Bromopride

Base Information

• Chemical Name: Bromopride
• CAS No.: 4093-35-0
• Molecular Formula: C14H22 Br N3 O2
• Molecular Weight: 344.252
• Hs Code.: 2924299090
• European Community (EC) Number: 223-842-2
• NSC Number: 758391
• UNII: 75473V2YZK
• DSSTox Substance ID: DTXSID0045383
• Nikkaji Number: J8.679G
• Wikipedia: Bromopride
• Wikidata: Q1958189
• NCI Thesaurus Code: C73035
• Metabolomics Workbench ID: 152090
• ChEMBL ID: CHEMBL399510
• Mol file: 4093-35-0.mol

Synonyms:bromoprid;bromopride;bromopride dihydrochloride;bromopride hydrochloride;Viaben

Chemical Property of Bromopride

Chemical Property:

• Vapor Pressure: 8.53E-08mmHg at 25°C
• Melting Point: 148-150?C
• Refractive Index: 1.6200 (estimate)
• Boiling Point: 435.8°Cat760mmHg
• PKA: 13.84±0.46(Predicted)
• Flash Point: 217.3°C
• PSA: 67.59000
• Density: 1.313g/cm³
• LogP: 3.08360
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 343.08954
• Heavy Atom Count: 20
• Complexity: 300

Purity/Quality:

99% ^*data from raw suppliers

Bromopride ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCN(CC)CCNC(=O)C1=CC(=C(C=C1OC)N)Br
• Recent ClinicalTrials: Efficacy of Bromopride and Simethicone Versus Bromopride in Functional Dyspepsia
• Description: Bromopride is a dopamine D2 receptor antagonist (Ki = 14 nM). It binds to bovine anterior pituitary membranes with an IC50 value of 2.13 μM. Bromopride inhibits cholinesterase activity in vitro in rat plasma and striatum homogenate (IC50s = 67.8 and 38.4 μM, respectively). It increases serum prolactin levels in rats by 100% when used at a dose of 0.02 mol/kg. Bromopride (2.5 mg/kg) decreases locomotion and rearing in an open field test and impairs acquistion, but not retention, of a conditioned avoidance response in a two-way active conditioned avoidance test in rats.
• Uses: An antiemetic.Bromopride is used in method and a system for analyzing neuropharmacology of a drug. An antiemetic
• Therapeutic Function: Antiemetic

Technology Process of Bromopride

There total 5 articles about Bromopride 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: 65.0%

→ bromopride (4093-35-0)

Guidance literature:

Reference yield:

carbon monoxide (201230-82-2) + 2-bromo-4-iodo-5-methoxyaniline (1285695-16-0) + N,N-diethylethylenediamine (100-36-7) → bromopride (4093-35-0)

Guidance literature:

With triethylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In 1,4-dioxane; at 80 ℃; Inert atmosphere; Sealed chamber;

DOI:10.1021/ja200818w

Reference yield:

4-bromo-3-nitroanizole (5344-78-5) → bromopride (4093-35-0)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogenchloride; iron / ethanol; water / 3 h / Reflux

2: tetramethylammonium dichloroiodate(I) / ethyl acetate / 96 h

3: triethylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾ / 1,4-dioxane / 80 °C / Inert atmosphere; Sealed chamber

With hydrogenchloride; tetramethylammonium dichloroiodate(I); iron; triethylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In 1,4-dioxane; ethanol; water; ethyl acetate;

DOI:10.1021/ja200818w

upstream raw materials:

carbon monoxide

2-bromo-4-iodo-5-methoxyaniline

N,N-diethylethylenediamine

4-bromo-3-nitroanizole

Refernces

• 1、 Hermange, Philippe,Lindhardt, Anders T.,Taaning, Rolf H.,Bjerglund, Klaus,Lupp, Daniel,Skrydstrup, Troels. "Ex situ generation of stoichiometric and substoichiometric 12CO and 13CO and its efficient incorporation in palladium catalyzed aminocarbonylations". supporting information; experimental part. p. 6061 - 6071. Retrieved 2011/06/19.