Suvarna Garge (Editor)

Paraxanthine

Updated on
Edit
Like
Comment
Share on FacebookTweet on TwitterShare on LinkedInShare on Reddit
Formula
  
C7H8N4O2

Molar mass
  
180.16 g/mol

Paraxanthine Paraxanthine Wikipedia

Paraxanthine, or 1,7-dimethylxanthine, is a dimethyl derivative of xanthine, structurally related to caffeine. Like caffeine, paraxanthine is a psychoactive central nervous system (CNS) stimulant. It possesses a potency roughly equal to that of caffeine and is likely involved in the mediation of the effects of caffeine itself.

Contents

Paraxanthine httpsqphecquoracdnnetmainqimgfe9f67348e61

Production and metabolism

Paraxanthine Paraxanthine 98 HPLC solid SigmaAldrich

Paraxanthine is not produced by plants and is only observed in nature as a metabolite of caffeine and theobromine in animals. After intake, roughly 84% of caffeine is demethylated at the 3-position to yield paraxanthine, making it the chief metabolite of caffeine in the body.

Paraxanthine Paraxanthine solution 10 mgmL in methanol ampule of 1 mL

Certain proposed synthetic pathways of caffeine make use of paraxanthine as a bypass intermediate. However, its absence in plant alkaloid assays implies that these are infrequently, if ever, directly produced by plants.

Physiological effects

Paraxanthine has a number of physiological effects on animals:

Paraxanthine BASi Method Development And Validation Of Caffeine And

  • Paraxanthine is a competitive nonselective phosphodiesterase inhibitor which raises intracellular cAMP, activates PKA, inhibits TNF-alpha and leukotriene synthesis, and reduces inflammation and innate immunity.
  • Paraxanthine is a nonselective adenosine receptor antagonist which raises plasma epinephrine and diastolic blood pressure.
  • Paraxanthine is responsible for the lipolytic properties of caffeine, and its presence in the blood causes an increase in serum free fatty acid concentration.
  • Paraxanthine, unlike caffeine, acts as an enzymatic effector of Na+/K+ ATPase. As a result, it is responsible for increased transport of potassium ions into skeletal muscle tissue. Similarly, the compound also stimulates increases in calcium ion concentration in muscle.

    • Toxicity

    Paraxanthine 12911png

    Paraxanthine is believed to exhibit a lower toxicity than caffeine. While blood levels commensurate with average intake appear to be fairly innocuous, high blood concentrations of paraxanthine have been linked to miscarriage in pregnant mothers.

    References

    Paraxanthine Wikipedia
    (Text) CC BY-SA