Tmic
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Record Information
Version2.0
Creation Date2009-03-06 18:58:09 UTC
Update Date2014-12-24 20:21:12 UTC
Accession NumberT3D0142
Identification
Common NameBromine
ClassSmall Molecule
DescriptionElemental bromine exists as a diatomic molecule, Br2. It is a dense, mobile, slightly transparent reddish-brown liquid, that evaporates easily at standard temperature and pressures to give an orange vapor (its color resembles nitrogen dioxide) that has a strongly disagreeable odor resembling that of chlorine. It is one of only two elements on the periodic table that are known to be liquids at room temperature (the other being mercury). Bromine is corrosive and toxic, with properties between those of chlorine and iodine. Free bromine does not occur in nature, but occurs as colorless soluble crystalline mineral halide salts, analogous to table salt. Bromine is used in the preparation of brominated flame retardants, it is also used in the preparation of gas additives and pesticides. Bromide compounds, especially potassium bromide, were frequently used as general sedatives in the 19th and early 20th century. Bromides in the form of simple salts are still used as anticonvulsants in both veterinary and human medicine, although the latter use varies from country to country. Bromine has been long believed to have no essential function in mammals, but recent research suggests that bromine is necessary for tissue development. In addition, bromine is used preferentially over chlorine by one antiparasitic enzyme in the human immune system. Organobromides are needed and produced enzymatically from bromide by some lower life forms in the sea, particularly algae.
Compound Type
  • Food Toxin
  • Halogen
  • Inorganic Compound
  • Lachrymator
  • Metabolite
  • Natural Compound
  • Non-Metal
  • Pesticide
Chemical Structure
Thumb
Synonyms
Synonym
Br2
Brom
Bromine gas
Bromine liquid
Dibromine
Chemical FormulaBr2
Average Molecular Mass159.808 g/mol
Monoisotopic Mass157.837 g/mol
CAS Registry Number7726-95-6
IUPAC Namedibromane
Traditional NameBrom
SMILESBrBr
InChI IdentifierInChI=1S/Br2/c1-2
InChI KeyInChIKey=GDTBXPJZTBHREO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of inorganic compounds known as homogeneous halogens. These are inorganic non-metallic compounds in which the largest atom is a nobel gas.
KingdomInorganic compounds
Super ClassHomogeneous non-metal compounds
ClassHomogeneous halogens
Sub ClassNot Available
Direct ParentHomogeneous halogens
Alternative ParentsNot Available
Substituents
  • Homogeneous halogen
Molecular FrameworkNot Available
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Microsome
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Metabolic PathwaysNot AvailableNot Available
ButyrophenonesNot AvailableNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateGas or Liquid
AppearanceRed liquid or orange vapour.
Experimental Properties
PropertyValue
Melting Point-7.25°C
Boiling Point59°C
Solubility35 mg/mL at 20 °C [MILLS, JF (1985)]
LogPNot Available
Predicted Properties
PropertyValueSource
logP1.38ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity17.47 m³·mol⁻¹ChemAxon
Polarizability6.64 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0900000000-910b678335ae6fededb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-bceda49410b6a9adda52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-bceda49410b6a9adda52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0900000000-bceda49410b6a9adda52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-ced64dc3e7ac6514aa80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-ced64dc3e7ac6514aa80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0900000000-ced64dc3e7ac6514aa80View in MoNA
Toxicity Profile
Route of ExposureOral (9) ; inhalation (9) ; dermal (9)
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. (9, 10, 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. (9)
Toxicity ValuesLD50: 85.2 ppm (Intraperitoneal, Rat) (2) LD50: 2600 mg/kg (Oral, Rat) (2) LC50: 750 ppm over 9 minutes (Inhalation, Mouse) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesBromine is used mainly in fire retardants and fine chemicals. Bromine salts have also been used as gasoline additives and pesticides. (8)
