3-Aminobenzamide

3-Aminobenzamide Basic information
Product Name:3-Aminobenzamide
Synonyms:m-Amino Benzamide 3-Amino Benzamide;3-AB, 3-ABA;3-Aminobenzamide,3-AB, 3-ABA;INO-1001;3-AMinobenzaMide, 98% 1GR;3-AMinobenzaMide, 98% 5GR;Benzamide, 3-amino- (9CI);3-Aminobenzamide,98%
CAS:3544-24-9
MF:C7H8N2O
MW:136.15
EINECS:222-586-9
Product Categories:A-AM;Amides;Bioactive Small Molecules;AMIDE;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Inhibitors;Inhibitor;Building Blocks;Carbonyl Compounds;Cell Biology;Chemical Synthesis;Organic Building Blocks
Mol File:3544-24-9.mol
3-Aminobenzamide Structure
3-Aminobenzamide Chemical Properties
Melting point 115-116 °C (lit.)
Boiling point 250.42°C (rough estimate)
density 1.1778 (rough estimate)
refractive index 1.5769 (estimate)
storage temp. room temp
solubility ethanol: 50 mg/mL, clear, faintly yellow
form powder
pka16.26±0.50(Predicted)
color white to off-white
Water Solubility Soluble in dimethylformamide (~30 mg/ml), dimethyl sulfoxide (~30 mg/ml), phosphate buffered saline (pH7.2) (~2 mg/ml), water (25 mg/ml), and ethanol (25 mg/ml).
Sensitive Light Sensitive
BRN 2802373
Stability:Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
LogP-0.330
CAS DataBase Reference3544-24-9(CAS DataBase Reference)
NIST Chemistry Reference3-NH2-C6H4CONH2(3544-24-9)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36-37/39
RIDADR 3077
WGK Germany 3
RTECS CU8992000
HS Code 29242990
Hazardous Substances Data3544-24-9(Hazardous Substances Data)
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
3-Aminobenzamide Usage And Synthesis
DescriptionThe poly(ADP-ribose) polymerases (PARPs) comprise a family of enzymes which post-translationally modify proteins by poly(ADP-ribosyl)ation. Since some PARPs are activated by DNA strand breaks, PARP signaling has roles in DNA repair, apoptosis, inflammation, and other cellular responses. 3-amino Benzamide is an inhibitor of PARPs (Ki = 1.8 μM). Through its effects on PARPs, 3-amino benzamide causes telomere shortening and stimulates angiogenesis. It has PARP-mediated actions in such diverse diseases as atherosclerosis, neurogenesis, and cancer.
Chemical Propertiesbeige powder
UsesThe poly(ADP-ribose) polymerases (PARPs) comprise a family of enzymes which post-translationally modify proteins by poly(ADP-ribosyl)ation. Since some PARPs are activated by DNA strand breaks, PARP signaling has roles in DNA repair, apoptosis, inflammation, and other cellular responses. 3-amino Benzamide is an inhibitor of PARPs (Ki = 1.8 μM). Through its effects on PARPs, 3-amino benzamide causes telomere shortening and stimulates angiogenesis. It has PARP-mediated actions in such diverse diseases as atherosclerosis, neurogenesis, and cancer.
Uses3-Aminobenzamide is used as an endogenous poly-ADP-ribosyltransferase inhibitor. Through its effects on PARPs, 3-amino benzamide causes telomere shortening and stimulates angiogenesis. It displays neuroprotective, anti-necrotic effects.
DefinitionChEBI: A substituted aniline that is benzamide in which one of the meta- hydrogens is replaced by an amino group.
Biochem/physiol Actions3-Aminobenzamide enhances cell death, unscheduled DNA synthesis and repair replication by interrupting the rejoining of DNA strand breaks induced by both ionizing radiations and several alkylating agents. It has an ability to inhibit the activity of nuclear enzyme poly (ADP-ribose) synthetase (PARS). 3-Aminobenzamide exhibits protective action against myocardial reperfusion injury and local inflammation.
References1) Purnell and Whish (1980), Novel inhibitors of poly(ADP-ribose) synthetase; Biochem. J., 185 775 2) Kuo et al. (1996), Inhibitors of poly(ADP-ribose) polymerase block nitric oxide-induced apoptosis but not differentiation in human leukemia HL-60 cells; Biochem. Biophys. Res. Commun., 219 502 3) Malorni et al. (1995), 3-Aminobenzamide protects cells from UV-B-induced apoptosis by acting on cytoskeleton and substrate adhesion; Biochem. Biophys. Res. Commun., 207 715 4) Heller et al. (1995), Inactivation of the poly(ADP-ribose) polymerase gene affects oxygen radical and nitric oxide toxicity in islet cells; J. Biol. Chem., 270 11176
3-Aminobenzamide Preparation Products And Raw materials
Raw materialsDichloromethane-->Sodium sulfate-->Aluminum oxide-->Methanesulfonic acid-->3-Aminobenzonitrile
Preparation Products3-NITROSOBENZAMIDE-->tert-Butyl 3-aminobenzylcarbamate
3-NITROBENZANILIDE N-[3-(acetylamino)phenyl]-2-aminobenzamide 1,2-DIHYDRO-5-NITROINDAZOL-3-ONE N1-[2-(4-pyridyl)ethyl]-2-aminobenzamide 4-AMINO-3,5-DINITROBENZAMIDE N-{4-[Acetyl(methyl)amino]phenyl}-3-aminobenzamide N-(3,5-DINITROBENZOYL)-DL-LEUCINE 4-CHLORO-3-NITROBENZANILIDE 2-[2-HYDROXY-3-(2,4-XYLYLCARBAMOYL)-1-NAPHTHYLAZO]PHENOL N1-(2-thienylmethyl)-2-aminobenzamide 3-Nitrophthalhydrazide 4-AMINO-N-METHYLPHTHALIMIDE N-{4-[Acetyl(methyl)amino]phenyl}-4-aminobenzamide 4-Nitrophthalhydrazide N-[4-(Acetylamino)phenyl]-4-aminobenzamide N-(4-Aminobutyl)-N-ethylisoluminol 2-[2-(4-AMINOBENZAMIDE)ETHYLSULFONYL]ETHANOL HYDROGEN SULFATE ESTER N,N-Diallyl-3-aminobenzamide

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