Amoxapine
- CAS No.
- 14028-44-5
- Chemical Name:
- Amoxapine
- Synonyms
- Amoxepine;amoxan;Demolox;cl67772;Asendis;Asendin;Moxadil;Defanyl;CL 67772;Ascendin
- CBNumber:
- CB5375947
- Molecular Formula:
- C17H16ClN3O
- Molecular Weight:
- 313.78
- MDL Number:
- MFCD00069210
- MOL File:
- 14028-44-5.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| 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 |
| Major Application | pharmaceutical (small molecule) |
| 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 |
| InChIKey | QWGDMFLQWFTERH-UHFFFAOYSA-N |
| SMILES | Clc1ccc2Oc3ccccc3N=C(N4CCNCC4)c2c1 |
| CAS DataBase Reference | 14028-44-5(CAS DataBase Reference) |
| FDA UNII | R63VQ857OT |
| NIST Chemistry Reference | Amoxapine(14028-44-5) |
| Proposition 65 List | Amoxapine |
| ATC code | N06AA17 |
| UNSPSC Code | 41116107 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H302 |
| Precautionary statements | P264-P270-P301+P312-P501 |
| 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 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral |
| Toxicity | LD50 in mice (mg/kg): 122 i.p.; 112 orally (Howell, 1972) |
Amoxapine price More Price(58)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | A129 | Amoxapine | 14028-44-5 | 5g | $1040 | 2026-04-30 | Buy |
| Sigma-Aldrich | A-123 | Amoxapine 1.0?mg/mL in methanol, certified reference material, Cerilliant? | 14028-44-5 | 1mL | $96.8 | 2026-04-30 | Buy |
| Sigma-Aldrich | 1031401 | Amoxapine United States Pharmacopeia (USP) Reference Standard | 14028-44-5 | 200mg | $422 | 2026-04-30 | Buy |
| TCI Chemical | A2499 | Amoxapine >97.0%(GC)(T) | 14028-44-5 | 1g | $93 | 2026-04-30 | Buy |
| TCI Chemical | A2499 | Amoxapine >97.0%(GC)(T) | 14028-44-5 | 5g | $423 | 2021-12-16 | Buy |
Amoxapine Chemical Properties,Uses,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.
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.
Pharmacology
The antidepressant action of amoxapine is comparable to that of imipramine and amitriptyline. It exhibits antagonistic activity on dopamine (D2) receptors.
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."
References
[1] E P PLVIMKI. Interactions of selective serotonin reuptake inhibitors with the serotonin 5-HT2c receptor.[J]. Psychopharmacology, 1996, 126 3: 234-240. DOI: 10.1007/bf02246453
Amoxapine Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| TCI (Shanghai) Development Co., Ltd. | 021-67121386 | Sales-CN@TCIchemicals.com | China | 24512 | 81 |
| Beijing HwrkChemical Technology Co., Ltd | 89508211 18501085097 | sales.bj@hwrkchemical.com | China | 9407 | 55 |
| Adamas Reagent, Ltd. | 400-6009262 15618770481 | yhx@titansci.com | China | 14098 | 59 |
| LGM Pharma | 1-(800)-881-8210 | inquiries@lgmpharma.com | United States | 2110 | 70 |
| Chemsky（shanghai）International Co.,Ltd. | 021-50135380 | shchemsky@sina.com | China | 32273 | 50 |
| XiaoGan ShenYuan ChemPharm co,ltd | 15527621225; 15527621225 | 1791901229@qq.com | China | 6746 | 52 |
| Syntechem Co.,Ltd | info@syntechem.com | China | 12973 | 57 | |
| China Langchem Inc. | 0086-21-58956006 | China | 7798 | 57 | |
| Sinopharm Chemical Reagent Co,Ltd. | 86-21-63210123 | sj_scrc@sinopharm.com | China | 9791 | 79 |
View Lastest Price from Amoxapine manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-06-02 | Amoxapine
14028-44-5
|
99.99% | 10g | TargetMol Chemicals Inc. | |||
 |
2021-07-13 | Amoxapine
14028-44-5
|
$10.00-15.00 | 1KG | 99%+ HPLC | Zhuozhou Wenxi import and Export Co., Ltd | ||
 |
2021-07-10 | Amoxapine
14028-44-5
|
$10.00-15.00 | 1KG | 99%+ HPLC | Zhuozhou Wenxi import and Export Co., Ltd |
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