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Chlorpheniramine maleate
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Name

Chlorpheniramine maleate

 EINECS 204-037-5
CAS No. 113-92-8 Density 1.107 g/cm3
PSA 90.73000 LogP 3.53040
Solubility 1-5 g/100 mL at 21 ºC Melting Point 130-135 ºC
Formula C20H23ClN2O4 Boiling Point 379 ºC at 760 mmHg
Molecular Weight 390.867 Flash Point 183 ºC
Transport Information UN 2811 6.1/PG 3 Appearance White crystalline powder
Safety 36/37/39-45 Risk Codes 25
Molecular Structure Molecular Structure of 113-92-8 (Chlorpheniramine maleate) Hazard Symbols ToxicT
Synonyms

2-Pyridinepropanamine,?-(4-chlorophenyl)-N,N-dimethyl- [132-22-9] but the (Z)-2-butenedioate (1:1);Prestwick_57;Allergin;Chlor-trimeton;Teldrin;Piriton;Chlorprophenpyridamine;but-2-enedioic acid; 3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-yl-propan-1-amine;Chlorpheniramine maleate (JP14/USP);[3-(4-chlorophenyl)-3-pyridin-2-yl-propyl]-dimethyl-azanium; (Z)-4-hydroxy-4-oxo-but-2-enoate;Chlor-Tripolon;Neorestamin;Chlor-trimeton (TN);2-Pyridinepropanamine,?-(4-chlorophenyl)-N,- N-dimethyl-,(2Z)-2-butenedioate (1:1);chlorphenamine hydrogen maleate;Teldrin (TN);

Article Data 9

Chlorpheniramine maleate Synthetic route

64-18-6

formic acid

20619-13-0

Didesmethylchlorpheniramine

110-16-7

maleic acid

113-92-8

chlorphenamine maleate

Conditions
ConditionsYield
Stage #1: formic acid; Didesmethylchlorpheniramine In water; N,N-dimethyl-formamide at 100℃; for 24h;
Stage #2: maleic acid In isopropyl alcohol at 80℃; for 2h;		88.8%
4350-41-8

2-(4-chlorobenzyl)pyridine

107-99-3

2-(dimethylamino)ethyl chloride

110-16-7

maleic acid

113-92-8

chlorphenamine maleate

Conditions
ConditionsYield
Stage #1: 2-(4-chlorobenzyl)pyridine With sodium amide In toluene Reflux;
Stage #2: 2-(dimethylamino)ethyl chloride In toluene for 6h; Reflux;
Stage #3: maleic acid In water		54.4%
Stage #1: 2-(4-chlorobenzyl)pyridine With sodium amide In toluene Reflux;
Stage #2: 2-(dimethylamino)ethyl chloride In toluene for 6h; Reflux;
Stage #3: maleic acid In toluene		22.4 g
140-53-4

p-chlorobenzyl cyanide

113-92-8

chlorphenamine maleate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: cobaltocene / 4 h / 150 - 170 °C / Autoclave
2.1: sodium amide / tetrahydrofuran / 1 h / 20 - 25 °C
2.2: 2 h / 30 - 45 °C
3.1: ethanol / 2.5 h / -2 - 0 °C
View Scheme
110-16-7

maleic acid

132-22-9

Chlorpheniramine

113-92-8

chlorphenamine maleate

Conditions
ConditionsYield
In ethanol at -2 - 0℃; for 2.5h;350 g
With pyrographite In ethanol at 80℃; for 1.5h; Temperature; Large scale;
With pyrographite In ethanol at 80℃; for 2h; Temperature;

2-(4-chlorobenzyl)pyridine

2-(4-chlorobenzyl)pyridine

110-16-7

maleic acid

chlorphenamine maleate

chlorphenamine maleate

Conditions
ConditionsYield
Stage #1: 2-(4-chlorobenzyl)pyridine With sodium amide In toluene Reflux;
Stage #2: 2-(N,N-dimethylamino)ethyl bromide In toluene for 6h; Reflux;
Stage #3: maleic acid In toluene		24.1 g