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. (8, 9, 10)
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. (9, 10)
TreatmentBromine should be washed with water from any areas of dermal or ocular contact. If inhaled, treatment is mainly symptomatic and may include maintaining an adequate airway, administering oxygen, antibronchospasm therapy, and/or antibiotics. (9)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB31434
PubChem Compound ID24408
ChEMBL IDNot Available
ChemSpider ID22817
KEGG IDC01324
UniProt IDNot Available
OMIM ID
ChEBI ID29224
BioCyc IDBR-
CTD IDD001966
Stitch IDBromine
PDB IDNot Available
ACToR ID8170
Wikipedia LinkBromine
References
Synthesis ReferenceNot Available
MSDSLink
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. Goodman AB: Retinoid receptors, transporters, and metabolizers as therapeutic targets in late onset Alzheimer disease. J Cell Physiol. 2006 Dec;209(3):598-603. [17001693 ]
  3. Lam KH, Gambari R, Yuen MC, Kan CW, Chan P, Xu L, Tang W, Chui CH, Cheng GY, Wong RS, Lau FY, Tong CS, Chan AK, Lai PB, Kok SH, Cheng CH, Chan AS, Tang JC: The preparation of 2,6-disubstituted pyridinyl phosphine oxides as novel anti-cancer agents. Bioorg Med Chem Lett. 2009 Apr 15;19(8):2266-9. doi: 10.1016/j.bmcl.2009.02.091. Epub 2009 Feb 27. [19321340 ]
  4. Gregoriadis GC, Apostolidis NS, Romanos AN, Paradellis TP: Postoperative changes in serum bromine value. Surg Gynecol Obstet. 1985 Mar;160(3):243-9. [3975796 ]
  5. European Chemicals Bureau (2007). IUCLID Dataset, Bromine (CAS # 7726-95-6).
  6. Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
  7. Duke, James A. (1992) Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
  8. Wikipedia. Bromine. Last Updated 9 June 2009. [Link]
  9. International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [Link]
  10. Wikipedia. Potassium bromide. Last Updated 9 June 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye. Contributes to intracellular pH regulation in the duodenal upper villous epithelium during proton-coupled peptide absorption. Stimulates the chloride-bicarbonate exchange activity of SLC26A6.
Gene Name:
CA2
Uniprot ID:
P00918
Molecular Weight:
29245.895 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory63000 uMNot AvailableBindingDB 26980
References
  1. Innocenti A, Zimmerman S, Ferry JG, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of the beta-class enzyme from the methanoarchaeon Methanobacterium thermoautotrophicum (Cab) with anions. Bioorg Med Chem Lett. 2004 Sep 6;14(17):4563-7. [15357993 ]
  2. Innocenti A, Lehtonen JM, Parkkila S, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of the newly isolated murine isozyme XIII with anions. Bioorg Med Chem Lett. 2004 Nov 1;14(21):5435-9. [15454240 ]
  3. Innocenti A, Firnges MA, Antel J, Wurl M, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of the membrane-bound human isozyme IV with anions. Bioorg Med Chem Lett. 2004 Dec 6;14(23):5769-73. [15501038 ]
  4. Innocenti A, Hilvo M, Parkkila S, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: the membrane-associated isoform XV is highly inhibited by inorganic anions. Bioorg Med Chem Lett. 2009 Feb 15;19(4):1155-8. doi: 10.1016/j.bmcl.2008.12.082. Epub 2008 Dec 25. [19128966 ]
  5. Bertucci A, Innocenti A, Scozzafava A, Tambutte S, Zoccola D, Supuran CT: Carbonic anhydrase inhibitors. Inhibition studies with anions and sulfonamides of a new cytosolic enzyme from the scleractinian coral Stylophora pistillata. Bioorg Med Chem Lett. 2011 Jan 15;21(2):710-4. doi: 10.1016/j.bmcl.2010.11.124. Epub 2010 Dec 4. [21208801 ]
  6. Luca VD, Vullo D, Scozzafava A, Carginale V, Rossi M, Supuran CT, Capasso C: An alpha-carbonic anhydrase from the thermophilic bacterium Sulphurihydrogenibium azorense is the fastest enzyme known for the CO2 hydration reaction. Bioorg Med Chem. 2013 Mar 15;21(6):1465-9. doi: 10.1016/j.bmc.2012.09.047. Epub 2012 Sep 29. [23078755 ]
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:
CA1
Uniprot ID:
P00915
