4-アミノアンチピリン

4-Aminoantipyrine

HCID 2151CAS 83-07-8

基本情報

標準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
単同位体質量
203.10586204

概要

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.

名称と識別子

優先名称
4-Aminoantipyrine
IUPAC
4-amino-1,5-dimethyl-2-phenylpyrazol-3-one
現地名
4-アミノアンチピリン
英語名
4-Aminoantipyrine
分子式
C11H13N3O
分子量
203.24

名称と別名

4-AminoantipyrineAMPYRONE83-07-84-AminophenazoneAminoantipyrineMetapirazoneAminoantipyrin4-AminoantipyreneSolvapyrin-AAminoazopheneAminoazophenazoneSolnapyrin-A
名称をさらに表示
4-アミノアンチピリン1,2-ジヒドロ-1,5-ジメチル-2-フェニル-4-アミノ-3H-ピラゾール-3-オン4-アミノ-1,2-ジヒドロ-1,5-ジメチル-2-フェニル-3H-ピラゾール-3-オン4-アミノ-1,5-ジメチル-2-フェニル-4-ピラゾリン-3-オン2,3-ジメチル-1-フェニル-4-アミノ-3-ピラゾリン-5-オンアンピロン4-アミノ-1-フェニル-2,3-ジメチル-1H-ピラゾール-5(2H)-オン4-アミノ-2,3-ジメチル-1-フェニル-3-ピラゾリン-5-オンアミノアンチピリン1,5-ジメチル-2-フェニル-4-アミノ-4-ピラゾリン-3-オン1,5-ジメチル-2-フェニル-4-アミノ-1,2-ジヒドロ-3H-ピラゾール-3-オン1,5-ジメチル-2-フェニル-4-アミノ-2,3-ジヒドロ-1H-ピラゾール-3-オン4-アミノ-1,5-ジメチル-2-フェニル-3(2H)-ピラゾロン1,5-ジメチル-4-アミノ-2-フェニル-1H-ピラゾール-3(2H)-オン4-アミノ-1,5-ジメチル-2-フェニル-1H-ピラゾール-3(2H)-オン1,5-ジメチル-2-フェニル-4-アミノ-1H-ピラゾール-3(2H)-オン4-アミノ-2,3-ジメチル-1-フェニル-5-ピラゾロン4-アミノフェナゾン4-アミノアンチピリン [生化学用]4‐アミノアンチピリン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

データベース識別子

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

物性

構造計算による物性

XLogP
0.1
極性表面積
49.6 Ų
水素結合供与体数
1
水素結合受容体数
3
回転可能結合数
1
重原子数
15

実験および物理化学的性質

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

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]+

物理化学的性質

融点
105 · 105-110 °C(lit.)
沸点
340 C · 340 C
比重(密度)
0.8 · 0.8
屈折率
1.493 · 1.4930 (estimate)
貯蔵温度
Keep in dark place,Inert atmosphere,Room temperature
溶解性
2 O: · H2O: 0.1 g/mL、透明

化学的性質

化学的特性It is an amber to pale yellow crystalline powder. It is soluble in water, benzene, and ethanol, and only slightly soluble in diethyl ether.

安全と法規制

GHS分類

GHS Classification · 5 件

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.

危険有害性情報

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%)

安全データ

F
8-9-23
wgk
3
tsca
TSCA listed
rtecs
CD2480000
毒性
LD50 orally in Rabbit: 1700 mg/kg
hs_code
29331190

化学と産業

薬理情報

ATC CodeN02BB03
MeSH Pharmacological Classification · 2 件

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)

用途と製造

Use Classification · 2 件

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
応用分野 · 4 件

用途フェノール定量、有機合成用。

用途アンピロン(英:Ampyrone)は、抗炎症剤、解熱鎮痛剤、解熱剤の特性を有するアミノピリンの代謝産物である。顆粒球減少症の危険性のために薬剤としての使用は推奨されていない。その代わりに、過酸化物またはフェノールを生成する生化学反応の試薬として使用されている。アンピロンは、肝ミクロソームを刺激し、また、細胞外液を測定するために使用されている。

使用4-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.

一般的な説明4-Aminoantipyrine forms heterocyclic Schiff bases, by reaction with various aldehydes and oximes. These Schiff bases form stable complexes with transition metals.

調製方法

製造方法synthesis 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.

純化方法It crystallises from EtOH or EtOH/ether. [Beilstein 25 III/IV 3554.]

サプライヤー50 社

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]
補足説明 · 1 件

定義ChEBI: 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.

関連反応

19 件

関連ノート

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