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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:58 UTC
HMDB IDHMDB0015367
Secondary Accession Numbers
  • HMDB15367
Metabolite Identification
Common NameBromodiphenhydramine
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 patientsBromodiphenhydramine 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.
Structure
Data?1582753289
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 Weight334.251
Monoisotopic Molecular Weight333.072826914
IUPAC Name{2-[(4-bromophenyl)(phenyl)methoxy]ethyl}dimethylamine
Traditional Namebromodiphenhydramine
CAS Registry Number1808-12-4
SMILES
CN(C)CCOC(C1=CC=CC=C1)C1=CC=C(Br)C=C1
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0034 g/LNot Available
LogP4Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+168.28330932474
DeepCCS[M-H]-165.92530932474
DeepCCS[M-2H]-198.81130932474
DeepCCS[M+Na]+174.37630932474
AllCCS[M+H]+173.732859911
AllCCS[M+H-H2O]+170.332859911
AllCCS[M+NH4]+176.832859911
AllCCS[M+Na]+177.732859911
AllCCS[M-H]-172.732859911
AllCCS[M+Na-2H]-172.832859911
AllCCS[M+HCOO]-173.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BromodiphenhydramineCN(C)CCOC(C1=CC=CC=C1)C1=CC=C(Br)C=C12986.0Standard polar33892256
BromodiphenhydramineCN(C)CCOC(C1=CC=CC=C1)C1=CC=C(Br)C=C12163.4Standard non polar33892256
BromodiphenhydramineCN(C)CCOC(C1=CC=CC=C1)C1=CC=C(Br)C=C12158.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Bromodiphenhydramine EI-B (Non-derivatized)splash10-0a4i-9000000000-53342d9a3abac3e5c1302017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Bromodiphenhydramine EI-B (Non-derivatized)splash10-0a4i-9000000000-53342d9a3abac3e5c1302018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bromodiphenhydramine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9170000000-a9ca360a39867bdc60e32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bromodiphenhydramine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bromodiphenhydramine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromodiphenhydramine 10V, Positive-QTOFsplash10-001i-1019000000-1f077c44d5a8983889d92016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromodiphenhydramine 20V, Positive-QTOFsplash10-008c-8198000000-4408b93513107a5fa2572016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromodiphenhydramine 40V, Positive-QTOFsplash10-00dl-9230000000-62fdc401b129d1d31d652016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromodiphenhydramine 10V, Negative-QTOFsplash10-001i-1029000000-87dd03a792f708d9d5602016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromodiphenhydramine 20V, Negative-QTOFsplash10-01q9-4298000000-6b6342526e6f4ecb97e72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromodiphenhydramine 40V, Negative-QTOFsplash10-0ufr-7940000000-034e1b52c692b487913f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromodiphenhydramine 10V, Positive-QTOFsplash10-000x-0094000000-3cf414b28e1dcbff7ea22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromodiphenhydramine 20V, Positive-QTOFsplash10-0006-0090000000-9617a3dfb8b832dc2bb32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromodiphenhydramine 40V, Positive-QTOFsplash10-0006-1090000000-cc1dcdb2d999990b63882021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromodiphenhydramine 10V, Negative-QTOFsplash10-001i-0019000000-ef5c1d55ed2ce8849a562021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromodiphenhydramine 20V, Negative-QTOFsplash10-0233-9272000000-29ea7428b9a497e3fd802021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bromodiphenhydramine 40V, Negative-QTOFsplash10-0a6u-3490000000-1cd8fd6f5553771b70e72021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01237 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01237 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 IDDB01237
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2350
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBromazine
METLIN IDNot Available
PubChem Compound2444
PDB IDNot Available
ChEBI ID59177
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Ullrich KJ, Rumrich G, David C, Fritzsch G: Bisubstrates: substances that interact with renal contraluminal organic anion and organic cation transport systems. I. Amines, piperidines, piperazines, azepines, pyridines, quinolines, imidazoles, thiazoles, guanidines and hydrazines. Pflugers Arch. 1993 Nov;425(3-4):280-99. [PubMed:8309790 ]