An active metabolite of caffeine
Related Products
Isomer(s)
22235Aminophylline 21745Theobromine 23760Theophylline
Labeled Version(s)
9003564Paraxanthine-d6
Parent Compound(s)
14118Caffeine
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Paraxanthine

Item No. 21068

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,7-dihydro-1,7-dimethyl-1H-purine-2,6-dione
CAS Number
611-59-6
Synonyms
  • 1,7-Dimethylxanthine
  • NSC 400018
Molecular Formula
C7H8N4O2
Formula Weight
180.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH 7.2) (1:3): 0.25 mg/mlEthanol: 0.5 mg/ml
λmax
269 nm
SMILES
O=C(C(N(C)C=N1)=C1N2)N(C)C2=O
InChi Code
InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)
InChi Key
QUNWUDVFRNGTCO-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    10 mg

    $49

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    25 mg

    $91

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    50 mg

    $130

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    100 mg

    $190

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    Product Description

    Paraxanthine is an active metabolite of caffeine (Item No. 14118).1 It is formed via N3-demethylation of caffeine by the cytochrome P450 (CYP) isoform CYP1A2. Paraxanthine is an adenosine A1 and A2 receptor antagonist (Kis = 35 and 22 µM, respectively).2 In vivo, paraxanthine (30 mg/kg) increases striatal cGMP and extracellular striatal dopamine levels and locomotor activity, as well as inhibits motor depression induced by the adenosine A1 agonist CPA (N6-cyclopentyladenosine; Item No. 21448) or the adenosine A2 receptor agonist CGS 21680 (Item No. 17126) in rats not habituated to caffeine.3 It also promotes wakefulness and increases locomotor activity and core temperature in narcoleptic transgenic mice without increasing behavioral anxiety.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tassaneeyakul, W., Birkett, D.J., McManus, M.E., et al. Caffeine metabolism by human hepatic cytochromes P450: contributions of 1A2, 2E1 and 3A isoforms. Biochem. Pharmacol. 47(10), 1767-1776 (1994).

    2. Chou, C.-C., and Vickroy, T.W. Antagonism of adenosine receptors by caffeine and caffeine metabolites in equine forebrain tissues. Am. J. Vet. Res. 64(2), 216-224 (2003).

    3. Orrú, M., Guitart, X., Karcz-Kubicha, M., et al. Psychostimulant pharmacological profile of paraxanthine, the main metabolite of caffeine in humans. Neuropharmacology 67, 476-484 (2013).

    4. Okuro, M., Fujiki, N., Kotorii, N., et al. Effects of paraxanthine and caffeine on sleep, locomotor activity, and body temperature in orexin/ataxin-3 transgenic narcoleptic mice. Sleep 33(7), 930-942 (2010).