Paraxanthine

Paraxanthine

Names
IUPAC name 1,7-Dimethyl-3H-purine-2,6-dione
Other names Paraxanthine, 1 ,7-Dimethylxanthine
Identifiers
CAS Number	611-59-6 N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:25858 Y
ChEMBL	ChEMBL1158 Y
ChemSpider	4525 Y
ECHA InfoCard	100.009.339
PubChem	4687
UNII	Q3565Y41V7 Y
InChI InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13) Y Key: QUNWUDVFRNGTCO-UHFFFAOYSA-N Y 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
SMILES O=C2Nc1ncn(c1C(=O)N2C)C
Properties
Chemical formula	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  (what is YN ?)
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.

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.

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.

Paraxanthine has a number of physiological effects on animals:

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.