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.
An antihistamine and also an inhibitor of serotonin reuptake
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.
Antihistaminic;H1 Antagonist
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.
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.
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.
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.
[1] THOMAS HOEGBERG. Synthesis of pyridylallylamines related to zimelidine and their inhibition of neuronal monoamine uptake[J]. Journal of Medicinal Chemistry, 1981, 24 12: 1499-1507. DOI:
10.1021/jm00144a025