113-92-8

chlorphenamine maleate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: manganese; trifluoroacetic acid / acetonitrile / 0.17 h
1.2: 12 h / 30 - 40 °C
2.1: sodium amide / toluene / Reflux
2.2: 6 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: manganese; trifluoroacetic acid / acetonitrile / 0.17 h
1.2: 12 h / 30 - 40 °C
2.1: sodium amide / toluene / Reflux
2.2: 6 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: manganese; trifluoroacetic acid / acetonitrile / 0.17 h
1.2: 12 h / 30 - 40 °C
2.1: sodium amide / toluene / Reflux
2.2: 6 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: manganese; trifluoroacetic acid / acetonitrile / 0.17 h
1.2: 12 h / 30 - 40 °C
2.1: sodium amide / toluene / 0.33 h / 20 °C
2.2: 8 h / Reflux
3.1: water; N,N-dimethyl-formamide / 24 h / 100 °C
3.2: 2 h / 80 °C
View Scheme
104-83-6

1-Chloro-4-(chloromethyl)benzene

113-92-8

chlorphenamine maleate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: manganese; trifluoroacetic acid / acetonitrile / 0.17 h
1.2: 12 h / 30 - 40 °C
2.1: sodium amide / toluene / Reflux
2.2: 6 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: manganese; trifluoroacetic acid / acetonitrile / 0.17 h
1.2: 12 h / 30 - 40 °C
2.1: sodium amide / toluene / 0.33 h / 20 °C
2.2: 8 h / Reflux
3.1: water; N,N-dimethyl-formamide / 24 h / 100 °C
3.2: 2 h / 80 °C
View Scheme
58498-12-7

4-(2-Pyridinylmethyl)phenylamine

113-92-8

chlorphenamine maleate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium nitrite; hydrogenchloride / water / 0.33 h / 0 - 5 °C
1.2: 4 h / 20 °C
2.1: sodium amide / toluene / Reflux
2.2: 6 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: sodium nitrite; hydrogenchloride / water / 0.33 h / 0 - 5 °C
1.2: 4 h / 20 °C
2.1: sodium amide / toluene / 0.33 h / 20 °C
2.2: 8 h / Reflux
3.1: water; N,N-dimethyl-formamide / 24 h / 100 °C
3.2: 2 h / 80 °C
View Scheme
4350-41-8

2-(4-chlorobenzyl)pyridine

113-92-8

chlorphenamine maleate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium amide / toluene / 0.33 h / 20 °C
1.2: 8 h / Reflux
2.1: water; N,N-dimethyl-formamide / 24 h / 100 °C
2.2: 2 h / 80 °C
View Scheme

potassium pentacyanonitrosylchromate(III) monohydrate

113-92-8

chlorphenamine maleate

{Cr(NO)(CN)2(chloropheniramine maleate)2(H2O)}

Conditions
ConditionsYield
With CH3COOH In acetic acid byproducts: CH3COOK, H2O, HCN; aq. acetic acid; 20-30 min, 80°C; CO2 bubbled (few h) to remove HCN; ppt. filtered, washed (H2O repeatedly; ethanol); dried (vac., over silica gel, room temp., to const. wt.); elem.anal.;55%

