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7,12-Dimethylbenz(a)anthracene

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7,12-Dimethylbenz(a)anthracene
Names
IUPAC name 7,12-dimethylbenzophenanthrene
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.326 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C20H16/c1-13-16-8-5-6-9-17(16)14(2)20-18(13)12-11-15-7-3-4-10-19(15)20/h3-12H,1-2H3Key: ARSRBNBHOADGJU-UHFFFAOYSA-N
  • InChI=1/C20H16/c1-13-16-8-5-6-9-17(16)14(2)20-18(13)12-11-15-7-3-4-10-19(15)20/h3-12H,1-2H3Key: ARSRBNBHOADGJU-UHFFFAOYAX
SMILES
  • c32c(c1ccccc1c(c2ccc4c3cccc4)C)C
Properties
Chemical formula C20H16
Molar mass 256.34104
Melting point 122–123 °C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards T (Toxic)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

7,12-Dimethylbenz(a)anthracene is an immunosuppressor and a powerful organ-specific laboratory carcinogen. Also known as 7,12-dimethylbenzanthracene or DMBA, this substance is widely used in many research laboratories studying cancer. DMBA serves as a tumor initiator by making necessary mutations. Tumor promotion can be induced with treatments of TPA (12-O-tetradecanoylphorbol-13-acetate) in some models of two-stage carcinogenesis. This allows for a greatly accelerated rate of tumor growth, making many cancer studies possible.

References

  1. 7,12-Dimethylbenz(a)anthracene at Sigma-Aldrich
  2. Miyata M, Furukawa M, Takahashi K, Gonzalez FJ, Yamazoe Y. (2001) Mechanism of 7, 12-Dimethylbenzanthracene-Induced Immunotoxicity: Role of Metabolic Activation at the Target Organ. Jpn J Pharmacol 86:302-309. Link
  3. Sung YM, He G, Fischer, SM. (2005) Lack of Expression of the EP2 but not EP3 Receptor for Prostaglandin E2 Results in Suppression of Skin Tumor Development. Cancer Res 65:9304-9311
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