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Assignment One: 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?...

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Assignment One:

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.

Assignment Two:

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.


Answered Same Day Dec 24, 2021

Solution

David answered on Dec 24 2021
111 Votes
Solution TTs280913_111028_3
O
CH3COO
CH3COO
N CH3
O
O
CH3COO
N CH3
O
CH3COO
O
N CH3
Phenolic Hydroxyl group
Allylic Hydroxyl group
Heroin
Alkaline
Hydrolysis
3,6-Diacetylmorphine
6-
Monoacetyl
morphine
3-Monoacetylmorphine
If a product is more stable than the other, the stable product will be formed
preferentially. Between 6-Monoacetylmorphine and 3-Monoacetylmorphine, the
former is resonance...
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