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<compound>
  <id type="integer">1995</id>
  <title>T3D1991</title>
  <common-name>2,2',3,3',4,4',5',6-Octabromobiphenyl</common-name>
  <description>2,2',3,3',4,4',5',6-Octabromobiphenyl belongs to the biphenyls and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. With an average molecular weight of 785.38 g/mol, 2,2',3,3',4,4',5',6-Octabromobiphenyl is a heavy molecule. This exogenous compound has the formula C12H2Br8 and exists as a solid at room temperature.

It acts on the aryl hydrocarbon receptor (AHR), which it binds to and activates. This process initiates the transcriptional upregulation of several genes, including the cytochrome P-450-dependent monooxygenases CYP1A1 and CYP1A2. Such activity affects cell cycle regulation, oxidative stress response, morphogenesis, and biochemical and endocrine pathways, resulting in toxic responses.</description>
  <cas>69278-61-1</cas>
  <pubchem-id>155279</pubchem-id>
  <chemical-formula>C12H2Br8</chemical-formula>
  <weight>777.362350</weight>
  <appearance>Colorless to white powder.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral (L628) ; inhalation (L628) ; dermal (L628)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>The exact mechanism of toxicty of PBBs varies depending on the specific congener. The predominant interaction is believed to involve the aryl hydrocarbon receptor (AhR). PBBs bind to and activate the AhR, which in turn initiates the transcriptional upregulation of a number of genes, affecting biochemical and endocrine pathways, cell cycle regulation, morphogenesis, oxidative stress response, and various other processes. This results in the numerous toxic responses characteristic of PBBs. Some of the known induced genes include the cytochrome P-450-dependent monooxygenases CYP1A1 and CYP1A2. (L628)</mechanism-of-toxicity>
  <metabolism>PBBs can be absorbed via oral, inhalation, and dermal routes. Due to their lipophilic nature, PBBs, especially the highly brominated congeners, tend to accumulate in lipid-rich tissues such as the liver, adipose, skin, and breast milk. Certain PBB compounds are metabolized by the microsomal monooxygenase system catalyzed by cytochrome P-450 of the type induced by phenobarbital. The rate of metabolism may depends on the bromine substitution pattern. PBB congeners of low bromine content are transformed into hydroxylated derivatives that are predominately eliminated in the urine. Highly brominated congeners are either retained or excreted unchanged in the feces. (L628) </metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>2A, probably carcinogenic to humans. (L135)</carcinogenicity>
  <use-source>PBBs can be used as flame retardants and may be added to the plastics used to make products like computer monitors, televisions, textiles, and plastic foams to make them difficult to burn. However, the use of PBBs is banned or restricted in most areas due to their toxicity and persistence in the environment. (L628, L629) </use-source>
  <min-risk-level>Acute Oral: 0.01 mg/kg/day (L134) </min-risk-level>
  <health-effects>PBB exposure may cause weight loss, skin disorders (such as acne), nervous and immune systems effects, and effects on the liver, kidneys, and thyroid gland. (L628) </health-effects>
  <symptoms>Symptoms of PBB exposure may include nausea, abdominal pain, loss of appetite, joint pain, fatigue, and weakness. (L629) </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">2009-06-24T17:05:49Z</created-at>
  <updated-at type="dateTime">2026-08-27T22:05:58Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>2,2',3,3',4,4',5',6-Octabromobiphenyl</stitch-id>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>BrC1=CC(Br)=C(C(Br)=C1Br)C1=CC(Br)=C(Br)C(Br)=C1Br</moldb-smiles>
  <moldb-formula>C12H2Br8</moldb-formula>
  <moldb-inchi>InChI=1S/C12H2Br8/c13-4-2-6(15)9(17)11(19)7(4)3-1-5(14)10(18)12(20)8(3)16/h1-2H</moldb-inchi>
  <moldb-inchikey>MOIDFYBXINJWHO-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">785.376</moldb-average-mass>
  <moldb-mono-mass type="decimal">777.36235124</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>9.1</logp>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id>136789</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"/>
  <chemdb-id>CHEM001738</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00123528</susdat-id>
  <iupac>1,2,3,4-tetrabromo-5-(2,3,4,6-tetrabromophenyl)benzene</iupac>
  <moldb-polar-surface-area>0</moldb-polar-surface-area>
  <moldb-refractivity>112.17660000000001</moldb-refractivity>
  <moldb-polarizability>44.146638399819</moldb-polarizability>
  <moldb-rotatable-bond-count>0</moldb-rotatable-bond-count>
  <moldb-acceptor-count>0</moldb-acceptor-count>
  <moldb-donor-count>0</moldb-donor-count>
  <moldb-pka-strongest-acidic nil="true"/>
  <moldb-pka-strongest-basic nil="true"/>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>2</moldb-number-of-rings>
  <moldb-alogps-logp>7.39</moldb-alogps-logp>
  <moldb-alogps-logs>-7.36</moldb-alogps-logs>
  <moldb-alogps-solubility>3.40e-05 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Benzenoids</superklass>
  <klass>Benzene and substituted derivatives</klass>
  <subklass>Biphenyls and derivatives</subklass>
  <paper-count type="integer">0</paper-count>
  <sync-id>CED0167373</sync-id>
  <structure-inchikey>MOIDFYBXINJWHO-UHFFFAOYSA-N</structure-inchikey>
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</structure-pickle>
  <structure-indexed-at type="dateTime">2026-09-19T04:00:19Z</structure-indexed-at>
</compound>
