Basic information
- CAS
118-23-0- Standard SMILES
CN(C)CCOC(c1ccccc1)c1ccc(Br)cc1- InChIKey
NUNIWXHYABYXKF-UHFFFAOYSA-N- Molecular formula
- C17H20BrNO
- Average molar mass
- 334.2 g/mol
- Monoisotopic mass
- 333.07283
Overview
Bromazine is a tertiary amino compound that is the 4-bromobenzhydryl ether of 2-(dimethylamino)ethanol. An antihistamine with antimicrobial properties, it is used in the control of cutaneous allergies. It has a role as an antimicrobial agent, a H1-receptor antagonist and a muscarinic antagonist. It is an organobromine compound and a tertiary amino compound. It contains a bromazine hydrochloride.
Names & identifiers
- Preferred name
- Bromodiphenhydramine
- IUPAC
- 2-[(4-bromophenyl)-phenylmethoxy]-N,N-dimethylethanamine
- English name
- N-2-(4-bromobenzhydryloxy)ethyldimethylamine
- Molecular formula
- C17H20BrNO
- Molecular weight
- 334.25
Names & synonyms
bromodiphenhydramineBromazineBromdiphenhydramine118-23-0HistabromamineDeserolBromazinaNeo-BenadrylBromazinumDTXSID6022688beta-(p-Bromobenzhydryloxy)ethyldimethylamine2-(p-bromo-alpha-phenylbenzyloxy)-N,N-dimethylethylamine
Show more names
2-[(RS)-(4-Bromophenyl)phenylmethoxy]-N,N-dimethylethanamineBromanautineBromo-BenadrylDimenhydrinate EP Impurity HDiphenhydramine EP Impurity CN-2-(4-bromobenzhydryloxy)ethyldimethylamine2-benzhydryloxy-N-(bromomethyl)-N-methylethanamine
beta-dimethylaminoethyl p-bromobenzhydryl etherT032BI7727DTXCID002688CHEBI:59177{2-[(4-bromophenyl)(phenyl)methoxy]ethyl}dimethylamineEthanamine, 2-((4-bromophenyl)phenylmethoxy)-N,N-dimethyl-Ethanamine, 2-[(4-bromophenyl)phenylmethoxy]-N,N-dimethyl-(2-((4-bromophenyl)(phenyl)methoxy)ethyl)dimethylamine
Database identifiers
- CAS
118-23-0、1808-12-4
Properties
Computed structural properties
- XLogP
- 4
- Topological polar surface area
- 12.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 6
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 258
Experimental & physicochemical properties
LogP4
Solubility3.45e-03 g/L
Human DrugsPharmaceuticals
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 151 · 151-154 °C(Press: 0.3 Torr)
- Density
- 1.259 · 1.259±0.06 g/cm3(Predicted)
- pka
- 8.64 · pKa 8.64(H2O t = 25 c = 0.002 to 0.01) (Uncertain)
- FDA UNII
- 32 BI7727 · T032BI7727
- ATC code
- 6 AA01 · R06AA01
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationEthanamine, 2-(4-bromophenyl)phenylmethoxy-N,N-dimethyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Toxicology
Exposure RoutesWell absorbed in the digestive tract.
Toxicity SummaryBromodiphenhydramine 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.
Signs and SymptomsSigns of overdose include wheezing, tightness in the chest, fever, itching, bad cough, blue skin color, fits, swelling of face, lips, tongue, or throat.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Chemistry & industry
Pharmacology
ATC Code
R - Respiratory system
QR - Respiratory system
Protein Binding96%
Pharmacodynamics
Bromodiphenhydramine is an antihistamine of the ethanolamine class. Ethanolamine antihistamines have significant antimuscarinic activity and produce marked sedation in most patients. In addition to the usual allergic symptoms, the drug also treats irritant cough and nausea, vomiting, and vertigo associated with motion sickness. It also is used commonly to treat drug-induced extrapyramidal symptoms as well as to treat mild cases of Parkinson's disease. Rather than preventing the release of histamine, as do cromolyn and nedocromil, Bromodiphenhydramine competes with free histamine for binding at HA-receptor sites. Bromodiphenhydramine competitively antagonizes the effects of histamine on HA-receptors in the GI tract, uterus, large blood vessels, and bronchial muscle. Ethanolamine derivatives have greater anticholinergic activity than do other antihistamines, which probably accounts for the antidyskinetic action of Bromodiphenhydramine. This anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown.
Mechanism of ActionBromodiphenhydramine 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.
Biological Half-Life1 to 4 hours
Metabolism/Metabolites
Hepatic (cytochrome P-450 system); some renal.
Hepatic (cytochrome P-450 system); some renal. Half Life: 1 to 4 hours
Absorption, Distribution and ExcretionWell absorbed in the digestive tract.
Cellular Locations
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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