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Amoxapine

Product Name
Amoxapine
CAS No.
14028-44-5
Chemical Name
Amoxapine
Synonyms
amoxan;Demolox;cl67772;Asendis;Asendin;Moxadil;Defanyl;CL 67772;Ascendin;Amoxepine
CBNumber
CB5375947
Molecular Formula
C17H16ClN3O
Formula Weight
313.78
MOL File
14028-44-5.mol
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Amoxapine Property

Melting point:
175-1760C
Boiling point:
469.9±55.0 °C(Predicted)
Density 
1.2613 (rough estimate)
refractive index 
1.5800 (estimate)
Flash point:
9℃
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
methanol: soluble
pka
pKa 7.6 (Uncertain)
form 
Solid
color 
Crystals from benzene/pet ether
Merck 
14,576
Stability:
Stable under recommended storage conditions., Stable Under Recommended Storage C
CAS DataBase Reference
14028-44-5(CAS DataBase Reference)
NIST Chemistry Reference
Amoxapine(14028-44-5)
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Safety

Hazard Codes 
Xn
Risk Statements 
22
Safety Statements 
36
RIDADR 
3249
WGK Germany 
3
RTECS 
HQ4025500
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
2934990002
Toxicity
LD50 in mice (mg/kg): 122 i.p.; 112 orally (Howell, 1972)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
A129
Product name
Amoxapine
Packaging
5g
Price
$942
Updated
2024/03/01
Sigma-Aldrich
Product number
A-123
Product name
Amoxapine
Purity
1.0?mg/mL in methanol, certified reference material, Cerilliant?
Packaging
1mL
Price
$76.9
Updated
2024/03/01
Sigma-Aldrich
Product number
1031401
Product name
Amoxapine
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
TCI Chemical
Product number
A2499
Product name
Amoxapine
Purity
>97.0%(GC)(T)
Packaging
1g
Price
$131
Updated
2024/03/01
TCI Chemical
Product number
A2499
Product name
Amoxapine
Purity
>97.0%(GC)(T)
Packaging
5g
Price
$423
Updated
2021/12/16
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Amoxapine Chemical Properties,Usage,Production

Description

Amoxapine is a tetracyclic antidepressant with a wide range of pharmacological effects. It inhibits norepinephrine and serotonin reuptake, binding the respective transporters with Kd values of 16 and 58 nM. It has also been shown to act as either an antagonist or inverse agonist at serotonin 5-HT2A, 2B, 2C, 3, 6, 7 (Kis = 1 and 2 nM for 5-HT2A and 5-HT2C, respectively), dopamine D2, 3, 4 (Kd = 160 nM for D2), α1-adrenergic (Kd = 50 nM), and histamine H1 (Kd = 25 nM) receptors.

Chemical Properties

Crystalline Solid

Originator

Asendin,Lederle,US,1980

Uses

Amoxapine is intended more for relieving symptoms in patients with neurotic or situational depression. It has a number of serious side effects.

Uses

A tricyclic norepinephrine uptake inhibitor

Uses

antidepressant, inhibits norepinephrine uptake

Definition

ChEBI: A dibenzooxazepine compound having a chloro substituent at the 2-position and a piperazin-1-yl group at the 11-position.

Manufacturing Process

A mixture of 125 g of o-(p-chlorophenoxy)aniline hydrochloride and 100 ml of dry pyridine is treated cautiously with a solution of 90 ml of ethyl chlorocarbonate in 150 ml of ether. The mixture is kept at room temperature for 3 days, diluted with about 500 ml of water and extracted with 300 ml of ether, The ethereal extract is washed with 300 ml of water, dried over calcium chloride, filtered and concentrated. The resulting ethyl o-(pchlorophenoxy) carbanilate is obtained in a viscous oil suitable for use in the next step without further purification.
A solution of 70 g of ethyl o-(p-chlorophenoxy)carbanilate and 120 g of Ncarbethoxypiperazine in 100 ml of benzene containing a little sodium methoxide is heated on a steam bath for about 5 days. The solvent is removed by distillation and the residue is triturated with water. The resulting solid is dissolved in ether and dried over sodium sulfate. Filtration and concentration then yields ethyl 4-[[o-(p-chlorophenoxy)phenyl]carbamoyl]-1- piperazinecarboxylate, melting at 89°C to 91°C, and suitable for cyclization.
A mixture of 10 g of the above piperazine carboxylate ester, 8 g of phosphorus pentoxide and 20 ml of phosphorus oxychloride is heated under reflux for about 1 day, diluted with 100 ml each of chloroform and benzene and quenched with 200 g of ice. The mixture is made basic with 10% sodium hydroxide. The organic layer is isolated and extracted with 150 ml of dilute hydrochloric acid. The product is precipitated from the aqueous layer by addition of 10% sodium hydroxide, extracted with benzene and dried over potassium carbonate. Recrystallization from benzene-petroleum ether gives 2- chloro-11-(1-piperazinyl)dibenz[b,f][1,4]oxazepine which melts at 175°C to 176°C.

brand name

Asendin (Lederle).

