Antipyrine
PHENAZONE · Antipyrin · Antipirin · ANTIPYRENE · Fenazone · Phenozone · ANALGESINE · Antypirine
Identifikatoren & physikalische Daten
| CAS No. | 60-80-0 |
|---|---|
| Summenformel | C11H12N2O |
| Durchschnittliche Molmasse | 188,23 g/mol |
| Monoisotopische Masse | 188,094963 g/mol |
| SMILES | Cc1cc(=O)n(-c2ccccc2)n1C |
| InChIKey | VEQOALNAAJBPNY-UHFFFAOYSA-N |
| PubChem CID | 2206 |
| ChEMBL | CHEMBL277474 |
| ChEBI | CHEBI:31225 |
| EC No. | 200-486-6 |
| DTXSID | DTXSID6021117 |
| Lokaler Name | Antipyrine |
Chemische & physikalische Eigenschaften
| XLogP | 0,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 23,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 266 |
| Stoffklassen | Pharmaceutical |
| Arzneimittel | DEA NFLIS-Drug Category -> AnalgesicsPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Metabolite of Metamizole |
| SpringerMaterials Properties | Crystal structure |
| LogP (Verteilungskoeffizient) | 0.380,230.42 |
| Dichte | Relative density (water = 1): 1.191,19 g/cm3 |
| Löslichkeit | 4.74e+01 g/LSolubility in water: very good25.2 [ug/mL] (The mean of the results at pH 7.4)H2O: soluble1 gm in less than 1ml1000 g/L (20 ºC) |
| Human Drugs | Breast FeedingLactationMilk, HumanAnti-Inflammatory Agents, Non-SteroidalPharmaceuticals |
| Siedepunkt | 319 °C |
| Schmelzpunkt | 114 °C113 °C109-111 °C(lit.) |
| Physical Description | SolidCOLOURLESS CRYSTALS OR WHITE POWDER. |
| Ionization Efficiency | Positive3.152.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Dissociation Constants | 1.4 |
| Brechungsindex | 1.5850 (estimate) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Crystalline Powder |
| pKa (Säurekonstante) | pKa 1.4 (Uncertain) |
| Farbe | White |
| Biologische Quelle | rabbit |
| Merck | 14,716 |
| BRN | 157775 |
| Stabilität | Stable. Incompatible with ammonia, strong acids, alkalies, strong oxidizing agents, metallic salts, phenol. |
| InChI | 1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3 |
| InChIKey | VEQOALNAAJBPNY-UHFFFAOYSA-N |
| SMILES | CN1N(C(=O)C=C1C)c2ccccc2 |
| LogP (Verteilungskoeffizient) | 0.380 |
| CAS Datenbank | 60-80-0(CAS DataBase Reference) |
| NIST chemische Informationen | Antipyrine(60-80-0) |
| EPA chemische Informationen | Antipyrine (60-80-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 0.5% (1 of 184) of reports.WarningH302 (99.5%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 184 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | REACH registered substance: Phenazone (EC: 200-486-6)3H-Pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 3H-Pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-: Environment tier I assessment |
| Brandgefahren | Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| Chemical Dangers | Decomposes on heating. This produces toxic and corrosive fumes of nitrogen oxides. Reacts with strong oxidants. |
| Physical Dangers | Dust explosion possible if in powder or granular form, mixed with air. |
| Hazard Classes and Categories | Acute Tox. 4 (99.5%) |
| Brandbekämpfung | Use water spray, powder, foam, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest.Rinse skin with plenty of water or shower.Rinse with plenty of water for several minutes (remove contact lenses if easily possible).Rinse mouth. Seek medical attention if you feel unwell. |
| Sichere Lagerung | Separated from strong oxidants. |
| Verschüttetes entsorgen | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
Anwendungen & Verwendung
History
Antipyrine (phenazone) was one of the first important synthetic Analgesic drugs that synthesis in Germany in 1884 by a pupil of Emil Fischer.
Verwenden
Antipyrine has been used for immunoblotting. It has also been used as an internal reference marker for studying the transport characteristics of platinum-containing drug, cisplatin in the human placenta in vitro. Antipyrine is an analgesic and antipyretic that has been given by mouth and as ear drops. It is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29)
Herstellung & Synthese
synthetische
Antipyrine (1) was prepared from the reaction of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one with methyl iodide in methanol or in acetonitrile containing sodium bicarbonate in water in 58% yield. The reaction of 1-methyl-2-phenylhydrazine (2) with methyl 3-oxobutanoate (3) in acetonitrile gave 1 and pyrazolone 4 . Krohn has been reported the synthesis of 1 from the reaction of 5 with dimethyl sulfate in 71% yield. The reaction of pyrazolone 6 with methanol in the presence of triphenylphosphine afforded 1 (14%) and pyrazole 7 (53%). The same reaction was reported by Pegurier et al by heating the reactants in methanol containing calcium monoxide. Knorr early reported also, the synthesis of antipyrine from heating of 1-phenyl-5-ethoxy-3- methylpyrazole (8) with methyl iodide in methanol.