BROMOPRIDE

BROMOPRIDE Basic information
Product Name:BROMOPRIDE
Synonyms:4-Amino-5-bromo-N-[2-(diethylamino)ethyl]-2-methoxybenzamide,Emepride,Emoril,Viadil;BROMOPRID;2-Methoxy-4-aMino-5-broMo-N,N-diethylaMinoethylbenzaMide;Opridan;Plesium;Praiden;4-azanyl-5-bromo-N-(2-diethylaminoethyl)-2-methoxy-benzamide;4-amino-5-bromo-n-(2-(diethylamino)ethyl)-2-methoxy-benzamid
CAS:4093-35-0
MF:C14H22BrN3O2
MW:344.25
EINECS:223-842-2
Product Categories:Intermediates & Fine Chemicals;Pharmaceuticals;Amines;Aromatics;EMEPRIDE
Mol File:4093-35-0.mol
BROMOPRIDE Structure
BROMOPRIDE Chemical Properties
Melting point 148-150?C
Boiling point 435.8±45.0 °C(Predicted)
density 1.4132 (rough estimate)
refractive index 1.6200 (estimate)
storage temp. 2-8°C
solubility Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form Solid
pka13.84±0.46(Predicted)
color White to Off-White
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22
Safety Statements 36
WGK Germany 3
RTECS BZ3280000
MSDS Information
ProviderLanguage
SigmaAldrich English
BROMOPRIDE Usage And Synthesis
DescriptionBromopride 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.
Chemical PropertiesWhite Solid
OriginatorPraiden,Italchemi,Italy,1977
UsesAn antiemetic.Bromopride is used in method and a system for analyzing neuropharmacology of a drug.
DefinitionChEBI: 4-amino-5-bromo-N-[2-(diethylamino)ethyl]-2-methoxybenzamide is a member of benzamides.
Manufacturing ProcessTo 119 g (0.45 mol) of N-(2-diethylaminoethyl)-2-methoxy-4-aminobenzamide dissolved in 200 cc of acetic acid are added in the cold in small portions 69 g of acetic anhydride (0.45 mol + 50% excess). The starting material is made by esterifying 4-aminosalicylic acid with methanol, then acetylating with acetic anhydride and then methylating with dimethyl sulfate. The solution obtained is heated for 2 hours on a water bath and then boiled for 15 minutes. It is cooled at 25°C. While agitating constantly and maintaining the temperature between 25° and 30°C, there is added to the solution drop by drop 72 g of bromine dissolved in 60 cc of acetic acid. It is agitated for one hour. The mixture obtained is added to one liter of water and the base is precipitated by the addition of 30% soda, The precipitated base is extracted with 40 cc of methylene chloride. After evaporation of the solvent, the residue is boiled for two hours with 390 g of concentrated hydrochloric acid in 780 cc of water. It is cooled, diluted with one liter of water, 12 g of charcoal are added, and the mixture filtered. The base is precipitated with 30% soda. The N-(2- diethylaminoethyl)-2-methoxy-4-amino-5-bromobenzamide formed crystallizes, is centrifuged and washed with water. A yield of 85 g of base having a melting point of 129°-130°C is obtained.
To produce the dihydrochloride, the free base is dissolved in 110 cc of absolute alcohol, 9.6 g of dry hydrochloric acid dissolved in 35 cc of alcohol are added, followed by 2.8 cc of water. The dihydrochloride precipitates, is centrifuged, washed, and dried at 40°C. It was a solid white material having a melting point of 134°-135°C.
Therapeutic FunctionAntiemetic
BROMOPRIDE Preparation Products And Raw materials
Raw materialsDimethyl sulfate-->4-Aminosalicylic acid-->Methanol-->Acetic anhydride
Saletamide 3-Bromo-N-methylbenzamide 98% Bromopride Hydrochloride (3-BROMOBENZYL)METHYLAMINE 5-BROMO-2-HYDROXYBENZYLAMINE 5-BROMO-2-METHOXYBENZYLAMINE procainamide N-Ethyl-3-bromobenzylamine 2-BROMO-5-METHOXYANILINE HCL 5-BROMOSALICYLAMIDE N-(5-BROMO-2-METHOXYBENZYL)-N-METHYLAMINE BROMOPRIDE 3-Bromo-N-ethylbenzamide 5-Bromosalicylaldehyde 5-Bromo-2-chlorobenzoic acid

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