Many popular nicotine gums also contain the sugar β

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absolutely awful. Many popular nicotine gums also contain the sugar β -cyclodextrin ( β CD), which has the following structure: As you can see, there is a big hole in the middle of this molecule into which other molecules can bind. This is what happens to nicotine in the presence of β CD: β CD ( aq ) + nicotine ( aq ) * ) β CD-nicotine ( aq ) . This keeps the nicotine away from the taste buds. The equilibrium constant for this reaction in water at 37 C is 194. 1 If 0.5 mg of nicotine (molar mass 162.23 g/mol) is dissolved in 1 mL of saliva with 50 mg β CD (molar mass 1134.98 g/mol), what percentage of the nicotine is free in solution? [10 marks] Hint: Start by calculating the concentrations of the three chemical species in solution. 1 J. Szejtli and L. Szente, Eur. J. Pharmaceutics Biopharmaceutics 61 , 115 (2005). This review article has the rather amusing title “Elimination of bitter, disgusting tastes of drugs and foods by cyclodextrins”. 2
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