Enantioseparation of nicotine alkaloids in cigarettes by CE using sulfated beta-CD as a chiral selector and a capillary coated with amino groups.
Nicotine (NC) and its related compounds (cotinine (CN), nornicotine (NN), anatabine (AT) and anabasine (AB)) were simultaneously enantioseparated by CE using a capillary with amino groups and sulfated beta-CD as a chiral selector. The optimum running conditions were found to be 30 mM acetate buffer (pH 5.0) containing 8% sulfated beta-CD with an applied voltage of +15 kV at 30 degrees C using direct detection at 260 nm. Using a capillary coated with amino groups, the EOF migrates toward the positive pole. However, when sulfated beta-CD was added to the BGE, it was found that the EOF migrated toward the negative pole due to ionic adsorption of sulfated beta-CD to amino groups on the capillary inner wall. All the cationic analytes migrated as anions, suggesting that they formed stable anionic complexes with sulfated beta-CD. With this system and a simple pretreatment with mini-cartridges, NC alkaloids in five cigarette samples were enantioseparated. As a result, each of the compounds except for CN was detected. In the case of NC, only (S)-NC was detected (more than 99.9%), but in the case of NN, AT and AB, the ratios of (S)-isomer to total isomers were in the ranges 58-70, 81-85 and 59-65%, respectively. On the other hand, only NC was detected in cigarette smoke and the ratio of (S)- and (R)-NCs was 96:4. The amounts of NC alkaloids in cigarettes suggest that the production of (R)-NC resulted from racemization due to the high temperature/burning of the cigarette.
Kodama
Shuji
S
Toyama Institute of Health, Toyama, Japan. shuji.kodama@pref.toyama.lg.jp
Morikawa
Atsushi
A
Nakagomi
Kazuya
K
Yamamoto
Atsushi
A
Sato
Atsushi
A
Suzuki
Kentaro
K
Yamashita
Tomohisa
T
Kemmei
Tomoko
T
Taga
Atsushi
A
D000470:Alkaloids / Q000032:analysis*; D000588:Amines / Q000737:chemistry; D003367:Cotinine / Q000032:analysis; D019075:Electrophoresis, Capillary / Q000379:methods*; D006801:Humans; D009538:Nicotine / Q000031:analogs & derivatives / Q000032:analysis*; D012680:Sensitivity and Specificity; D013237:Stereoisomerism; D013431:Sulfates / Q000737:chemistry; D014026:Nicotiana / Q000737:chemistry*
D000470:Alkaloids; D000588:Amines; D013431:Sulfates; D009538:Nicotine; D003367:Cotinine