3-Aminobenzamide

3-Aminobenzamide
Names
Other names
  • meta-Aminobenzamide
  • 3-AB
  • 3-ABA
Identifiers
3544-24-9
ChEBI CHEBI:64042
ChemSpider 1583
EC Number 222-586-9
Jmol interactive 3D Image
PubChem 1645
Properties
C7H8N2O
Molar mass 136.15 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
Xi
R-phrases R36/37/38
S-phrases S26-36
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
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

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

Preparation

3-Aminobenzamide can be prepared though the catalytic hydrogenation of 3-nitrobenzamide.[1]

Uses

It is known since 1980[2] that 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 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.[3] 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.[4]

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. ↑ Purnell, MR; Whish, WJ (1980). "Novel inhibitors of poly(ADP-ribose) synthetase". Biochemical Journal 185 (3): 775–777. doi:10.1042/bj1850775. PMC 1161458. PMID 6248035.
  3. ↑ 3-Aminobenzamide Product Information, Sigma-Aldrich, Accessed October 19, 2012
  4. ↑ 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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