Aminophenazone

Base Information

• Chemical Name: Aminophenazone
• CAS No.: 58-15-1
• Deprecated CAS: 144574-10-7
• Molecular Formula: C13H17N3O
• Molecular Weight: 231.297
• Hs Code.: 29331190
• European Community (EC) Number: 200-365-8
• NSC Number: 757388,4993
• UN Number: 2811
• UNII: 01704YP3MO
• DSSTox Substance ID: DTXSID7020504
• Nikkaji Number: J2.331K
• Wikipedia: Aminophenazone
• Wikidata: Q416503
• NCI Thesaurus Code: C76792
• Pharos Ligand ID: 55CTRHQHJC51
• Metabolomics Workbench ID: 43553
• ChEMBL ID: CHEMBL288470
• Mol file: 58-15-1.mol

Synonyms:1,5-Dimethyl-4-dimethylamino-2-phenyl-3-pyrazolone;1-Phenyl-2,3-dimethyl-4-dimethylaminopyrazol-5-one;3-Keto-1,5-dimethyl-4-dimethylamino-2-phenyl-2,3-;4-(Dimethylamino)antipyrine;Dimethylamino-analgesine;

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Chemical Property of Aminophenazone

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.000333mmHg at 25°C
• Melting Point: 107-109 °C(lit.)
• Refractive Index: 1.614
• Boiling Point: 319.7 °C at 760 mmHg
• PKA: pKa 5.0 (Uncertain)
• Flash Point: 125.9 °C
• PSA: 30.17000
• Density: 1.17 g/cm³
• LogP: 1.55040
• Storage Temp.: Refrigerator
• Sensitive.: Air & Light Sensitive
• Water Solubility.: 5.55 g/100 mL
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 231.137162174
• Heavy Atom Count: 17
• Complexity: 343
• Transport DOT Label: Poison

Purity/Quality:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-21/22
• Safety Statements: 26-36-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)N(N1C)C2=CC=CC=C2)N(C)C
• Uses: Aminopyrine is used as an antipyretic and analgesic drug. It belongs to the pyrazolone derivatives having a most toxic and most dangerous analgesic effect and it is a non-narcotic drug. Due to strong adverse effects, its single medicine preparation is gradually replaced by compound preparation.

Technology Process of Aminophenazone

There total 62 articles about Aminophenazone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-dimethylamino-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one; compound with 3,3-diethyl-1H-pyridine-2,4-dione (81944-03-8,69401-33-8,8015-18-7) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → diethylbarbituric acid (57-44-3) + aminopyrine (58-15-1)

Guidance literature:

Reference yield:

aminopyrine (58-15-1) + chlorpromazine semiquinone cation radical → 2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine (50-53-3) + aminopyrine radical cation (58-15-1)

Guidance literature:

Rate constant; pH 6;

DOI:10.1039/P29880001579

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 1,5-dimethyl-4-nitroso-2-phenyl-1,2-dihydro-pyrazol-3-one (885-11-0) → aminopyrine (58-15-1)

Guidance literature:

With water; copper(II) sulfate; zinc; Reagens 4: H₂SO₄;

upstream raw materials:

methyl iodide

dimethyl sulfate

4-hydrazinyl-N,N-dimethylbenzenamine

5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-ylamine

Downstream raw materials:

4-dimethylamino-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one; compound with 5-allyl-5-isopropyl-barbituric acid

N,N,N',N'-Tetramethyl-benzene-1,4-diamine

2-Dimethylamino-2-methoxy-3-[(E)-methylimino]-N-phenyl-butyramide

phenolate

Refernces

• 1、 Goodwin, Douglas C.,Grover, Thomas A.,Aust, Steven D.. "Redox mediation in the peroxidase-catalyzed oxidation of aminopyrine: Possible implications for drug-drug interactions". . p. 476 - 483. Retrieved 1996.
• 2、 Choudhary, Muhammad Iqbal,Rizvi, Fazila,Shaikh, Muniza,Siddiqui, Hina,Yousuf, Sammer,Zafar, Humaira. "Microwave assisted Biology-Oriented Drug Synthesis (BIODS) of new N,N′-disubstituted benzylamine analogous of 4-aminoantipyrine against leishmaniasis – In vitro assay and in silico-predicted molecular interactions with key metabolic targets". . . Retrieved 2022/01/25.
• 3、 Pegurier, Cecile,Collart, Philippe,Danhaive, Pierre,Defays, Sabine,Gillard, Michel,Gilson, Frederic,Kogej, Thierry,Pasau, Patrick,Van Houtvin, Nathalie,Van Thuyne, Marc,van Keulen, BerendJan. "Pyrazolone methylamino piperidine derivatives as novel CCR3 antagonists". . p. 4228 - 4231. Retrieved 2008/02/09.