7-Nitroindazole Chemical Properties

Melting point:

185-186°C

Boiling point:

290.19°C (rough estimate)

Density 

1.4141 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

-20°C

solubility 

Soluble to 100 mM in DMSO and to 20 mM in ethanol

pka

10.03±0.40(Predicted)

form 

powder to crystal

color 

Light yellow to Brown

Water Solubility 

slightly soluble

BRN 

6809

InChI

InChI=1S/C7H5N3O2/c11-10(12)6-3-1-2-5-4-8-9-7(5)6/h1-4H,(H,8,9)

InChIKey

PQCAUHUKTBHUSA-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC=C2[N+]([O-])=O)C=N1

CAS DataBase Reference

2942-42-9(CAS DataBase Reference)

NIST Chemistry Reference

7-Nitroindazole(2942-42-9)

Safety Information

Hazard Codes 

T

Risk Statements 

60-40

Safety Statements 

53-22-36/37/39-45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

NK7962200

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

29339900

MSDS

• Language:English Provider:7-Nitro-1H-indazole
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

7-Nitroindazole Usage And Synthesis

Description

7-Nitroindazole is a non-selective inhibitor of NOS isoforms in vitro. However, it shows good anti-nociceptive effects in vivo without affecting blood pressure via inhibition of eNOS. The IC₅₀ values for inhibition of rat nNOS, bovine eNOS, and rat iNOS are 0.71, 0.78, and 5.8 μM, respectively.

Chemical Properties

yellow powder or Yellow orange solid soluble in DMSO.

Uses

7-nitroindazole is a specific inhibitor of neural nitric oxide synthase (nNOS), an enzyme that converts arginine to citrulline and nitric oxide (NO) in neuronal tissue. NO is a key player in the hippocampal long-term potentiation (LTP) and in general cell signaling.

Definition

7-Nitroindazole is a heterocyclic small molecule containing an indazole ring that has been nitrated at the 7 position. It is a potent, selective brain inhibitor of mouse cerebellar Nitric Oxide Synthase, a hemoprotein enzyme that, in neuronal tissue, converts arginine to citrulline and nitric oxide (NO).

Biological Activity

Sodium salt of the non-selective NOS inhibitor 7-nitroindazole (7-Nitroindazole).

Synthesis

General procedure for the synthesis of 7-nitroindazole from 2-methyl-6-nitroaniline: To a stirred solution of 2-methyl-6-nitroaniline (10 g, 0.065 mol) in acetic acid (470 ml, 47 times the volume) was slowly added an aqueous solution (9 ml) of sodium nitrite (1.54 g, 0.06 mol, 1.1 equiv). The reaction mixture was stirred at room temperature for 30-45 min. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent 30% ethyl acetate/hexane, Rf=0.7). After completion of the reaction, acetic acid was removed by distillation under reduced pressure. The obtained residue was dissolved in ice water (200 ml), the precipitated solid was filtered, washed with cold water and dried under vacuum to afford the target product 7-nitroindazole as a yellow solid (10 g, 98% yield).

References

[1] Synlett, 2007, # 8, p. 1203 - 1206
[2] Patent: WO2010/127855, 2010, A1. Location in patent: Page/Page column 124; 125
[3] Archives of Pharmacal Research, 2018, vol. 41, # 1, p. 46 - 56
[4] European Journal of Medicinal Chemistry, 1986, vol. 21, # 4, p. 359 - 362
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 5, p. 339 - 345

7-Nitroindazole(2942-42-9)Related Product Information

• 3-Nitroacetophenone
• 4-Nitrobenzoic acid
• 3-BROMO-7-NITROINDAZOLE
• TRITON
• Nitrobenzene
• NITROGEN DIOXIDE
• Nitromethane
• 2-methyl-7-nitro-2H-indazole
• Nitroethane
• 4-Nitroaniline
• 5-Nitroindazole
• 1-METHYL-6-NITROINDAZOLE
• 4-Nitro-1H-indazole
• 3-HYDROXY-6-NITROINDAZOLE
• 3-Nitro-1H-indazole ,97%
• 3-Methyl-6-nitroindazole
• 5-NITROINDAZOLE-3-CARBOXYLIC ACID
• 6-Nitroindazole