Chlorpheniramine maleate Chemical Properties

 
IUPAC Name: (Z)-But-2-enedioic acid; 3-(4-Chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
Molecular Formula: C20H23ClN2O4
Molecular Weight: 390.86 g/mol
Canonical SMILES: c1([C@@H](c2ccccn2)CCN(C)C)ccc(Cl)cc1.C(=C\C(O)=O)\C(O)=O
InChI: InChI=1/C16H19ClN2.C4H4O4/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13;5-3(6)1-2-4(7)8/h3-9,11,15H,10,12H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+
EINECS: 204-037-5
Classification Code: Antihistaminic; Drug / Therapeutic Agent; Mutation data; Reproductive Effect; Tumor data
Product Categories: Intermediates & Fine Chemicals; Pharmaceuticals; Antagonists; Histaminergics; Neurotransmitters
Index of Refraction: 1.565 
Molar Refractivity: 80.8 cm3 
Molar Volume: 248 cm3 
Polarizability: 32.03×10-24 cm3 
Surface Tension: 42.1 dyne/cm 
Density: 1.107 g/cm3 
Flash Point: 183 °C 
Enthalpy of Vaporization: 62.7 kJ/mol 
Boiling Point: 379 °C at 760 mmHg 
Melting Point: 130-135 °C(lit.)
Water Solubility: 1-5 g/100 mL at 21 °C
Vapour Pressure of Chlorpheniramine maleate (CAS NO.113-92-8): 6.04E-06 mmHg at 25 °C

Chlorpheniramine maleate Uses

  Chlorpheniramine maleate (CAS NO.113-92-8) is used as antihistaminic.

Chlorpheniramine maleate Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 75mg/kg (75mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
dog LD50 intravenous 97600ug/kg (97.6mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Journal of Pharmacology and Experimental Therapeutics. Vol. 113, Pg. 72, 1955.
guinea pig LD50 intravenous 68mg/kg (68mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 113, Pg. 313, 1958.
guinea pig LD50 oral 198mg/kg (198mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Journal of Pharmacology and Experimental Therapeutics. Vol. 113, Pg. 72, 1955.
guinea pig LD50 subcutaneous 101mg/kg (101mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Journal of Pharmacology and Experimental Therapeutics. Vol. 113, Pg. 72, 1955.
mouse LD50 intraperitoneal 76700ug/kg (76.7mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT		 Journal of Pharmacology and Experimental Therapeutics. Vol. 113, Pg. 72, 1955.
mouse LD50 intravenous 26100ug/kg (26.1mg/kg)   Toxicology and Applied Pharmacology. Vol. 23, Pg. 537, 1972.
mouse LD50 oral 130mg/kg (130mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 1644, 1978.
mouse LD50 subcutaneous 104mg/kg (104mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT		 Journal of Pharmacology and Experimental Therapeutics. Vol. 113, Pg. 72, 1955.
rat LD50 oral 306mg/kg (306mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT		 Kiso to Rinsho. Clinical Report. Vol. 12, Pg. 1371, 1978.
rat LD50 subcutaneous 365mg/kg (365mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.

Chlorpheniramine maleate Safety Profile

Poison by ingestion, intravenous, and subcutaneous routes. Experimental reproductive effects. Used as an antihistamine. Mutation data reported. When heated to decomposition it emits very toxic fumes of Cl− and NOx.
Hazard Codes: ToxicT
Risk Statements: 25 
R25: Toxic if swallowed.
Safety Statements: 36/37/39-45 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: US6504000
HazardClass: 6.1(b)
PackingGroup of Chlorpheniramine maleate (CAS NO.113-92-8): III

Chlorpheniramine maleate Specification

 Chlorpheniramine maleate (CAS NO.113-92-8), its Synonyms are Anaplex HD ; Azimycin (Veterinary) ; Bayer Select Allergy-Sinus ; Bayer Select Flu Relief ; Brexin L.A. ; Cerose-DM ; Chlor-Trimeton Decongestant ; Chlor-Trimeton Sinus ; Sudafed Plus ; Teldrin Timed-Release Allergy Capsules ; TheraFlu ; Triaminic ; 1-(N,N-Dimethylamino)-3-(p-chlorophenyl-3-alpha-pyridyl)propane maleate ; 1-(p-Chlorphenyl)-1-(2-pyridyl)-3-dimethylaminopropan maleat ; dl-Chlorpheniramine maleate . It is odorless white crystalline solid or white powder with a bitter taste. 

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