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A129

Sigma-Aldrich

Amoxapine

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C17H16ClN3O
Numéro CAS:
14028-44-5
Poids moléculaire :
313.78
Numéro CE :
237-867-1
Numéro MDL:
MFCD00069210
Code UNSPSC :
12352200
ID de substance PubChem :
24278075
Nomenclature NACRES :
NA.77

Forme

powder

Niveau de qualité

100

Solubilité

methanol: soluble

Auteur

Wyeth

Chaîne SMILES 

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

Clé InChI

QWGDMFLQWFTERH-UHFFFAOYSA-N

Informations sur le gène

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
Imran B Chaudhry et al.
Journal of clinical psychopharmacology, 27(6), 575-581 (2007-11-16)
It has been proposed that the lack of extrapyramidal side effects of atypical antipsychotic drugs is caused by their fast dissociation or low affinity for the D2 receptor or their concomitant high affinity for other receptors, for example, 5HT2 and
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
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