Therapeutic Function

Antidepressant

General Description

Consideration of the structure of amoxapine, 2-chloro-11-(1-piperazinyl)dibenz-[b,f] [1,4]oxazepine (Asendin), reinforcesthe fact that many antidepressants are very closelyrelated to antipsychotics. Indeed, some, including amoxapine,have significant effects at D2 receptors. The Nmethyl–substituted relative of amoxapine is the antipsychoticloxapine (Loxitane). The 8-hydroxy metabolite ofamoxapine is reportedly active as an antidepressant and asa D2 receptor blocker.

Mechanism of action

Additionally, it is the N-desmethyl metabolite of the antipsychotic loxapine. Amoxapine differs structurally from the other secondary TCAs in that it has both a nitrogen and an oxygen atom in its 7-membered central ring and a piperazinyl ring rather than a propylamino side chain attached to the central ring.Amoxapine is a less potent inhibitor of neuronal NE reuptake compared with the other secondary TCAs, with a mechanism of action similar to that of desipramine.

Pharmacology

The antidepressant action of amoxapine is comparable to that of imipramine and amitriptyline. It exhibits antagonistic activity on dopamine (D2) receptors.

Pharmacokinetics

Amoxapine shares the toxic potentials of the TCAs, and the usual precautions of TCA administration should be observed. Amoxapine resembles the atypical antipsychotic drugs in its intermediate affinity as an antagonist of dopamine-2 and of 5-HT2 receptors. Amoxapine is rapidly and almost completely absorbed from the gastrointestinal (GI) tract. Amoxapine and its 8-hydroxyamoxapine metabolite have been detected in human milk at concentrations below steady-state therapeutic concentrations.

Clinical Use

Amoxapine is a dibenzoxazepine TCA with antidepressant and antipsychotic effects that has shown therapeutic effectiveness in patients with delusional depression.

Safety Profile

Poison by ingestion andintraperitoneal routes. Human systemic effects byingestion: acute renal failure, acute tubular necrosis, BPlowering, coma, convulsions, decreased body temperature,EKG changes, excitement, fasciculations, heart ratechanges, hype

Synthesis

Amoxapine, 2-chloro-11-(1-piperazinyl)-dibenz[b,f]oxazepine (7.3.2), is a direct analog of the neuroleptic loxapine (6.5.3), differing only in the absence of a methyl group in the piperazine region of the molecule. On the other hand, it could be included in the class of tricyclic antidepressants, the main difference being the presence of a side chain on the central 7-membered ring of the tricyclic system. Amoxapine, like loxapine, is synthesized from 2-(4-chlorobenzoxy)aniline, which as in loxapine synthesis is acidified with chlorocarbonic acid into (6.5.1) and further transformed into ureide (7.3.1) upon reaction with 1-carboethoxypiperazine. Cyclization by a mixture of phosphorous pentoxide and phosphorous oxychloride into the dibenzoxazepine and subsequent alkaline hydrolysis gives amoxapine (7.3.2) [50¨C53].

Metabolism

Amoxapine has the shortest elimination time (~8 hours) of the secondary TCAs. It is metabolized in the liver principally to 8-hydroxyamoxapine and to 7-hydroxyamoxapine. Both of these metabolites are pharmacologically active and have half-lives of 30 and 6.5 hours, respectively. The hydroxylation of amoxapine is inhibited by ketoconazole, suggesting the involvement of CYP3A4."

Amoxapine Preparation Products And Raw materials

Raw materials

Piperazine Ethyl chloroformate Ethyl N-piperazinecarboxylate PHENYLURETHANE

Preparation Products

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Amoxapine Suppliers

Americas 1 Belgium 2 Canada 2 China 140 Czech Republic 1 Europe 3 France 3 Germany 6 India 27 Japan 2 Spain 1 Switzerland 3 Turkey 1 United Kingdom 14 United States 26 USA 1 Venezuela 1 Global 234
TCI Chemicals (India) Pvt. Ltd.
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Dharani Export-Import Services (P) Ltd.
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S.Zhaveri Pharmakem Pvt. Ltd
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Anlon Healthcare Pvt., Ltd.
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18
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58
Mehta Pharmaceutical Industries
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atul@mehtapharma.com
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58
Placid Pharmachem
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Clearsynth Labs
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58
Innovative Synthetic Molecules
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Parth Overseas
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CENTAUR PHARMACEUTICALS PRIVATE LTD
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centaur@centaurlab.com
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Pharma Affiliates
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Simson Pharma
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Shreeji Pharma International
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Orient Pharma
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Athos Chemicals
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Merit International
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SynZeal Research Pvt Ltd
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Indogulf Group
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Di Bombay Pharma
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Pharmaffiliates Analytics and Synthetics P. Ltd
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A.J Chemicals
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OCEAN TRADING CORPORATION
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View Lastest Price from Amoxapine manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
Amoxapine 14028-44-5
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10
Zhuozhou Wenxi import and Export Co., Ltd
Product
Amoxapine 14028-44-5
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-09
Career Henan Chemical Co
Product
Amoxapine 14028-44-5
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
1000KGS
Release date
2019-12-23

14028-44-5, AmoxapineRelated Search:

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