안티피린
안티피린 · PHENAZONE · Antipyrin · Antipirin · ANTIPYRENE · Fenazone · Phenozone · ANALGESINE
식별자 및 물리적 특성
| CAS No. | 60-80-0 |
|---|---|
| 분자식 | C11H12N2O |
| 평균 분자량 | 188.23 g/mol |
| 단동위원소 질량 | 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 |
| 현지명 | 안티피린 |
화학 및 물리적 성질
| XLogP | 0.4 |
|---|---|
| 극성 표면적 | 23.6 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 1 |
| 무거운 원자 수 | 14 |
| 형식 전하 | 0 |
| 복잡도 | 266 |
| 물질 분류 | Pharmaceutical |
| 의약품 | DEA NFLIS-Drug Category -> AnalgesicsPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Metabolite of Metamizole |
| SpringerMaterials Properties | Crystal structure |
| LogP(분배 계수) | 0.380,230.42 |
| 밀도 | Relative density (water = 1): 1.191,19 g/cm3 |
| 용해도 | 4.74e+01 g/LSolubility in water: very good25.2 [ug/mL] (The mean of the results at pH 7.4)H2O: 1ml 미만에 용해되는 1gm |
| Human Drugs | Breast FeedingLactationMilk, HumanAnti-Inflammatory Agents, Non-SteroidalPharmaceuticals |
| 끓는 점 | 319 °C |
| 녹는점 | 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 |
| 굴절률 | 1.5850 (estimate) |
| 저장 조건 | 2-8°C |
| 물리적 상태 | 결정성 분말 |
| pKa(산도 계수) | pKa 1.4 (Uncertain) |
| 색상 | 하얀색 |
| 생물학적 소스 | rabbit |
| 용해도 | 1000g/L(20℃) |
| Merck | 14,716 |
| BRN | 157775 |
| 안정성 | 안정적인. 암모니아, 강산, 알칼리, 강산화제, 금속염, 페놀과 호환되지 않습니다. |
| 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(분배 계수) | 0.380 |
| NIST | Antipyrine(60-80-0) |
| EPA | Antipyrine (60-80-0) |
화학적 성질
Colorless crystal or white crystalline powder. Soluble in benzene, ethanol, water, chloroform, slightly soluble in ether. Odorless, slightly bitter.
안전 및 규제
| GHS 분류 | 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. |
|---|---|
| 규제 정보 | 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 |
| 기타 안전 정보 | IMAP assessments - 3H-Pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-: Environment tier I assessment |
| 화재 위험 | 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%) |
| 소화 | Use water spray, powder, foam, carbon dioxide. |
| 응급 조치 | 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. |
| 안전 보관 | Separated from strong oxidants. |
| 누출 처리 | 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. |
| Eye Prevention | Wear safety spectacles. |
| Fire Prevention | NO open flames. |
| Inhalation Risk | Evaporation at 20 °C is negligiblea harmful concentration of airborne particles can, however, be reached quickly when dispersed, especially if powdered. |
| Skin Prevention | Protective gloves. |
| Exposure Prevention | PREVENT DISPERSION OF DUST! |
| Ingestion Prevention | Do not eat, drink, or smoke during work. |
| Inhalation Prevention | Use ventilation, local exhaust or breathing protection. |
| Effects of Long Term Exposure | The substance may have effects on the blood. This may result in anaemia. |
| 노출 경로 | The substance can be absorbed into the body by inhalation of dust and by ingestion. |
| Signs and Symptoms | Cough.No acute symptoms expected.Redness. |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| USGS Health-Based Screening Levels for Evaluating Water-Quality | AntipyrinePharmaceuticalSmith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP |
| 수질 위해 등급(WGK) | 1 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | CD2450000 |
| 운송 번호(UN) | 3249 |
| 독성 | LD50 orally in rats: 1.8 g/kg (Hart) |
| 관세 코드 | 29331190 |
| 위험 문구(R) | 22-36/37/38 |
| 위험 표시 | Xn |
| 안전 문구(S) | 26-36-37/39 |
| 포장분류 | III |
| 위험 등급 | 6.1(b)Acute Tox. 4 Oral |
| 기존화학 물질 | KE-10627 |
| F 고인화성물질 | 10 |
| 저장 분류 | 11 - Combustible Solids |
용도
역사
Antipyrine (phenazone) was one of the first important synthetic Analgesic drugs that synthesis in Germany in 1884 by a pupil of Emil Fischer.
용도
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)
일반 설명
Antipyrine is an antipyretic agent used for the symptomatic treatment of acute otitis media, most commonly in combination with benzocaine. One of the earliest widely used analgesics and antipyretics, antipyrine was gradually replaced in common use by other medications including phenacetin (itself later withdrawn because of safety concerns), aspirin, paracetamol and modern NSAIDs such as ibuprofen.
제조 및 합성 방법
제조 방법
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.