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Brompheniramine hydrogen maleate

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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
  • RS-brompheniramine maleate
  • dimotane
  • g-(4-bromophenyl)-N,N-dimethyl-2-pyridinepropanaminemaleate
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
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Brompheniramine hydrogen maleate Chemical Properties

Melting point:
134-135°C
Flash point:
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 
Solid
color 
White to Off-White
λmax
261nm(lit.)
Merck 
14,1443
Stability:
Hygroscopic
InChIKey
SRGKFVAASLQVBO-BTJKTKAUSA-N
LogP
3.565 (est)
CAS DataBase Reference
980-71-2(CAS DataBase Reference)
EPA Substance Registry System
2-Pyridinepropanamine, .gamma.-(4-bromophenyl)-N,N-dimethyl-, (2Z)-2-butenedioate (1:1) (980-71-2)
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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

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Brompheniramine hydrogen maleate Usage And Synthesis

Description

Brompheniramine 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 Properties

White Solid

Originator

Dimetane,Robins,US,1957

Uses

This 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.

Uses

Antihistaminic;H1 Antagonist

Uses

An antihistamine and also an inhibitor of serotonin reuptake

Definition

ChEBI: 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 Process

Initially, 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 name

Dimetane (Wyeth).

Therapeutic Function

Antihistaminic

General Description

Brompheniraminemaleate, (+)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 effects

The 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.

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