7-Nitroindazole

HCID 1893CAS 2942-42-9

Basic information

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

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

Safety & regulation

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

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.

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
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).

Related reactions

12 records

Linked notes

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