DEXCHLORPHENIRAMINE Chemical Properties

alpha 

D25 +49.8° (c = 1 in DMF)

Boiling point:

142 °C(Press: 1.0 Torr)

Density 

1.107±0.06 g/cm3(Predicted)

pka

9.33±0.28(Predicted)

Safety Information

Hazardous Substances Data

25523-97-1(Hazardous Substances Data)

DEXCHLORPHENIRAMINE Usage And Synthesis

Originator

Polaramine,Schering,US,1958

Uses

Antihistaminic.

Uses

Activity of this drug is approximately twice that of chlorpheniramine. Dexchlorpheniramine is also used for allergy symptoms, rhinitis, and dermatitis.

Definition

ChEBI: Dexchlorpheniramine is a chlorphenamine. It is an enantiomer of a levochlorpheniramine.

Manufacturing Process

Twenty grams of d-phenylsuccinic acid and 28 grams of 3-(2-pyridyl)-3-pchlorophenyl-N,N-dimethylpropylamine are dissolved in 400 ml of absolute ethyl alcohol and allowed to stand at room temperature until crystallization is effected. The crystals are filtered, washed with absolute ethyl alcohol and recrystallized from 300 ml of this solvent in the same manner. The crystals are recrystallized twice from 80% ethyl alcohol using 3.5 ml per gram of compound in the manner described above and pure d-3-(2-pyridyl)-3-pchlorophenyl-N,Ndimethylpropylamine-d-phenylsuccinate is obtained, melting point 145-147°C.
This salt is shaken with 100 ml of diethyl ether and 50 ml of 20% aqueous potassium carbonate; the ether layer is separated, dried over anhydrous potassium carbonate, filtered and the ether is removed in vacuo. The d-3-(2- pyridyl)-3-p-chlorophenyl-N,N-dimethylpropylamine so obtained is a mobile oil.
4.3 grams of the above base and 1.8 grams of maleic acid are dissolved in 20 ml isopropyl acetate and kept at room temperature until crystallization is complete. The crystals are filtered, washed with ethyl acetate and recrystallized from 15 ml of this solvent in the same manner. The crystalline d-3-(2-pyridyl)-3-p-chlorophenyl-N,N-dimethylpropylamine maleate so formed is then filtered off and dried. MP 113-115°C from US Patent 3,030,371.

brand name

Mylaramine (Morton Grove); Polaramine (Schering).

Therapeutic Function

Antihistaminic

DEXCHLORPHENIRAMINE(25523-97-1)Related Product Information

• HexanitrodiphenylaMine
• BROMPHENIRAMINE MALEATE IMP. B (EP) AS MALEATE: DEXCHLORPHENIRAMINE MALEATE
• IMP. B (EP): DEXCHLORPHENIRAMINE CL
• DEXCHLORPHENIRAMINE TANNATE
• DEXCHLORPHENIRAMINE MALEATE IMP. A (EP) AS MALEATE: (3RS)-N,N-DIMETHYL-3-PHENYL-3-(PYRIDIN-2-YL)PROPAN-1-AMINE MALEATE
• Dexchlorpheniramine Maleate
• Pheniramine maleate
• DEXCHLORPHENIRAMINE