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

Biochemistry
9th Edition
ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
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Propose a mechanism for the conversion of (C) to (D). (Note: It is not acceptable to propose a primary carbocation as an intermediate.)

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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