Question 1)
Heroin is 3, 6-diacetylmorphine. Heroin is 2-3 times more potent than morphine.
In vitro and in vivo, to which product does heroin hydrolyze first, (3- or 6-acetylmorphine), and why?
Hint: What are the acidic pKa values of the respective hydroxyl products? Look up the structures on the internet or use the UF library online e-journals.
Question 2)
Acetylsulfisoxazole, is readily hydrolyzed in vivo to sulfisoxazole. On the other hand, the acyl group in amikacin, is stable to hydrolysis in vivo. Both acetylsulfisoxazole and amikacin are acyl derivatives where the acyl group is attached to nitrogen.
Why is one stable and the other not?
Hint: What are the acidic pKa values of the respective N-H groups formed on hydrolysis. Look up the structures on the internet or use the UF library online e-journals.