944-73-0

Usage

Uses

Used in Pharmaceutical Industry:
1,3-Dimethyluric acid is used as a research compound for studying the effects of caffeine and its metabolites on the human body. It can be utilized in the development of new drugs or therapies that target the same pathways as caffeine, potentially offering similar benefits with reduced side effects.
Used in Nutraceutical Industry:
1,3-Dimethyluric acid can be used as an ingredient in nutraceutical products, such as dietary supplements or functional foods, that aim to provide the stimulating effects of caffeine with a lower risk of side effects. It may be particularly useful for individuals who are sensitive to caffeine or for those seeking an alternative source of energy.
Used in Cosmetic Industry:
1,3-Dimethyluric acid may be used in cosmetic products for its potential skin benefits, such as improving skin elasticity and reducing the appearance of fine lines and wrinkles. Its effects on the skin can be attributed to its similarity to caffeine, which is known to have vasoconstrictive properties and can help tighten the skin.
Used in Research and Development:
1,3-Dimethyluric acid is used as a research tool in scientific studies to better understand the metabolic pathways of caffeine and its effects on various physiological processes. This knowledge can contribute to the development of new treatments and interventions for a range of health conditions.

InChI:InChI=1/C7H8N4O3/c1-10-4-3(8-6(13)9-4)5(12)11(2)7(10)14/h1-2H3,(H2,8,9,13)

Upstream product

• 861553-89-1 (1,3-dimethyl-2,4,6-trioxo-hexahydro-pyrimidin-5-yl)-urea 
• 144-62-7 oxalic acid 
• 108-24-7 acetic anhydride 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 49810-21-1 (6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-carbamic acid ethyl ester 
• 10381-75-6 8-bromotheophylline 
• 72944-43-5 Dehydro-1,3-dimethyluric acid 
• 58-55-9 theophylline 
• 106887-61-0 5-chloro-1,3-dimethyl-5,7-dihydro-3H-purine-2,6,8-trione 
• 5440-00-6 4,5-Diamino-1,3-dimethyluracil 
• 3197-61-3 N-formylimidazole 
• 616-38-6 carbonic acid dimethyl ester 
• 57-13-6 urea 
• 708-79-2 1-methyluric acid 

Downstream Products

• 708-79-2 1-methyluric acid 
• 2757-85-9 1,3-dimethylalloxan 
• 57-13-6 urea 
• 585-05-7 oxaluric acid 
• 144-62-7 oxalic acid 
• 74-89-5 methylamine 
• 10381-75-6 8-bromotheophylline 
• 2309-49-1 theacrine 
• 127652-61-3 5-mentoxy-1,3-dimethyl-5,7-dihydro-3H-purine-2,6,8-trione 
• 127652-60-2 5-menthoxy-1,3-dimethyl-5,7-dihydro-3H-purine-2,6,8-trione 
• 32282-45-4 1,3-dimethylallantoin 
• 5176-82-9 1,3-dimethylparabanic acid 
• 600-39-5 dimethyloxamide 
• 85-18-7 8-chlorotheophylline 

Relevant academic research and scientific papers

Synthesis of dehydro-1,3-dimethyluric acid

Pyrolytic dehydrochlorination of 5-chloro-1,3-dimethyl-isouric acid (1) gave dehydro-1,3-dimethyluric acid (2b) as the first example of a quinonoid redox state in uric acid series.

Pharmacokinetics of intravenous theophylline in mutant Nagase analbuminemic rats

It was obtained from our laboratories that the expression of hepatic microsomal cytochrome P450 (CYP) 1A2 increased approximately 3.5 times in mutant Nagase analbuminemic rats (NARs, an animal model for human familial analbuminemia), and theophylline was reported to be metabolized to 1,3-dimethyluric acid (1,3-DMU) and 1-methylxanthine (which was further metabolized to 1-methyluric acid, 1-MU, via xanthine oxidase) via CYP1A2 in rats. Hence, the pharmacokinetic parameters of theophylline, 1,3-DMU and 1-MU were compared after intravenous administration of aminophylline, 5 mg/kg as theophylline, to control Sprague-Dawley rats and NARs. In NARs, the total area under the plasma concentration-time curve from time zero to time infinity (AUC) of theophylline was significantly smaller (1040 versus 1750 μg min/ml) than that in control rats and this could be due to significantly faster renal clearance (CLR, 1.39 versus 0.571 ml/min/kg, due to inhibition of renal reabsorption of unchanged theophylline) and nonrenal clearance (CLNR, 3.36 versus 2.25 ml/min/kg, due to 3.5-fold increase in CYP1A2) than those in control rats. Based on in vitro hepatic microsomal studies, the intrinsic 1,3-DMU formation clearance was significantly faster in NARs than that in control rats (267 versus 180 × 10-6 ml/min). After intravenous administration of 1,3-DMU, the renal secretion of 1,3-DMU was inhibited in NARs. Inhibition of renal secretion or reabsorption of various compounds in NARs was also discussed.

