Enantiomeric composition of nicotine in smokeless tobacco, medicinal products, and commercial reagents

Abstract

The enantiomeric composition of nicotine in 18 smokeless tobaccos, 3 strains of tobacco leaf, 8 pharmaceutical products, and 4 commercial reagents was determined. The relative amount of the minor enantiomeric component, (R)-(+)-nicotine, ranged from ∼0.1% to ∼1.2% of the total nicotine in all samples. In some cases it appears that (R)-(+)-nicotine may be considered one of the five most common alkaloids in tobacco products. The highest level of (R)-(+)-nicotine was found in a commercial transdermal patch. The extraction and purification processes used in obtaining commercial (S)-(−)-nicotine supplies from tobacco do not appear to decrease the amount of (R)-(+)-nicotine present. Chirality 10:587–591, 1998. © 1998 Wiley-Liss, Inc.