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Chlorpheniramine maleate structure
Chlorpheniramine maleate structure

Chlorpheniramine maleate

Iupac Name:but-2-enedioic acid;3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
CAS No.: 113-92-8
Molecular Weight:390.864
Modify Date.: 2022-11-10 14:52
Introduction: Chlorpheniramine maleate is an histamine H1 receptor antagonist with IC50 of 12 nM.Target: Histamine H1 ReceptorChlorpheniramine inhibits the proliferation of MCF-7, MDA-MB 231, and Ehrlich cells in a dose-response manner, and significantly reduces the ornithine decarboxylase mRNA translation by 50%-70% at the 250 μM [1]. Chlorpheniramine displaces of [3H]pyrilamine from human histamine receptor subtype 1 expressed in CHO cells with IC50 of 66 nM. Chlorpheniramine displays antimalarial a View more+
1. Names and Identifiers
1.1 Name
Chlorpheniramine maleate
1.2 Synonyms

)-Chlorpheniramine)-Chlorpheniramine maleate (+/-)-CHLORPHENIRAMINE MALEATE SALT (+/-)-CHLORPHENIRAMINE-D6 MALEATE [3-(4-chlorophenyl)-3-(2-pyridyl)propyl]dimethylamine 1-(N,N-Dimethylamino)-3-(p-chlorophenyl-3-a-pyridyl)propane Maleate 1-(p-Chlorophenyl)-1-(2-pyridyl)-3-dimethy-laminopropanebimaleate 1-Parachlorophenyl-1-(2-pyridyl)-3-dimethylaminopropane maleate 2-[p-Chloro-a-(2-dimethylaminoethyl)benzyl]pyridine 2-Pyridinepropanamine 2-pyridinepropanamine, g-(4-chlorophenyl)-N,N-dimethyl- 2-pyridinepropanamine, g-(4-chlorophenyl)-N,N-dimethyl-, (2Z)-2-butenedioate (1:1) 2-Pyridinepropanamine, Γ-(4-chlorophenyl)-N,N-dimethyl- 2-Pyridinepropanamine, γ-(4-chlorophenyl)-N,N-dimethyl-, (2Z)-2-butenedioate (1:1) 2-Pyridinepropanamine, γ-(4-chlorophenyl)-N,N-dimethyl-, (Z)-2-butenedioate (1:1) 3-(4-Chlorophenyl)-N,N-dimethyl-3-(2-pyridinyl)-1-propanamine 3-(4-Chlorophenyl)-N,N-dimethyl-3-(2-pyridinyl)-1-propanamine (2Z)-2-butenedioate (1:1) 3-(4-chlorophenyl)-N,N-dimethyl-3-(pyridin-2-yl)propan-1-amine 3-(4-Chlorophenyl)-N,N-dimethyl-3-(pyridin-2-yl)propan-1-amine (2Z)-but-2-enedioate (1:1) 3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine 4-Chloropheniramine allergin Allergisan alunex BISACODYL Chlorcaps T.D. Chlorophenamine CHLOROPHENAMINEMALEATE Chloropheniramine maleate chlorphenamine CHLORPHENAMINE HYDROGEN MALEATE, WHO STANDARD Chlorphenamine Maleate CHLORPHENAMINE MALEATES chlorpheniramine Chlorpheniramine (maleate) CHLORPHENIRAMINE HYDROGEN MALEATE CHLORPHENIRAMINE MALEATE REFERENCE STANDARD Chlorpheniramine Maleate Salt CHLORPHENIRAMINE-D4 MALEATE ChlorpheniramineMaleate Chlorprophenpyridamine maleate Chlortrimeton Cloropiril Cloropiril M.P. c-meton D-2-(p-Chloro-α-(2-dimethylaminoethyl)benzyl)pyridine d-chlorpheniramine maleate dexchlorpheniramine maleate dl-Chlorpheniramine EINECS 205-054-0 g-(4-Chlorophenyl)-g-(2-pyridyl)propyldimethylamine g-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine Haynon Histadur ibioton lorphen M.P. chlorcaps T.D. MFCD00069225 P-CHLORO(2-DIMETHYLAMINOETHYL)BENZYLPYRIDINE MALEATE piriex piriton Puermin teldrin UNII:V1Q0O9OJ9Z

