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Brompheniramine hydrogen maleate

Brompheniramine hydrogen maleate Basic information
Product Name:Brompheniramine hydrogen maleate
Synonyms:2-(p-bromo-alpha-(2-(dimethylamino)ethyl)benzyl)pyridinemaleate(1:1);2-(p-bromo-alpha-(2-(dimethylamino)ethyl)benzyl)-pyridinmaleate(1:1);dimegan;dimetane;dimetanemaleate;dimotane;g-(4-bromophenyl)-N,N-dimethyl-2-pyridinepropanaminemaleate;gamma-(4-bromophenyl)-n,n-dimethyl-2-pyridinepropanamin(z)-2-butenedioate
CAS:980-71-2
MF:C20H23BrN2O4
MW:435.31
EINECS:213-562-9
Product Categories:Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:980-71-2.mol
Brompheniramine hydrogen maleate Structure
Brompheniramine hydrogen maleate Chemical Properties
Melting point 134-135°C
Fp 9℃
storage temp. Inert atmosphere,Room Temperature
solubility Soluble in water, freely soluble in ethanol (96 per cent), in methanol and in methylene chloride.
form neat
color White to Off-White
λmax261nm(lit.)
Merck 14,1443
Stability:Hygroscopic
InChIKeySRGKFVAASLQVBO-BTJKTKAUSA-N
LogP3.565 (est)
CAS DataBase Reference980-71-2(CAS DataBase Reference)
EPA Substance Registry System2-Pyridinepropanamine, .gamma.-(4-bromophenyl)-N,N-dimethyl-, (2Z)-2-butenedioate (1:1) (980-71-2)
Safety Information
Hazard Codes Xn,Xi,T,F
Risk Statements 22-39/23/24/25-23/24/25-11
Safety Statements 36-45-36/37-16-7
RIDADR 3249
WGK Germany 3
RTECS US4025000
TSCA Yes
HazardClass 6.1(b)
PackingGroup III
HS Code 38220090
MSDS Information
ProviderLanguage
SigmaAldrich English
Brompheniramine hydrogen maleate Usage And Synthesis
DescriptionBrompheniramine is a first generation antihistamine of the propylamine class. It antagonizes histamine H1 receptors (Ki = 6.06 nM) and also inhibits the reuptake of serotonin and norepinephrine.
Chemical PropertiesWhite Solid
OriginatorDimetane,Robins,US,1957
UsesAn antihistamine and also an inhibitor of serotonin reuptake
UsesThis drug is only available in combination with other medications: Bromfed, Dimetane, Dimetapp, Drixomed, Histatab, Nasahist. The only difference between this agent and chlorpheniramine is the substitution of a bromine for a chlorine atom in brompheniramine.
UsesAntihistaminic;H1 Antagonist
DefinitionChEBI: The maleic acid salt of brompheniramine. A histamine H1 receptor antagonist, it is used for the symptomatic relief of allergic conditions, including rhinitis and conjunctivitis.
Manufacturing ProcessInitially, 4-bromobenzyl-cyanide is reacted with sodium amide and 2- chloropyridine to give bromophenyl-pyridyl acetonitrile. This is then reacted with sodium amide then dimethyl amino ethyl chloride to give 4-bromophenyldimethylaminoethyl- pyridyl acetonitrile. This intermediate is then hydrolyzed and decarboxylated to bromphenirame using 80% H2SO4 at 140°-150°C for 24 hours. The brompheniramine maleate may be made by reaction with maleic acid in ethanol followed by recrystallization from pentanol.
Brand nameDimetane (Wyeth).
Therapeutic FunctionAntihistaminic
General DescriptionBrompheniraminemaleate, (+)2-[p-bromo-α-[2-(dimethylamino)ethyl]benzyl]pyridine bimaleate (Dimetane), differs fromchlorpheniramine by the substitution of a bromine atom forthe chlorine atom. Its actions and uses are like those of chlorpheniramine.It has a half-life of 25 hours, which is almosttwice that of chlorpheniramine.
Side effectsThe side effects of this medication are similar to other classes of sedative antihistamines. Some medications include parabens. Patients sensitive to parabens may develop a sensitivity reaction.
Brompheniramine hydrogen maleate Preparation Products And Raw materials
Raw materials2-Chloropyridine-->Sulfuric acid-->Sodium amide-->N,N-DIMETHYLAMINOETHYL CHLORIDE-->Maleic acid-->4-Bromophenylacetonitrile
Rosiglitazone maleate Polybutene Chlorodimethylphenylsilane Propane Brompheniramine CI 46045 Enalapril maleate Brompheniramine hydrogen maleate Maleic anhydride Hydrogen peroxide DIMETHYLAMINOPYRIDINE, POLYMER-BOUND (-)-2-[METHYLAMINO]-1-PHENYLPROPANE Disodium fumarate Cinepazide maleate D/L-AMPHETAMINE HYDROCHLORIDE Trimebutine maleate 2,6-Lutidine HYDROGEN CYANIDE
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