944-73-0

Basic information

• Product Name: 1,3-DIMETHYLURIC ACID
• Synonyms: 1,3-DIMETHYL-2,6,8-TRIHYDROXYPURINE;1,3-DIMETHYLURIC ACID;1,3-Dimethyl-7,9-dihydro-1H-purine-2,6,8(3H)-trione;7,9-dihydro-1,3-dimethyl-1h-purine-2,6,8(3h)-trione;8(3h)-trione,7,9-dihydro-1,3-dimethyl-1h-purine-6;Ba 2751;ba2751;Oxytheophylline
• CAS NO: 944-73-0
• Molecular Formula: C₇H₈N₄O₃
• Molecular Weight: 196.16
• EINECS: 213-410-1
• Mol File: 944-73-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: ≥300 °C(lit.)
• Boiling Point: 333.04°C (rough estimate)
• Flash Point: 268.4 °C
• Appearance: /
• Density: 1.4375 (rough estimate)
• Vapor Pressure: 1.93E-11mmHg at 25°C
• Refractive Index: 1.6700 (estimate)
• Storage Temp.: −20°C
• Solubility: 1 M NH4OH: soluble50mg/mL, clear to slightly hazy, colorless to
• PKA: 5.61±0.50(Predicted)
• CAS DataBase Reference: 1,3-DIMETHYLURIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIMETHYLURIC ACID(944-73-0)
• EPA Substance Registry System: 1,3-DIMETHYLURIC ACID(944-73-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 2
• RTECS: UP0783700
• Hazardous Substances Data: 944-73-0(Hazardous Substances Data)

Usage

Uses

1,3-Dimethyluric Acid, is a metabolite of Caffeine (C080100), that is shown to have some of Its similar effects.

Definition

ChEBI: 1,3-dimethyluric acid is an oxopurine that is 7,9-dihydro-1H-purine-2,6,8(3H)-trionesubstituted by methyl groups at N-1 and N-3. It has a role as a metabolite. It derives from a 7,9-dihydro-1H-purine-2,6,8(3H)-trione. It is a conjugate acid of a 1,3-dimethylurate anion.

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 
• 58-55-9 theophylline 
• 5440-00-6 4,5-Diamino-1,3-dimethyluracil 
• 3197-61-3 N-formylimidazole 
• 616-38-6 carbonic acid dimethyl ester 
• 102-09-0 bis(phenyl) carbonate 
• 6632-68-4 6-amino-1,3-dimethyl-5-nitroso-1H-pyrimidine-2,4-dione 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 298-12-4 Glyoxilic acid 
• 57-13-6 urea 
• 106887-61-0 5-chloro-1,3-dimethyl-5,7-dihydro-3H-purine-2,6,8-trione 

Downstream Products

• 2757-85-9 1,3-dimethylalloxan 
• 57-13-6 urea 
• 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 
• 585-05-7 oxaluric acid 
• 144-62-7 oxalic acid 
• 74-89-5 methylamine 
• 5176-82-9 1,3-dimethylparabanic acid 
• 600-39-5 dimethyloxamide 
• 708-79-2 1-methyluric acid 
• 85-18-7 8-chlorotheophylline 

Relevant articles and documents

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.

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.

Reaction of 5-Nitroso-6-Aminouracils with Glyoxylic Acid – A Simple Synthetic Pathway to Uric Acid Derivatives

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