The antidepressant amitriptyline inhibits the reuptake of norepinephrine and serotonin from the synaptic cleft. Because the reuptake of these neurotransmitters is inhibited, their effects are potentiated; they remain available to interact with serotonin and norepinephrine receptor sites longer and continue to cause excitation of sero- tonin- and norepinephrine-mediated neural pathways. Following is a synthesis for amitriptyline. H,PO, COOH (A) (B) HBr НО Br `NMe, (C) (D) Amitriptyline

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter22: Reactions Of Benzene And Its Derivatives
Section: Chapter Questions
Problem 22.53P
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Is amitriptyline chiral? If so, how many of the possible stereoisomers are formed in this synthesis?

The antidepressant amitriptyline inhibits the reuptake of norepinephrine and
serotonin from the synaptic cleft. Because the reuptake of these neurotransmitters is
inhibited, their effects are potentiated; they remain available to interact with serotonin
and norepinephrine receptor sites longer and continue to cause excitation of sero-
tonin- and norepinephrine-mediated neural pathways. Following is a synthesis for
amitriptyline.
H,PO,
COOH
(A)
(B)
HBr
НО
Br
`NMe,
(C)
(D)
Amitriptyline
Transcribed Image Text:The antidepressant amitriptyline inhibits the reuptake of norepinephrine and serotonin from the synaptic cleft. Because the reuptake of these neurotransmitters is inhibited, their effects are potentiated; they remain available to interact with serotonin and norepinephrine receptor sites longer and continue to cause excitation of sero- tonin- and norepinephrine-mediated neural pathways. Following is a synthesis for amitriptyline. H,PO, COOH (A) (B) HBr НО Br `NMe, (C) (D) Amitriptyline
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