Br?nsted acid catalysis in the oxidation of purine based alkaloids by Mn(VII) in aqueous acetonitrile and sodium fluoride medium: A kinetic approach

Br?nsted acid (HClO4, H2SO4) catalyzed Mn(VII) oxidation of purine alkaloids such as caffeine, theophylline and theobromine in aqueous acetonitrile and sodium fluoride medium revealed first order kinetics in both [(Mn(VII)] and [Alkaloid] at constant acidity and temperature. Sodium fluoride was added to the reaction mixture in order to avoid/suppress auto catalytic reaction due to the generation of Mn(III) and Mn(IV) species during the course of Mn(VII) oxidations in acidic solutions. An increase in the Br?nsted acids (HClO4, H2SO4) concentration accelerated the rate of oxidation. Rate enhancements observed here in are analyzed by Zucker-Hammett, Bunnett and Bunnett-Olsen criteria of acidity functions. On the basis of observed Bunnett-Olsen criteria of acidity functions, the most plausible mechanism has been proposed with the involvement of water molecule in the slow step (as proton transferring agent).

1,3-dimethyl uric acid synthesis method

The invention discloses a 1,3-dimethyl uric acid synthesis method, which comprises: carrying out an acylation reaction on 1,3-dimethyl-5,6-diaminouracil as a raw material and an acylation reagent under the action of an acid binding agent to obtain an intermediate 1,3-dimethyl-5-amino-6-N-alkoxycarbonyluracil; and carrying out a cyclization reaction on the intermediate 1,3-dimethyl-5-amino-6-N-alkoxycarbonyluracil under the action of an alkali to obtain 1,3-dimethyl uric acid, wherein the acylation reaction and the cyclization reaction are performed under the action of a solvent. According to the present invention, 1,3-dimethyl uric acid is synthesized by using the two-step method through the optimized design and test research, such that the process is reasonable and feasible, the reactiontemperature is moderately controllable, the yield is high, and the method is suitable for large-scale industrial production.

One-step synthesis method of 1,3-dimethyl uric acid

The invention discloses a one-step synthesis method of 1,3-dimethyl uric acid. 1,3-Dimethyl-5,6-diaminouracil is taken as a raw material to carry out cyclization reaction with urea under the action of a solvent to obtain the 1,3-dimethyluric acid. The solvent in the cyclization reaction is any one or a mixture of more than one of ethylene glycol, DMSO and DMF. The 1,3-Dimethyl-5,6-diaminouracil is taken as the raw material to carry out cyclization reaction with the urea to directly obtain the 1,3-dimethyluric acid on the basis of optimized design and experimental research, the process flow is reasonable and feasible, cheap and easily available raw materials are used, the one-step synthesis method is economical and practical, the formula design is reasonable, the post-treatment is simple, the product quality is good, the yield is high, and the one-step synthesis method is suitable for large-scale industrial production.

Total synthesis method for theacrine

The invention relates to a total synthesis method for theacrine. The total synthesis method comprises the following steps: 6-amino-1,3-dimethyluracil is taken as a raw material and subjected to a nitrosation reaction, and an intermediate 6-amino-1,3-dimethyl-5-nitrosouracil is obtained; 6-amino-1,3-dimethyl-5-nitrosouracil is subjected to a reduction reaction, and an intermediate 1,3-dimethyl-5,6-diaminouracil is obtained; 1,3-dimethyl-5,6-diaminouracil is subjected to a cyclization reaction, and an intermediate 1,3-dimethyluric acid is obtained; 1,3-dimethyluric acid is reacted with a methylation reagent, and a product is obtained. Theacrine prepared with the method can be synthesized massively in industrial application without restriction of raw materials; the conversion rate and the yield are high, the synthesis is convenient, post-processing is simpler, and the method is suitable for large-scale production and can be widely popularized and applied; the method is not needed to be performed under a high pressure condition, has low requirement for equipment and reduces the incidence rate of danger; with adoption of recrystallization for preparing the target product, the product purity is high.

