26351-04-2

Usage

Uses

Used in Pharmaceutical Research:
CAFFEINE-D3 is used as a research tool for studying the effects of caffeine on the central nervous system and its interactions with acetylcholinesterase. The labeled version allows for easier tracking and analysis in scientific experiments.
Used in Drug Development:
CAFFEINE-D3 serves as a starting point for the development of new drugs with similar stimulant properties or as a modified version with improved pharmacological profiles. The labeled compound can be used to study the metabolism, distribution, and excretion of caffeine in the body.
Used in Diagnostic Applications:
In the medical field, CAFFEINE-D3 can be employed as a diagnostic aid to monitor the function of the central nervous system and the activity of acetylcholinesterase, which is an important enzyme in the nervous system.
Used in Sports Performance Enhancement Research:
CAFFEINE-D3 can be utilized in research aimed at understanding the effects of caffeine on athletic performance and endurance, as well as its potential benefits and drawbacks for athletes.
Used in Toxicology Studies:
The labeled CAFFEINE-D3 can be used in toxicology studies to investigate the potential adverse effects of caffeine on human health and to establish safe dosage levels for consumption.

Upstream product

• 58-55-9 theophylline 
• 865-50-9 iodomethane-d3 
• 86180-42-9 3,7,9-trimethylxanthinium betaine 
• 86180-43-0 3-methyl-7,9-bisdeuteromethylxanthinium betaine 

Relevant academic research and scientific papers

Digitally enhanced thin layer chromatography: Further development and some applications in isotopic chemistry

Improvements to thin layer chromatography (TLC) analysis can be made easily and cheaply by the application of digital colour photography and image analysis. The combined technique, digitally enhanced TLC (DE-TLC), is applicable to the accurate quantificat

Collision-induced dissociation studies of caffeine in positive electrospray ionisation mass spectrometry using six deuterated isotopomers and one N1-ethylated homologue

Rationale: In order to deepen the understanding of electrospray ionisation collision-induced dissociation (ESI-CID) fragmentation reactions of xanthine derivatives for the identification of metabolites using low-resolution liquid chromatography/mass spectrometry (LC/MS) analysis, basic experiments using caffeine (1,3,7-trimethylxanthine) as model compound have been performed. Methods: Six deuterium isotopomers and one N1-ethylated homologue of caffeine have been synthesized and their ESI fragmentation spectra have been obtained by using LC/MS in combination with either standard or perdeuterated eluent mixtures. RESULTS One result of these studies is the finding that the positive charges of the ESI-CID caffeine fragments are caused by the addition of protons. Furthermore, the performed experiments allow the determination of all molecular formulae of each ESI-CID caffeine fragment. Conclusions: As basic CID reactions of caffeine have been elucidated in this work, the developed fragmentation scheme may serve as a valuable tool for the interpretation of ESI-CID fragmentation spectra of more complex xanthine derivatives and their respective metabolites. Copyright

Easy preparative scale syntheses of labelled xanthines: Caffeine, theophylline and theobromine

Several easy preparative scale (0.5-1.5 g) syntheses of deuterium labelled caffeine, theophylline and theobromine are described. Some new selective syntheses of theophylline and theobromine have been developed. Labelled xanthines are of great interest in qualitative or quantitative isotope dilution-mass spectrometry, coupled with gas or liquid chromatography, currently performed in anti-doping and forensic laboratories. Copyright

Mechanism of free radical oxidation of caffeine in aqueous solution

The oxidation of caffeine with persulfate and hydroxyl radicals in aqueous solution has been studied by EPR spectroscopy and HPLC analysis. In both cases the formation of 1,3,7-trimethyluric acid is observed as the main final product. A C8-OH radical adduct is postulated as the intermediate after reaction with OH., and leads to the final product after further oxidation. This radical is too short-lived to be observed by EPR After oxidation of caffeine with SO4.- its radical cation is detected by EPR. This radical reacts with water to produce the above mentioned C8-OH radical adduct after deprotonation. In the presence of dibasic phosphate a spectrum attributed to the C8-phosphate radical adduct is observed. This radical results from the nucleophilic attack of the buffer on the radical cation of caffeine. Hydrolysis and oxidation of the phosphate radical intermediate results in the formation of 1,3,7-trimethyluric acid.

ISOMERIZATION AND DEALKYLATION OF METHYLATED XANTHINIUM DERIVATIVES

The isomerization or dealkylation of methylated xanthinium derivatives takes place with the participation of nucleophiles and is facilitated in the presence of a sterically hindered configuration.When heated, 7,9-dimethyl- and 1,7,9-trimethylxanthinium salts isomerize to theobromine and caffeine respectively.Under these conditions 3,7,9-trimethyl- and 1,3,7,9-tetramethylxanthinium salts are dealkylated.The 1,7,9- and 3,7,9-trimethylxanthinium betaines are isomerized quantitatively to caffeine.The role of the nucleophile under these conditions is played by the negatively charged fragment in the pyridine part of molecule.An intermolecular mechanism of rearrangement of the 3,7,9-trimethylxanthinium betaine is demonstrated.The sterically overloaded 1,3,8,9-tetramethylxanthine and 1,3,9-trimethyl-8-azaxanthine and not the charged compounds undergo rearrangement.In these cases the nucleophilic center is the doubly bonded N7 atom in the five-membered ring.