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

1,7-DIMETHYLXANTHINE, also known as Paraxanthine, is a xanthine derivative and a major metabolite of caffeine. It is a central nervous system stimulant and an inhibitor of phosphodiesterase 9 (PDE9). Paraxanthine is characterized by its off-white to pale yellow solid appearance and plays a significant role in various applications due to its unique properties.

Uses

Used in Pharmaceutical Applications:
1,7-DIMETHYLXANTHINE is used as an adenosine receptor agonist and a central nervous system (CNS) stimulant for promoting wakefulness and increasing locomotor activity.
Used in Clinical Toxicology and Urine Drug Testing:
1,7-DIMETHYLXANTHINE is used as a reference solution for the quantification of caffeine in clinical toxicology or urine drug testing by high-performance liquid chromatography (HPLC), LC-MS/MS, or GC/MS.
Used in Research and Development:
1,7-DIMETHYLXANTHINE is used as an adenosine receptor ligand in research, particularly in the study of its effects on motor depression, striatal cGMP, and extracellular striatal dopamine concentrations in vivo.
Used in Environmental Contaminant Analysis:
Paraxanthine, as a contaminant of emerging concern (CECs), is used in the analysis and monitoring of environmental contaminants in various settings.
Used in Drug Delivery Systems:
Although not explicitly mentioned in the provided materials, Paraxanthine's stimulant properties could potentially be utilized in the development of drug delivery systems to enhance the therapeutic outcomes of certain medications by increasing their bioavailability and delivery efficiency.

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

• 858221-03-1 5-amino-3-methyl-3H-imidazole-4-carboxylic acid methylamide 
• 541-41-3 chloroformic acid ethyl ester 
• 7051-59-4 2-ethoxy-1,7-dimethyl-1,7-dihydro-purin-6-one 
• 54828-05-6 1-methyl-4-nitro-1H-imidazole-5-carboxylic acid 
• 58-08-2 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione 
• 97184-73-1 1,7-Dimethyl-2-propoxy-1,7-dihydro-purin-6-one 
• 97184-72-0 1,7-dimethyl-2-methoxy-6-oxo-1,6-dihydropurine 
• 2239-26-1 5-formylamino-6-methylamino-3-methyluracil 
• 130557-57-2 1,7-dimethyl-3-aminoxanthine 
• 7499-88-9 1,7-Dimethyl-3-benzylxanthine 
• 16017-75-7 2-chloro-6-oxo-1,6-dihydro-1,7-dimethylpurine 
• 5472-54-8 8-chloro-1,7-dimethyl-1H-purine-2,6(3H,7H)-dione 
• 19143-71-6 1,7-dimethyl-2-thioxo-1,2,3,7-tetrahydro-purin-6-one 
• 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 
• 33868-03-0 1,7-dimethyluric acid 
• 58-08-2 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione 
• 7501-74-8 3-(2-hydroxy-ethyl)-1,7-dimethyl-3,7-dihydro-purine-2,6-dione 
• 139927-96-1 3-(4-hydroxy-3-nitrobenzyl)-1,7-dimethylxanthine 
• 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.