519-32-4

Usage

Uses

Used in Pharmaceutical Industry:
ISOCAFFEINE is used as a secondary standard for quality control in pharmaceutical laboratories and manufacturers. It serves as a convenient and cost-effective alternative to the preparation of in-house working standards, ensuring the accuracy and reliability of pharmaceutical products containing caffeine.
Used in Research and Development:
ISOCAFFEINE is used as a research compound in the development of new drugs and therapies involving caffeine or its derivatives. Its presence as an impurity in caffeine allows researchers to study its effects and interactions with other compounds, potentially leading to the discovery of novel applications and treatments.
Used in Quality Control and Testing:
ISOCAFFEINE is used as a reference material in the quality control and testing of caffeine-containing products. It helps to ensure that the purity and concentration of caffeine in these products meet the required standards, maintaining the safety and efficacy of the final product for consumers.

Biochem/physiol Actions

1,3,9-Trimethylxanthine is an adenosine receptor antagonist.

InChI:InChI=1/C8H10N4O2/c1-10-4-9-5-6(10)11(2)8(14)12(3)7(5)13/h4H,1-3H3

Upstream product

• 186581-53-3 diazomethane 
• 1198-33-0 9-methylxanthine 
• 2564-54-7 1,3,9-trimethyl-8-thio-uric acid 
• 84346-90-7 Toluene-4-sulfonate7-cyanomethyl-1,3,9-trimethyl-2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-7-ium; 
• 886-38-4 diphenylcyclopropenone 
• 84346-94-1 Toluene-4-sulfonate7-methoxycarbonylmethyl-1,3,9-trimethyl-2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-7-ium; 
• 84346-81-6 C₁₆H₁₆N₄O₃ 
• 1811-38-7 3-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)propanenitrile 
• 77-78-1 dimethyl sulfate 
• 5440-00-6 4,5-Diamino-1,3-dimethyluracil 
• 769-42-6 1,3-dimethylbarbituric acid 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 
• 6972-27-6 1,3-Dimethyl-6-chlorouracil 
• 64-18-6 formic acid 

Downstream Products

• 7464-93-9 1,3,9-trimethyluric acid 
• 1073148-20-5 [(NH3)5RuTMX][ZnCl4]Cl 

Relevant academic research and scientific papers

ETHYNYLXANTHINES, PREPARATION AND USE AS CALCIUM ION CHANNEL MODULATORS

The present invention relates to novel pharmaceutical compounds, which exhibit ability to act as calcium ion channel modulators, methods for their synthesis and the treatment and/or prevention of various diseases and disorders including deregulated calcium ion channel activity.

Michael adducts in regioselective synthesis of N-substituted azoles

Michael adducts of azoles (4-phenyl-, 4-methyl- and 4-nitroimidazole, 4-methylbenzimidazole, 1,2,4-triazole and theophylline) are shown to be valuable substrates for obtaining the N-substituted derivatives of the parent heterocycles by a quaternization-Hofmann elimination sequence. The effectiveness of the procedure is dependent on the regiochemical outcome of the first, N-protective step, i.e. the Michael addition. By choosing the appropriate Michael acceptor, alkylating agent and deprotection conditions, the thermodynamically less stable regioisomers of N-substituted azoles have been obtained in high yields.

Generation and Properties of N7-Xanthinium Ylides: Reactions of N7-Xanthinium Ylides with Diphenylcyclopropenone and Acetylenic Compounds

Xanthinium N7-ylides were generated in situ from 7-substituted 9-methylxanthinium tosylates (2) using n-BuLi in tetrahydrofuran or Et3N in MeCN.The xanthinium N7-ylides (3) generated using Et3N in MeCN reacted with diphenylcyclopropenone to give pyrone derivatives and isocaffeine in good yields.The reactions of 3a-b with dimethyl acetylenedicarboxylate or methyl propiolate (MP) afforded 5-pyrrol-1-yluracils in moderate yields.N7-Methoxycarbonylmethylide (3c) reacted with MP to give a pyrrolopteridine derivative together with a 5-pyrrol-1-yluracil derivative.Furthermore, the dihydropyrrolopurine derivative (7) , a primary 1,3-dipolar cycloaddition product, was detected by nuclear magnetic resonance measurement of the products.Keywords - xantinium N7-ylide; cycloaddition; dimethyl acetylenedicarboxylate; methyl propiolate; diphenylcyclopropenone; 5-pyrrol-1-yluracil; pyrrolopteridine; isocaffeine