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A129

Sigma-Aldrich

Amoxapine

Synonym(s):

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

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100 MG
$54.30
500 MG
$214.00
5 G
$968.00

About This Item

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

$54.30

Available to ship onMay 01, 2025Details

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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.[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.[3] It is a tricyclic antidepressant that inhibits the uptake of norepinephrine[4] and blocks 5- hydroxytryptamine (HT2 ) serotonergic receptors.[3]

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_germany

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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Rogelio Apiquian et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 30(12), 2236-2244 (2005-06-16)
Amoxapine is marketed as an antidepressant. However, its in-vitro profile, receptor occupancy and preclinical effects are very similar to atypical antipsychotics. Amoxapine has also shown efficacy as an atypical antipsychotic in open trials. The objective of this study was to
Xiao-Pen Lee et al.
Journal of separation science, 31(12), 2265-2271 (2008-06-12)
A method for the simultaneous extraction of four tricyclic antidepressants from human plasma samples using pipette tip SPE with MonoTip C(18) tips is presented. Human plasma (0.1 mL) containing four tricyclic antidepressants (amitriptyline, amoxapine, imipramine, and trimipramine) and an internal
Merve Kasap et al.
Neuroscience research (2020-07-19)
Two-pore domain K+ channels (K2Ps) regulate the resting membrane potential in excitable cells and determine ease of depolarization. Gain-of-function (gf) mutations in one of these channels (unc-58) in C. elegans switch it to a Na+ conductance channel and cause tremors
Guang Yang et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 28(1), 163-174 (2011-08-26)
Although tricyclic antidepressants amoxapine is proposed to target 5-HT and D2 receptors, very few studies have addressed the effect of amoxapine on molecular and cellular mechanisms via receptor pathways. In this study, we test the effect of amoxapine on rat
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
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