Paraxanthine

Base Information

• Chemical Name: Paraxanthine
• CAS No.: 611-59-6
• Molecular Formula: C7H8N4O2
• Molecular Weight: 180.166
• European Community (EC) Number: 210-271-9
• NSC Number: 400018
• UNII: Q3565Y41V7
• DSSTox Substance ID: DTXSID2052281
• Nikkaji Number: J2.991B
• Wikipedia: Paraxanthine
• Wikidata: Q419223
• Metabolomics Workbench ID: 37896
• ChEMBL ID: CHEMBL1158
• Mol file: 611-59-6.mol

Synonyms:1,7-dimethylxanthine;paraxanthine

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Chemical Property of Paraxanthine

Chemical Property:

• Appearance/Colour: off-white to pale yellow solid
• Melting Point: 294-296 °C(lit.)
• Refractive Index: 1.737
• Boiling Point: 312.97°C (rough estimate)
• PKA: pKa 8.5 (Uncertain)
• Flash Point: 9℃
• PSA: 72.68000
• Density: 1.6 g/cm³
• LogP: -1.03970
• Storage Temp.: -20°C Freezer
• Solubility.: ethanol: 0.6mg/mL
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 180.06472551
• Heavy Atom Count: 13
• Complexity: 267

Purity/Quality:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 22-39/23/24/25-23/24/25-11
• Safety Statements: 22-24/25-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Purines
• Canonical SMILES: CN1C=NC2=C1C(=O)N(C(=O)N2)C
• Description: Paraxanthine is an inhibitor of phosphodiesterase 9 (PDE9) and an antagonist of adenosine receptors A1 and A2 (Kis = 35 and 22 μM, respectively in equine forebrain tissues). It is the main metabolite of caffeine in humans, making up 80% of the three dimethylxanthine metabolites produced by caffeine demethylation. Paraxanthine increases locomotor activity and counteracts adenosine receptor agonist-induced motor depression in rats not habituated to caffeine. At a dose of 30 mg/kg, paraxanthine induces a significant increase in striatal cGMP and extracellular striatal dopamine concentrations in vivo. It also promotes wakefulness and increases locomotor activity and core temperature in narcoleptic transgenic mice without increasing behavioral anxiety.
• Uses: adenosine receptor agonist, CNS stimulant 1,7-Dimethylxanthine has been used for the quantification of caffeine by high-performance liquid chromatography (HPLC). Paraxanthine is an adenosine receptor ligand and a major metabolite of caffeine.This compound is a contaminant of emerging concern (CECs).

Technology Process of Paraxanthine

There total 46 articles about Paraxanthine 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: 90.0%

1,7-Dimethyl-3-benzylxanthine (7499-88-9) → paraxanthine (611-59-6)

Guidance literature:

With boron tribromide; In toluene; at 80 ℃; for 2h; Reagent/catalyst; Temperature; Solvent;

Reference yield: 74.0%

1,7-dimethyl-3-aminoxanthine (130557-57-2) → paraxanthine (611-59-6)

Guidance literature:

With hydrogenchloride; sodium nitrite; at 0 - 5 ℃; for 1h;

Reference yield: 60.0%

5-formylamino-6-methylamino-3-methyluracil (2239-26-1) → paraxanthine (611-59-6)

Guidance literature:

With formic acid; formamide; for 0.5h; Heating;

DOI:10.1002/jhet.5570300509

upstream raw materials:

5-amino-3-methyl-3H-imidazole-4-carboxylic acid methylamide

chloroformic acid ethyl ester

1,7-dimethyl-2-thioxo-1,2,3,7-tetrahydro-purin-6-one

8-chloro-1,7-dimethyl-1H-purine-2,6(3H,7H)-dione

Downstream raw materials:

3-(3-(3-hydroxyphenyl)prop-2-yn-1-yl)-1,7-dimethyl-8-(methylsulfonyl)-3,7-dihydro-1H-purine-2,6-dione

8-chloro-1,7-dimethyl-1H-purine-2,6(3H,7H)-dione

Refernces

• 1、 -. "Preparation method of 1,7-dimethylxanthine". Paragraph 0045; 0048; 0049; 0052; 0061; 0064; 0065; 0068. . Retrieved 2019/06/27.
• 2、 -. "MLKL INHIBITORS". Paragraph 0613-0614; 0725-0726. . Retrieved 2018/09/26.