Amoxapine

Base Information

• Chemical Name: Amoxapine
• CAS No.: 14028-44-5
• Molecular Formula: C17H16ClN3O
• Molecular Weight: 313.787
• Hs Code.: 2934990002
• European Community (EC) Number: 237-867-1
• NSC Number: 759559
• UNII: R63VQ857OT
• DSSTox Substance ID: DTXSID7022598
• Nikkaji Number: J3.129A
• Wikipedia: Amoxapine
• Wikidata: Q58356
• NCI Thesaurus Code: C47397
• RXCUI: 722
• Pharos Ligand ID: 289V2KZN46SC
• Metabolomics Workbench ID: 42880
• ChEMBL ID: CHEMBL1113
• Mol file: 14028-44-5.mol

Synonyms:2-Chloro-11-(1-piperazinyl)dibenz(b,f)(1,4)oxazepine;Amoxapine;Asendin;Asendis;CL 67,772;CL-67,772;CL67,772;Défanyl;Demolox;Desmethylloxapine

Chemical Property of Amoxapine

Chemical Property:

• Appearance/Colour: Crystalline solid
• Vapor Pressure: 5.32E-09mmHg at 25°C
• Melting Point: 175-176 °C
• Refractive Index: 1.685
• Boiling Point: 469.9 °C at 760 mmHg
• PKA: pKa 7.6 (Uncertain)
• Flash Point: 238 °C
• PSA: 36.86000
• Density: 1.37 g/cm³
• LogP: 3.13150
• Storage Temp.: -20°C Freezer
• Solubility.: methanol: soluble
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 313.0981898
• Heavy Atom Count: 22
• Complexity: 424

Purity/Quality:

Amoxapine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antidepressant Agents
• Canonical SMILES: C1CN(CCN1)C2=NC3=CC=CC=C3OC4=C2C=C(C=C4)Cl
• 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.
• Uses: Amoxapine is intended more for relieving symptoms in patients with neurotic or situational depression. It has a number of serious side effects. A tricyclic norepinephrine uptake inhibitor antidepressant, inhibits norepinephrine uptake
• Therapeutic Function: Antidepressant
• Clinical Use: Amoxapine is a dibenzoxazepine TCA with antidepressant and antipsychotic effects that has shown therapeutic effectiveness in patients with delusional depression.

Technology Process of Amoxapine

There total 4 articles about Amoxapine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

loxapine (1977-10-2) → amoxapine (14028-44-5)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. HCl / 16 h / Heating

2: POCl₃, PhNMe₂ / 5 h / Heating

3: xylene / 5 h / Heating

With hydrogenchloride; N,N-dimethyl-aniline; trichlorophosphate; In xylene;

DOI:10.1002/hlca.19670500131

Reference yield:

2-chlorodibenzo[b,f][1,4]oxazepin-11(10H)-one (3158-91-6) → amoxapine (14028-44-5)

Guidance literature:

Multi-step reaction with 2 steps

1: POCl₃, PhNMe₂ / 5 h / Heating

2: xylene / 5 h / Heating

With N,N-dimethyl-aniline; trichlorophosphate; In xylene;

DOI:10.1002/hlca.19670500131

Reference yield:

piperazine (110-85-0) + 2,11-dichloro-dibenzo[b,f][1,4]oxazepine (3455-14-9) → amoxapine (14028-44-5)

Guidance literature:

In xylene; for 5h; Heating;

DOI:10.1002/hlca.19670500131

upstream raw materials:

piperazine

2,11-dichloro-dibenzo[b,f][1,4]oxazepine

loxapine

2-chlorodibenzo[b,f][1,4]oxazepin-11(10H)-one

Downstream raw materials:

2-chlorodibenzo[b,f][1,4]oxazepin-11(10H)-one

Refernces