3-Aminobenzamide

3-Aminobenzamide
Names
	Preferred IUPAC name 3-Aminobenzamide
	Other names meta-Aminobenzamide; 3-AB; 3-ABA;
Identifiers
CAS Number	3544-24-9;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:64042;
ChemSpider	1583;
ECHA InfoCard	100.020.534
EC Number	222-586-9;
PubChem CID	1645;
CompTox Dashboard (EPA)	DTXSID90188922 ;
	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−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
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H315, H319, H335
Precautionary statements	P338, P351
NFPA 704 (fire diamond)	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 [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 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

^ ^a ^b 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.
^ 3-Aminobenzamide Product Information, Sigma-Aldrich, Accessed October 19, 2012
^ 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.

[Purnell1980-1] 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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