42297-40-5

Usage

Classification

Xanthine alkaloid, specifically a methylxanthine

Natural occurrence

Found in coffee, tea, and various other beverages and foods

Mechanism of action

Blocks the action of adenosine, a neurotransmitter that relaxes the brain and induces drowsiness

Effects

Increases alertness, temporarily reduces feelings of fatigue, improves mental alertness, enhances physical performance

Potential adverse effects

Anxiety, insomnia, rapid heart rate (with excessive consumption)

Usage

Commonly used for its stimulating effects and to alleviate fatigue

Upstream product

• 58-08-2 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione 
• 2099-73-2 8-nitrotheophylline 
• 74-88-4 methyl iodide 
• 58-55-9 theophylline 

Downstream Products

• 4921-49-7 8-chlorocaffeine 
• 10381-82-5 8-bromocaffeine 
• 37789-28-9 8-Aminocaffeine 
• 5415-44-1 1,3,7-trimethyluric acid 
• 155581-81-0 4-acetylamino-N-(1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-benzenesulfonamide 
• 78146-62-0 7-methyl-8-dimethylaminotheophylline 
• 577-66-2 8-Ethoxy-3,7-dihydro-1,3,7-trimethyl-1H-purin-2,6-dion 

Relevant academic research and scientific papers

Purines. XIV [1]. Synthesis and properties of 8-nitroxanthine and its N- methyl derivatives

Xanthine (1) and its N-methyl derivatives 2-16 have been nitrated to the corresponding 8-nitro derivatives 17-32 under different reaction conditions. Nitration in glacial acetic acid with nitric acid works well with the N-7 unsubstituted and some of the 9-methylxanthines, respectively, whereas the 7- methylxanthine derivatives react best with nitronium tetrafluoroborate in sulfolane or glacial acetic acid. The 8-nitro group can be displaced nucleophilically to form 8-chloro-, 33, 34, 8-ethoxy-, 35, 36, and uric acid derivatives 37-40, respectively. The newly synthesized 8-nitroxanthines have been characterized by elemental analyses, pK-determinations and uv and 1H- nmr spectra.

Synthesis and Properties of 8-Nitro-7-Alkylated Theophylline Derivatives

8-Nitrotheophylline (3) was alkylated with alkylhalides to obtain the corresponding 8-nitro-7-alkylated theophylline derivatives (4a-d).The reduction of 4a-d provided 8-aminoderivatives (5a-d).Heating 4a-d in the concentrated HCl gave the corresponding 8-chloroderivatives (6a-d).The products 5a and 5b reacted with 4-acetamidobenzenesulphonyl chloride to provide 8-(4'-acetamidobenzenesulphonamido)theophyllines (7a) and (7b).The acid hydrolysis of 7a and 7b gave the corresponding 8-(4'-aminobenzenesulphonamido)theophyllines (8a) and (8b), which were also products of the reaction of 6b and 6c with 4-acetamidobenzenesulphonamide, followed by the acid hydrolysis.The reaction of 6a and 6b with benzylamine in dimethylformamide resulted unexpectedly in the 8-dimethylaminoderivatives (9a) and (9b), respectively. Key words: 8-nitrotheophylline, alkylhalides, HCl, acid hydrolysis.