Enantioseparation of the antidepressant reboxetine
by
Cannazza G, Braghiroli D, Carrozzo MM, Parenti C,
Sabbioni C, Mandrioli R, Fanali S, Raggi MA.
Department of Pharmaceutical Sciences,
University of Modena and Reggio Emilia,
Via Campi 183, 41100 Modena, Italy
J Pharm Biomed Anal. 2008 Jul 11.


ABSTRACT

The enantioseparation of reboxetine by HPLC was investigated using chiral stationary phases (CSPs) containing cellulose Tris(3,5-dimethylphenyl)carbamate on silica gel (Chiralcel OD column) as the chiral selector. Reversed phase HPLC was the technique of choice for the analytical enantioseparation of reboxetine, while the chiral semipreparative separation was obtained with the same CSP, but in normal phase conditions. The effects of the mobile phase pH and composition on analytical retention, enantioselectivity and resolution were investigated. The best performance was obtained using a mobile phase composed of 0.5M sodium perchlorate at pH 6 and acetonitrile in the 60/40 (v/v) ratio. The semipreparative separation has allowed obtaining pure enantiomers, but required the preparation of reboxetine free base. Different n-hexane/alcohol mixtures were tested as mobile phases, varying both the nature of the alcohol and its percentage in the mobile phase. Different n-hexane/alcohol mixtures were tested as mobile phase and the best results were obtained by using a mobile phase composed of n-hexane and 2-propanol (80:20, v/v).


Enantiomers
NARIs and SSRIs
Sexual side-effects
Noradrenaline and mood
Catecholamine depletion
Selectivity or multiplicity?
Reboxetine and the elderly
Noradrenaline reuptake inhibition
Sexual function: paroxeine v reboxetine




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