Chlorpheniramine
Title: Chlorpheniramine
CAS Registry Number: 132-22-9
CAS Name: g-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine
Additional Names: 2-[p-chloro-a-(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; g-(4-chlorophenyl)-g-(2-pyridyl)propyldimethylamine; chlorprophenpyridamine; chlorphenamine
Trademarks: Haynon (Rosemont)
Molecular Formula: C16H19ClN2
Molecular Weight: 274.79
Percent Composition: C 69.93%, H 6.97%, Cl 12.90%, N 10.19%
Literature 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).
Properties: Oily liquid, bp1.0 142°.
Boiling point: bp1.0 142°
 
Derivative Type: Maleate
CAS Registry Number: 113-92-8
Trademarks: Allergisan (Pharmacia); Chlor-Trimeton (Schering-Plough); Piriton (GSK); Teldrin (SKB)
Molecular Formula: C16H19ClN2.C4H4O4
Molecular Weight: 390.86
Percent Composition: 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 (e 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).
Melting point: mp 130-135°
Absorption maximum: uv max (water): 261 nm (e 5760)
Toxicity data: LD50 orally in mice: 162 mg/kg (Smith)
 
Derivative Type: d-Form
CAS Registry Number: 25523-97-1
Additional Names: Dexchlorpheniramine; d-chlorpheniramine
Properties: Oily liquid. [a]D25 +49.8° (c = 1 in DMF).
Optical Rotation: [a]D25 +49.8° (c = 1 in DMF)
 
Derivative Type: d-Form maleate
CAS Registry Number: 2438-32-6
Trademarks: Phenamin (Nycomed); Polamin (Schering-Plough); Polaramine (Schering-Plough); Polaronil (Schering-Plough)
Properties: Crystals from ethyl acetate, mp 113-115°. [a]D25 +44.3° (c = 1 in dimethylformamide). pH of 1% soln 4-5.
Melting point: mp 113-115°
Optical Rotation: [a]D25 +44.3° (c = 1 in dimethylformamide)
 
Therap-Cat: Antihistaminic.
Therap-Cat-Vet: Antihistaminic.
Keywords: Antihistaminic; Alkylamine Derivatives.

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