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Amoxapine

Name: Amoxapine
Brand: SIGMA

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

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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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This Item	C6305	D5676	1031401
Sigma-Aldrich A129 Amoxapine	Sigma-Aldrich C6305 Clozapine	Sigma-Aldrich D5676 N-Desmethylclozapine	USP 1031401 Amoxapine
form powder	form powder	form powder	form -
Quality Level 100	Quality Level 300	Quality Level 200	Quality Level -
solubility methanol: soluble	solubility ethanol: 1 mg/mL, 0.1 M HCl: 30 mg/mL, DMSO: 4.8 mg/mL	solubility -	solubility -
originator Wyeth	originator Novartis	originator -	originator -
Gene Information human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816), HTR2A(3356), HTR2B(3357), HTR2C(3358), SLC6A2(6530), SLC6A4(6532)	Gene Information human ... ADRA1A(148), ADRA2A(150), ADRA2C(152), CHRM1(1128), DRD2(1813), DRD3(1814), DRD4(1815), HRH1(3269), HRH4(59340), HTR2A(3356), HTR2C(3358), HTR3A(3359), HTR3B(9177), HTR3C(170572), HTR3D(200909), HTR3E(285242), HTR6(3362), HTR7(3363), KCNH1(3756), KCNH2(3757), UGT1A4(54657) rat ... Adra1a(29412), Adra2a(25083), Adrb1(24925), Chrm1(25229), Drd1a(24316), Drd2(24318), Drd3(29238), Drd4(25432), Hrh1(24448), Htr1a(24473), Htr1b(25075), Htr2a(29595), Htr2b(29581), Htr2c(25187), Htr3a(79246), Htr7(65032), Slc6a4(25553)	Gene Information human ... KCNH1(3756)	Gene Information human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816), SLC6A2(6530), SLC6A4(6532)

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.[1] It has also been used as an antipsychotic drug to test its effect on the viability of glioblastoma cells.[2]

Biochem/physiol Actions

Amoxapine, a structural analog of clozapine, is a human ether a-go-go (hERG) channel blocker.[1] It is also an N-methylated metabolite of loxapine. It is a tricyclic antidepressant that inhibits the uptake of norepinephrine[3] 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

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

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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Determination of amoxapine and nortriptyline in blood plasma and serum by salt-assisted liquid-liquid microextraction and high-performance liquid chromatography.

Manju Gupta et al.

Journal of separation science, 33(23-24), 3774-3780 (2010-11-18)

A new, selective and sensitive method has been developed for the determination of tricyclic antidepressant drugs, amoxapine and nortriptyline, in human blood plasma and serum, involving their reaction with allyl isothiocyanate and extraction of thiourea derivatives with water-miscible organic solvent

Evaluation of the interaction between β-cyclodextrin and psychotropic drugs by surface plasmon resonance assay with a Biacore ® system.

Hiroaki Kobayashi et al.

Journal of pharmaceutical and biomedical analysis, 54(1), 258-263 (2010-09-15)

Phase-solubility studies have been used to evaluate the solubilizing effects of cyclodextrins (CDs) on lipophilic, water-insoluble drugs. However, large amounts of CDs and drugs are required to measure solubility by phase-solubility studies. Thus, more efficient approaches to evaluate the interaction

Successful treatment of amoxapine-induced refractory status epilepticus with propofol (diprivan)

K S Merigian et al.

Academic emergency medicine : official journal of the Society for Academic Emergency Medicine, 2(2), 128-133 (1995-02-01)

Tonic-clonic seizure activity is a recognized complication of amoxapine overdose. Refractory drug-induced status epilepticus is associated with significant morbidity and mortality. Standard regimens for controlling status epilepticus may be ineffective for aborting drug-induced seizures. The authors report the case of

Amoxapine (Asendin, Lederle Laboratories).

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

Amoxapine: a review of its pharmacology and efficacy in depressed states.

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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Global Trade Item Number

SKU	GTIN
A129-500MG	04061832088549
A129-5G	04061832088556
A129-100MG	04061832088532

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