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Record Information
Version3.6
Creation Date2006-05-18 09:07:14 UTC
Update Date2016-02-11 01:05:08 UTC
HMDB IDHMDB01941
Secondary Accession NumbersNone
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
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 KeyInChIKey=ZDIGNSYAACHWNL-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
  • Phenylpropylamine
  • Aralkylamine
  • Halobenzene
  • Bromobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl bromide
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organobromide
  • Organohalogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
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 mg/mLALOGPS
logP3.63ALOGPS
logP3.75ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity83.67 m3·mol-1ChemAxon
Polarizability32.08 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
MSMass Spectrum (Electron Ionization)splash10-0002-5490000000-9c3b804de0b552198b85View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot 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
NuGOwiki LinkHMDB01941
Metagene LinkHMDB01941
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