Extraction of radio-labelled xanthine derivatives by artificial receptors: Deep insight into the association behaviour

Association constants for the interaction of almost insoluble substrates with triphenylene ketal-based receptors in toluene have been determined by means of an extraction method employing the corresponding radio-labelled substrates. Flexible and more polar receptors tend to aggregate and exhibit inferior extraction qualities. Binding constants in toluene were found to be in the range 105-107 M-1, which is significantly higher than in dichloromethane. X-ray analyses indicate the direct participation of a water molecule in the binding process, which may account for the surprisingly small effect of moisture in the solvent on the stability of the complexes.

Highly efficient C-8 oxidation of substituted xanthines with substitution at the 1-, 3-, and 7- Positions using biocatalysts

A bacterial consortium consisting of strains belonging to the genus Klebsiella and Rhodococcus quantitatively converts 1-, 3- and 7-substituted xanthines to their respective 8-oxo compounds.

Metabolism of theophylline and its inhibition by fluoroquinolones in rat hepatic microsomes

1. The effects of β-naphthoflavone, dexamethasone, phenobarbitone and isosafrole on the metabolism of theophylline by rat liver microsomes have been studied. Only β-naphthoflavone, a known P4501A inducer, increased the rate of 1-methylxanthine formation (3-fold), whereas all the inducers studied increased the rate of 1,3-dimethyluric acid production (2.5-3-fold). 2. To study the effects of a range of fluoroquinolones on theophylline metabolism, β-naphthoflavone-induced microsomes mere used, as the ratio for metabolite production rates was similar to that of untreated microsomes (4:1,3-dimethyluric acid: 1-methylxanthine at 2 mM theophylline). High concentrations of fluoroquinolones (0.5-1.5 mM) were required to affect microsomal theophylline metabolism. 1-Methylxanthine was more sensitive to fluoroquinolone inhibition by enoxacin, ciprofloxacin, norfloxacin and pipemidic acid than 1,3-dimethyluric acid; CP67015, had a significant effect on 1,3-dimethyluric acid production only; binfloxacin had no effect on either pathway. 3. Ethoxycoumarin, a rapidly metabolized substrate, was also investigated as a surrogate for theophylline in in vitro experiments. Fluoroquinolone inhibition of ethoxycoumarin O-de-ethylation in β-naphthoflavone-induced microsomes was quantitatively greater but qualitatively similar to theophylline metabolism (IC(50s) 440-870 μM at 2 μM 7-ethoxycoumarin). 4. These data are comparable with previous rat experiments in vivo, indicating that enoxacin, ciprofloxacin and norfloxacin have similar intrinsic activity in the inhibition of theophylline metabolism.

Multiplicity of cytochrome P-450 species involved in theophylline metabolism in mouse hepatic microsomes

To ascertain the multiplicity of the cytochrome P-450 (P-450) species participating in the individual metabolic conversion of theophylline by 8-hydroxylation, 3-demethylation and 1-demethylation in mice, kinetics were studied under various conditions using untreated and inducer-treated mouse hepatic microsomes. Eadie-Hofstee plots of 1-demethylation in untreated microsomes exhibited a straight line, whereas those of 8-hydroxylation and 3-demethylation were curved lines. The biphasic kinetics indicated the contribution of two P-450 populations to the respective metabolic pathways; one characterized by high affinity and low capacity, the other by low affinity and high capacity. The high affinity population was efficiently induced by β-naphthoflavone (β-NF), and was highly susceptible to inhibition by a specific CYP1A inhibitor. The low affinity population was sensitive to induction by phenobarbital (PB), and was markedly inhibited by preferential inhibitors for PB-inducible P-450 species. The present results indicated that two P-450 populations contributed to the theophylline metabolism in mouse hepatic microsomes, and that the high and low affinity populations corresponded, respectively, to CYP1A, and a PB-inducible P-450 species having a much higher capacity than CYP1A.