title: Enantiomeric separation of tolperisone and eperisone by reversed-phase HPLC with cellulose tris(3-chloro-4-methylphenylcarbamate)-coated chiral column.
abstract: 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 mm ammonium acetate in H2 O (pH 8.0 and 7.0, respectively)-CH3 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.
authors.affiliation: Department of Clinical Science, Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi-shi, Chiba, 274-8510, Japan.
authors.forename: Yuri
authors.initials: Y
authors.lastname: Owada
authors.forename: Mizuho
authors.initials: M
authors.lastname: Takahashi
authors.forename: Sumiko
authors.initials: S
authors.lastname: Iwasa
authors.forename: Hideaki
authors.initials: H
authors.lastname: Ichiba
authors.forename: Kiyomi
authors.initials: K
authors.lastname: Sadamoto
authors.forename: Takeshi
authors.initials: T
authors.lastname: Fukushima
mesh_terms: D002482:Cellulose / Q000031:analogs & derivatives / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods*; D056148:Chromatography, Reverse-Phase / Q000295:instrumentation / Q000379:methods*; D048448:Phenylcarbamates / Q000737:chemistry; D011427:Propiophenones / Q000737:chemistry* / Q000302:isolation & purification; D013237:Stereoisomerism; D014049:Tolperisone / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D048448:Phenylcarbamates; D011427:Propiophenones; C538979:cellulose tris(3-chloro-4-methylphenylcarbamate); C030848:eperisone; D002482:Cellulose; D014049:Tolperisone
keywords: Chiralcel OZ-RH; HPLC; enantiomer; eperisone; tolperisone