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HPLC enantioseparation of α,α‐diphenyl‐2‐pyrrolidinemethanol and methylphenidate using a chiral fluorescent derivatization reagent and its application to the analysis of rat plasma
Author(s) -
Inagaki Shinsuke,
Taniguchi Sayuri,
Hirashima Haruo,
Higashi Tatsuya,
Min Jun Zhe,
KikuraHanajiri Ruri,
Goda Yukihiro,
Toyo'oka Toshimasa
Publication year - 2010
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.201000479
Subject(s) - derivatization , reagent , chemistry , chromatography , high performance liquid chromatography , fluorescence , resolution (logic) , detection limit , quantitative analysis (chemistry) , organic chemistry , physics , quantum mechanics , artificial intelligence , computer science
Enantioseparation of α,α‐diphenyl‐2‐pyrrolidinemethanol (D2PM) and methylphenidate (MPH; Ritalin ® ) using ( R )‐(−)‐4‐( N , N ‐dimethylaminosulfonyl)‐7‐(3‐isothiocyanatopyrrolidin‐1‐yl)‐2,1,3‐benzoxadiazole as the chiral derivatization reagent has been achieved for the first time, and a simple, reliable detection method using HPLC with fluorescence detection has been developed. D2PM and MPH have been derivatized with ( R )‐(−)‐4‐( N , N ‐dimethylaminosulfonyl)‐7‐(3‐isothiocyanatopyrrolidin‐1‐yl)‐2,1,3‐benzoxadiazole at 55°C for 15 min. The derivatives of D2PM and MPH have been separated, completely and rapidly, using a reversed‐phase system within 16 min (resolution factor ( R s )=1.60 and 2.53, respectively). The detection limits of ( R )‐ and ( S )‐D2PM were found to be 6.8 and 13 ng/mL, respectively, and those of D ‐ and L ‐ threo ‐MPH were 61 and 66 ng/mL, respectively ( S / N =3). The proposed method was successfully applied to the analysis of rat plasma, where the rats were separately dosed with D2PM and MPH (Ritalin).