Chemistry:Methylliberine

Methylliberine

Names
Preferred IUPAC name 2-Methoxy-1,7,9-trimethyl-7,9-dihydro-1H-purine-6,8-dione
Other names O(2),1,7,9-Tetramethylurate; Tetramethyluric acid; Dynamine
Identifiers
CAS Number	51168-26-4 N[ChemSpider]
3D model (JSmol)	Interactive image
ChemSpider	43515875
PubChem CID	15872156
UNII	RY9AJC5PA7 Y
InChI InChI=1S/C9H12N4O3/c1-11-5-6(12(2)9(11)15)10-8(16-4)13(3)7(5)14/h1-4H3 Key: ZVQXCXPGLSBNCX-UHFFFAOYSA-N InChI=1/C9H12N4O3/c1-11-5-6(12(2)9(11)15)10-8(16-4)13(3)7(5)14/h1-4H3 Key: ZVQXCXPGLSBNCX-UHFFFAOYAY
SMILES CN1C2=C(N=C(N(C2=O)C)OC)N(C1=O)C
Properties
Chemical formula	C9H12N4O3
Molar mass	224.22 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tracking categories (test):

• SizeSet

Methylliberine is an isolate of coffee beans, tea, cola nuts, guarana, cocoa, and yerba mate. It is structurally related to Liberine.

Based on its structural similarity to caffeine and theacrine methylliberine is widely believed to be an adenosine receptor antagonist, although as of 2023 no scientific studies have been done to establish this. Methylliberine has a short half-life of only 1.5 hours compared to the 5-7 hour half life of caffeine. An interaction study showed concamitant administration of both caffeine and methylliberine increases the half-life of caffeine by about 2 fold. This is likely due to inhibition of the CYP1A2 enzyme. Safety studies of methyliberine have been conducted in rats and it is approved for use as a dietary supplement in the US.