<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">1811</id>
  <title>T3D1807</title>
  <common-name>o-Xylyl bromide</common-name>
  <description>o-Xylyl bromide, also known as methylbenzyl bromide or T-stoff, is a poisonous organic chemical compound, formerly used as a tear gas. Physically it is a colourless liquid (melting point 21 °C) with a pleasant aromatic odour. o-Xylyl bromide is highly toxic, irritant and lachrymatory, and has been incorporated in chemical weapons since the early months of World War I. The first extensive use of xylyl bromide was the firing by German forces of 18,000 "T-shells" at Russian positions in the Battle of Bolimów in January 1915. In the absence of clarification, the name "xylyl bromide" may refer to any one of 3 xylyl isomers (o-Xylyl, p-Xylyl, m-Xylyl) or a mixture of all three.</description>
  <cas>89-92-9</cas>
  <pubchem-id>6992</pubchem-id>
  <chemical-formula>C8H9Br</chemical-formula>
  <weight>183.988760</weight>
  <appearance>Colorless liquid.</appearance>
  <melting-point>21°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral (L626) ; inhalation (L626) ; dermal (L626)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Organobromide compounds such as o-Xylyl bromide are strong alkylating agents.  Consequently they can readily modify free thiols (cysteines) and methionine residues of the surfaces of proteins leading to the disruption of enzyme, transporter or membrane functions. One of the most probable protein targets is the TRPA1 ion channel that is expressed in sensory nerves (trigeminal nerve) of the eyes, nose, mouth and lungs.</mechanism-of-toxicity>
  <metabolism>Bromine 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. (L626)</metabolism>
  <toxicity></toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>No indication of carcinogenicity (not listed by IARC). (L135)</carcinogenicity>
  <use-source>Occupational exposure to xylyl bromide may occur through inhalation and dermal contact with this compound at workplaces where xylyl bromide is produced or used.</use-source>
  <min-risk-level></min-risk-level>
  <health-effects>Strong lachrymator. Strong irritant to eyes, skin and soft tissues. Highly toxic if inhaled, swallowed or absorbed through skin</health-effects>
  <symptoms>Causes severe eye and skin burns. Irritating to eyes, skin, and respiratory system. Acute exposure (ingestion or inhalation) can lead to coma, nausea, vomiting, and metabolic acidosis may occur.</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">2009-06-22T16:08:38Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:24:40Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia></wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id>CPD-1125</biocyc-id>
  <ctd-id></ctd-id>
  <stitch-id>o-Xylyl bromide</stitch-id>
  <drugbank-id></drugbank-id>
  <pdb-id></pdb-id>
  <actor-id></actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CC1=CC=CC=C1CBr</moldb-smiles>
  <moldb-formula>C8H9Br</moldb-formula>
  <moldb-inchi>InChI=1S/C8H9Br/c1-7-4-2-3-5-8(7)6-9/h2-5H,6H2,1H3</moldb-inchi>
  <moldb-inchikey>InChIKey=WGVYCXYGPNNUQA-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">185.061</moldb-average-mass>
  <moldb-mono-mass type="decimal">183.988762935</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Liquid</state>
  <logp></logp>
  <hmdb-id></hmdb-id>
  <chembl-id></chembl-id>
  <chemspider-id>6726</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>
