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7-Nitro-1H-indazol

7-Nitroindazole

HCID 1893
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Grundinformationen

CAS
2942-42-9
Standard-SMILES
O=[N+]([O-])c1cccc2cn[nH]c12
InChIKey
PQCAUHUKTBHUSA-UHFFFAOYSA-N
Summenformel
C7H5N3O2
Durchschnittliche Molmasse
163,13 g/mol
Monoisotopische Masse
163,0381764

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
7-Nitroindazole
IUPAC
7-nitro-1H-indazole
Lokaler Name
7-Nitro-1H-indazol
Englischer Name
7-Nitroindazole
Summenformel
C7H5N3O2
Molmasse
163.13

Namen und Synonyme

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,8
Polarare Oberfläche (TPSA)
74,5 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
0
Schwere Atome
12
Formalladung
0
Komplexität
192

Experimentelle und physikochemische Eigenschaften

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]

Physikochemische Eigenschaften

Schmelzpunkt
185 · 185-186°C
Siedepunkt
290.19 °C · 290.19°C (rough estimate)
Dichte
1.4141 · 1.4141 (rough estimate)
Brechungsindex
1.55 · 1.5500 (estimate)
storage temp.
-20 °C · -20°C
Löslichkeit
100 mM · Soluble to 100 mM in DMSO and to 20 mM in ethanol
pka
10.03 · 10.03±0.40(Predicted)
Aggregatzustand
powder to crystal
Farbe
Light yellow to Brown
Wasserlöslichkeit
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 Datenbank
2942 · 2942-42-9(CAS DataBase Reference)
NIST chemische Informationen
7 · 7-Nitroindazole(2942-42-9)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 3 (86.7%)

Sicherheitsdaten

wgk
3
ridadr
UN 2811 6.1/PG 3
hs_code
29339900
RTECS-Nr.
NK7962200
risk_code
60-40
hazard_code
T
safety_code
53-22-36/37/39-45
hazard_class
IRRITANT
packing_group
Ⅲ

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 5 Einträge

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.

Anwendungen · 2 Einträge

Beschreibung7-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.

Verwenden7-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.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

NatriumnitritEssigsure6-Nitro-o-toluidin

Nachgelagerte Produkte

2-Methyl-2H-indazol-7-ylamine3‐chloro‐1‐methyl‐7‐nitro‐1H‐indazole
Ergänzende Hinweise · 1 Eintrag

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).

Zugehörige Reaktionen

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Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 206161
HRID 206161als EduktTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
Reaktionsgleichung von HRID 270915
HRID 270915als Eduktuspto-grants-2008_11
Reaktionsgleichung von HRID 296458
HRID 296458als EduktTraining data from https://doi.org/10.1039/C8SC04228D (8/10)
Reaktionsgleichung von HRID 482343
HRID 482343als Eduktuspto-grants-1998_08
Reaktionsgleichung von HRID 1116142
HRID 1116142als EduktTraining data from https://doi.org/10.1039/C8SC04228D (7/10)
Reaktionsgleichung von HRID 1200344
HRID 1200344als EduktTraining data from https://doi.org/10.1039/C8SC04228D (5/10)
Reaktionsgleichung von HRID 1267002
HRID 1267002als Eduktuspto-grants-2003_04
Reaktionsgleichung von HRID 1372131
HRID 1372131als Eduktuspto-grants-2007_01
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