4-(dimethylamino)-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one

• ChemBase编号: 1232
• 分子式: C13H17N3O
• 平均质量: 231.29358
• 单一同位素质量: 231.13716218
• SMILES: O=c1n(n(c(c1N(C)C)C)C)c1ccccc1
• Canonical SMILES: CN(c1c(C)n(n(c1=O)c1ccccc1)C)C
• InChI: InChI=1S/C13H17N3O/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11/h5-9H,1-4H3
• InChIKey: RMMXTBMQSGEXHJ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-(dimethylamino)-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one
• IUPAC传统名: aminophenazone
• 别名: 4-二甲氨基-2,3-二甲氧-1-苯基吡唑-5-酮; 4-Dimethylamino-2,3-dimethyl-1-phenylpyrazol-5-one; 4-(Dimethylamino)antipyrine; 4-Dimethylaminoantipyrine; Aminopyrine; Dipyrine; Aminophenazone; 4-Dimethylamino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one; 4-DIMETHYLAMINOANTIPYRINE; AMINOPYRINE; 4-Dimethylaminoantipyrine; Amidopyrine

登记号

• CAS号: 58-15-1
• EC号: 200-365-8
• MDL号: MFCD00003142
• 默克索引号: 14474
• PubChem SID: 24894178; 160964692; 46504975
• PubChem CID: 6009

理论计算性质

JChem

• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 1.1466073
• LogD (pH = 7.4): 1.1505445
• Log P: 1.150595
• 摩尔折射率: 70.111 cm^3
• 极化性: 25.711367 Å^3
• 极化表面积: 26.79 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.94
• LOG S: -1.01
• 溶解度: 2.25e+01 g/l

分子性质

理化性质

• 溶解度: 54.4 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• 熔点: 105-109°C; 107-109
• 疏水性(logP): 1.00 [HANSCH,C ET AL. (1995)]

安全信息

• 保存条件: Room Temperature (15-30°C), Protect from light
• 保存注意事项: Air & Light Sensitive
• RTECS编号: CD2625000
• 欧盟危险性物质标志: X; 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811; UN2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3; III
• 危险公开号: 22; 22-36/37/38; R:22
• 安全公开号: 26-36; 36; S:36/37/39
• TSCA收录: 是
• GHS危险品标识: GHS06; GHS07
• GHS警示词: Danger
• GHS危险声明: H301-H315-H319-H335; H302
• GHS警示性声明: P261-P301 + P310-P305 + P351 + P338; P264-P270-P301+P312-P330-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

药理学性质

• 作用靶点: Others

产品相关信息

• 纯度: 98+%
• 成盐信息: Free Base

详细说明

MP Biomedicals - 02157785

Free Base
Crystalline

MP Biomedicals - 05214044

MP Biomedicals Rare Chemical collection

DrugBank - DB01424

• Drug Groups: approved; withdrawn
• Description: A pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of agranulocytosis. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of cytochrome P-450 metabolic activity in liver function tests. [PubChem]
• Indication: Formerly widely used as an antipyretic and analgesic in rheumatism, neuritis, and common colds. Currently used to measure total body water.
• Pharmacology: Aminophenazone is a pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of agranulocytosis. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of cytochrome P-450 metabolic activity in liver function tests. [Wikipedia]
• Toxicity: Can cause life-threatening agranulocytosis.
• Affected Organisms: Humans and other mammals
• References: Rating D, Langhans CD: Breath tests: concepts, applications and limitations. Eur J Pediatr. 1997 Aug;156 Suppl 1:S18-23. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - D8015

Biochem/physiol Actions
Antipyrine was found to be nonmutagenic when screened against Salmonella typhimurium tester strains TA100, TA98, TA97, TA102 and TA104.3
Application
Oxidation by Fe(VI) has potential to remove N-nitrosodimethylamine precursors, including 4-dimethylaminoantipyrine, from drinking water.1 4-Dimethylaminoantipyrine is itself an effective scavenger of reactive nitrogen compounds nitric oxide and peroxynitrite, important in the inflammatory response.2

参考文献

• Rating D, Langhans CD: Breath tests: concepts, applications and limitations. Eur J Pediatr. 1997 Aug;156 Suppl 1:S18-23. Pubmed