Molecular Weight:
28870.0 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory4000 uMNot AvailableBindingDB 26980
References
  1. Innocenti A, Zimmerman S, Ferry JG, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of the beta-class enzyme from the methanoarchaeon Methanobacterium thermoautotrophicum (Cab) with anions. Bioorg Med Chem Lett. 2004 Sep 6;14(17):4563-7. [15357993 ]
  2. Innocenti A, Lehtonen JM, Parkkila S, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of the newly isolated murine isozyme XIII with anions. Bioorg Med Chem Lett. 2004 Nov 1;14(21):5435-9. [15454240 ]
  3. Innocenti A, Firnges MA, Antel J, Wurl M, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of the membrane-bound human isozyme IV with anions. Bioorg Med Chem Lett. 2004 Dec 6;14(23):5769-73. [15501038 ]
  4. Innocenti A, Hilvo M, Parkkila S, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: the membrane-associated isoform XV is highly inhibited by inorganic anions. Bioorg Med Chem Lett. 2009 Feb 15;19(4):1155-8. doi: 10.1016/j.bmcl.2008.12.082. Epub 2008 Dec 25. [19128966 ]
  5. Bertucci A, Innocenti A, Scozzafava A, Tambutte S, Zoccola D, Supuran CT: Carbonic anhydrase inhibitors. Inhibition studies with anions and sulfonamides of a new cytosolic enzyme from the scleractinian coral Stylophora pistillata. Bioorg Med Chem Lett. 2011 Jan 15;21(2):710-4. doi: 10.1016/j.bmcl.2010.11.124. Epub 2010 Dec 4. [21208801 ]
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid.
Gene Name:
CA4
Uniprot ID:
P22748
Molecular Weight:
35032.075 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory90 uMNot AvailableBindingDB 26980
Inhibitory52000 uMNot AvailableBindingDB 26980
References
  1. Innocenti A, Firnges MA, Antel J, Wurl M, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of the membrane-bound human isozyme IV with anions. Bioorg Med Chem Lett. 2004 Dec 6;14(23):5769-73. [15501038 ]
  2. Innocenti A, Hilvo M, Parkkila S, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: the membrane-associated isoform XV is highly inhibited by inorganic anions. Bioorg Med Chem Lett. 2009 Feb 15;19(4):1155-8. doi: 10.1016/j.bmcl.2008.12.082. Epub 2008 Dec 25. [19128966 ]
  3. Innocenti A, Zimmerman S, Ferry JG, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of the beta-class enzyme from the methanoarchaeon Methanobacterium thermoautotrophicum (Cab) with anions. Bioorg Med Chem Lett. 2004 Sep 6;14(17):4563-7. [15357993 ]
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide. Its role in saliva is unknown.
Gene Name:
CA6
Uniprot ID:
P23280
Molecular Weight:
35366.615 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory730 uMNot AvailableBindingDB 26980
References
  1. Bertucci A, Innocenti A, Scozzafava A, Tambutte S, Zoccola D, Supuran CT: Carbonic anhydrase inhibitors. Inhibition studies with anions and sulfonamides of a new cytosolic enzyme from the scleractinian coral Stylophora pistillata. Bioorg Med Chem Lett. 2011 Jan 15;21(2):710-4. doi: 10.1016/j.bmcl.2010.11.124. Epub 2010 Dec 4. [21208801 ]
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide.
Gene Name:
CA7
Uniprot ID:
P43166
Molecular Weight:
29658.235 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory1060 uMNot AvailableBindingDB 26980
References
  1. Vullo D, Ruusuvuori E, Kaila K, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of the cytosolic human isozyme VII with anions. Bioorg Med Chem Lett. 2006 Jun 15;16(12):3139-43. Epub 2006 Apr 18. [16621537 ]
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide. Participates in pH regulation. May be involved in the control of cell proliferation and transformation. Appears to be a novel specific biomarker for a cervical neoplasia.
Gene Name:
CA9
Uniprot ID:
Q16790
Molecular Weight:
49697.36 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory16000 uMNot AvailableBindingDB 26980
References
  1. Innocenti A, Firnges MA, Antel J, Wurl M, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: inhibition of the membrane-bound human isozyme IV with anions. Bioorg Med Chem Lett. 2004 Dec 6;14(23):5769-73. [15501038 ]
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]