and conformations was performed on the basis of the 'octant rule' and UV spectra. In accord with published data, it was established that, on protonation, the phenyl group of the ketamine molecule occupies an axial position, while for the base form, the ratio of conformers containing axial/equatorial aryl moieties is strongly solvent-dependent. The CD and UV spectra indicate the presence of an intramolecular H-bond C=O ···· H-N in the conformer with axial aryl moiety.

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