This study examined the relationship between oral smokeless tobacco (ST) topographical measures and biomarkers of tobacco and carcinogen exposure. During 2 weeks of baseline ad libitum ST use, 54 male participants (mean age=32.1 ± 7.5 years) were required to record the time each dip was placed in and removed from their mouths. Urine samples were collected twice during baseline and analyzed for nicotine, cotinine, and their glucuronides (total nicotine and total cotinine) and for metabolites of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol and its glucuronides (total NNAL). The results suggest that frequency and duration measures of ST use (p<.01 to p<.001), particularly total dip duration, are significantly correlated with total cotinine, total nicotine, and total NNAL. These results suggest that how long a ST user has tobacco in his mouth is most predictive of tobacco toxin exposure.