ChemicalBook > CAS DataBase List > Amoxapine

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
More
Less

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)
More
Less

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)
More
Less

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..…

More
Less

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
More
Less

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

Preparation Products

More
Less

Amoxapine Suppliers

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Fax
021-64823266
Email
chenyj@titansci.com
Country
China
ProdList
14103
Advantage
59
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
XiaoGan ShenYuan ChemPharm co,ltd
Tel
15527768850
Email
1791901229@qq.com
Country
China
ProdList
8836
Advantage
52
Syntechem Co.,Ltd
Tel
Fax
E-Mail Inquiry
Email
info@syntechem.com
Country
China
ProdList
12984
Advantage
57
China Langchem Inc.
Tel
0086-21-58956006
Fax
0086-21-58956100
Country
China
ProdList
7811
Advantage
57
Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
Email
sj_scrc@sinopharm.com
Country
China
ProdList
9815
Advantage
79
Hangzhou Yuhao Chemical Technology Co., Ltd
Tel
0571-82693216
Fax
+86-571-82880190
Email
info@yuhaochemical.com
Country
China
ProdList
9387
Advantage
52
More
Less

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:


  • 2-Chloro-11-(1-piperazinyl)dibenzo[b,f][1,4]oxazepine
  • amoxan
  • Amoxepine
  • Ascendin
  • Asendin
  • Asendis
  • CL 67772
  • CL-67.772
  • cl67772
  • Demolox
  • Dibenz[b,f][1,4]oxazepine, 2-chloro-11-(1-piperazinyl)-
  • 8-chloro-6-(1-piperazinyl)benzo[b][1,4]benzoxazepine
  • f)(1,4)oxazepine,2-chloro-11-(1-piperazinyl)-dibenz(
  • Moxadil
  • AMOXAPINE
  • 2-CHLORO-11-(1-PIPERAZINYL)DIBENZ(B,F)(1,4)OXAZEPINE
  • AMOXAPINE TRICYCLIC ANTIDEPRESS
  • Defanyl
  • 8-Chloro-6-piperazin-1-ylbenzo[b][1,5]benzoxazepine
  • ENC2378671
  • 2-Chloro-11-(1-piperazinyl)dibenzo[b,f][1,4]
  • Amixapine (Minimum Pack)
  • Amoxapine (200 mg)
  • 13-chloro-10-(piperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaene
  • 2-chloro-11-(piperazin-1-yl)dibenzo[b,f][1,4]oxazepine
  • Amoxapine &gt
  • Amoxapine Amoxapine
  • AmoxapineQ: What is Amoxapine Q: What is the CAS Number of Amoxapine Q: What is the storage condition of Amoxapine Q: What are the applications of Amoxapine
  • high quality Amoxapine
  • Amoxapine (1031401)
  • Amoxapine/CL-67772
  • Amoxapine, ≥ 97.0%
  • 14028-44-5
  • C17H16ClN3O
  • ASENDIN
  • Adrenoceptor
  • Intermediates & Fine Chemicals
  • Pharmaceuticals