Tmic
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Toxin, Toxin Target Database.
Record Information
Version2.0
Creation Date2009-03-06 18:57:57 UTC
Update Date2014-12-24 20:20:56 UTC
Accession NumberT3D0035
Identification
Common Name1,2-Dibromoethane
ClassSmall Molecule
Description1,2-Dibromoethane, also known as ethylene dibromide (EDB), is the organobromine compound with the chemical formula (CH2Br)2. Although trace amounts occur naturally in the ocean, where it is formed probably by algae and kelp, it is mainly synthetic. It is a colorless liquid with a sweet odor, detectable at 10 ppm, is a widely used and sometimes-controversial fumigant. The effects on people of breathing high levels are not known, but animal studies with short-term exposures to high levels caused depression and collapse, indicating effects on the brain.
Compound Type
  • Bromide Compound
  • Gasoline Additive/Component
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Organobromide
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
1,2,Dibromoethane
1,2-Dibromoethane(Ethylene bromide)
1,2-Dibromomethane
1,2-Ethylene dibromide
Alpha,beta-dibromoethane
Alpha,omega-dibromoethane
Bromofume
Celmide
DBE
Dibromoethane
Dibromoethylene
Dowfume
Edabrom
EDB
Ethylene Bromide
Ethylene Dibromide
Garden dowfume
Glycol bromide
Glycol dibromide
Iscobrome D
Kopfume
Nefis
Nephis
Sanhyuum
Soilbrom
Soilfume
SYM dibromoethane
SYM-dibromoethane
Unifume
Chemical FormulaC2H4Br2
Average Molecular Mass187.861 g/mol
Monoisotopic Mass185.868 g/mol
CAS Registry Number106-93-4
IUPAC Name1,2-dibromoethane
Traditional Namedibromoethane
SMILESBrCCBr
InChI IdentifierInChI=1S/C2H4Br2/c3-1-2-4/h1-2H2
InChI KeyInChIKey=PAAZPARNPHGIKF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as organobromides. These are compounds containing a chemical bond between a carbon atom and a bromine atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassOrganobromides
Sub ClassNot Available
Direct ParentOrganobromides
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Organobromide
  • Alkyl halide
  • Alkyl bromide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point9.9°C
Boiling PointNot Available
Solubility3.91 mg/mL at 25 °C [HORVATH,AL et al. (1999)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.06 g/LALOGPS
logP2.08ALOGPS
logP1.87ChemAxon
logS-1.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity26.62 m³·mol⁻¹ChemAxon
Polarizability10.74 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-0900000000-2ee3f4bc49d4cb3289c7View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-5900000000-0f8e5929b65c18ffe174View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-0900000000-2ee3f4bc49d4cb3289c7View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-5900000000-0f8e5929b65c18ffe174View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-3900000000-703ca88896dc7f353fc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-9059cc10a7a8eb687facView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-ee5e7d28ff43cd849c39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0900000000-2578b34097bd653c4d1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-51a6eb4c9e7aa0216f9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-541ce06a61a5a4e27f0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0900000000-c16dec5f28cf43cf1857View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a6r-7900000000-505389611033d5f531b3View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureOral (3) ; inhalation (3) ; dermal (3)
Mechanism of ToxicityThe metabolite 2-bromoacetaldehyde produces liver damage by binding to cellular proteins. S-(2-bromoethyl)glutathione, another metabolite, exerts genotoxic and carcinogenic effects by binding to DNA. Antispermatogenic effects of 1,2-dibromoethanes metabolites may be caused by their covalent binding to thiol groups of nucleoproteins in nuclei of spermatozoa. Such adduct formation interferes with DNA, causing improper packing of the chromatin. (3)
Metabolism1,2-Dibromoethane is rapidly absorbed by ingestion, inhalation, and dermal routes, then distributed mainly to the kidneys, liver, and spleen. It can be metabolized by either the cytochrome P-450 system or the glutathione S-transferase system. Many of the metabolites are toxic, and include 2-bromoacetaldehyde and S-(2-bromoethyl)glutathione. These metabolites may be further broken down and excreted in the urine. (3)
Toxicity ValuesLD50: 108 mg/kg (Oral, Rat) (2) LD50: 300 mg/kg (Dermal, Rat) (2) LD50: 220 mg/kg (Intraperitoneal, Mouse) (2) LC50: 14 300 mg/m3 over 30 minutes (Inhalation, Rat) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2A, probably carcinogenic to humans. (4)
Uses/Sources1,2-Dibromoethane was once widely used as an additive in leaded gasoline and a pesticide, however, today it's use is restricted to only certain pesticides (treatment of logs for termites and beetles, control of moths in beehives) and dye preparations. (3)
Minimum Risk LevelNot Available
Health EffectsLong term exposure can result in liver, kidney, and reproductive system damage. 1,2-Dibromoethane is also known to have adverse effects on the brain. (3)
SymptomsRedness and inflammation, including skin blisters and mouth and stomach ulcers, can occur if large amounts of 1,2-dibromoethane are swallowed. Breathing high levels may cause depression and collapse. (3)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB60334
PubChem Compound ID7839
ChEMBL IDCHEMBL452370
ChemSpider ID7551
KEGG IDC11088
UniProt IDNot Available
OMIM ID
ChEBI ID28534
BioCyc IDCPD-8985
CTD IDD015946
Stitch ID1,2-Dibromoethane
PDB IDNot Available
ACToR ID418
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D0035.pdf
General References
  1. Magrane M, Consortium U: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [21447597 ]
  2. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  3. ATSDR - Agency for Toxic Substances and Disease Registry (1992). Toxicological profile for 1,2-dibromoethane. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  4. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
  2. Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors α and β: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
Gene Name:
ESR2
Uniprot ID:
Q92731
Molecular Weight:
59215.765 Da
References
  1. Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
  2. Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors α and β: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.
3. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1992). Toxicological profile for 1,2-dibromoethane. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
General Function:
Methyltransferase activity
Specific Function:
Involved in the cellular defense against the biological effects of O6-methylguanine (O6-MeG) in DNA. Repairs alkylated guanine in DNA by stoichiometrically transferring the alkyl group at the O-6 position to a cysteine residue in the enzyme. This is a suicide reaction: the enzyme is irreversibly inactivated.
Gene Name:
MGMT
Uniprot ID:
P16455
Molecular Weight:
21645.83 Da
References
  1. Liu L, Pegg AE, Williams KM, Guengerich FP: Paradoxical enhancement of the toxicity of 1,2-dibromoethane by O6-alkylguanine-DNA alkyltransferase. J Biol Chem. 2002 Oct 4;277(40):37920-8. Epub 2002 Jul 31. [12151404 ]
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
References
  1. Kaphalia BS, Ansari GA: Covalent binding of ethylene dibromide and its metabolites to albumin. Toxicol Lett. 1992 Sep;62(2-3):221-30. [1412507 ]