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
Show more names
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
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
- 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
Safety & regulation
GHS classification
GHS Classification
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
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
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
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
Downstream products
Suppliers50 total
Additional notes
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
Linked notes
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