Vanoxerine dihydrochloride

Base Information

• Chemical Name: Vanoxerine dihydrochloride
• CAS No.: 67469-78-7
• Deprecated CAS: 110872-73-6
• Molecular Formula: C28H32F2N2O^.2HCl
• Molecular Weight: 523.494
• UNII: MWO1IP03EV
• DSSTox Substance ID: DTXSID1042570
• Wikidata: Q23054713
• Pharos Ligand ID: X3Z4X23VJL4Y
• ChEMBL ID: CHEMBL543876
• Mol file: 67469-78-7.mol

Synonyms:1-(2 (bis(4-fluorophenyl)methoxy)ethyl)-4-(3-phenylpropyl)piperazine;1-(2 (bis(4-fluorophenyl)methoxy)ethyl)-4-(3-phenylpropyl)piperazine dihydrochloride;GBR 12909;GBR-12909;I 893;I-893;vanoxeamine;vanoxerine

Chemical Property of Vanoxerine dihydrochloride

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 7.7E-12mmHg at 25°C
• Melting Point: 221 °C
• Boiling Point: 542.7 °C at 760 mmHg
• Flash Point: 282 °C
• PSA: 15.71000
• LogP: 6.80100
• Storage Temp.: Desiccate at RT
• Solubility.: DMSO: >5 mg/mL Solutions freshly prepared daily
• Water Solubility.: Soluble in DMSO to 50mM. Soluble to 5mM in water with warming.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 522.2016254
• Heavy Atom Count: 35
• Complexity: 498

Purity/Quality:

98%,99%, ^*data from raw suppliers

GBR 12909 dihydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CN(CCN1CCCC2=CC=CC=C2)CCOC(C3=CC=C(C=C3)F)C4=CC=C(C=C4)F.Cl.Cl
• Description: GBR 12909 is a potent inhibitor that blocks dopamine uptake (IC50 = 1-51 nM). It is more than 100-fold less effective at blocking serotonin or noradrenaline uptake. GBR 12909 effectively inhibits dopamine uptake in vivo, leading to consequent stimulation of dopamine receptors. GBR 12909 also inhibits pyrilamine binding to the histamine H1 receptor (IC50 = 18 nM) but poorly inhibits ligand binding to dopamine, adrenergic, acetylcholine, serotonin, and γ-aminobutyric acid receptors. It also blocks ligand binding to sigma receptors in rat brain (IC50 = 48 nM).
• Uses: Antidepressant;Dopamine reuptake inhibitor Dopamine uptake inhibitor

Technology Process of Vanoxerine dihydrochloride

There total 7 articles about Vanoxerine dihydrochloride 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: 60.0%

1-Bromo-3-phenylpropane (637-59-2) + 1-[2-(bis(4-fluorophenyl)methoxy)ethyl]piperazine (61897-33-4) → 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine dihydrochloride (67469-78-7)

Guidance literature:

With hydrogenchloride; potassium carbonate; In ethanol; for 3h; Heating;

Reference yield:

1-(2-(di(4-fluorophenyl)-methoxy)-ethyl)-4-(3-phenylpropyl)piperazine (67469-69-6) → 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine dihydrochloride (67469-78-7)

Guidance literature:

With hydrogenchloride; In ethanol; at 15 - 25 ℃; for 2h; Concentration; Large scale;

DOI:10.1021/op020211j

Reference yield:

1-Bromo-3-phenylpropane (637-59-2) → 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine dihydrochloride (67469-78-7)

Guidance literature:

Multi-step reaction with 4 steps

1: acetonitrile / 8 h / 75 - 80 °C / Large scale

2: hydrogenchloride / ethanol / 2 h / 20 - 30 °C / Large scale

3: sodium carbonate / water; butanone / 24 h / 75 - 80 °C / Large scale

4: hydrogenchloride / ethanol / 2 h / 15 - 25 °C / Large scale

With hydrogenchloride; sodium carbonate; In ethanol; water; acetonitrile; butanone;

DOI:10.1021/op020211j

upstream raw materials:

1-Bromo-3-phenylpropane

1-[2-(bis(4-fluorophenyl)methoxy)ethyl]piperazine

1-(2-(di(4-fluorophenyl)-methoxy)-ethyl)-4-(3-phenylpropyl)piperazine

2-[bis(4-fluorophenyl)methoxy]ethyl iodide

Refernces

• 1、 Van Der Zee,Koger,Gootjes,Hespe. "Aryl 1,4-dialk(en)ylpiperazines as selective and very potent inhibitors of dopamine uptake". . p. 363 - 370. Retrieved 2007/10/02.