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7-Nitroindazole

HCID 1893
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
2942-42-9
Standard SMILES
O=[N+]([O-])c1cccc2cn[nH]c12
InChIKey
PQCAUHUKTBHUSA-UHFFFAOYSA-N
Molecular formula
C7H5N3O2
Average molar mass
163.13 g/mol
Monoisotopic mass
163.0381764

Overview

7-nitroindazole is a member of the class of indazoles that is 1H-indazole substituted by a nitro group at position 7. It is a nitric oxide synthase (NOS) inhibitor. It has a role as an antinociceptive agent, an anxiolytic drug, an analgesic, an EC 1.14.13.39 (nitric oxide synthase) inhibitor and a neuroprotective agent. It is a C-nitro compound and a member of indazoles.

Names & identifiers

Preferred name
7-Nitroindazole
IUPAC
7-nitro-1H-indazole
English name
7-Nitroindazole
Molecular formula
C7H5N3O2
Molecular weight
163.13

Names & synonyms

7-nitroindazole7-Nitro-1H-indazole2942-42-97-nitro-indazoleUX0N37CMVHDTXSID30183638NSC-728437-Nitro-2H-indazoleRefChem:546919DTXCID70106129220-934-41H-Indazole, 7-nitro-
Show more names
NITROINDAZOLE187-NitroinazoleINDAZOLE, 7-NITRO-7-nitro-1h-indazol7-Nitroindazole>7-NITROINDAZOLE 97+%
7-NIMFCD00022789Spectrum2_0017157-Nitroindazole (7-NI)NITROINDAZOLE, 7-BSPBio_003580SPECTRUM1505342MLS000028452

Database identifiers

CAS
2942-42-9
PubChem CID
1893
DTXSID
DTXSID30183638
ChEMBL
CHEMBL247378
ChEBI
CHEBI:40287
UNII
UX0N37CMVH
EC Number
220-934-4
Nikkaji
J2.168G

Properties

Computed structural properties

XLogP
1.8
Topological polar surface area
74.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
12
Formal charge
0
Complexity
192

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Solubility>24.5 [ug/mL] (The mean of the results at pH 7.4)
Collision Cross Section126.82 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
185 · 185-186°C
Boiling point
290.19 °C · 290.19°C (rough estimate)
Density
1.4141 · 1.4141 (rough estimate)
refractive index
1.55 · 1.5500 (estimate)
storage temp.
-20 °C · -20°C
solubility
100 mM · Soluble to 100 mM in DMSO and to 20 mM in ethanol
pka
10.03 · 10.03±0.40(Predicted)
form
powder to crystal
color
Light yellow to Brown

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H301 (86.7%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P264, P264+P265, P270, P280, P301+P316, P302+P352, P305+P351+P338, P318, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (86.7%)

Safety data

wgk
3
rtecs
NK7962200
ridadr
UN 2811 6.1/PG 3
hs_code
29339900
risk_code
60-40
Signal word
Danger
Symbol(GHS)
GHS06,GHS08
hazard_code
T
safety_code
53-22-36/37/39-45
hazard_class
IRRITANT
packing_group
Ⅲ
Hazard statements
H301-H319-H351-H360
Precautionary statements
P201-P301+P310+P330-P305+P351+P338

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 5 items

Compounds capable of relieving pain without the loss of CONSCIOUSNESS.

Drugs used to prevent SEIZURES or reduce their severity.

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here.

Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.

Applications · 2 items

Description7-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.

Uses7-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.

Upstream & downstream products

Upstream raw materials

Sodium nitriteAcetic acid2-Methyl-6-nitroaniline

Downstream products

Related reactions

12 records
New reaction record
HRID 206161 reaction equation
HRID 206161As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 270915 reaction equation
HRID 270915As reactantuspto-grants-2008_11
HRID 296458 reaction equation
HRID 296458As reactantTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
HRID 482343 reaction equation
HRID 482343As reactantuspto-grants-1998_08
HRID 1116142 reaction equation
HRID 1116142As reactantTraining data from https://doi.org/10.1039/C8SC04228D (7/10)
HRID 1200344 reaction equation
HRID 1200344As reactantTraining data from https://doi.org/10.1039/C8SC04228D (5/10)
HRID 1267002 reaction equation
HRID 1267002As reactantuspto-grants-2003_04
HRID 1372131 reaction equation
HRID 1372131As reactantuspto-grants-2007_01
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Compound notes

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Water Solubility
slightly soluble
BRN
6809 · 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 · 2942-42-9(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
0 N37CMVH · UX0N37CMVH
NIST Chemistry Reference
7 · 7-Nitroindazole(2942-42-9)
UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
Symbol(GHS)
6 · GHS06,GHS08
Signal word
Danger
Hazard statements
301 · H301-H319-H351-H360
Precautionary statements
201 · P201-P301+P310+P330-P305+P351+P338
Hazard Codes
T
Risk Statements
60 · 60-40
Safety Statements
53 · 53-22-36/37/39-45
RIDADR
2811 · UN 2811 6.1/PG 3
WGK Germany
3 · 3
RTECS
7962200 · NK7962200
HazardClass
IRRITANT
PackingGroup
Ⅲ
HS Code
29339900 · 29339900
2-Methyl-2H-indazol-7-ylamine3‐chloro‐1‐methyl‐7‐nitro‐1H‐indazole
Additional notes · 1 item

Definition7-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).