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A129

Sigma-Aldrich

Amoxapine

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C17H16ClN3O
Número CAS:
14028-44-5
Peso molecular:
313.78
Número CE:
237-867-1
Número MDL:
MFCD00069210
Código UNSPSC:
12352200
ID de substância PubChem:
24278075
NACRES:
NA.77

forma

powder

Nível de qualidade

100

solubilidade

methanol: soluble

originador

Wyeth

cadeia de caracteres 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

chave InChI

QWGDMFLQWFTERH-UHFFFAOYSA-N

Informações sobre genes

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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Aplicação

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.

Ações bioquímicas/fisiológicas

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.

Características e benefícios

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.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H302

Declarações de precaução

P264 - P270 - P301 + P312 - P501

Classificações de perigo

Acute Tox. 4 Oral

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

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

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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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
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
Yan-Lin He et al.
The Journal of pharmacology and experimental therapeutics, 332(2), 437-445 (2009-11-17)
Ion channels are known to be modulated by antidepressant drugs, but the molecular mechanisms are not known. We have shown that the antidepressant drug amoxapine suppresses rectifier outward K(+) (I(K)) currents in mouse cortical neurons. At a concentration of 10
F Jenck et al.
Progress in neuro-psychopharmacology & biological psychiatry, 18(3), 563-574 (1994-05-01)
A variety of antidepressants of different chemical classes were tested for their in vivo and in vitro activity at 5-HT1C receptors in the brain. Conventional tricyclic antidepressants (imipramine, desipramine, maprotiline, clomipramine, trimipramine, amitriptyline, nortriptyline, doxepin, amoxapine, oxaprotiline) and two atypical
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