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Name Description
id 31
T3DB ID T3D0035
Name 1,2-Dibromoethane
Class SmallMolecule
Description 1,2-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.
Categories "Pesticide", "Industrial/Workplace Toxin", "Pollutant", "Airborne Pollutant", "Synthetic Toxin"
Types "Organic Compound", "Organochloride", "Gasoline Additive/Component", "Pesticide", "Organobromide", "Bromide Compound", "Pollutant", "Metabolite", "Industrial/Workplace Toxin", "Synthetic Compound"
Synonyms "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"
CAS Number 106-93-4
Chemical Formula C2H4Br2
Average Molecular Mass 187.86
Monoisotopic Mass 185.87
IUPAC Name 1,2-dibromoethane
Traditional Name dibromoethane
SMILES BrCCBr
InChI Identifier InChI=1S/C2H4Br2/c3-1-2-4/h1-2H2
InChI Key InChIKey=PAAZPARNPHGIKF-UHFFFAOYSA-N
Kingdom Organic Compounds
Super Class Organohalogen Compounds
Class Organobromides
Sub Class
Direct Parent Alkyl Bromides
Alternate Parents "Alkyl Bromides"
Geometric Description Aliphatic Acyclic Compounds
Substituents "organobromide", "alkyl bromide", "Aliphatic Acyclic Compound", "Alkyl Halide"
Descriptors "bromoalkane (ChEBI)", "a bromide (MetaCyc)"
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Cytoplasm", "Extracellular"
Biofluids
Tissues
Pathways
State Liquid
Appearance Colorless liquid.
Melting Point 9.9°C
Boiling Point
Solubility 3.91 mg/mL at 25 °C [HORVATH,AL et al. (1999)]
LogP
Route of Exposure Oral (L120) ; inhalation (L120) ; dermal (L120)
Mechanism of Toxicity The 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. (L120)
Metabolism 1,2-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. (L120)
Toxicity LD50: 108 mg/kg (Oral, Rat) (T14) LD50: 300 mg/kg (Dermal, Rat) (T14) LD50: 220 mg/kg (Intraperitoneal, Mouse) (T14) LC50: 14 300 mg/m3 over 30 minutes (Inhalation, Rat) (T14)
Lethal Dose
Carcinogenicity 2A, probably carcinogenic to humans. (L135)
Uses/Sources 1,2-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. (L120)
Minimum Risk Level
Health Effects Long term exposure can result in liver, kidney, and reproductive system damage. 1,2-Dibromoethane is also known to have adverse effects on the brain. (L120)
Symptoms Redness 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. (L120)
Treatment
DrugBank ID
HMDB ID HMDB60334
PubChem Compound ID 7839
ChEMBL ID CHEMBL452370
ChemSpider ID 7551
KEGG Compound ID C11088
UniProt ID 0
OMIM ID 0
ChEBI ID 28534
BioCyc ID CPD-8985
CTD ID D015946
Stitch ID 1,2-Dibromoethane
PDB ID
ACToR ID 418
Wikipedia Link
Creation Date 2009-03-06 18:57:57
Update Date 2014-12-24 20:20:56