基本信息
- 标准SMILES
Cc1c(N)c(=O)n(-c2ccccc2)n1C- InChIKey
RLFWWDJHLFCNIJ-UHFFFAOYSA-N- 分子式
- C11H13N3O
- 平均分子量
- 203.24 g/mol
- 单同位素质量
- 203.10586204
概述
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.
名称与标识
- 首选名称
- 4-Aminoantipyrine
- IUPAC
- 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one
- 中文名
- 4-氨基安替比林
- 英文名
- 4-Aminoantipyrine
- 分子式
- C11H13N3O
- 分子量
- 203.24
名称与别名
展开更多名称
数据库标识
- CAS
83-07-8- PubChem CID
- 2151
- DTXSID
DTXSID8048860- ChEMBL
CHEMBL1165011- ChEBI
CHEBI:59026- UNII
- 0M0B7474RA
- EC Number
- 201-452-3
- Nikkaji
- J796J
性质
结构计算性质
- XLogP
- 0.1
- 极性表面积
- 49.6 Ų
- 氢键供体
- 1
- 氢键受体
- 3
- 可旋转键
- 1
- 重原子
- 15
- 形式电荷
- 0
- 复杂度
- 305
实验与物化性质
Collision Cross Section
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]+
物理化学性质
- 熔点
- 105 · 105-110 °C(lit.)
- 沸点
- 340 C · 340 C
- 密度
- 0.8 · 0.8
- 堆积密度
- 430 kg/m3 · 430kg/m3
- 折射率
- 1.493 · 1.4930 (estimate)
- 储存条件
- Keep in dark place,Inert atmosphere,Room temperature
- 溶解度
- 2 O: · H2O: 0.1 g/mL, clear
- 酸度系数(pKa)
- 1 · pK1: 4.94(+1) (25°C)
- 形态
- Powder or Crystals
- 颜色
- Yellow to yellow-brown
- PH值
- 7.1 · 7.1 (100g/l, H2O, 20℃)(slurry)
- 气味 (Odor)
- Odorless
- 水溶解性
- 500 g/L · ca. 500 g/L (20 ºC)
- Merck
- 14 · 14,591
- BRN
- 181635 · 181635
- 稳定性
- Stable. May be light sensitive.
- InChI
- 1S/C11H13N3O/c1-8-10(12)11(15)14(13(8)2)9-6-4-3-5-7-9/h3-7H,12H2,1-2H3
- InChIKey
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N
- SMILES
- CN1N(c2ccccc2)C(=O)C(N)=C1C
- LogP
- -0.257 · -0.257 (est)
- CAS 数据库
- 83 · 83-07-8(CAS DataBase Reference)
- NIST化学物质信息
- Aminoantipyrene(83-07-8)
- EPA化学物质信息
- 4 · 4-Aminoantipyrene (83-07-8)
化学性质
淡黄色结晶。熔点109℃。溶于水、苯和乙醇,微溶于乙醚。
安全与法规
GHS分类
GHS Classification
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.
危害信息
安全数据
- F
- 8-9-23
- wgk
- 3
- tsca
- TSCA listed
- 毒性
- LD50 orally in Rabbit: 1700 mg/kg
- RTECS号
- CD2480000
- hazard_note
- Harmful
- 存储类别
- 11 - Combustible Solids
- 安全说明
- 26-36-36/37/39
- 海关编码
- 29331190
- 危险品标志
- Xn
- 危险性类别
- Acute Tox. 4 Oral
- 危险类别码
- 22-36/37/38-20/21/22
毒性防护
急性毒性口服-大鼠LD50: 1700 毫克/公斤; 口服-小鼠LD50: 800 毫克/公斤
包装储运
可燃性危险特性可燃;燃烧产生有毒氮氧化物烟雾
储运特性库房通风低温干燥
灭火剂干粉、泡沫、砂土、二氧化碳, 雾状水
化学与工业
药理信息
MeSH Pharmacological Classification
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)
用途与制造
Use Classification
Pharmaceuticals -> Nervous System -> Analgesics -> Pyrazolones -> Transformation products
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
应用领域
用途4-氨基安替比林用于检定醇与胺类,测大气及水中酚类化合物,显色原理主要是其中的氨基与苯酚对位形成偶合反应,产生氮氮双键的偶氮化合物,为一种红色染料。
用途用作药物安乃近的中间体,也用以测定醇、苯酚和胺及其同系物;色谱测定烷基苯酚;测定 H2O2;在苯酚和过氧化物酶存在的情况下测定葡萄糖。
制备方法
生产方法安替比林经亚硝酸钠亚硝化,经亚硫酸氢铵与亚硫酸铵还原,经硫酸水解,最后用液氨中和,得到4-氨基安替比林。工艺过程如下:安替比林与50%硫酸配成溶液,其中含安替比林38%-40%、含硫酸11%-12%。将此溶液与亚硝酸钠溶液同时流入亚硝化反应器,控制两者的流量,控制反应温度45-50℃,搅拌下反应,并用碘粉淀粉试纸测反应终点以调节水流量。亚硝化生成的亚硝基安替比林立即流入还原罐,与罐内配好的还原剂亚硫酸氢铵与亚硫酸铵的水溶液反应。取样测pH值及还原度,pH值在5.4-5.8之间,还原度约为15(即1ml还原液消耗0.1N碘液的毫升数)。还原结束后,pH值调节至5.8-6.0,还原度为5左右。升温至100℃,水解3h。降温至80℃,用液氨中和至pH7-7.5,静置分层。分去废水,得4-氨基安替比林油(含量80%以上)。将其压入结晶罐,搅拌、冷却结晶、过滤,得4-氨基安替比林。收率96%。
上下游产品信息
上游原料
下游产品
试剂价格
- A13846 · 100g
- 4-氨基安替比林, 97% 4-Aminoantipyrine, 97% — 820元
- 10315 · 25g
- 4-氨基安替比林4-Aminoantipyrine, 98%, Thermo Scientific Chemicals — 502元
供应商50 家
相关反应
关联笔记
加载中…