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Basic Information

Molecular Structure:
CAS No.:	113-92-8
Name:	Chlorpheniramine maleate
Article Data:	9
Cas Database

Formula:	C₂₀H₂₃ClN₂O₄
Molecular Weight:	390.867
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:	T
Risk Codes:	25
Safety:	36/37/39-45
Transport Information:	UN 2811 6.1/PG 3
PSA:	90.73000
LogP:	3.53040

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formic acid

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maleic acid

: 113-92-8
chlorphenamine maleate

Conditions

Conditions	Yield
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%

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: 4350-41-8
2-(4-chlorobenzyl)pyridine

: 107-99-3
2-(dimethylamino)ethyl chloride

: 110-16-7
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chlorphenamine maleate

Conditions

Conditions	Yield
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

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p-chlorobenzyl cyanide

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chlorphenamine maleate

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

...Expand

: 113-92-8
chlorphenamine maleate

Conditions

Conditions	Yield
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

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1-Chloro-4-(chloromethyl)benzene

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Conditions

Conditions	Yield
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

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4-(2-Pyridinylmethyl)phenylamine

: 113-92-8
chlorphenamine maleate

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

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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 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

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 NO_x.
Hazard Codes: Toxic T
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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