4-Amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-on

4-Aminoantipyrine

HCID 2151CAS 83-07-8
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Grundinformationen

Standard-SMILES
Cc1c(N)c(=O)n(-c2ccccc2)n1C
InChIKey
RLFWWDJHLFCNIJ-UHFFFAOYSA-N
Summenformel
C11H13N3O
Durchschnittliche Molmasse
203,24 g/mol
Monoisotopische Masse
203,10586204

Überblick

4-aminoantipyrine is a pyrazolone, a member of the class of pyrazoles that is antipyrine substituted at C-4 by an amino group. It is a metabolite of aminopyrine and of metamizole. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antipyretic, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, an antirheumatic drug, a drug metabolite, a peripheral nervous system drug and a marine xenobiotic metabolite. It is a primary amino compound and a pyrazolone. It is functionally related to an antipyrine.

Namen und Bezeichner

Bevorzugter Name
4-Aminoantipyrine
IUPAC
4-amino-1,5-dimethyl-2-phenylpyrazol-3-one
Lokaler Name
4-Amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-on
Englischer Name
4-Aminoantipyrine
Summenformel
C11H13N3O
Molmasse
203.24

Namen und Synonyme

4-AminoantipyrineAMPYRONE83-07-84-AminophenazoneAminoantipyrineMetapirazoneAminoantipyrin4-AminoantipyreneSolvapyrin-AAminoazopheneAminoazophenazoneSolnapyrin-A
Weitere Namen anzeigen
4-AMINOANTIPYRIN4-AMINO-1,5-DIMETHYL-2-PHENYL-1,2-DIHYDRO-PYRAZOL-3-ONENSC 60242
4-AAP4-Amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one3H-Pyrazol-3-one, 4-amino-1,2-dihydro-1,5-dimethyl-2-phenyl-4-Amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-oneDTXSID8048860CHEBI:590260M0B7474RANSC-60242

Datenbank-Bezeichner

CAS
83-07-8
PubChem CID
2151
DTXSID
DTXSID8048860
ChEMBL
CHEMBL1165011
ChEBI
CHEBI:59026
UNII
0M0B7474RA
EC Number
201-452-3
Nikkaji
J796J

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,1
Polarare Oberfläche (TPSA)
49,6 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
1
Schwere Atome
15

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Metabolite of Metamizole
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section · 3 Einträge

151.49 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

142.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

142.48 Ų [M+H]+

Physikochemische Eigenschaften

Schmelzpunkt
105 · 105-110 °C(lit.)
Siedepunkt
340 C · 340 C
Dichte
0.8 · 0.8
Brechungsindex
1.493 · 1.4930 (estimate)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit
2 O: · H2O: 0.1 g/mL, clear

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 1% (1 of 105) of reports.

Warning

H302 (99%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 105 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information4-Amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 3H-Pyrazol-3-one, 4-amino-1,2-dihydro-1,5-dimethyl-2-phenyl-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (99%)

Sicherheitsdaten

F
8-9-23
wgk
3
tsca
TSCA listed
hs_code
29331190
RTECS-Nr.
CD2480000
risk_code
22-36/37/38-20/21/22

Chemie und Industrie

Pharmakologische Informationen

ATC CodeN02BB03
MeSH Pharmacological Classification · 2 Einträge

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)

Verwendung und Herstellung

Use Classification · 2 Einträge

Pharmaceuticals -> Nervous System -> Analgesics -> Pyrazolones -> Transformation products

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

General Manufacturing Information3H-Pyrazol-3-one, 4-amino-1,2-dihydro-1,5-dimethyl-2-phenyl-: ACTIVE
Anwendungen · 1 Eintrag

Verwenden4-Aminoantipyrine is a metabolite of aminopyrine, having both analgesic and anti-inflammatory properties. It readily forms metal complexes due to its amino nitrogen, a strong coordination site.4-aminoantipyrine forms Schiff bases when treated with aldehydes/ketones, which are used in chemosensing applications.Coupling Reagent for Trinder's reagent in colorimetric hydrogen peroxide detectionassays.Forms highly stable dyes by coupling with Trinder's reagent in presence of Peroxidase and H2O2. Therefore suitable for use in test strip and solution diagnostics.

Darstellung

synthetischesynthesis of 4-aminoantipyrine: Antipyrine is nitrosated by sodium nitrite, reduced by ammonium bisulfite and ammonium sulfite, hydrolyzed by sulfuric acid, and finally neutralized with liquid ammonia to obtain 4-aminoantipyrine.

Vor- und nachgelagerte Produkte

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 4-aminoantipyrine is a pyrazolone, a member of the class of pyrazoles that is antipyrine substituted at C-4 by an amino group. It is a metabolite of aminopyrine and of metamizole. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antirheumatic drug, a peripheral nervous system drug, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, an antipyretic, a drug metabolite and a marine xenobiotic metabolite. It is a primary amino compound and a pyrazolone. It derives from an antipyrine.

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