| Identification | More | [Name]
1-Aminobenzotriazole | [CAS]
1614-12-6 | [Synonyms]
1-AMINOBENZOTRIAZOLE
1-BENZOTRIAZOLAMINE
1H-1,2,3-BENZOTRIAZOL-1-YLAMINE
ABT
RARECHEM AQ NN 0550
TIMTEC-BB SBB004208
1-Benzotriazolylamine
1H-Benzotriazol-1-amine
1H-Benzotriazole,1-amino-
Benzotriazol-1-ylamine
1-Aminobenzotriazole 97%
ABT, 1-Benzotriazoleamine
1-Benzotriazolamine, ABT
1-(Thiophen-2-yl)-4-[(2-aminoethyl)amino]-1-butanone
4-[(2-Aminoethyl)amino]-1-(2-thienyl)butan-1-one
1-Amino-1H-benzotriazole | [Molecular Formula]
C6H6N4 | [MDL Number]
MFCD00132902 | [Molecular Weight]
134.14 | [MOL File]
1614-12-6.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow to beige or light brown crystalline powder | [Melting point ]
81-84 °C (lit.) | [Boiling point ]
237.24°C (rough estimate) | [density ]
1.2769 (rough estimate) | [refractive index ]
1.7000 (estimate) | [RTECS ]
DM1235000 | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Soluble in DMSO (up to 30mg/ml) | [form ]
Crystalline Powder | [pka]
2.09±0.30(Predicted) | [color ]
Yellow to beige or light brown | [Water Solubility ]
slightly soluble | [BRN ]
607843 | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month. | [InChI]
InChI=1S/C6H6N4/c7-10-6-4-2-1-3-5(6)8-9-10/h1-4H,7H2 | [InChIKey]
JCXKHYLLVKZPKE-UHFFFAOYSA-N | [SMILES]
N1(N)C2=CC=CC=C2N=N1 | [CAS DataBase Reference]
1614-12-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [Description]
1-Aminobenztriazole (1614-12-6) is a pan-specific cytochrome P450 inhibitor acting as a suicide substrate.1,2?Blocks omega-oxidation of arachidonic acid but not its epoxidation.3 | [Chemical Properties]
yellow to beige or light brown crystalline powder | [Uses]
1-Aminobenzotriazole is used as a Suicide inhibitor of cytochrome P450 and chloroperoxidase, an inhibitor of oxidative drug metabolism in biochemical pharmacology and toxicology studies. | [Biochem/physiol Actions]
1-Aminobenzotriazole (1-ABT) is used as an in vitro tool in drug discovery. It can differentiate the P450 from non-P450 enzyme systems. 1-ABT exhibits inhibitory action by covalent alteration of the heme prosthetic group in the P450 enzyme. | [Synthesis]
To a solution of benzotriazole (5 g, 42.01 mmol) and potassium hydroxide (11.76 g, 0.21 mol) in water (50 mL) was added hydroxylamine-O-sulfonic acid (9.49 g, 84.02 mmol) in batches while controlling the temperature of the reaction not to exceed 50 °C. After the addition was completed, the reaction mixture was stirred at room temperature for 2 hours. The precipitate was collected by filtration and washed well with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography using petroleum ether: ethyl acetate (300:1) as eluent to afford 1H-benzo[d][1,2,3]triazol-1-amine as a white solid (1.52 g, 27% yield). Mass spectrum (ESI) m/z: 135 [M + H]+. | [in vivo]
Oral 1-Aminobenzotriazole (ABT) (100 mg/kg, 2 h predose) decreases the clearance of intravenous procainamide (45%) in rats, accompanied by a decreased N-acetylprocainamide-to-procainamide ratio in urine (0.74 versus 0.21) and plasma (area under the curve ratio 0.59 versus 0.11). The urinary recovery of procainamide increases from 18 to 30%, whereas the recovery of N-acetylprocainamide in urine decreases from 13.3 to 6.5% with 1-Aminobenzotriazole[2]. Pretreatment of rats with 100 mg/kg oral 1-Aminobenzotriazole (ABT) administered 2 hours before a semisolid caloric test meal markedly delays gastric emptying. 1-Aminobenzotriazole also increases stomach weights by 2-fold[3]. | [IC 50]
CYP2; CYP3 | [References]
1) Mugford?et al.?(1995),?1-Aminobenzotriazole-Induced Destruction of Hepatic and Renal Cytochrome P450 in Male Sprague-Dawley Rats; Fundam. Appl. Tox.,?19?43
2) Emoto?et al.?(2005),?In Vitro Inhibitory Effect of 1-Aminobenzotriazole on Drug Oxidations in Human Liver Microsomes: A Comparison With SKF-525A; Drug Metab. Pharmacokinet.,?20?351
3) Su?et al.?(1998),?Inhibition of Renal Arachidonic Acid Omega-Hydroxylase Activity With ABT Reduces Blood Pressure in the SHR; Am. J. Physiol.,?275?R426 |
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