Bromobimane (T3D1780)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2009-06-22 16:08:35 UTC
Update Date2014-12-24 20:24:37 UTC
Accession NumberT3D1780
Identification
Common NameBromobimane
ClassSmall Molecule
DescriptionBromobimane is an organobromide compound. 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. (3)
Compound Type
  • Amide
  • Bromide Compound
  • Ester
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
9,10-Dioxa-syn-(bromomethyl,methyl)(methyl,methyl)bimane
Bimane monobromide
MBB
MBBR
Monobromobimane
Thiolyte MB
Thiolyte® MB reagent
Chemical FormulaC10H11BrN2O2
Average Molecular Mass271.111 g/mol
Monoisotopic Mass270.000 g/mol
CAS Registry Number71418-44-5
IUPAC Name3-(bromomethyl)-2,5,6-trimethyl-1H,7H-[1,2]diazolo[1,2-a]pyrazole-1,7-dione
Traditional Namemonobromobimane
SMILESCC1=C(C)C(=O)N2N1C(CBr)=C(C)C2=O
InChI IdentifierInChI=1S/C10H11BrN2O2/c1-5-7(3)12-8(4-11)6(2)10(15)13(12)9(5)14/h4H2,1-3H3
InChI KeyInChIKey=AHEWZZJEDQVLOP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrazolopyrazoles. These are polycyclic aromatic compounds containing to pyrazole rings fused to each other. Pyrazole is 5-membered ring consisting of three carbon atoms and two adjacent nitrogen centers.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrazolopyrazoles
Sub ClassNot Available
Direct ParentPyrazolopyrazoles
Alternative Parents
Substituents
  • Pyrazolopyrazole
  • Pyrazolinone
  • Azole
  • Pyrazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Azacycle
  • Alkyl bromide
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organobromide
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alkyl halide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.6 g/LALOGPS
logP1.06ALOGPS
logP1.11ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.62 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity61.78 m³·mol⁻¹ChemAxon
Polarizability23.49 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-88a7306e117528e59ec92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-410d2f6736bdca05c0022016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9360000000-abd471d9c14aee1dfe762016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0290000000-ff223b4a13c4ad986a672016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-0590000000-ba56f5967b8038fa0ac52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-1970000000-5f47fb5212ed31081bea2016-08-03View Spectrum
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4)
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. (4, 5, 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. (4)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
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. (3, 4, 5)
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. (4, 5)
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.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID114810
ChEMBL IDCHEMBL1649730
ChemSpider ID102775
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID62825
BioCyc IDNot Available
CTD IDC028381
Stitch IDBromobimane
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1780.pdf
General References
  1. Ziouzenkova O, Orasanu G, Sharlach M, Akiyama TE, Berger JP, Viereck J, Hamilton JA, Tang G, Dolnikowski GG, Vogel S, Duester G, Plutzky J: Retinaldehyde represses adipogenesis and diet-induced obesity. Nat Med. 2007 Jun;13(6):695-702. Epub 2007 May 27. [17529981 ]
  2. Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
  3. Wikipedia. Bromine. Last Updated 9 June 2009. [Link]
  4. International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [Link]
  5. Wikipedia. Potassium bromide. Last Updated 9 June 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available