<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">45</id>
  <title>T3D0044</title>
  <common-name>1,2-Dibromo-3-chloropropane</common-name>
  <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)</description>
  <cas>96-12-8</cas>
  <pubchem-id>7280</pubchem-id>
  <chemical-formula>C3H5Br2Cl</chemical-formula>
  <weight>233.844650</weight>
  <appearance>Colorless liquid.</appearance>
  <melting-point>6°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility>1.23 mg/mL at 20 °C [MUNNECKE,DE &amp; VANGUNDY,SD (1979)]</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral (L125) ; inhalation (L125) ; dermal (L125)</route-of-exposure>
  <target nil="true"/>
  <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)</mechanism-of-toxicity>
  <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)</metabolism>
  <toxicity>LD50: 100 mg/kg (Oral, Rabbit) (T25)
LC50: 1480 mg/m3 over 1 hour (Inhalation, Rat) (T25)</toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>2B, possibly carcinogenic to humans. (L135)</carcinogenicity>
  <use-source>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)</use-source>
  <min-risk-level>Intermediate Inhalation: 0.0002 ppm (L134)
Intermediate Oral: 0.002 mg/kg/day (L134)</min-risk-level>
  <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)</health-effects>
  <symptoms>Symptoms of 1,2-dibromo-3-chloropropane exposure include headaches, nausea, lightheadedness, and weakness. (L125)</symptoms>
  <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.</treatment>
  <created-at type="dateTime">2009-03-06T18:57:58Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:20:57Z</updated-at>
  <interacting-proteins>Glutathione S-transferase P (P09211) 
Glutathione S-transferase Mu 1 (P09488) 
Glutathione S-transferase A1 (P08263) 
Glutathione S-transferase theta-2 (P30712) 
Glutathione S-transferase Mu 4 (Q03013) 
Glutathione S-transferase theta-1 (P30711) 
Glutathione S-transferase A4 (O15217) 
Glutathione S-transferase A2 (P09210) 
Glutathione S-transferase A3 (Q16772) 
Glutathione S-transferase Mu 3 (P21266) 
Glutathione S-transferase omega-1 (P78417) 
Glutathione S-transferase kappa 1 (Q9Y2Q3) 
Glutathione S-transferase Mu 2 (P28161) 
Glutathione S-transferase omega-2 (Q9H4Y5) 
Glutathione S-transferase A5 (Q7RTV2) 
Glutathione S-transferase Mu 5 (P46439) 
Glutathione S-transferase theta-4 (A8MPT4) 
Maleylacetoacetate isomerase (O43708) 
Microsomal glutathione S-transferase 1 (P10620) 
Microsomal glutathione S-transferase 2 (Q99735) 
Microsomal glutathione S-transferase 3 (O14880) 
(L125)</interacting-proteins>
  <wikipedia>http://en.wikipedia.org/wiki/1,2-Dibromo-3-chloropropane</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C14336</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id>BETA-AMINOPROPIONITRILE</biocyc-id>
  <ctd-id>C007318</ctd-id>
  <stitch-id>1,2-Dibromo-3-chloropropane</stitch-id>
  <drugbank-id></drugbank-id>
  <pdb-id></pdb-id>
  <actor-id>416</actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins>Glutathione S-transferase P (P09211) 
Glutathione S-transferase Mu 1 (P09488) 
Glutathione S-transferase A1 (P08263) 
Glutathione S-transferase theta-2 (P30712) 
Glutathione S-transferase Mu 4 (Q03013) 
Glutathione S-transferase theta-1 (P30711) 
Glutathione S-transferase A4 (O15217) 
Glutathione S-transferase A2 (P09210) 
Glutathione S-transferase A3 (Q16772) 
Glutathione S-transferase Mu 3 (P21266) 
Glutathione S-transferase omega-1 (P78417)
Glutathione S-transferase kappa 1 (Q9Y2Q3)
Glutathione S-transferase Mu 2 (P28161) 
Glutathione S-transferase omega-2 (Q9H4Y5)
Glutathione S-transferase A5 (Q7RTV2) 
Glutathione S-transferase Mu 5 (P46439) 
Glutathione S-transferase theta-4 (A8MPT4)
Maleylacetoacetate isomerase (O43708) 
Microsomal glutathione S-transferase 1 (P10620) 
Microsomal glutathione S-transferase 2 (Q99735) 
Microsomal glutathione S-transferase 3 (O14880) 
(L125)</metabolizing-proteins>
  <transporting-proteins nil="true"/>
  <moldb-smiles>ClCC(Br)CBr</moldb-smiles>
  <moldb-formula>C3H5Br2Cl</moldb-formula>
  <moldb-inchi>InChI=1/C3H5Br2Cl/c4-1-3(5)2-6/h3H,1-2H2</moldb-inchi>
  <moldb-inchikey>InChIKey=WBEJYOJJBDISQU-UHFFFAOYNA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">236.333</moldb-average-mass>
  <moldb-mono-mass type="decimal">233.844653161</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Liquid</state>
  <logp></logp>
  <hmdb-id></hmdb-id>
  <chembl-id></chembl-id>
  <chemspider-id>136192</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
