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

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-->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.

journal_name

Chirality

journal_title

Chirality

authors

Zsila F,Hollósi M,Gergely A

doi

10.1002/1520-636X(2000)12:10<720::AID-CHIR4>3.0.CO

subject

Has Abstract

pub_date

2000-11-01 00:00:00

pages

720-6

issue

10

eissn

0899-0042

issn

1520-636X

pii

10.1002/1520-636X(2000)12:10<720::AID-CHIR4>3.0.CO

journal_volume

12

pub_type

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