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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-18 09:20:41 UTC
Update Date2022-03-07 02:49:11 UTC
HMDB IDHMDB0001944
Secondary Accession Numbers
  • HMDB0004994
  • HMDB01944
  • HMDB04994
Metabolite Identification
Common NameChlorpheniramine
DescriptionChlorpheniramine 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.
Structure
Data?1582752219
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 Weight274.788
Monoisotopic Molecular Weight274.123676325
IUPAC Name[3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
Traditional Namechlorpheniramine
CAS Registry Number113-92-8
SMILES
CN(C)CCC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1
InChI Identifier
InChI=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
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point130 - 135 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility160 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available163.461http://allccs.zhulab.cn/database/detail?ID=AllCCS00000970
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+162.04432859911
AllCCS[M-H]-168.09232859911
DeepCCS[M+H]+160.78430932474
DeepCCS[M-H]-158.42630932474
DeepCCS[M-2H]-191.31230932474
DeepCCS[M+Na]+166.87730932474
AllCCS[M+H]+162.032859911
AllCCS[M+H-H2O]+158.332859911
AllCCS[M+NH4]+165.632859911
AllCCS[M+Na]+166.632859911
AllCCS[M-H]-168.132859911
AllCCS[M+Na-2H]-168.232859911
AllCCS[M+HCOO]-168.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ChlorpheniramineCN(C)CCC(C1=CC=C(Cl)C=C1)C1=CC=CC=N12892.2Standard polar33892256
ChlorpheniramineCN(C)CCC(C1=CC=C(Cl)C=C1)C1=CC=CC=N12036.8Standard non polar33892256
ChlorpheniramineCN(C)CCC(C1=CC=C(Cl)C=C1)C1=CC=CC=N11978.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Chlorpheniramine EI-B (Non-derivatized)splash10-0zfr-6290000000-2ca3230cde716588805e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Chlorpheniramine EI-B (Non-derivatized)splash10-0zfr-6290000000-2ca3230cde716588805e2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlorpheniramine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9380000000-f4a0f7b13adeafb1762d2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlorpheniramine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlorpheniramine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chlorpheniramine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0zfr-6490000000-8e58cd1c686f23a7dac62014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpheniramine Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-01b9-3900000000-ea4ccfd2afe05f49fc7a2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpheniramine Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-004i-0090000000-9e46eb080de95d4f8f8e2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpheniramine Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-014i-1920000000-d2d2acf559d9070a1d472012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpheniramine EI-B (Unknown) , Positive-QTOFsplash10-0zfr-6190000000-2ca3230cde716588805e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpheniramine LC-ESI-qTof , Positive-QTOFsplash10-0uy0-0960000000-1f750af75fe542c6c06f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpheniramine , positive-QTOFsplash10-001i-0290000000-03651b7b90a1745fdf232017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpheniramine , positive-QTOFsplash10-0uy0-0960000000-1f750af75fe542c6c06f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Chlorpheniramine 35V, Positive-QTOFsplash10-001i-0490000000-3d28aeb0e77391e8e9b22021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpheniramine 10V, Positive-QTOFsplash10-004i-0090000000-9b4d486e9c2c7712ca4d2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpheniramine 20V, Positive-QTOFsplash10-0059-0190000000-2c96b165338a445b284d2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpheniramine 40V, Positive-QTOFsplash10-0ue9-3960000000-73025748bd5a004599382017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpheniramine 10V, Negative-QTOFsplash10-00di-0090000000-90a6e640c735788d17ca2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpheniramine 20V, Negative-QTOFsplash10-00di-1090000000-89ac3cf688134ba8a50b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpheniramine 40V, Negative-QTOFsplash10-01tc-6490000000-4242ef7cec7b0b0a73932017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpheniramine 10V, Positive-QTOFsplash10-001i-0090000000-c38223f80e776a39c8402021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpheniramine 20V, Positive-QTOFsplash10-001i-0090000000-5c9ac02f7374772460c82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpheniramine 40V, Positive-QTOFsplash10-0ue9-1290000000-cc70655f6b19de3dc41d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpheniramine 10V, Negative-QTOFsplash10-00di-0090000000-df52e539d08e1efa7d952021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpheniramine 20V, Negative-QTOFsplash10-00di-4390000000-4b1316bcb291af4998c92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chlorpheniramine 40V, Negative-QTOFsplash10-0ue9-8490000000-4bf6d67eb7d38a21b96b2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Epidermis
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01114
Phenol Explorer Compound IDNot Available
FooDB IDFDB022759
KNApSAcK IDNot Available
Chemspider ID2624
KEGG Compound IDC06905
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChlorpheniramine
METLIN ID1734
PubChem Compound2725
PDB IDNot Available
ChEBI ID52010
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bantz EW, Dolen WK, Chadwick EW, Nelson HS: Chronic chlorpheniramine therapy: subsensitivity, drug metabolism, and compliance. Ann Allergy. 1987 Nov;59(5):341-6. [PubMed:3688558 ]
  2. 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. [PubMed:12417888 ]
  3. MSDS [Link]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
General function:
Involved in transport
Specific function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc
Gene Name:
ALB
Uniprot ID:
P02768
Molecular weight:
69365.9
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The H4 subclass of histamine receptors could mediate the histamine signals in peripheral tissues. Displays a significant level of constitutive activity (spontaneous activity in the absence of agonist)
Gene Name:
HRH4
Uniprot ID:
Q9H3N8
Molecular weight:
44495.4