Bromodiphenhydramine (CHEM002384)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:43 UTC
Update Date2016-11-09 01:08:46 UTC
Accession NumberCHEM002384
Identification
Common NameBromodiphenhydramine
ClassSmall Molecule
DescriptionBromodiphenhydramine is only found in individuals that have used or taken this drug. It is an ethanolamine antihistamine with antimicrobial property. Bromodiphenhydramine is used in the control of cutaneous allergies. Ethanolamine antihistamines produce marked sedation in most patients. Bromodiphenhydramine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Bromide Compound
  • Drug
  • Ether
  • Histamine Antagonist
  • Metabolite
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(p-Bromo-alpha-phenylbenzyloxy)-N,N-dimethylethylamineChEBI
beta-(p-Bromobenzhydryloxy)ethyldimethylamineChEBI
beta-Dimethylaminoethyl p-bromobenzhydryl etherChEBI
BromazinaChEBI
BromazinumChEBI
2-(p-Bromo-a-phenylbenzyloxy)-N,N-dimethylethylamineGenerator
2-(p-Bromo-α-phenylbenzyloxy)-N,N-dimethylethylamineGenerator
b-(p-Bromobenzhydryloxy)ethyldimethylamineGenerator
Β-(p-bromobenzhydryloxy)ethyldimethylamineGenerator
b-Dimethylaminoethyl p-bromobenzhydryl etherGenerator
Β-dimethylaminoethyl p-bromobenzhydryl etherGenerator
AmodrylHMDB
BromazinHMDB
BromazineHMDB
BromdiphenhydramineHMDB
Bromodiphenhydramine hydrochlorideHMDB
AmbodrylHMDB
Chemical FormulaC17H20BrNO
Average Molecular Mass334.251 g/mol
Monoisotopic Mass333.073 g/mol
CAS Registry Number118-23-0
IUPAC Name{2-[(4-bromophenyl)(phenyl)methoxy]ethyl}dimethylamine
Traditional Namebromodiphenhydramine
SMILESCN(C)CCOC(C1=CC=CC=C1)C1=CC=C(Br)C=C1
InChI IdentifierInChI=1S/C17H20BrNO/c1-19(2)12-13-20-17(14-6-4-3-5-7-14)15-8-10-16(18)11-9-15/h3-11,17H,12-13H2,1-2H3
InChI KeyNUNIWXHYABYXKF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Benzylether
  • Bromobenzene
  • Halobenzene
  • Aryl bromide
  • Aryl halide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Dialkyl ether
  • Organobromide
  • Organohalogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility3.45e-03 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.0034 g/LALOGPS
logP4.16ALOGPS
logP4.42ChemAxon
logS-5ALOGPS
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity87.55 m³·mol⁻¹ChemAxon
Polarizability33.48 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-53342d9a3abac3e5c130Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-53342d9a3abac3e5c130Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9170000000-a9ca360a39867bdc60e3Spectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1029000000-87dd03a792f708d9d560Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-4298000000-6b6342526e6f4ecb97e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-7940000000-034e1b52c692b487913fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-ef5c1d55ed2ce8849a56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0233-9272000000-29ea7428b9a497e3fd80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-3490000000-1cd8fd6f5553771b70e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1019000000-1f077c44d5a8983889d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-008c-8198000000-4408b93513107a5fa257Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9230000000-62fdc401b129d1d31d65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000x-0094000000-3cf414b28e1dcbff7ea2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0090000000-9617a3dfb8b832dc2bb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-1090000000-cc1dcdb2d999990b6388Spectrum
Toxicity Profile
Route of ExposureWell absorbed in the digestive tract.
Mechanism of ToxicityBromodiphenhydramine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding.
MetabolismHepatic (cytochrome P-450 system); some renal. Half Life: 1 to 4 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor management of symptoms related to hay fever and other types of allergy and used to help bring up phlegm, thin secretions, and make a cough productive.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSigns of overdose include wheezing, tightness in the chest, fever, itching, bad cough, blue skin color, fits, swelling of face, lips, tongue, or throat.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01237
HMDB IDHMDB0015367
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBromazine
Chemspider ID2350
ChEBI ID59177
PubChem Compound ID2444
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

DrugSyn.org

MSDSNot Available
General ReferencesNot Available