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Name Description
id 40
T3DB ID T3D0044
Name 1,2-Dibromo-3-chloropropane
Class SmallMolecule
Description 1,2-Dibromo-3-chloropropane is a manufactured chemical and the active ingredient in the nematicide Nemagon, also known as Fumazone. Nemagon is a soil fumigant formerly used in agriculture but banned to most areas today. (L126)
Categories "Pesticide", "Pollutant", "Airborne Pollutant", "Synthetic Toxin"
Types "Organic Compound", "Organochloride", "Pesticide", "Organobromide", "Bromide Compound", "Pollutant", "Synthetic Compound"
Synonyms "1,2-Dibromo-3-chloropropane (DBCP)", "1,2-Dibromochloropropane", "1,3-Dibromo-3-chloropropane", "1-Chloro-2,3-dibromopropane", "2,3-Dibromo-1-chloropropane", "3-Chloro-1,2-dibromopropane", "Fumagon", "Fumazone", "Gro-tone nematode granular", "Nemabrom", "Nemafume", "Nemagon", "Nemagon soil fumigant", "Nemagone", "Nemanax", "Nemanex", "Nemapaz", "Nemaset", "Nematocide", "Nematox", "Nemazon"
CAS Number 96-12-8
Chemical Formula C3H5Br2Cl
Average Molecular Mass 236.33
Monoisotopic Mass 233.84
IUPAC Name 1,2-dibromo-3-chloropropane
Traditional Name 1,2-dibromo-3-chloropropane
InChI Identifier InChI=1/C3H5Br2Cl/c4-1-3(5)2-6/h3H,1-2H2
Kingdom Organic Compounds
Super Class Organohalogen Compounds
Class Organochlorides
Sub Class
Direct Parent Organochlorides
Alternate Parents "Organobromides", "Alkyl Chlorides", "Alkyl Bromides"
Geometric Description Aliphatic Acyclic Compounds
Substituents "organochloride", "alkyl chloride", "organobromide", "alkyl bromide", "Aliphatic Acyclic Compound", "Alkyl Halide"
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Cytosol", "Membrane", "Microsome", "Mitochondrion"
Pathways "Apoptosis"
State Liquid
Appearance Colorless liquid.
Melting Point 6°C
Boiling Point
Solubility 1.23 mg/mL at 20 °C [MUNNECKE,DE & VANGUNDY,SD (1979)]
Route of Exposure Oral (L125) ; inhalation (L125) ; dermal (L125)
Mechanism of Toxicity The initial metabolism of 1,2-dibromo-3-chloropropane to reactive epoxide metabolites that bind to DNA and other macromolecules may be responsible for its hepatotoxicity and nephrotoxicity. The mechanism of 1,2-dibromo-3-chloropropane's testicular toxicity is believed to be due to either the inhibition of sperm carbohydrate metabolism, probably at the step of nicotinamide adenine dinucleotide (NADH) dehydrogenase activity in the mitochondrial electron transport chain, or drect DNA damage caused by its metabolites. (L125, A13)
Metabolism 1,2-Dibromo-3-chloropropane is absorbed via oral, inhalation, and dermal routes. It accumulates mainly in the kidney, liver, and adipose tissues. 1,2-Dibromo-3-chloropropane is intially converted to epoxy derivatives, which are further hydrolyzed and debrominated. Glutathione (GSH) conjugation of epoxide intermediates in the liver is believed to produce precursors to toxic intermediates. The metabolites are excreted mainly in the urine. (L125)
Toxicity LD50: 100 mg/kg (Oral, Rabbit) (T25) LC50: 1480 mg/m3 over 1 hour (Inhalation, Rat) (T25)
Lethal Dose
Carcinogenicity 2B, possibly carcinogenic to humans. (L135)
Uses/Sources 1,2-Dibromo-3-chloropropane is the active ingredient in the nematicide Nemagon, also known as Fumazone. Nemagon is a soil fumigant formerly used in agriculture. (L125)
Minimum Risk Level Intermediate Inhalation: 0.0002 ppm (L134) Intermediate Oral: 0.002 mg/kg/day (L134)
Health Effects Breathing high levels of 1,2-dibromo-3-chloropropane causes reproductive damage, including reduced sperm counts, birth defects, and infertility. It may also damage the stomach, liver, kidneys, brain, spleen, blood, and lungs, and cause skin and eye damage from direct contact. (L125)
Symptoms Symptoms of 1,2-dibromo-3-chloropropane exposure include headaches, nausea, lightheadedness, and weakness. (L125)
Treatment EYES: 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.
DrugBank ID
PubChem Compound ID 7280
ChemSpider ID 136192
KEGG Compound ID C14336
UniProt ID 0
CTD ID C007318
Stitch ID 1,2-Dibromo-3-chloropropane
ACToR ID 416
Wikipedia Link http://en.wikipedia.org/wiki/1,2-Dibromo-3-chloropropane
Creation Date 2009-03-06 18:57:58
Update Date 2014-12-24 20:20:57