611-59-6

Basic information

• Product Name: 1,7-DIMETHYLXANTHINE
• Synonyms: 1,7-Dimethyl-1H-purine-2,6-dione, 1,7-Dimethylxanthine, 2,6-Dihydroxy-1,7-dimethylpurine, Paraxanthine;1,7-Dimethyl-1H-purine-2,6-dione, 2,6-Dihydroxy-1,7-dimethylpurine, Paraxanthine;1,7-Dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione;1,7-Dimethylxanthine-[13C4,15N3] (para-xanthine);1,7-Dimethylxanthine-[2H6] (para-xanthine);Paraxanthine-d3;IMp. F (EP): 1,7-DiMethyl-3,7-dihydro-1H-purine-2,6-dione(Paraxanthine;Caffeine IMpurity F
• CAS NO: 611-59-6
• Molecular Formula: C₇H₈N₄O₂
• Molecular Weight: 180.16
• EINECS: 210-271-9
• Product Categories: Amines;Heterocycles;Metabolites & Impurities;Phosphorylating and Phosphitylating Agents;Isolabel;Various Metabolites and Impurities;Metabolites
• Mol File: 611-59-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: 294-296 °C(lit.)
• Boiling Point: 312.97°C (rough estimate)
• Flash Point: 9℃
• Appearance: white/solid
• Density: 1.3640 (rough estimate)
• Refractive Index: 1.6700 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: ethanol: 0.6mg/mL
• PKA: pKa 8.5 (Uncertain)
• Stability: Store tightly sealed at RT
• BRN: 197907
• CAS DataBase Reference: 1,7-DIMETHYLXANTHINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,7-DIMETHYLXANTHINE(611-59-6)
• EPA Substance Registry System: 1,7-DIMETHYLXANTHINE(611-59-6)

Safety Data

• 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
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 3
• RTECS: RV9380000
• Hazardous Substances Data: 611-59-6(Hazardous Substances Data)

Usage

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.

Chemical Properties

Off-White to Pale Yellow Solid

Uses

Different sources of media describe the Uses of 611-59-6 differently. You can refer to the following data:
1. adenosine receptor agonist, CNS stimulant
2. 1,7-Dimethylxanthine has been used for the quantification of caffeine by high-performance liquid chromatography (HPLC).
3. Paraxanthine is an adenosine receptor ligand and a major metabolite of caffeine.This compound is a contaminant of emerging concern (CECs).

General Description

Paraxanthine is a major plasma and urinary metabolite of caffeine. This xanthine derivative is, along with caffeine, a central nervous system stimulant. This Snap-N-Spike? reference solution is applicable for caffeine quantitation in clinical toxicology or urine drug testing by LC-MS/MS or GC/MS.

Biochem/physiol Actions

Adenosine receptor ligand; major metabolite of caffeine

Safety Profile

An experimental teratogen. Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)

Upstream product

• 19143-71-6 1,7-dimethyl-2-thioxo-1,2,3,7-tetrahydro-purin-6-one 
• 5472-54-8 8-chloro-1,7-dimethyl-1H-purine-2,6(3H,7H)-dione 
• 97184-72-0 1,7-dimethyl-2-methoxy-6-oxo-1,6-dihydropurine 
• 7051-59-4 2-ethoxy-1,7-dimethyl-1,7-dihydro-purin-6-one 
• 16017-76-8 2-chloro-7-methyl-6-oxo-1,6-dihydropurine 
• 61982-18-1 4-amino-1-methylimidazole-5-carboxylate ethyl ester 
• 40648-96-2 1-methyl-4-nitro-1H-imidazole-5-carbonitrile 
• 58-08-2 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione 
• 105-40-8 Ethyl N-methylcarbamate 
• 16017-75-7 2-chloro-6-oxo-1,6-dihydro-1,7-dimethylpurine 
• 858221-03-1 5-amino-3-methyl-3H-imidazole-4-carboxylic acid methylamide 
• 541-41-3 chloroformic acid ethyl ester 
• 130557-57-2 1,7-dimethyl-3-aminoxanthine 
• 118-00-3 G 

Downstream Products

• 7464-77-9 3-isopropyl-1,7-dimethyl-3,7-dihydro-purine-2,6-dione 
• 7499-88-9 1,7-Dimethyl-3-benzylxanthine 
• 7464-76-8 3-Propyl-1,7-dimethylxanthine 
• 7464-75-7 3-allyl-1,7-dimethyl-3,7-dihydro-purine-2,6-dione 
• 139927-95-0 3-<(4-methoxymethoxy)-3-nitrobenzyl>-1,7-dimethylxanthine 
• 7499-82-3 1,7-Dimethyl-3-(3'-methylbutyl)xanthine 
• 7501-74-8 3-(2-hydroxy-ethyl)-1,7-dimethyl-3,7-dihydro-purine-2,6-dione 
• 2093393-05-4 3-(3-(3-hydroxyphenyl)prop-2-yn-1-yl)-1,7-dimethyl-8-(methylsulfonyl)-3,7-dihydro-1H-purine-2,6-dione 
• 5472-54-8 8-chloro-1,7-dimethyl-1H-purine-2,6(3H,7H)-dione 

Relevant articles and documents

Preparation method of paraxanthine

The invention discloses a preparation method of paraxanthine, which comprises the following steps: carrying out N methylation on 7-site and 1-site of guanine nucleoside (V), hydrolyzing glycosyl to obtain a compound (II), reacting the compound (II) with a diazotization reagent, and hydrolyzing to obtain the paraxanthine (I). The raw materials and the auxiliary materials are cheap and easy to obtain, and the industrial price of the main raw material guanosine is only 90 yuan/KG; the steps are short, and the total yield is not less than 70%; the reaction conditions are mild, and the method is safe and reliable; and the method is simple to operate, stable in process and suitable for industrialization.

Preparation methods of 1, 7-dimethylxanthine and intermediate thereof, and intermediate

The invention provides two preparation methods of 1, 7-dimethylxanthine, an intermediate thereof and a preparation method of the intermediate. The two preparation methods of 1, 7-dimethylxanthine, provided by the invention, have advantages of convenient o

Discovery of a new class of highly potent necroptosis inhibitors targeting the mixed lineage kinase domain-like protein

We report the development of novel Mixed Lineage Kinase Domain-Like protein (MLKL) inhibitors with single nanomolar potency (compound 15 is also named as TC13172). Using the converting biochemistry to chemistry activity-based protein profiling (BTC-ABPP) method, we were able to determine that the inhibitors covalently bind to Cysteine86 (Cys-86) of MLKL. This is the first example of the use of LC-MS/MS to identify the binding site of an MLKL inhibitor. The novel MLKL inhibitors provide powerful tools to study the biological function of MLKL and demonstrate that MLKL should be viewed as a druggable target.