1-Aminobenzotriazole Chemical Properties

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29349990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

1-Aminobenzotriazole Usage And Synthesis

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.

Uses

1-Aminobenzotriazole has been used as a cytochrome P450 inhibitor to study the effects of estrogen on H₂O₂-induced premature senescence of vascular smooth muscle cells from old rats It has also been used to study the estrogen receptor-mediated effects of 17β-estradiol.

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

IC 50

CYP2; CYP3

References

[1] CHERYL A. MUGFORD . 1-Aminobenzotriazole-induced destruction of hepatic and renal cytochromes P450 in male Sprague-Dawley rats[J]. Fundamental and Applied Toxicology, 1992, 19 1: Pages 43-49. DOI:10.1016/0272-0590(92)90026-e
[2] CHIE EMOTO. In Vitro Inhibitory Effect of 1-Aminobenzotriazole on Drug Oxidations in Human Liver Microsomes: a Comparison with SKF-525A[J]. Drug Metabolism and Pharmacokinetics, 2005, 20 5: Pages 351-357. DOI:10.2133/dmpk.20.351
[3] P SU  D L K  K M Kaushal. Inhibition of renal arachidonic acid omega-hydroxylase activity with ABT reduces blood pressure in the SHR.[J]. American Journal of Physiology, 1998, 275 2: R426-38. DOI:10.1152/ajpregu.1998.275.2.r426

1-Aminobenzotriazole(1614-12-6)Related Product Information

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