1443. Brompheniramine

Nomenclature

CAS number: 86-22-6
γ-(4-Bromophenyl)-N,N-dimethyl-2-pyridinepropanamine; 2-[p-bromo-α-(2-dimethylaminoethyl)benzyl]pyridine; 1-(p-bromophenyl)-1-(2-pyridyl)-3-dimethylaminopropane; 3-(p-bromophenyl)-3-(2-pyridyl)-N,N-dimethylpropylamine; parabromdylamine.
C16H19BrN2; mol wt 319.24.
C 60.20%, H 6.00%, Br 25.03%, N 8.78%.

Description and references

Prepn from α-(p-bromophenyl)-α-(β-dimethylaminoethyl)-2-pyridylacetonitrile: Sperber et al., US 2567245 (1951); US 2676964 (1954 to Schering). Prepn of d-form: L. A. Walter, US 3061517 (1962 to Schering).

Chemical structure

Properties

Oily liquid. Slightly yellow color. Characteristic amine-like odor. bp0.5 147-152°. Soluble in dilute acids.

Derivative

Maleate.

Nomenclature

CAS number: 980-71-2
Dimegan (Dexo); Dimetane (Robins); Dimotane (Robins); Ilvin (Merck KGaA); Nagemid (Dexo); Symptom 3 (Parke-Davis); Veltane (Lannett).
C16H19BrN2.C4H4O4; mol wt 435.31.
C 55.18%, H 5.33%, Br 18.36%, N 6.44%, O 14.70%.

Properties

Crystals, mp 132-134°. Sol in water, somewhat less sol in alcohol. pH of a 2% aq soln about 5.

Derivative

d-Form.

Nomenclature

CAS number: 132-21-8
Dexbrompheniramine; (+)-parabromdylamine.

Properties

Oily liquid. [α]D25 +42.7° (c = 1 in DMF).

Derivative

d-Form maleate.

Nomenclature

CAS number: 2391-03-9
Disomer (Schering); Ebalin (Allergopharma).
C16H19BrN2.C4H4O4; mol wt 435.31.
C 55.18%, H 5.33%, Br 18.36%, N 6.44%, O 14.70%.

Properties

Crystals, mp 103-113°.

Therapeutic Category

Antihistaminic.

Keywords

Antihistaminic; Alkylamine Derivatives