1-Methylxanthine

Base Information

• Chemical Name: 1-Methylxanthine
• CAS No.: 6136-37-4
• Molecular Formula: C6H6N4O2
• Molecular Weight: 166.139
• Hs Code.: 29335990
• European Community (EC) Number: 228-108-5
• UNII: 7EE8WCA32U
• DSSTox Substance ID: DTXSID30210271
• Nikkaji Number: J492.512B,J2.241A
• Wikidata: Q27136943
• Metabolomics Workbench ID: 41117
• ChEMBL ID: CHEMBL1250
• Mol file: 6136-37-4.mol

Synonyms:1-methylxanthine

Chemical Property of 1-Methylxanthine

Chemical Property:

• Appearance/Colour: faint yellow solid
• Melting Point: ≥300 °C
• Refractive Index: 1.626
• PKA: pK1:7.70;pK2:12.0 (25°C)
• PSA: 83.54000
• Density: 1.539 g/cm³
• LogP: -1.05010
• Storage Temp.: -20°C Freezer
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly)
• XLogP3: -0.3
• 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%,99%, ^*data from raw suppliers

1-Methylxanthine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Purines
• Canonical SMILES: CN1C(=O)C2=C(NC1=O)N=CN2
• Uses: A metabolite of Theophylline.

Technology Process of 1-Methylxanthine

There total 18 articles about 1-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: 42.0%

5,6‐diamino‐2‐methoxy‐3‐methylpyrimidin‐4(3H)‐one (85357-27-3) + formamide (77287-34-4,77287-35-5,60100-09-6) → 1-methylxanthine (6136-37-4)

Guidance literature:

With hydrogenchloride; for 12h; Heating;

Reference yield:

3-methyl-6-aminouracil (21236-97-5) → 1-methylxanthine (6136-37-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / NaNO₂, conc. HCl / dimethylformamide; H₂O / 1 h / 30 °C

2: Na₂S₂O₄, 12.5percent aq. NH₄OH / 0.33 h / 70 °C

3: 4 h / Heating

With hydrogenchloride; ammonium hydroxide; sodium dithionite; sodium nitrite; In water; N,N-dimethyl-formamide;

Reference yield:

5-nitroso-6-amino-3-methyl-1,3-dihydropyrimidine-2,4-dione (61033-04-3) → 1-methylxanthine (6136-37-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Na₂S₂O₄, 12.5percent aq. NH₄OH / 0.33 h / 70 °C

2: 4 h / Heating

With ammonium hydroxide; sodium dithionite;

upstream raw materials:

6-amino-3-methyl-5-(N-formylamino)uracil

formamide

8-chlorocaffeine

5,6-diamino-3-methylpyrimidine-2,4(1H,3H)-dione

Downstream raw materials:

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

1-Methyl-uramil

7-benzyl-1-methyl-3,7-dihydro-purine-2,6-dione

1-Methyl-7-(3'-methyl-2'-butenyl)xanthine

Refernces

• 1、 Ogiso,Iwaki,Uno. "Inhibition kinetics of theophylline metabolism by mexiletine and its metabolites". . p. 75 - 81. Retrieved 2007/10/03.
• 2、 Zhang, Zhi-Yi,Kaminsky, Laurence S.. "Characterization of Human Cytochromes P450 Involved in Theophylline 8-Hydroxylation". . p. 205 - 212. Retrieved 2007/10/03.