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3-Aminobenzamide

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3-Aminobenzamide
Names
Preferred IUPAC name 3-Aminobenzamide
Other names
  • meta-Aminobenzamide
  • 3-AB
  • 3-ABA
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.020.534 Edit this at Wikidata
EC Number
  • 222-586-9
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H8N2O/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,8H2,(H2,9,10)
SMILES
  • C1=CC(=CC(=C1)N)C(=O)N
Properties
Chemical formula C7H8N2O
Molar mass 136.154 g·mol
Appearance Off-white powder
Density 1.233g/cm
Melting point 115 to 116 °C (239 to 241 °F; 388 to 389 K)
Boiling point 329 °C (624 °F; 602 K)
log P 0.33
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Danger
Hazard statements H302, H315, H319, H335
Precautionary statements P338, P351
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2 0 0
Lethal dose or concentration (LD, LC):
LD50 (median dose) 1000mg/kg (oral, bird)
Safety data sheet (SDS) Sigma-Aldrich
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

3-Aminobenzamide is a benzamide. It is an off-white powder and has the chemical formula C7H8N2O.

Preparation

3-Aminobenzamide can be prepared through the reduction of 3-nitrobenzamide by catalytic hydrogenation.

Uses

3-Aminobenzamide is an inhibitor of poly ADP ribose polymerase (PARP), an enzyme responsible for DNA repair, transcription control, and programmed cell death. When PARP is activated it rapidly uses up stores of nicotinamide adenine dinucleotide (NAD) in the cell as it performs DNA repair. Low levels of NAD deplete the amount of ATP found in the cell which can lead to cell death. The structure of 3-aminobenzamide is similar to that of NAD so it binds to PARP and prevents it from using up NAD. PARP is often a target of cancer therapy and so 3-aminobenzamide could potentially be used as an anticancer drug.

References

  1. ^ Purnell, M. R; Whish, W. J. D. (1980). "Novel inhibitors of poly(ADP-ribose) synthetase". Biochem. J. 185 (3): 775–777. doi:10.1042/bj1850775. PMC 1161458. PMID 6248035.
  2. 3-Aminobenzamide Product Information Archived 2016-02-03 at the Wayback Machine, Sigma-Aldrich, Accessed October 19, 2012
  3. Karlberg, T.; Hammarström, M.; Schütz, P.; Scensson, L.; Schüler, H. (2010). "Crystal Structure of the catalytic domain of human PARP2 in complex with PARP inhibitor ABT-888". Biochemistry. 49 (6): 1056–1058. doi:10.1021/bi902079y. PMID 20092359.
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