Paraxanthine

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Paraxanthine
Skeletal formula of paraxanthine
Ball-and-stick model of the paraxanthine model
Names
IUPAC name
1,7-dimethyl-3H-purine-2,6-dione
Other names
paraxanthine,
1 ,7-Dimethylxanthine
Identifiers
611-59-6 N
ChEBI CHEBI:25858 YesY
ChEMBL ChEMBL1158 YesY
ChemSpider 4525 YesY
Jmol 3D model Interactive image
PubChem 4687
UNII Q3565Y41V7 YesY
  • InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13) YesY
    Key: QUNWUDVFRNGTCO-UHFFFAOYSA-N YesY
  • InChI=1/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)
    Key: QUNWUDVFRNGTCO-UHFFFAOYAS
  • O=C2Nc1ncn(c1C(=O)N2C)C
Properties
C7H8N4O2
Molar mass 180.17 g·mol−1
Melting point 351 to 352 °C (664 to 666 °F; 624 to 625 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

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.

Production and metabolism

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.[1]

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.[citation needed]

Physiological effects

Paraxanthine has a number of physiological effects on animals:

Toxicity

Paraxanthine is believed to exhibit a lower toxicity than caffeine.[7] 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.[8]

References

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