3-Methylxanthine

Base Information

• Chemical Name: 3-Methylxanthine
• CAS No.: 1076-22-8
• Molecular Formula: C6H6N4O2
• Molecular Weight: 166.139
• Hs Code.: 29335990
• European Community (EC) Number: 214-058-1
• NSC Number: 515466
• UNII: WS6X982OEC
• DSSTox Substance ID: DTXSID90148107
• Nikkaji Number: J492.513K,J3.360J
• Wikidata: Q27888118
• Metabolomics Workbench ID: 37909
• ChEMBL ID: CHEMBL619
• Mol file: 1076-22-8.mol

Synonyms:3-methylxanthine;3-methylxanthine, methyl-(13)C-labeled;3-methylxanthine, monopotassium salt;3-methylxanthine, monosodium salt

Chemical Property of 3-Methylxanthine

Chemical Property:

• Appearance/Colour: white to cream solid
• Vapor Pressure: 2.23E-05mmHg at 25°C
• Melting Point: >300 °C
• Refractive Index: 1.827
• Boiling Point: 322.4oC at 760 mmHg
• PKA: pK1:8.10;pK2:11.3 (25°C)
• Flash Point: 148.8oC
• PSA: 83.54000
• Density: 1.54 g/cm³
• LogP: -1.05010
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly)
• Water Solubility.: Insoluble in water.
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 166.04907545
• Heavy Atom Count: 12
• Complexity: 242

Purity/Quality:

98%min ^*data from raw suppliers

3-Methylxanthine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T+
• Hazard Codes: Xn,T+
• Statements: 22-26/27/28
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C2=C(C(=O)NC1=O)NC=N2
• Uses: 3-Methylxanthine is a Xanthine derivative with diuretic, cardiac stimulant and smooth muscle relaxant activities; isomeric with theobromine.They can also act as Bronchodilator.

Technology Process of 3-Methylxanthine

There total 40 articles about 3-Methylxanthine 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: 95.12%

4-(N-methylamino)-1H-imidazole-5-carboxamide (90801-87-9) → 3-methylxanthine (1076-22-8)

Guidance literature:

With formic acid; perchloric acid adsorbed on silica gel; In ethanol; at 20 ℃; for 0.333333h; Solvent;

Reference yield: 94.1%

formic acid (64-18-6) + 5,6-diamino-1-methyluracil (6972-82-3) → 3-methylxanthine (1076-22-8)

Guidance literature:

formic acid; 5,6-diamino-1-methyluracil; In water; at 105 ℃; for 3h;

With sodium hydroxide; In water; at 105 ℃; for 1h;

Reference yield: 90.0%

7-benzyl-3-methylxanthine (56025-86-6) → 3-methylxanthine (1076-22-8)

Guidance literature:

With 20 % Pd(OH)2/C; hydrogen; In acetic acid; ethyl acetate; at 90 ℃; for 0.416667h; under 75007.5 Torr; H-Cube reactor;

DOI:10.1039/c0nj00612b

upstream raw materials:

formaldehyd

5,6-diamino-1-methyluracil

formamide

6-amino-1-methyl-5-nitrosouracil

Downstream raw materials:

3,7,9-trimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purinium; toluene-4-sulfonate

theobromine /

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

3,7-dihydro-7-(4-methoxybenzyl)-3-methyl-1H-purine-2,6-dione

Refernces

• 1、 Szolomajer, Janos,Paragi, Gabor,Batta, Gyula,Guerra, Celia Fonseca,Bickelhaupt, F. Matthias,Kele, Zoltan,Padar, Petra,Kupihar, Zoltan,Kovacs, Lajos. "3-Substituted xanthines as promising candidates for quadruplex formation: Computational, synthetic and analytical studies". . p. 476 - 482. Retrieved 2011.
• 2、 Tanabe et al.. "-". . p. 3224. Retrieved 1976.
• 3、 Zhang, Zhi-Yi,Kaminsky, Laurence S.. "Characterization of Human Cytochromes P450 Involved in Theophylline 8-Hydroxylation". . p. 205 - 212. Retrieved 1995.
• 4、 Andosov, V. V.,Kirilyus, I. V.,Frangulyan, G. A.. "ELECTROCHEMICAL REDUCTION OF NITROSO PRODUCTS OF THE MANUFACTURE OF THEOPHYLLINE AND THEOBROMINE". . p. 268 - 269. Retrieved 1981.
• 5、 Abramova et al.. "-". . . Retrieved 1975.
• 6、 Konishi,Morita,Yamaji. "Multiplicity of cytochrome P-450 species involved in theophylline metabolism in mouse hepatic microsomes". . p. 576 - 580. Retrieved 1995.
• 7、 Reichman,Bergmann,Neiman. "Alkaline hydrolysis of methylthiopurines bearing oxo groups in the ring". . p. 3367 - 3371,3367,3370. Retrieved 1973.
• 8、 -. "Preparation method of hypoglycemic drug linagliptin intermediate". Paragraph 0049-0057. . Retrieved 2021/04/21.