Description
A 3-methylxanthine tautomer where the imidazole proton is located at the 7-position.
Chemical properties
| Chemical formula | Net charge | Average mass |
|---|---|---|
| C6H6N4O2 | 0 | 166.13740 |
Nomenclature
| IUPAC | SMILES | InChI | InChIKey | Synonyms |
|---|---|---|---|---|
| 3-methyl-3,7-dihydro-1H-purine-2,6-dione | Cn1c2nc[nH]c2c(=O)[nH]c1=O | InChI=1S/C6H6N4O2/c1-10-4-3(7-2-8-4)5(11)9-6(10)12/h2H,1H3,(H,7,8)(H,9,11,12) | GMSNIKWWOQHZGF-UHFFFAOYSA-N |
|
Citations
- Cavallaro, RA, et al. 1999. Potentiation of cADPR-induced Ca(2+)-release by methylxanthine analogues. Journal of Medicinal Chemistry. 42(14).
- Chappe, V, et al. 1998. Structural basis for specificity and potency of xanthine derivatives as activators of the CFTR chloride channel. British Journal of Pharmacology. 123(4).
- Georgopoulou, E, et al. 2010. Purine substrate recognition by the nucleobase-ascorbate transporter signature motif in the YgfO xanthine permease: ASN-325 binds and ALA-323 senses substrate. The Journal of Biological Chemistry. 285(25).
- Geraets, L, et al. 2006. Caffeine metabolites are inhibitors of the nuclear enzyme poly(ADP-ribose)polymerase-1 at physiological concentrations. Biochemical Pharmacology. 72(7).
- Guerreiro, S, et al. 2008. Paraxanthine, the primary metabolite of caffeine, provides protection against dopaminergic cell death via stimulation of ryanodine receptor channels. Molecular Pharmacology. 74(4).
- Lee, SW, et al. 2010. Ultrafast dynamics show that the theophylline and 3-methylxanthine aptamers employ a conformational capture mechanism for binding their ligands. Biochemistry. 49(13).
- Liu, W, et al. 1997. Structure-activity relationship of xanthines and skeletal muscle ryanodine receptor/Ca2+ release channel. Pharmacology. 54(3).
- Morimoto, T, et al. 2003. Effect of St. John's wort on the pharmacokinetics of theophylline in healthy volunteers. Journal of Clinical Pharmacology. 44(1).
- Niki, Y, et al. 1998. Effects of DU-6859a, a new quinolone antimicrobial, on theophylline metabolism in in vitro and in vivo studies. Antimicrobial Agents and Chemotherapy. 42(7).
- Ogiso, T, et al. 1995. Inhibition kinetics of theophylline metabolism by mexiletine and its metabolites. Biological & Pharmaceutical Bulletin. 18(1).
- Yao, C, et al. 2001. Fluvoxamine-theophylline interaction: gap between in vitro and in vivo inhibition constants toward cytochrome P4501A2. Clinical Pharmacology and Therapeutics. 70(5).