Metamizole

Base Information

• Chemical Name: Metamizole
• CAS No.: 50567-35-6
• Deprecated CAS: 7061-45-2,129-84-0
• Molecular Formula: C13H17 N3 O4 S
• Molecular Weight: 311.362
• European Community (EC) Number: 256-627-7
• UNII: 934T64RMNJ
• DSSTox Substance ID: DTXSID6044143
• Wikipedia: Metamizole
• Wikidata: Q56719288
• RXCUI: 3523
• Pharos Ligand ID: 6YJ77KZ9JQ45
• Metabolomics Workbench ID: 61987
• ChEMBL ID: CHEMBL461522
• Mol file: 50567-35-6.mol

Synonyms:Algopyrin;Analgin;Biopyrin;Dipyrone;Dipyronium;Metamizol;Metamizole;Metamizole Sodium;Methamizole;Methampyrone;Narone;Noramidopyrine Methanesulfonate;Noramidopyrine Methanesulfonate Sodium;Normelubrine;Novalgetol;Novalgin;Novamidazophen;Novaminsulfone;Optalgin;Pyralgin;Sulpyrin;Sulpyrine

Chemical Property of Metamizole

Chemical Property:

• Melting Point: 131-132 °C (decomp)
• Refractive Index: 1.611
• PKA: 1.32±0.50(Predicted)
• PSA: 92.92000
• Density: 1.379g/cm³
• LogP: 1.84670
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 311.09397721
• Heavy Atom Count: 21
• Complexity: 546

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)N(N1C)C2=CC=CC=C2)N(C)CS(=O)(=O)O
• Recent ClinicalTrials: Evaluation of the Added Value of Metamizole to Standard Postoperative Treatment After Ambulant Shoulder Surgery
• Recent EU Clinical Trials: Evaluation of the added value of Metamizole to standard postoperative treatment after ambulant shoulder surgery: a double-blind, randomized controlled trial

Technology Process of Metamizole

There total 4 articles about Metamizole 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: 98.5%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-methylaminoantipyrine (519-98-2) → Metamizol (50567-35-6)

Guidance literature:

With sulfur dioxide; water; In ethanol; at 60 - 80 ℃; under 2068.65 - 3102.97 Torr; Solvent; Pressure;

Reference yield: 93.3%

metamizol (68-89-3) → Metamizol (50567-35-6)

Guidance literature:

With hydrogenchloride; In ethanol; at 20 - 30 ℃; for 1h; Solvent; Reagent/catalyst;

Reference yield:

4-methylaminoantipyrine (519-98-2) → Metamizol (50567-35-6)

Guidance literature:

/BRN= 290808/;

upstream raw materials:

4-methylaminoantipyrine

metamizol

formaldehyd

Downstream raw materials:

1-diketobutyryl-1-phenyl-2-methyl-2-nitrosohydrazine

1-acetyl-1-methyl-2-nitroso-2-phenylhydrazine

4-(N-methyl-N-nitroso)aminoantipyrine

Oxalsaeure-mono(2-acetyl-2-methyl-1-phenyl)hydrazid

Refernces

Tandem one-pot synthesis of polysubstituted pyridines using the blaise reaction intermediate and 1,3-enynes

10.1021/ol202691b

The study presents a novel tandem one-pot method for the synthesis of polysubstituted pyridines, which are important components in natural products, pharmaceuticals, and functional materials. The process involves the sequential reactions of nitriles with Reformatsky reagents and 1,3-enynes, utilizing the Blaise reaction intermediate. The chemicals used include various aromatic nitriles, Reformatsky reagents with different R2 groups, and a range of 1,3-enynes. These chemicals serve to construct pyridine rings with controllable substitution patterns around the pyridine core, offering a flexible and efficient synthetic approach. The purpose of these chemicals is to enable the selective control of substitution patterns in the pyridine moiety through a series of reactions that include regio- and chemoselective addition, isomerization, cyclization, and aromatization. This method not only simplifies the synthetic steps but also minimizes waste generation, and it allows for the divergent construction of two different heterocyclic rings, pyridine and pyridone, within a single molecule.