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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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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

form

powder

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

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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
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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