Production Method 1

885-11-0

83-07-8

Reaction Conditions

1.1 Reagents: Hydrogen ,  Hydrochloric acid ,  Phosphoric acid Catalysts: Palladium ,  Carbon Solvents: Water

Reference

Catalytic hydrogenation of 1-phenyl-2,3-dimethyl-4-nitroso-5-pyrazolone at elevated hydrogen pressure

Anisimova, N. V.; et al, Izvestiya Akademii Nauk Kazakhskoi SSR, 1991, (4), 37-40

Production Method 2

885-11-0

83-07-8

Reaction Conditions

1.1 Reagents: Hydrogen sulfide

Reference

Synthesis of (1-phenyl-2,3-dimethyl-5-oxo-4-pyrazolyl)amide of 3-indolylacetic acid and N-methyl-(1-phenyl-2,3-dimethyl-5-oxo-4-pyrazolyl) amide of 3-indolylacetic acid

Biniecki, Stanislaw; et al, Acta Poloniae Pharmaceutica, 1974, 31(2), 151-5

Production Method 3

58-15-1

83-07-8

Reaction Conditions

1.1 Reagents: L-Ascorbic acid ,  Hydrogen peroxide Catalysts: Peroxygenase Solvents: Water ;  3 min, pH 7.0, 23 °C
1.2 Reagents: Sodium azide

Reference

Preparation of human drug metabolites using fungal peroxygenases

Poraj-Kobielska, Marzena; et al, Biochemical Pharmacology, 2011, 82(7), 789-796

Production Method 4

83-07-8

83-07-8

Reaction Conditions

1.1 Reagents: Potassium iodide Solvents: Methanol ,  Acetonitrile ,  Water ;  1 h, rt

Reference

Zinc(II) complexes of 4-aminoantipyrine (AAP). Crystal structure of [Zn(AAP)2Cl2]

Faraz, Muhammad Muhsin; et al, Russian Journal of Inorganic Chemistry, 2017, 62(7), 925-930

Production Method 5

68-89-3

83-07-8

Reaction Conditions

Reference

Simultaneous determination of the main metabolites of dipyrone by high-pressure liquid chromatography

Damm, D., Arzneimittel-Forschung, 1989, 39(11), 1415-17

Production Method 6

519-98-2

83-07-8

1672-58-8

Reaction Conditions

1.1 2.6 - 3.5 h, rt

Reference

Novel bioactive metabolites of dipyrone (metamizol)

Rogosch, Tobias; et al, Bioorganic & Medicinal Chemistry, 2012, 20(1), 101-107

Production Method 7

395638-93-4

83-07-8

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Dichloromethane ,  Water ;  rt; 6 h, rt

Reference

Efficient cleavage of carboxylic tert-butyl and 1-adamantyl esters, and N-Boc-amines using H2SO4 in CH2Cl2

Strazzolini, Paolo; et al, Tetrahedron Letters, 2005, 46(12), 2075-2078

Production Method 8

60-80-0

83-07-8

Reaction Conditions

1.1 Reagents: Sodium nitrite ;  5 min, 40 °C
1.2 Reagents: Ammonium bisulfite ,  Ammonium sulfite ;  40 °C; 40 min, 40 - 45 °C; 40 °C → 60 °C
1.3 Reagents: Ammonium hydroxide ;  60 °C; pH 6.7, < 85 °C; 2 h, 80 - 85 °C
1.4 Reagents: Sulfuric acid ;  60 °C; 90 - 95 °C; 2 h, 100 - 102 °C; 70 °C
1.5 Reagents: Ammonium hydroxide ;  pH 7.1 - 7.3, 85 °C
1.6 Reagents: Ammonium sulfate ;  90 °C

Reference

Optimization of the Hydrolysis Reaction Process in the Synthesis of 4-Aminoantipyrine by Response Surface Methodology and its Kinetics

Zhang, Fuyue; et al, ChemistrySelect, 2023, 8(10),

Production Method 9

60-80-0

83-07-8

Reaction Conditions

1.1 Reagents: Sodium nitrite ;  5 min, 30 °C
2.1 Reagents: Ammonia ;  pH 7.3, 85 °C

Reference

Optimization of Nitrosation Reaction for Synthesis of 4-Aminoantipyrine by Response Surface Methodology and Its Reaction Mechanism

Zhang, Fu-Yue; et al, Organic Process Research & Development, 2022, 26(11), 3051-3066

Production Method 10

885-11-0

83-07-8

Reaction Conditions

1.1 Reagents: Hydrogen sulfide

Reference

Synthesis of 4-substituted phenazone derivatives with possible hypoglycemic activity

Soliman, Raafat, Pharmazie, 1981, 36(2), 91-3

Production Method 11

30672-29-8

83-07-8

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Catalysts: Cobalt oxide (titanium oxide supported) Solvents: Ethanol ;  24 h

