Brompheniramine (CHEM003514)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (6)XML
Record Information
Version1.0
Creation Date2014-08-30 21:03:45 UTC
Update Date2026-05-14 16:50:13 UTC
Accession NumberCHEM003514
Identification
Common NameBrompheniramine
ClassSmall Molecule
DescriptionHistamine H1 antagonist used in treatment of allergies, rhinitis, and urticaria. [PubChem]
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Anti-Allergic Agent
  • Bromide Compound
  • Drug
  • Food Toxin
  • Histamine H1 Antagonist
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
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
Chemical FormulaC16H19BrN2
Average Molecular Mass319.239 g/mol
Monoisotopic Mass318.073 g/mol
CAS Registry Number86-22-6
IUPAC Name[3-(4-bromophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
Traditional Namebrompheniramine
SMILESCN(C)CCC(C1=CC=C(Br)C=C1)C1=CC=CC=N1
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
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
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point< 25 °C
Boiling Point149.5 °C at 5.00E-01 mm Hg
SolubilityFreely soluble (maleate salt)
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 RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9081000000-bc4d350922643027fea6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-014i-4954000000-f0a4889ab8cd0d5dcaccSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-00di-0090000000-02a74d4d4927d8e443aaSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-014i-0920000000-ad3d20cb0f1b7362fbc3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0029000000-fa060b2610f05fd6963aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01b9-0197000000-90a5b62f5a9e47f95802Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fef-3690000000-914dbc7e9fc6b1ce196aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-1bc9f3a3603646c31504Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1019000000-14a32020bd62ee6fb3b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fi4-7591000000-cd391d2ec4970c9e8b8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-615031c9863c28108e0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-6369000000-b40c997a38a0f9eb2fdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9480000000-6c5bc7bd482fbd292a0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0094000000-c8e61a4d45703ee2c906Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-363f1320fc00a31daef8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-1290000000-3b9b35511af51a9e3bb5Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-5490000000-9c3b804de0b552198b85Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureAntihistamines are well absorbed from the gastrointestinal tract after oral administration.
Mechanism of ToxicityBrompheniramine works by acting as an antagonist of the H1 histamine receptors. It also functions as a moderately effective anticholingeric agent, likely an antimuscarinic agent similar to other common antihistamines such as diphenhydramine. Its effects on the cholinergic system may include side-effects such as drowsiness, sedation, dry mouth, dry throat, blurred vision, and increased heart rate.
MetabolismHepatic (cytochrome P-450 system), some renal.
Toxicity ValuesOral, Rat: LD50 = 318 mg/kg.
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of the symptoms of the common cold and allergic rhinitis, such as runny nose, itchy eyes, watery eyes, and sneezing.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSigns of overdose include fast or irregular heartbeat, mental or mood changes, tightness in the chest, and unusual tiredness or weakness.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00835
HMDB IDHMDB0001941
FooDB IDFDB022756
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID1383
PDB IDNot Available
Wikipedia LinkBrompheniramine
Chemspider ID6573
ChEBI ID3183
PubChem Compound ID6834
Kegg Compound IDC06857
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Sperber, N., Papa, D. and Schwenk, E.; US. Patent 2,567,245; September 11, 1951; assigned
to Schering Corporation.
Sperber, N., Papa, D. and Schwenk, E.; U.S. Patent 2,676,964: April 27,1954; assigned to
Schering Corporation.

MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=2570152
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=2579237
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=6458703
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=9526560