Gabapentin, an anticonvulsant used in the treatment of epilepsy, is structurally related to the neurotransmitter 4-aminobutanoic acid (GABA). -NH2 -NH, B -СООН COOH Gabapentin 4-Aminobutanoic acid (y-Aminobutyric acid, GABA) Gabapentin was designed specifically to be more lipophilic than GABA and therefore more likely to cross the blood-brain barrier, the lipidlike protective membrane that sur- rounds the capillary system in the brain and prevents hydrophilic (water-loving) com- pounds from entering the brain by passive diffusion. Given the following retrosynthetic analysis, propose a synthesis for gabapentin. -NH, -NH2 CN COOH -COOEt COOEt Gabapentin COOEt COOE. O + COOEt COOEt Cyclohexanone Diethyl malonate
Gabapentin, an anticonvulsant used in the treatment of epilepsy, is structurally related to the neurotransmitter 4-aminobutanoic acid (GABA). -NH2 -NH, B -СООН COOH Gabapentin 4-Aminobutanoic acid (y-Aminobutyric acid, GABA) Gabapentin was designed specifically to be more lipophilic than GABA and therefore more likely to cross the blood-brain barrier, the lipidlike protective membrane that sur- rounds the capillary system in the brain and prevents hydrophilic (water-loving) com- pounds from entering the brain by passive diffusion. Given the following retrosynthetic analysis, propose a synthesis for gabapentin. -NH, -NH2 CN COOH -COOEt COOEt Gabapentin COOEt COOE. O + COOEt COOEt Cyclohexanone Diethyl malonate
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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![Gabapentin, an anticonvulsant used in the treatment of epilepsy, is structurally related
to the neurotransmitter 4-aminobutanoic acid (GABA).
-NH2
-NH,
B
-СООН
COOH
Gabapentin
4-Aminobutanoic acid
(y-Aminobutyric acid, GABA)
Gabapentin was designed specifically to be more lipophilic than GABA and therefore
more likely to cross the blood-brain barrier, the lipidlike protective membrane that sur-
rounds the capillary system in the brain and prevents hydrophilic (water-loving) com-
pounds from entering the brain by passive diffusion. Given the following retrosynthetic
analysis, propose a synthesis for gabapentin.
-NH,
-NH2
CN
COOH
-COOEt
COOEt
Gabapentin
COOEt
COOE.
O +
COOEt
COOEt
Cyclohexanone
Diethyl
malonate](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fb9589126-4bce-4246-8e7e-106818903ca0%2Fb3569859-9643-4a4c-afbf-4e1a0b09f476%2Fexxs64.jpeg&w=3840&q=75)
Transcribed Image Text:Gabapentin, an anticonvulsant used in the treatment of epilepsy, is structurally related
to the neurotransmitter 4-aminobutanoic acid (GABA).
-NH2
-NH,
B
-СООН
COOH
Gabapentin
4-Aminobutanoic acid
(y-Aminobutyric acid, GABA)
Gabapentin was designed specifically to be more lipophilic than GABA and therefore
more likely to cross the blood-brain barrier, the lipidlike protective membrane that sur-
rounds the capillary system in the brain and prevents hydrophilic (water-loving) com-
pounds from entering the brain by passive diffusion. Given the following retrosynthetic
analysis, propose a synthesis for gabapentin.
-NH,
-NH2
CN
COOH
-COOEt
COOEt
Gabapentin
COOEt
COOE.
O +
COOEt
COOEt
Cyclohexanone
Diethyl
malonate
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