3-Aminobenzamide

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

3-Aminobenzamide
Names
Preferred IUPAC name
3-Aminobenzamide
Other names
  • meta-Aminobenzamide
  • 3-AB
  • 3-ABA
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.020.534
EC Number
  • 222-586-9
UNII
Properties
C7H8N2O
Molar mass 136.154 g·mol−1
Appearance Off-white powder
Density 1.233g/cm3
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
Safety data sheet Sigma-Aldrich
GHS pictograms
GHS Signal word Danger
H302, H315, H319, H335
P351, P338
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
2
0
Lethal dose or concentration (LD, LC):
1000mg/kg (oral, bird)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Preparation

3-Aminobenzamide can be prepared through the reduction of 3-nitrobenzamide by catalytic hydrogenation.[1]

Uses

3-Aminobenzamide is an inhibitor of poly ADP ribose polymerase (PARP), an enzyme responsible for DNA repair, transcription control, and programmed cell death.[1] 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.[2] 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.[3]

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, 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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