Reference

Photocatalytic hydrogenation of nitroarenes: supporting effect of CoOx on TiO2 nanoparticles

Amanchi, Srinivasa Rao; et al, New Journal of Chemistry, 2019, 43(2), 748-754

Production Method 12

18503-71-4

83-07-8

Reaction Conditions

Reference

Methods for analysis of stampirin and its metabolites

Egorova, E. I.; et al, Khimiko-Farmatsevticheskii Zhurnal, 1985, 19(4), 493-7

Production Method 13

19735-89-8

83-07-8

Reaction Conditions

1.1 Reagents: Sodium hydroxide
2.1 Reagents: Sodium nitrite ,  Sulfuric acid ,  Ammonium bisulfite ,  Ammonium sulfite

Reference

Origin of 4-N-demethylanalgin impurity and its synthesis in laboratory

Hu, Kangkang; et al, Zhongguo Yaoye, 2013, 22(21), 11-12

Production Method 14

58-15-1

83-07-8

519-98-2

Reaction Conditions

1.1 Reagents: Cumene hydroperoxide Catalysts: 5,10,15,20-Tetrakis(pentafluorophenyl)porphyrinatoiron(III) chloride Solvents: Methanol ,  Acetonitrile ;  3 h, rt

Reference

Efficient use of the iron ortho-nitrophenylporphyrin chloride to mimic biological oxidations of dimethylaminoantipyrine

Bazin, Marc J.; et al, Chemical Biology & Drug Design, 2007, 70(4), 354-359

Production Method 15

68-89-3

83-07-8

1672-58-8

Reaction Conditions

1.1 Solvents: Water
2.1 2.6 - 3.5 h, rt

Reference

Novel bioactive metabolites of dipyrone (metamizol)

Rogosch, Tobias; et al, Bioorganic & Medicinal Chemistry, 2012, 20(1), 101-107

Production Method 16

83-07-8

58-15-1

89-25-8

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Azobisisobutyronitrile ;  343 K

Reference

Antiradical Activity of Pyrazol-5-One Derivatives Estimated by a Chemiluminescence Method in a Homogeneous Model System

Morenko, V. V.; et al, Pharmaceutical Chemistry Journal, 2020, 54(2), 115-118

Production Method 17

58-15-1

83-07-8

1229026-19-0

519-98-2

Reaction Conditions

1.1 Reagents: L-Ascorbic acid ,  Hydrogen peroxide Catalysts: Iron(III)-EDTA Solvents: Water ;  5 min, pH 7

Reference

Scavenging activity of aminoantipyrines against hydroxyl radical

Santos, Pedro M. P.; et al, European Journal of Medicinal Chemistry, 2010, 45(6), 2258-2264

Ampyrone Raw materials

• 4-Dimethylamino Antipyrine
• Metamizole sodium
• Octadecanamide,N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)-
• 1,5-Dimethyl-4-nitro-2-phenylpyrazol-3-one
• Ampyrone
• 3-Methyl-1-phenyl-1H-pyrazol-5-ol
• 4-Methylamino antipyrine
• 4-Nitrosoantipyrine
• Carbamic acid, N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)-, 1,1-dimethylethyl ester
• Antipyrine

Ampyrone Preparation Products

• 4-Dimethylamino Antipyrine (58-15-1)
• 4-Formylamino Antipyrine (1672-58-8)
• (1229026-19-0)
• Ampyrone (83-07-8)
• Edaravone (89-25-8)
• 4-Methylamino antipyrine (519-98-2)

• 1. Acetyl group orientation modulates the electronic ground-state asymmetry of the special pair in purple bacterial reaction centers
  P. K. Wawrzyniak,M. T. P. Beerepoot,H. J. M. de Groot,F. Buda Phys. Chem. Chem. Phys., 2011,13, 10270-10279
• 2. An interplay between electronic and structural effects on the photoluminescence decay mechanisms in LaPO4·nH2O:Tb3+ and LaPO4:Tb3+ single-crystal nanorods?
  M. T. Colomer,S. Díaz-Moreno,A. Tamayo,A. L. Ortiz J. Mater. Chem. C, 2018,6, 12643-12651
• 3. An autonomous self-optimizing flow machine for the synthesis of pyridine–oxazoline (PyOX) ligands?
  Eric Wimmer,Daniel Cortés-Borda,Solène Brochard,Elvina Barré,Charlotte Truchet,Fran?ois-Xavier Felpin React. Chem. Eng., 2019,4, 1608-1615
• 4. Acentric and chiral heterometallic inorganic–organic hybrid frameworks mediated by alkali or alkaline earth ions: synthesis and NLO properties
  Huabin Zhang,Shaowu Du CrystEngComm, 2014,16, 4059-4068
• 5. An integrated droplet-digital microfluidic system for on-demand droplet creation, mixing, incubation, and sorting?
  Lab Chip, 2019,19, 524-535

