Chiral HPLC analysis of milnacipran and its FMOC-derivative on cellulose-based stationary phases.
The HPLC enantioseparation of the last generation antidepressive drug milnacipran (+/-)-1 was investigated on different cellulose-based chiral stationary phases (CSPs). On carbamate-type columns, Chiralcel OD and OD-H (+/-)-1 could be separated with alpha value about 1.20 but the resolution was quite low because of the tailing of the peaks. Direct determination of (+/-)-1 with high selectivity and resolution was obtained on Chiralcel OJ in normal phase mode elution. Precolumn derivatization of milnacipran with Fmoc-Cl gave compound (+/-)-2 which was enantioseparated on all the investigated CSPs and allowed enhanced UV or fluorimetric detection. The Chiralpak IB, that could be considered the immobilized version of Chiralcel OD-H, was found completely ineffective in the chiral recognition of (+/-)-1 and moderately efficient in the separation of (+/-)-2.
Patti
Angela
A
Istituto di Chimica Biomolecolare del CNR, Via del Santuario 110, I-95028 Valverde CT, Italy. angela.patti@icb.cnr.it
Pedotti
Sonia
S
Sanfilippo
Claudia
C
D000818:Animals; D002482:Cellulose / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003521:Cyclopropanes / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification*; D005449:Fluorenes / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification; D006801:Humans; D000078764:Milnacipran; D055095:Optics and Photonics; D013237:Stereoisomerism
D003521:Cyclopropanes; D005449:Fluorenes; D002482:Cellulose; C054007:1-(9-fluorenyl)methyl chloroformate; D000078764:Milnacipran