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113-92-8

Basic Information
CAS No.: 113-92-8
Name: Chlorpheniramine maleate
Molecular Structure:
Molecular Structure of 113-92-8 (Chlorpheniramine maleate)
Formula: C20H23ClN2O4
Molecular Weight: 390.86
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);
EINECS: 204-037-5
Density: 1.107 g/cm3
Melting Point: 130-135 ºC
Boiling Point: 379 ºC at 760 mmHg
Flash Point: 183 ºC
Solubility: 1-5 g/100 mL at 21 ºC
Appearance: White crystalline powder
Hazard Symbols: ToxicT
Risk Codes: 25
Safety: 36/37/39-45
Transport Information: UN 2811 6.1/PG 3
PSA: 90.73000
LogP: 3.53040
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%

cobalt(II) nitrate hexahydrate

122630-45-9, 150063-91-5, 7361-93-5

salicylaldehyde anthranilic acid

113-92-8

chlorphenamine maleate

151958-93-9

Co(OC6H4CHNC6H4COO)(C5H4NCH(CH2CH2N(CH3)2)C6H4Cl)(H2O)*(HCCOOH)2

Conditions
ConditionsYield
In ethanol byproducts: HNO3; refluxing ethanolic solns. of metal salt, schiff base and heterocyclic base in 1:1:1 molar ratio for 2-5 h, pptn.; filtn., washing with ethanol, drying in vacuo, elem. anal.;53%

tetracyanodinitrosylmolybdate(0)

113-92-8

chlorphenamine maleate

Mo(NO)2(CN)2(C5H4NCH(CH2CH2N(CH3)2)C6H4Cl)2*2(CHCOOH)2*2H2O=(Mo(NO)2(CN)2(C16H19N2Cl)2)*((CHCOOH)2)2*2H2O

Conditions
ConditionsYield
In water; acetic acid addn. of ligand in a mixt. of water/acetic acid to a filtered aq. soln. of molybdate with shaking, refluxing for 4-5 h over a hot plate at 80°C; filtn. by suction, washing several times with dilute acetic acid, finally with water, drying in vacuo at room temp. to a constant weight, elem. anal.;52%

cobalt(II) nitrate hexahydrate

113-92-8

chlorphenamine maleate

3449-05-6

2-(salicylideneamino)thiophenol

151987-76-7

Co(OC6H4CHNC6H4S)(C5H4NCH(CH2CH2N(CH3)2)C6H4Cl)(H2O)*(HCCOOH)2

Conditions
ConditionsYield
In ethanol byproducts: HNO3; refluxing ethanolic solns. of metal salt, schiff base and heterocyclic base in 1:1:1 molar ratio for 2-5 h, pptn.; filtn., washing with ethanol, drying in vacuo, elem. anal.;50%
113-92-8

chlorphenamine maleate

A

2438-32-6

dextrochlorpheniramine maleate

B

23095-76-3

(-)-Chlorpheniramine maleate

Conditions
ConditionsYield
With sodium dihydrogenphosphate; phosphoric acid In methanol; water pH=2.75; Reagent/catalyst; Ionic liquid; Resolution of racemate;
With maleic anhydride-β-cyclodextrin modified Fe3O4 Resolution of racemate; Optical yield = 13.7 %ee;
With tetramethylammonium hydroxyproline; clindamycin phosphate In methanol; water at 20℃; pH=7.6; pH-value; Solvent; Temperature; Resolution of racemate; enantioselective reaction;
With β‐cyclodextrin In aq. phosphate buffer pH=2.5; Resolution of racemate;
113-92-8

chlorphenamine maleate

2C16H19ClN2*2C4H4O4*2Na(1+)*C20H6Br4O5(2-)

Conditions
ConditionsYield
In water at 23℃; for 0.166667h; pH=3.72; Solvent; pH-value; Temperature;
Downstream Products
2438-32-6
23095-76-3
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Chemistry

 
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 cm
Polarizability: 32.03×10-24 cm
Surface Tension: 42.1 dyne/cm 
Density: 1.107 g/cm
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

Uses

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

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.

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

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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