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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-18 09:07:14 UTC
Update Date2017-10-23 19:03:55 UTC
HMDB IDHMDB0001941
Secondary Accession Numbers
  • HMDB01941
Metabolite Identification
Common NameBrompheniramine
DescriptionBrompheniramine (also known as Bromfed, Bromfenex, and Dimetane) is an antihistamine drug of the propylamine class. It is commonly available over the counter and is indicated for the treatment of the symptoms of the common cold and allergic rhinitis, such as runny nose, itchy eyes, watery eyes, and sneezing. It is a first-generation antihistamine; Brompheniramine (also known as Bromfed, Bromfenex, and Dimetane) is an antihistamine drug of the propylamine class. It is commonly available over the counter and is indicated for the treatment of the symptoms of the common cold and allergic rhinitis, such as runny nose, itchy eyes, watery eyes, and sneezing. It is a first-generation antihistamine. -- Wikipedia; Histamine H1 antagonist used in treatment of allergies, rhinitis, and urticaria.
Structure
Thumb
Synonyms
ValueSource
1-(P-Bromophenyl)-1-(2-pyridyl)-3-dimethylaminopropaneChEBI
2-(P-bromo-alpha-(2-Dimethylaminoethyl)benzyl)pyridineChEBI
3-(4-Bromophenyl)-N,N-dimethyl-3-(2-pyridinyl)-1-propanamineChEBI
3-(P-Bromophenyl)-3-(2-pyridyl)-N,N-dimethylpropylamineChEBI
[3-(4-bromo-Phenyl)-3-pyridin-2-yl-propyl]-dimethyl-amineChEBI
BromfeniraminaChEBI
BrompheniraminumChEBI
2-(P-bromo-a-(2-Dimethylaminoethyl)benzyl)pyridineGenerator
2-(P-bromo-α-(2-dimethylaminoethyl)benzyl)pyridineGenerator
Antihistamine compoundHMDB
Brompheniramine maleateHMDB
D-BrompheniramineHMDB
DexbromfeniraminaHMDB
DexbrompheniramineHMDB
Dexbrompheniramine brompheniramineHMDB
Dexbrompheniramine maleateHMDB
Dexbrompheniramine maleate saltHMDB
DexbrompheniraminumHMDB
DimetaneHMDB
Dimetane-tenHMDB
Dimetapp allergyHMDB
IlvinHMDB
ParabromdylamineHMDB
ParabromodylamineHMDB
VeltaneHMDB
Dimetane tenMeSH
Maleate, brompheniramineMeSH
Whitehall-robins brand OF brompheniramine maleateMeSH
Para bromdylamineMeSH
ChlorphedMeSH
Brompheniramine maleate (1:1)MeSH
Oraminic 2MeSH
Oraminic-2MeSH
Roberts brand OF brompheniramine maleateMeSH
Robins brand OF brompheniramine maleateMeSH
P BromdylamineMeSH
P-BromdylamineMeSH
Vortech brand OF brompheniramine maleateMeSH
Para-bromdylamineMeSH
Chemical FormulaC16H19BrN2
Average Molecular Weight319.239
Monoisotopic Molecular Weight318.073161265
IUPAC Name[3-(4-bromophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
Traditional Namebrompheniramine
CAS Registry Number86-22-6
SMILES
CN(C)CCC(C1=CC=C(Br)C=C1)C1=CC=CC=N1
InChI Identifier
InChI=1S/C16H19BrN2/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 KeyZDIGNSYAACHWNL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pheniramines. These 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
  • Bromobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl bromide
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organobromide
  • Organohalogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP3.63ALOGPS
logP3.75ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity83.67 m³·mol⁻¹ChemAxon
Polarizability32.08 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9081000000-bc4d350922643027fea6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-014i-4954000000-f0a4889ab8cd0d5dcaccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-00di-0090000000-02a74d4d4927d8e443aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-014i-0920000000-ad3d20cb0f1b7362fbc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0029000000-fa060b2610f05fd6963aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01b9-0197000000-90a5b62f5a9e47f95802View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fef-3690000000-914dbc7e9fc6b1ce196aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-1bc9f3a3603646c31504View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1019000000-14a32020bd62ee6fb3b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fi4-7591000000-cd391d2ec4970c9e8b8aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0002-5490000000-9c3b804de0b552198b85View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Brompheniramine H1-Antihistamine ActionPw058500Pw058500 greyscalePw058500 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.024 +/- 0.0021 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022756
KNApSAcK IDNot Available
Chemspider ID6573
KEGG Compound IDC06857
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBrompheniramine
METLIN ID1383
PubChem Compound6834
PDB IDNot Available
ChEBI ID3183
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

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