Chlorpheniramine (CHEM002350)

Record Information
Version1.0
Creation Date2009-07-21 20:28:24 UTC
Update Date2026-05-14 16:57:56 UTC
Accession NumberCHEM002350
Identification
Common NameChlorpheniramine
ClassSmall Molecule
Description
Chlorpheniramine is a histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than Promethazine. -- Pubchem; Chlorphenamine or chlorpheniramine, commonly marketed as its salt chlorphenamine maleate (Chlor- Trimeton, Piriton, Chlor- Tripolon), is a first generation antihistamine used in the prevention of the symptoms of allergic conditions such as rhinitis and urticaria.- wikipedia.
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Amine
  • Anti-Allergic Agent
  • Antipruritic
  • Drug
  • Food Toxin
  • Histamine Antagonist
  • Histamine H1 Antagonist
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(p-Chlorophenyl)-1-(2-pyridyl)-3-dimethylaminopropaneChEBI
1-(p-Chlorophenyl)-1-(2-pyridyl)-3-N,N-dimethylpropylamineChEBI
2-[p-Chloro-alpha-[2-(dimethylamino)ethyl]benzyl]pyridineChEBI
3-(p-Chlorophenyl)-3-(2-pyridyl)-N,N-dimethylpropylamineChEBI
ChlorophenylpyridamineChEBI
ChlorphenaminChEBI
ChlorphenaminumChEBI
ChlorpheniraminumChEBI
ClofeniraminaChEBI
ClorfenaminaChEBI
ClorfeniraminaChEBI
gamma-(4-Chlorophenyl)-gamma-(2-pyridyl)propyldimethylamineChEBI
gamma-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamineChEBI
HaynonChEBI
ChlorphenamineKegg
2-[p-Chloro-a-[2-(dimethylamino)ethyl]benzyl]pyridineGenerator
2-[p-Chloro-α-[2-(dimethylamino)ethyl]benzyl]pyridineGenerator
g-(4-Chlorophenyl)-g-(2-pyridyl)propyldimethylamineGenerator
Γ-(4-chlorophenyl)-γ-(2-pyridyl)propyldimethylamineGenerator
g-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamineGenerator
Γ-(4-chlorophenyl)-N,N-dimethyl-2-pyridinepropanamineGenerator
Chlor-trimetonHMDB
Chloropheniramine maleateHMDB
Chlorphenamine hydrogen maleateHMDB
Chlorphenamine maleateHMDB
Chlorpheniaramine maleateHMDB
Chlorpheniramine maleateHMDB
TeldrinHMDB
Aller-chlorHMDB
Chlor-tripolonHMDB
ChlorproHMDB
Cloro-trimetonHMDB
KlorominHMDB
Maleate, chlorpheniramineHMDB
PiritonHMDB
Rugby brand OF chlorpheniramine maleateHMDB
Schering-plough brand OF chlorpheniramine maleateHMDB
Tannate, chlorpheniramineHMDB
Bayer brand OF chlorpheniramine maleateHMDB
Chlo-amineHMDB
Hogil brand 1 OF chlorpheniramine maleateHMDB
Llorens brand OF chlorpheniramine maleateHMDB
Schering brand OF chlorpheniramine maleateHMDB
Vortech brand 1 OF chlorpheniramine maleateHMDB
Antihistaminico llorensHMDB
ChlorprophenpyridamineHMDB
Chlorspan 12HMDB
Chlortab-4HMDB
Halsey drug brand OF chlorpheniramine maleateHMDB
Stafford-miller brand OF chlorpheniramine maleateHMDB
Vortech brand 3 OF chlorpheniramine maleateHMDB
Chlor-100HMDB
Chlorpheniramine tannateHMDB
Efidac 24HMDB
Hogil brand 2 OF chlorpheniramine maleateHMDB
Intra brand OF chlorpheniramine maleateHMDB
Schein brand OF chlorpheniramine maleateHMDB
Vortech brand 2 OF chlorpheniramine maleateHMDB
Chemical FormulaC16H19ClN2
Average Molecular Mass274.788 g/mol
Monoisotopic Mass274.124 g/mol
CAS Registry Number132-22-9
IUPAC Name[3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
Traditional Namechlorpheniramine
SMILESCN(C)CCC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1
InChI IdentifierInChI=1S/C16H19ClN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3
InChI KeySOYKEARSMXGVTM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pheniramines. Pheniramines are compounds containing a pheniramine moiety, which is structurally characterized by the presence of a 2-benzylpyridine linked to an dimethyl(propyl)amine to form a dimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine skeleton.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPheniramines
Direct ParentPheniramines
Alternative Parents
Substituents
  • Pheniramine
  • Chlorobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl chloride
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Skin
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point130 - 135°C
Boiling Point142°C
Solubility5500 mg/L (at 37°C)
Predicted Properties
PropertyValueSource
Water Solubility0.052 g/LALOGPS
logP3.74ALOGPS
logP3.58ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)9.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity80.85 m³·mol⁻¹ChemAxon
Polarizability30.82 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureWell absorbed in the gastrointestinal tract.
Mechanism of ToxicityChlorpheniramine binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.
MetabolismPrimarily hepatic via Cytochrome P450 (CYP450) enzymes. Half Life: 21-27 hours
Toxicity ValuesOral LD50 (rat): 306 mg/kg Oral LD50 (mice): 130 mg/kg Oral LD50 (guinea pig): 198 mg/kg LD50: 306 mg/kg (Human) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed used in the prevention of the symptoms of allergic conditions such as rhinitis, urticaria, allergy, common cold, asthma and hay fever.
Minimum Risk LevelNot Available
Health EffectsChlorpheniramine posesses serotonergic and norepinephrinergic effects. It has been shown to work as a serotonin-norepinephrine reuptake inhibitor or SNRI. [Wikipedia]
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB01114
HMDB IDHMDB0001944
FooDB IDFDB022759
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID1734
PDB IDNot Available
Wikipedia LinkChlorpheniramine
Chemspider ID2624
ChEBI ID52010
PubChem Compound ID2725
Kegg Compound IDC06905
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Anil M. Salpekar, John Johnson, “Acetaminophen compositions containing low doses of chlorpheniramine maleate, method for preparing same and tablets formed therefrom.” U.S. Patent US4631284, issued April, 1975.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10796091
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11284026
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16119587
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=16413139
5. Bantz EW, Dolen WK, Chadwick EW, Nelson HS: Chronic chlorpheniramine therapy: subsensitivity, drug metabolism, and compliance. Ann Allergy. 1987 Nov;59(5):341-6.
6. Simons FE, Silver NA, Gu X, Simons KJ: Clinical pharmacology of H1-antihistamines in the skin. J Allergy Clin Immunol. 2002 Nov;110(5):777-83.
7. MSDS: http://msds.orica.com/pdf/shess-en-cds-010-000000033835.pdf