A cGMP PDE inhibitor and metabolite of theophylline and caffeine
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3-Methylxanthine

Item No. 34288

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,9-dihydro-3-methyl-1H-purine-2,6-dione
CAS Number
1076-22-8
Synonyms
  • 3-MTX
  • 3-MX
  • NSC 515466
Molecular Formula
C6H6N4O2
Formula Weight
166.1
Purity
≥98%
Formulation (Request formulation change)
A solid
λmax
272 nm
SMILES
O=C1NC(N(C)C2=C1NC=N2)=O
InChi Code
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)
InChi Key
GMSNIKWWOQHZGF-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 g

    $41

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    10 g

    $75

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    25 g

    $178

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    Cayman Chemical
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    Product Description

    3-Methylxanthine is a cGMP phosphodiesterase (PDE) inhibitor and a metabolite of theophylline (Item No. 23760) and caffeine (Item No. 14118).1,2,3 It is formed from theophylline by the cytochrome P450 (CYP) isoform CYP1A2 and from caffeine via 6A5NF-1,3-dimethyluracil, 1,3,7-trimethyluric acid, or theobromine intermediates. 3-Methylxanthine inhibits cGMP PDE in isolated guinea pig trachealis muscle with an IC50 value of 920 µM.1 It is neurotoxic to mice, inducing convulsions with an ED50 value of 1,107 nmol/kg.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tanaka, H., Ogawa, K., Takagi, K., et al. Inhibition of cyclic GMP phosphodiesterase by xanthine derivatives relaxes guinea-pig trachealis smooth muscle. Clin. Exp. Pharmacol. Physiol. 18(3), 163-168 (1991).

    2. Camandola, S., Plick, N., and Mattson, M.P. Impact of coffee and cacao purine metabolites on neuroplasticity and neurodegenerative disease. Neurochem. Res. 44(1), 214-227 (2019).

    3. Ha, H.R., Chen, J., Freiburghaus, A.U., et al. Metabolism of theophylline by cDNA-expressed human cytochromes P-450. Br. J. Clin. Pharmacol. 39(3), 321-326 (1995).

    4. 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).