An active metabolite of caffeine and theophylline
Related Products
Isomer(s)
195841,7-Dimethyluric Acid
Parent Compound(s)
14118Caffeine 23760Theophylline
Technical Support & Resources

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1,3-Dimethyluric Acid

Item No. 36167

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7,9-dihydro-1,3-dimethyl-1H-purine-2,6,8(3H)-trione
CAS Number
944-73-0
Synonyms
  • Ba 2751
  • 1,3-DMU
  • 1,3-DMUA
  • NSC 95854
Molecular Formula
C7H8N4O3
Formula Weight
196.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Slightly soluble
λmax
232, 289 nm
SMILES
O=C1NC(C(N2C)=O)=C(N1)N(C)C2=O
InChi Code
InChI=1S/C7H8N4O3/c1-10-4-3(8-6(13)9-4)5(12)11(2)7(10)14/h1-2H3,(H2,8,9,13)
InChi Key
OTSBKHHWSQYEHK-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    50 mg

    $74

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    100 mg

    $132

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    250 mg

    $257

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    Cayman Chemical
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    Product Description

    1,3-Dimethyluric acid is an active metabolite of the methylxanthine alkaloids caffeine (Item No. 14118) and theophylline (Item No. 23760).1 It is formed from caffeine and theophylline by the cytochrome P450 (CYP) isoforms CYP1A2 and CYP2E1.2,3 1,3-Dimethyluric acid (500 µM) scavenges hydroxyl radicals in a cell-free assay and inhibits t-butyl hydroperoxide-induced lipid peroxidation by 77% in isolated human erythrocyte membranes.4 It induces contractions in isolated rabbit duodenal, jejunal, and ileal preparations, but induces relaxation in isolated rabbit ascending colon preparations, in a concentration-dependent manner.5 Intracerebral administration of 1,3-dimethyluric acid induces clonic convulsions in mice (ED50 = 360 nmol/animal).6 It has been found in urinary caliculi.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cornish, H.H., and Christman, A.A. A study of the metabolism of theobromine, theophylline, and caffeine in man. The Journal of Biological Chemisty 228(1), 315-323 (1957).

    2. Caubet, M.-S., Elbast, W., Dubuc, M.-C., et al. Analysis of urinary caffeine metabolites by HPLC-DAD: The use of metabolic ratios to assess CYP1A2 enzyme activity. J. Pharm. Biomed. Anal. 27(1-2), 261-270 (2002).

    3. Fuhr, U., Doehmer, J., Battula, N., et al. Biotransformation of methylxanthines in mammalian cell lines genetically engineered for expression of single cytochrome P450 isoforms. Allocation of metabolic pathways to isoforms and inhibitory effects of quinolones. Toxicology 82(1-3), 169-189 (1993).

    4. Bhat, V.B., Sridhar, G.R., and Madyastha, K.M. Efficient scavenging of hydroxyl radicals and inhibition of lipid peroxidation by novel analogues of 1,3,7-trimethyluric acid. Life Sci. 70(4), 381-393 (2001).

    5. Psarra, T.A., Batzias, G.C., Peeters, T.L., et al. Theophylline and its metabolites produce a stimulating cholinergic effect on the small intestine and a nonadrenergic noncholinergic relaxing effect on the colon: A comparative study in the rabbit intestine. J. Vet. Pharmacol. Ther. 30(6), 541-519 (2007).

    6. Yamamoto, K., Toyama, E., Kawakami, J., et al. Neurotoxic convulsions induced by theophylline and its metabolites in mice. Biol. Pharm. Bull. 19(6), 869-872 (1996).

    7. Safranow, K., and Machoy, Z. Methylated purines in urinary stones. Clin. Chem. 51(8), 1493-1498 (2005).