Record Information
Version1.0
Creation date2011-09-21 00:19:07 UTC
Update date2015-10-09 22:31:18 UTC
Primary IDFDB022756
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. [HMDB]
CAS Number86-22-6
Structure
Thumb
Synonyms
SynonymSource
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
BrotaneKegg
2-(p-Bromo-a-(2-dimethylaminoethyl)benzyl)pyridineGenerator
2-(p-Bromo-α-(2-dimethylaminoethyl)benzyl)pyridineGenerator
Antihistamine compoundHMDB
Brompheniramine maleateHMDB, MeSH
D-BrompheniramineHMDB
DexbromfeniraminaHMDB
DexbrompheniramineHMDB
Dexbrompheniramine brompheniramineHMDB
Dexbrompheniramine maleateHMDB
Dexbrompheniramine maleate saltHMDB
DexbrompheniraminumHMDB
DimetaneHMDB, MeSH
Dimetane-tenHMDB, MeSH
Dimetapp allergyHMDB, MeSH
IlvinHMDB
ParabromdylamineHMDB
ParabromodylamineHMDB
VeltaneHMDB
Dimetane tenMeSH, HMDB
Maleate, brompheniramineMeSH, HMDB
Whitehall-robins brand OF brompheniramine maleateMeSH, HMDB
Para bromdylamineMeSH, HMDB
ChlorphedMeSH, HMDB
Brompheniramine maleate (1:1)MeSH, HMDB
Oraminic 2MeSH, HMDB
Oraminic-2MeSH, HMDB
Roberts brand OF brompheniramine maleateMeSH, HMDB
Robins brand OF brompheniramine maleateMeSH, HMDB
P BromdylamineMeSH, HMDB
P-BromdylamineMeSH, HMDB
Vortech brand OF brompheniramine maleateMeSH, HMDB
Para-bromdylamineMeSH, HMDB
1-(P-Bromophenyl)-1-(2-pyridyl)-3-dimethylaminopropaneChEBI
2-(P-Bromo-a-(2-dimethylaminoethyl)benzyl)pyridineGenerator
2-(P-Bromo-alpha-(2-dimethylaminoethyl)benzyl)pyridineChEBI
2-(P-Bromo-α-(2-dimethylaminoethyl)benzyl)pyridineGenerator
3-(P-Bromophenyl)-3-(2-pyridyl)-N,N-dimethylpropylamineChEBI
Brompheniramine Maleatehmdb
Dexbrompheniramine Brompheniraminehmdb
dexbrompheniramine maleatehmdb
Dexbrompheniramine Maleate Salthmdb
Dimetane-Tenhmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H19BrN2
IUPAC name[3-(4-bromophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
InChI IdentifierInChI=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
Isomeric SMILESCN(C)CCC(C1=CC=C(Br)C=C1)C1=CC=CC=N1
Average Molecular Weight319.239
Monoisotopic Molecular Weight318.073161265
Classification
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
  • 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
Disposition

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0002-5490000000-9c3b804de0b552198b852014-09-20View Spectrum
Predicted GC-MSBrompheniramine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4l-9081000000-bc4d350922643027fea6Spectrum
Predicted GC-MSBrompheniramine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBrompheniramine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-014i-4954000000-f0a4889ab8cd0d5dcacc2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-00di-0090000000-02a74d4d4927d8e443aa2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-014i-0920000000-ad3d20cb0f1b7362fbc32012-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0029000000-fa060b2610f05fd6963a2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01b9-0197000000-90a5b62f5a9e47f958022017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fef-3690000000-914dbc7e9fc6b1ce196a2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-1bc9f3a3603646c315042017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1019000000-14a32020bd62ee6fb3b72017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fi4-7591000000-cd391d2ec4970c9e8b8a2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-615031c9863c28108e0f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-6369000000-b40c997a38a0f9eb2fdb2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9480000000-6c5bc7bd482fbd292a0c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0094000000-c8e61a4d45703ee2c9062021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-363f1320fc00a31daef82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-1290000000-3b9b35511af51a9e3bb52021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID6573
ChEMBL IDCHEMBL811
KEGG Compound IDC06857
Pubchem Compound ID6834
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00835
HMDB IDHMDB01941
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDBrompheniramine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Histamine H1 receptorHRH1P35367
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference