2180. Chlorpheniramine

Nomenclature

CAS number: 132-22-9
γ-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine; 2-[p-chloro-α-(2-dimethylaminoethyl)benzyl]pyridine; 1-(p-chlorophenyl)-1-(2-pyridyl)-3-dimethylaminopropane; 1-(p-chlorophenyl)-1-(2-pyridyl)-3-N,N-dimethylpropylamine; 3-(p-chlorophenyl)-3-(2-pyridyl)-N,N-dimethylpropylamine; γ-(4-chlorophenyl)-γ-(2-pyridyl)propyldimethylamine; chlorprophenpyridamine; chlorphenamine; Haynon (Rosemont).
C16H19ClN2; mol wt 274.79.
C 69.93%, H 6.97%, Cl 12.90%, N 10.19%.

Description and references

Synthesis: Sperber et al., US 2567245, US 2676964 (1951, 1954, both to Schering). Prepn of d-form: L. A. Walter, US 3061517 (1962 to Schering). Solutions: Foley, Ilavsky, US 2766174 (1956 to Schering). Pharmacology: F. E. Roth, W. M. Govier, J. Pharmacol. Exp. Ther. 124, 347 (1958). Toxicity data: R. B. Smith et al., Toxicol. Appl. Pharmacol. 28, 240 (1974). Comprehensive description: C. G. Eckhart, T. McCorkle, Anal. Profiles Drug Subs. 7, 43-80 (1978).

Chemical structure

Properties

Oily liquid, bp1.0 142°.

Derivative

Maleate.

Nomenclature

CAS number: 113-92-8
Allergisan (Pharmacia); Chlor-Trimeton (Schering-Plough); Piriton (GSK); Teldrin (SKB).
C16H19ClN2.C4H4O4; mol wt 390.86.
C 61.46%, H 5.93%, Cl 9.07%, N 7.17%, O 16.37%.

Properties

Crystals, mp 130-135°. uv max (water): 261 nm (ε 5760). Soly in mg/ml at 25°: ethanol 330; chloroform 240; water 160; methanol 130. Slightly sol in benzene, ether. pH of a 2% aq soln about 5. LD50 orally in mice: 162 mg/kg (Smith).

Derivative

d-Form.

Nomenclature

CAS number: 25523-97-1
Dexchlorpheniramine; d-chlorpheniramine.

Properties

Oily liquid. [α]D25 +49.8° (c = 1 in DMF).

Derivative

d-Form maleate.

Nomenclature

CAS number: 2438-32-6
Phenamin (Nycomed); Polamin (Schering-Plough); Polaramine (Schering-Plough); Polaronil (Schering-Plough).

Properties

Crystals from ethyl acetate, mp 113-115°. [α]D25 +44.3° (c = 1 in dimethylformamide). pH of 1% soln 4-5.

Therapeutic Category

Antihistaminic.

Therapeutic Category (Veterinary)

Antihistaminic.

Keywords

Antihistaminic; Alkylamine Derivatives