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Merck
CN

A129

Amoxapine

Synonym(s):

2-Chloro-11-(1-piperazinyl)dibenz[b,f][1,4]oxazepine

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About This Item

Empirical Formula (Hill Notation):
C17H16ClN3O
CAS Number:
14028-44-5
Molecular Weight:
313.78
NACRES:
NA.77
PubChem Substance ID:
24278075
UNSPSC Code:
12352200
EC Number:
237-867-1
MDL number:
MFCD00069210
Form:
powder
Quality level:
100

Key Documents

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form

powder

Quality Level

100

solubility

methanol: soluble

originator

Wyeth

SMILES string

Clc1ccc2Oc3ccccc3N=C(N4CCNCC4)c2c1

InChI

1S/C17H16ClN3O/c18-12-5-6-15-13(11-12)17(21-9-7-19-8-10-21)20-14-3-1-2-4-16(14)22-15/h1-6,11,19H,7-10H2

InChI key

QWGDMFLQWFTERH-UHFFFAOYSA-N

Gene Information

human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816), HTR2A(3356), HTR2B(3357), HTR2C(3358), SLC6A2(6530), SLC6A4(6532)

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Application

Amoxapine has been used as an antidepressant drug to test its effect on locomotion and egg release in response to gain-of-functional mutations in potassium (K+) channels (unc-58) of C. elegans. It has also been used as an antipsychotic drug to test its effect on the viability of glioblastoma cells.

Biochem/physiol Actions

Amoxapine, a structural analog of clozapine, is a human ether a-go-go (hERG) channel blocker. It is also an N-methylated metabolite of loxapine. It is a tricyclic antidepressant that inhibits the uptake of norepinephrine and blocks 5- hydroxytryptamine (HT2 ) serotonergic receptors.

Features and Benefits

This compound is featured on the Biogenic Amine Transporters page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Wyeth. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBB6438
BCBB6438V
121K1611
071K1160

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J E Dugas et al.
Drug intelligence & clinical pharmacy, 16(3), 199-204 (1982-03-01)
Amoxapine is a tricyclic antidepressant agent, which is chemically related to the antipsychotic agent loxapine, but which appears to block selectively the neuronal reuptake of norepinephrine; it is qualitatively similar to desipramine. In studies of patients with mixed depressive illnesses
S G Jue et al.
Drugs, 24(1), 1-23 (1982-07-01)
Amoxapine is an N-demethylated dibenzoxazepine closely related in the neuroleptic loxapine. Its tricyclic structure appears to give it antidepressant properties resembling imipramine and amitriptyline. In uncontrolled trials it was shown to have antidepressant activity in usual doses up to 200
T A Ban et al.
International pharmacopsychiatry, 15(3), 166-170 (1980-01-01)
Amoxapine, a new antidepressant, is a tricyclic debenzoxazepine compound, the demethylated metabolite of the neuroleptic loxapine. In animal pharmacological studies, amoxapine has shown striking similarities to imipramine. In contrast to the prototype antidepressant drug, however, amoxapine does not interact with
Sabrina Obers et al.
Naunyn-Schmiedeberg's archives of pharmacology, 381(5), 385-400 (2010-03-17)
The antidepressant amoxapine has been linked to cases of QT prolongation, acute heart failure, and sudden death. Inhibition of cardiac hERG (Kv11.1) potassium channels causes prolonged repolarization and is implicated in apoptosis. Apoptosis in association with amoxapine has not yet
S Kapur et al.
Biological psychiatry, 45(9), 1217-1220 (1999-05-20)
All currently available atypical antipsychotics have, at clinically relevant doses: i) high serotonin (5-HT)2 occupancy; ii) greater 5-HT2 than dopamine (D)2 occupancy; and iii) a higher incidence of extrapyramidal side effects when their D2 occupancy exceeds 80%. A review of
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Global Trade Item Number

SKUGTIN
A129-500MG04061832088549
A129-100MG04061832088532
A129-5G04061832088556

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