Zsila F, Hollósi M, Gergely A
Department of Molecular Pharmacology, Institute of Chemistry, Budapest, Hungary.
Chirality. 2000 Nov;12(10):720-6. doi: 10.1002/1520-636X(2000)12:10<720::AID-CHIR4>3.0.CO;2-2.
The stereochemistry of tolperisone, a chiral aryl-alkyl basic ketone was investigated by means of circular dichroism (CD) and ultraviolet (UV) spectroscopy. The unusually high optical activity of tolperisone hydrochloride in the n-->pi* region is interpreted by the presence of a chiral conformer in solution. For stereochemical reasons, the C = O group and the aromatic moiety lack coplanarity by forming an inherently dissymetric chromophore, of M helicity. Similar helicity prevails in the crystal phase, according to the solid-state CD spectrum of (-)-tolperisone HCl salt. The chirality rule proposed by Snatzke for nonplanar benzoyl chromophores predicts the absolute configuration of (-)-tolperisone hydrochloride to be R, in agreement with other alpha-methyl-beta-amino-ketones.