1.3 CAS No.
113-92-8
1.4 CID
5281068
1.5 EINECS(EC#)
204-037-5
1.6 Molecular Formula
C20H23ClN2O4 (isomer)
1.7 Inchi
InChI=1S/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-
1.8 InChkey
DBAKFASWICGISY-BTJKTKAUSA-N
1.9 Canonical Smiles
CN(C)CCC(C1=CC=C(C=C1)Cl)C2=CC=CC=N2.C(=CC(=O)O)C(=O)O
1.10 Isomers Smiles
CN(C)CCC(C1=CC=C(C=C1)Cl)C2=CC=CC=N2.C(=C\C(=O)O)\C(=O)O
2. Properties
2.1 Density
1.107
2.1 Melting point
130-135℃
2.1 Boiling point
379 oC at 760 mmHg
2.1 Refractive index
1.6800 (estimate)
2.1 Flash Point
183 oC
2.1 Precise Quality
390.13500
2.1 PSA
90.73000
2.1 logP
3.53040
2.1 Solubility
1-5 g/100 mL at 21 oC
2.2 Appearance
Odorless white crystalline solid or white powder with a bitter taste.
2.3 Storage
Ambient temperatures.
2.4 Chemical Properties
White Solid
2.5 Color/Form
Powder
2.6 PH
4.0~5.5 (10g/l, 25℃)
2.7 Water Solubility
1-5 G/100 ML AT 21 oC
2.8 StorageTemp
2-8°C
3. Use and Manufacturing
3.1 Usage
An antagonist of the histamine H1-receptor
4. Safety and Handling
4.1 Symbol
GHS07
4.1 Hazard Codes
T
4.1 Signal Word
Warning
4.1 Risk Statements
R25
4.1 Safety Statements
S36/37/39;S45
4.1 Packing Group
III
4.1 Fire Hazard
Flash point data for Chlorpheniramine maleate are not available; however, Chlorpheniramine maleate is probably combustible.
4.2 Hazard Class
6.1(b)
4.2 Hazard Declaration
H302
4.2 RIDADR
UN 2811
4.2 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 Cland NOx.
4.3 Caution Statement
P301 + P312 + P330
4.3 WGK Germany
3
4.3 RTECS
US6504000
4.3 Safety

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

4.4 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.?

4.5 Toxicity

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.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H301 Toxic if swallowed

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

Response

P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P330 Rinse mouth.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

7. Other Information
7.0 Usage
An antihistaminic agent
7.1 Merck
14,2180
7.2 Description
Chlorpheniramine is a histamine H1 receptor antagonist with an IC75 value of 0.0016 μg/ml for reversal of histamine-induced spasms in isolated guinea pig ileum. It protects against intravenous histamine-induced death (PD50 = 0.15 mg/kg) and delays induction of aerosolized histamine-induced coughing (ED100sec = 0.44 mg/kg) in guinea pigs. Chlorpheniramine (20 mg/kg, i.p.) prevents histamine-induced passive cutaneous anaphylaxis (PCA) in rabbits. It also reduces respiratory resistance and hypersecretion of tracheobronchial fluid in a dog model of histamine-induced asthma. Formulations containing chlorpheniramine have been used in the treatment of seasonal allergies.
7.3 Chemical Properties
White Solid
7.4 Uses
An antagonist of the histamine H1-receptor
7.5 Uses
Antihistaminic
7.6 Uses
(±)-Chlorpheniramine maleate salt has been used:
  • as H1 receptor antagonist to determine the receptor function
  • to block the effect of compound 48/80 on plasma IGF-I
  • as a standard for fast sensing and determination by sequential injector coupled with potentiometer

8. Computational chemical data
  • Molecular Weight: 390.864g/mol
  • Molecular Formula: C20H23ClN2O4
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 390.1346349
  • Monoisotopic Mass: 390.1346349
  • Complexity: 368
  • Rotatable Bond Count: 7
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 6
  • Topological Polar Surface Area: 90.7
  • Heavy Atom Count: 27
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 1
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 2
  • CACTVS Substructure Key Fingerprint: AAADceB7OAAEAAAAAAAAAAAAAAAAAAAAAAA8QAAAAAAAAAABwAAAHgIACAAADQrBniQ+iJMIEgCoAzT3TACCgCAxByAI2CA4ZtgIJOLBk5GEMAhggADI2YcQgMAOhAAAAAAAAAAIAAAAAAAAAAAAAAAAAA==
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