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Enantiomeric separation of tolperisone and eperisone by reversed‐phase HPLC with cellulose tris(3‐chloro‐4‐methylphenylcarbamate)‐coated chiral column
Author(s) -
Owada Yuri,
Takahashi Mizuho,
Iwasa Sumiko,
Ichiba Hideaki,
Sadamoto Kiyomi,
Fukushima Takeshi
Publication year - 2014
Publication title -
biomedical chromatography
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.4
H-Index - 65
eISSN - 1099-0801
pISSN - 0269-3879
DOI - 10.1002/bmc.2892
Subject(s) - chemistry , enantiomer , chromatography , elution , chiral column chromatography , high performance liquid chromatography , ammonium acetate , moiety , optical rotation , resolution (logic) , tris , circular dichroism , cellulose , phase (matter) , column chromatography , chiral derivatizing agent , organic chemistry , stereochemistry , biochemistry , artificial intelligence , computer science
Enantiomeric separations of centrally acting muscle relaxants, that is, tolperisone (TOL) and eperisone (EP), that are marketed as racemates were investigated by reversed‐phase high‐performance liquid chromatography (HPLC) on a polysaccharide‐based chiral column. Both TOL and EP are basic drugs because they contain a tertiary amino group and have similar chemical structures with the exception of the p ‐methylphenyl and p ‐ethylphenyl groups in TOL and EP, respectively. A reversed‐phase chiral column, that is, a Chiralcel OZ‐RH column, which bears cellulose tris(3‐chloro‐4‐methylphenylcarbamate) as the chiral moiety, was effective for the enantiomeric separation of TOL and EP enantiomers. The separation factor and resolution values obtained for TOL were 1.22 and 1.66, respectively, and those for EP were 1.21 and 2.24, respectively, using a 20 m m ammonium acetate in H 2 O (pH 8.0 and 7.0, respectively)–CH 3 CN (70:30) mobile phase. Using the proposed HPLC conditions, it was found that ( R )‐TOL eluted faster than ( S )‐TOL, as revealed by the optical rotation and circular dichroism spectroscopy. In contrast, EP was easily racemized under the experimental conditions, and hence, the elution order was not determined. Copyright © 2013 John Wiley & Sons, Ltd.