A possible relation between pKa1 and lipid solubility and the amounts excreted in urine of some tobacco alkaloids given to man

Abstract

The amount of unchanged (—)-nicotine, (—)-nornicotine, (—)-methylanabasine and (—)-anabasine excreted in the urine after oral administration to man was dependent on urinary pH while that of (—)-cotinine depended on urinary pH and on urine flow rate. No unchanged β-nicotyrine, β-nornicotyrine or myosmine was detected in urine. More nornicotine and anabasine than their corresponding tertiary amines nicotine and methylanabasine were excreted unchanged in the urine. Correlations of pKa1 and lipid solubility and the urinary excretion of these compounds were made.