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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-18 09:07:14 UTC
Update Date2022-03-07 02:49:11 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
Data?1582752218
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 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
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

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available166.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00001064
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+169.85432859911
AllCCS[M-H]-171.1932859911
DeepCCS[M+H]+160.93230932474
DeepCCS[M-H]-158.57430932474
DeepCCS[M-2H]-191.4630932474
DeepCCS[M+Na]+167.02530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BrompheniramineCN(C)CCC(C1=CC=C(Br)C=C1)C1=CC=CC=N12982.4Standard polar33892256
BrompheniramineCN(C)CCC(C1=CC=C(Br)C=C1)C1=CC=CC=N11991.3Standard non polar33892256
BrompheniramineCN(C)CCC(C1=CC=C(Br)C=C1)C1=CC=CC=N12084.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Brompheniramine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9081000000-bc4d350922643027fea62017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Brompheniramine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Brompheniramine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-5490000000-9c3b804de0b552198b852014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Brompheniramine Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-014i-4954000000-f0a4889ab8cd0d5dcacc2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Brompheniramine Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-00di-0090000000-02a74d4d4927d8e443aa2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Brompheniramine Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-014i-0920000000-ad3d20cb0f1b7362fbc32012-07-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brompheniramine 10V, Positive-QTOFsplash10-014i-0029000000-fa060b2610f05fd6963a2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brompheniramine 20V, Positive-QTOFsplash10-01b9-0197000000-90a5b62f5a9e47f958022017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brompheniramine 40V, Positive-QTOFsplash10-0fef-3690000000-914dbc7e9fc6b1ce196a2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brompheniramine 10V, Negative-QTOFsplash10-014i-0009000000-1bc9f3a3603646c315042017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brompheniramine 20V, Negative-QTOFsplash10-014i-1019000000-14a32020bd62ee6fb3b72017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brompheniramine 40V, Negative-QTOFsplash10-0fi4-7591000000-cd391d2ec4970c9e8b8a2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brompheniramine 10V, Negative-QTOFsplash10-014i-0009000000-615031c9863c28108e0f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brompheniramine 20V, Negative-QTOFsplash10-016r-6369000000-b40c997a38a0f9eb2fdb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brompheniramine 40V, Negative-QTOFsplash10-004j-9480000000-6c5bc7bd482fbd292a0c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brompheniramine 10V, Positive-QTOFsplash10-00di-0094000000-c8e61a4d45703ee2c9062021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brompheniramine 20V, Positive-QTOFsplash10-00di-0090000000-363f1320fc00a31daef82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brompheniramine 40V, Positive-QTOFsplash10-006t-1290000000-3b9b35511af51a9e3bb52021-09-24Wishart 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 Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.024 +/- 0.0021 uMAdult (>18 years old)BothNormal details
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 IDDB00835
Phenol Explorer Compound IDNot Available
FooDB 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
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 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