Record Information
Version1.0
Creation Date2009-06-22 16:08:37 UTC
Update Date2026-05-14 19:34:37 UTC
Accession NumberCHEM001547
Identification
Common NameDibrompropamidine
ClassSmall Molecule
DescriptionDibrompropamidine is an organobromide compound. It is an antiseptic and disinfectant. As dibrompropamidine isethionate, it is also used in eyedrops and ointment for the treatment of infections. Bromine is a halogen element with the symbol Br and atomic number 35. Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock. (2, 5)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Bromide Compound
  • Ether
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
BrulidineMeSH
DibromopropamidineMeSH
BroleneMeSH
Dibrompropamidine isethionateMeSH
Dibropropamidine isethionateMeSH
1,3-Di(4-amidino-2-bromophenoxy)propane di-2-hydroxyethanesulfonateMeSH
Dibromopropamidine isethionateMeSH
Dibrompropamidine hydrochlorideMeSH
Dibrompropamidine isetionateMeSH
Chemical FormulaC17H18Br2N4O2
Average Molecular Mass470.158 g/mol
Monoisotopic Mass467.980 g/mol
CAS Registry Number496-00-4
IUPAC Name3-bromo-4-[3-(2-bromo-4-carbamimidoylphenoxy)propoxy]benzene-1-carboximidamide
Traditional Namebrolene
SMILESNC(=N)C1=CC=C(OCCCOC2=CC=C(C=C2Br)C(N)=N)C(Br)=C1
InChI IdentifierInChI=1S/C17H18Br2N4O2/c18-12-8-10(16(20)21)2-4-14(12)24-6-1-7-25-15-5-3-11(17(22)23)9-13(15)19/h2-5,8-9H,1,6-7H2,(H3,20,21)(H3,22,23)
InChI KeyGMJFVGRUYJHMCO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Bromobenzene
  • Halobenzene
  • Aryl bromide
  • Aryl halide
  • Monocyclic benzene moiety
  • Amidine
  • Carboximidamide
  • Carboxylic acid amidine
  • Ether
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organohalogen compound
  • Organobromide
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP2.36ALOGPS
logP2.9ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)11.81ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area118.2 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity126.53 m³·mol⁻¹ChemAxon
Polarizability40.74 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0020900000-4e27395f08642e69729eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07vi-0190700000-cffa581a34ee8e3b61a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fv-4490000000-5615b11f0b05a3f1b9d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0040900000-90572efd4494e3536bcfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0191400000-f4ec0a2d7b83ed827dd5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-4390000000-950ac975bd087a4e626eSpectrum
Toxicity Profile
Route of ExposureOral (3) ; inhalation (3) ; dermal (3)
Mechanism of ToxicityBromine is a powerful oxidizing agent and is able to release oxygen free radicals from the water in mucous membranes. These free radicals are also potent oxidizers and produce tissue damage. In additon, the formation of hydrobromic and bromic acids will result in secondary irritation. The bromide ion is also known to affect the central nervous system, causing bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes. (3, 4, 1)
MetabolismBromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (3)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesAs dibrompropamidine isethionate, it is also used in eyedrops and ointment for the treatment of infections. Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock.
Minimum Risk LevelNot Available
Health EffectsBromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (2, 3, 4)
SymptomsBromine vapour causes irritation and direct damage to the mucous membranes. Symptoms include lacrimation, rhinorrhoea, eye irritation with mucous secretions from the oropharyngeal and upper airways, coughing, dyspnoea, choking, wheezing, epistaxis, and headache. The bromide ion is a central nervous system depressant producing ataxia, slurred speech, tremor, nausea, vomiting, lethargy, dizziness, visual disturbances, unsteadiness, headaches, impaired memory and concentration, disorientation and hallucinations. This is called bromism. (3, 4)
TreatmentEYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Concentrations
Not Available
DrugBank IDDB13548
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDibrompropamidine
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID11974
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available