ContaminantDB: Bromodiphenhydramine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:43 UTC

Update Date

2026-05-14 16:58:58 UTC

Accession Number

CHEM002384

Identification

Common Name

Bromodiphenhydramine

Class

Small Molecule

Description

Bromodiphenhydramine 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(p-Bromo-alpha-phenylbenzyloxy)-N,N-dimethylethylamine	ChEBI
beta-(p-Bromobenzhydryloxy)ethyldimethylamine	ChEBI
beta-Dimethylaminoethyl p-bromobenzhydryl ether	ChEBI
Bromazina	ChEBI
Bromazinum	ChEBI
2-(p-Bromo-a-phenylbenzyloxy)-N,N-dimethylethylamine	Generator
2-(p-Bromo-α-phenylbenzyloxy)-N,N-dimethylethylamine	Generator
b-(p-Bromobenzhydryloxy)ethyldimethylamine	Generator
Β-(p-bromobenzhydryloxy)ethyldimethylamine	Generator
b-Dimethylaminoethyl p-bromobenzhydryl ether	Generator
Β-dimethylaminoethyl p-bromobenzhydryl ether	Generator
Amodryl	HMDB
Bromazin	HMDB
Bromazine	HMDB
Bromdiphenhydramine	HMDB
Bromodiphenhydramine hydrochloride	HMDB
Ambodryl	HMDB

Chemical Formula

C₁₇H₂₀BrNO

Average Molecular Mass

334.251 g/mol

Monoisotopic Mass

333.073 g/mol

CAS Registry Number

118-23-0

IUPAC Name

{2-[(4-bromophenyl)(phenyl)methoxy]ethyl}dimethylamine

Traditional Name

bromodiphenhydramine

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 Key

NUNIWXHYABYXKF-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

organobromine compound (CHEBI:59177 )
tertiary amino compound (CHEBI:59177 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	3.45e-03 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.0034 g/L	ALOGPS
logP	4.16	ALOGPS
logP	4.42	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	8.87	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	87.55 m³·mol⁻¹	ChemAxon
Polarizability	33.48 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-53342d9a3abac3e5c130	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-53342d9a3abac3e5c130	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9170000000-a9ca360a39867bdc60e3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1019000000-1f077c44d5a8983889d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-008c-8198000000-4408b93513107a5fa257	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-9230000000-62fdc401b129d1d31d65	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1029000000-87dd03a792f708d9d560	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q9-4298000000-6b6342526e6f4ecb97e7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ufr-7940000000-034e1b52c692b487913f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000x-0094000000-3cf414b28e1dcbff7ea2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0090000000-9617a3dfb8b832dc2bb3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-1090000000-cc1dcdb2d999990b6388	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0019000000-ef5c1d55ed2ce8849a56	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0233-9272000000-29ea7428b9a497e3fd80	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-3490000000-1cd8fd6f5553771b70e7	Spectrum

Toxicity Profile

Route of Exposure

Well absorbed in the digestive tract.

Mechanism of Toxicity

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.

Metabolism

Hepatic (cytochrome P-450 system); some renal. Half Life: 1 to 4 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For 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 Level

Not Available

Health Effects

Not Available

Symptoms

Signs of overdose include wheezing, tightness in the chest, fever, itching, bad cough, blue skin color, fits, swelling of face, lips, tongue, or throat.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01237

HMDB ID

HMDB0015367

FooDB ID

Not Available

Phenol Explorer ID