Stereochemical study of tolperisone, a muscle relaxant agent, by circular dichroism and ultraviolet spectroscopy

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Abstract

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→π* 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 α-methyl-β-amino-ketones. (C) 2000 Wiley-Liss, Inc.

Original languageEnglish
Pages (from-to)720-726
Number of pages7
JournalChirality
Volume12
Issue number10
DOIs
Publication statusPublished - Nov 8 2000

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Keywords

  • Absolute configuration
  • Chiral conformer
  • Circular dichroism and ultraviolet spectroscopy
  • Dipole-dipole interaction
  • Nonplanar benzoyl chromophore
  • Tolperisone

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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