DEXBROMPHENIRAMINE Property

alpha 

D25 +42.7° (c = 1 in DMF)

pka

pKa 9.3 (Uncertain)

Hazard and Precautionary Statements (GHS)

DEXBROMPHENIRAMINE Chemical Properties,Usage,Production

Originator

Disomer,White,US,1959

Uses

Antihistaminic.

Definition

ChEBI: The (pharmacologically active) (S)-(+)-enantiomer of brompheniramine. A histamine H1 receptor antagonist, it is used (commonly as its maleate salt) for the symptomatic relief of allergic conditions, including rhinitis nd conjunctivitis.

Manufacturing Process

The following is taken from US Patent 3,061,517. Sixteen grams of racemic 3- (2-pyridyl)-3-p-bromophenyl-N,N,-dimethylpropylamine and 9.7 grams of dphenylsuccinic acid are dissolved in 150 ml of absolute alcohol and kept at room temperature until crystallization is effected. The crystals are filtered,washed with absolute ethyl alcohol, and recrystallized from the same solvent using 5 ml there of per gram of solid. Three subsequent crystallizations from 80% alcohol give d-3-(2-pyridyl)-3-p-bromophenyl-N,N-dimethylpropylamined-phenylsuccinate; MP 152-154°C; [α]D25 91 (concentration, 1% in dimethylformamide).
The free base, d-3-(2-pyridyl)-3-p-bromophenyl-N,N-dimethylpropylamine, is obtained from this salt with diethyl ether and aqueous potassium carbonate; [α]D25 +42.7 (concentration, 1% in dimethylformamide). The free base is then reacted with maleic acid.

brand name

Disomer (Schering).

Therapeutic Function

Antihistaminic