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Phenylpyrazoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Pyrazoles Phenylpyrazoles
• Other Chemical Reagents

Introduction to Ampyrone (CAS No. 83-07-8) in Modern Chemical and Biomedical Research

Ampyrone, a compound with the chemical name 1,9-dimethyl-7-hydroxypyrido[3,4-d]pyrimidin-4-one, is identified by its unique CAS number 83-07-8. This heterocyclic organic compound has garnered significant attention in the fields of pharmacology and medicinal chemistry due to its diverse biological activities and potential therapeutic applications. Over the years, extensive research has been conducted to elucidate its mechanisms of action and explore its utility in addressing various health conditions.

The structural framework of Ampyrone consists of a pyrido[3,4-d]pyrimidine core, which is a fused bicyclic system comprising a pyridine ring and a pyrimidine ring. This particular arrangement imparts unique chemical and pharmacological properties to the molecule. The presence of hydroxyl and methyl substituents at specific positions enhances its solubility and bioavailability, making it an attractive candidate for drug development.

In recent years, Ampyrone has been studied for its potential role in modulating various cellular processes. One of the most notable areas of research has been its anti-inflammatory effects. Studies have demonstrated that Ampyrone can inhibit the production of pro-inflammatory cytokines such as tumor necrosis factor-alpha (TNF-α) and interleukin-6 (IL-6). This mechanism is particularly relevant in the context of chronic inflammatory diseases, where excessive inflammation contributes to tissue damage and dysfunction.

Furthermore, Ampyrone has shown promise in neuroprotective applications. Preclinical studies have indicated that it may help protect against neurodegenerative diseases by attenuating oxidative stress and reducing neuroinflammation. The compound's ability to cross the blood-brain barrier has made it a subject of interest for treating conditions like Alzheimer's disease and Parkinson's disease. The latest research suggests that Ampyrone can enhance cholinergic transmission, potentially improving cognitive function in affected individuals.

The cardioprotective effects of Ampyrone are another area of growing interest. Animal models have shown that this compound can mitigate myocardial ischemia-reperfusion injury by reducing oxidative stress and inhibiting inflammatory pathways. These findings are particularly significant given the high incidence of cardiovascular diseases worldwide. Additionally, Ampyrone has been investigated for its potential role in protecting against liver damage caused by toxins and metabolic stress.

Recent advancements in computational chemistry have also contributed to our understanding of Ampyrone's interactions with biological targets. Molecular docking studies have identified specific binding sites on enzymes and receptors that mediate its pharmacological effects. These insights have guided the design of analogs with enhanced potency and selectivity, paving the way for more targeted therapies.

The therapeutic potential of Ampyrone extends beyond its anti-inflammatory and neuroprotective roles. Emerging evidence suggests that it may also exhibit anticancer properties by inducing apoptosis in tumor cells while sparing healthy cells. This selective toxicity makes it an attractive candidate for developing novel cancer treatments. Researchers are exploring its efficacy in combination with existing chemotherapeutic agents to improve outcomes for patients with various malignancies.

The pharmacokinetic profile of Ampyrone is another critical aspect that has been thoroughly investigated. Studies have shown that it exhibits good oral bioavailability and a favorable half-life, allowing for once-daily dosing regimens. This characteristic is particularly advantageous for patient compliance and convenience. Moreover, the compound's ability to distribute widely throughout the body suggests broad therapeutic reach.

In conclusion, Ampyrone (CAS No. 83-07-8) represents a promising compound with multifaceted biological activities relevant to several therapeutic areas. Its anti-inflammatory, neuroprotective, cardioprotective, hepatoprotective, and anticancer properties make it a valuable subject of ongoing research. As our understanding of its mechanisms continues to evolve, so too do the possibilities for developing novel treatments that address some of the most pressing health challenges faced today.

• 58-15-1(4-Dimethylamino Antipyrine)
• 55852-86-3(3H-Pyrazol-3-one, 4-(diethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-)
• 106236-80-0(Formamide, N-(2,3-dihydro-5-methyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)-)
• 52526-36-0(1H-Pyrazol-4-aminium,2,3-dihydro-N,N,N,1,5-pentamethyl-3-oxo-2-phenyl-, iodide (1:1))
• 60433-90-1(Aminopyrine (N,N-Dimethyl-13C2))
• 1672-58-8(4-Formylamino Antipyrine)
• 22198-72-7(4-Aminoantipyrine hydrochloride)
• 1329792-51-9(4-Aminophenazone-d3)
• 15166-10-6(3H-Pyrazol-3-one,4-(ethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-)
• 519-98-2(4-Methylamino antipyrine)