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
3D model (JSmol)
ChemSpider
UNII
  • 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
  • CN1C2=C(N=C(N(C2=O)C)OC)N(C1=O)C
Properties
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).

Methylliberine is an isolate of coffee beans, tea, cola nuts, guarana, cocoa, and yerba mate.[1] 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.[2] Methylliberine has a short half-life of only 1.5 hours compared to the 5-7 hour half life of caffeine.[3] An interaction study showed concamitant administration of both caffeine and methylliberine increases the half-life of caffeine by about 2 fold.[3] This is likely due to inhibition of the CYP1A2 enzyme.[3] Safety studies of methyliberine have been conducted in rats and it is approved for use as a dietary supplement in the US.[4]


References

  1. ^ "Minor alkaloids in caffeine-containing beverages". Deutsche Lebensmittel-Rundschau. 96 (11): 363–368. 2000. Archived from the original on 2014-12-10. Retrieved 2013-10-16.
  2. ^ VanDusseldorp, Trisha A.; Stratton, Matthew T.; Bailly, Alyssa R.; Holmes, Alyssa J.; Alesi, Michaela G.; Feito, Yuri; Mangine, Gerald T.; Hester, Garrett M.; Esmat, Tiffany A.; Barcala, Megan; Tuggle, Karleena R.; Snyder, Michael; Modjeski, Andrew S. (28 February 2020). "Safety of Short-Term Supplementation with Methylliberine (Dynamine®) Alone and in Combination with TeaCrine® in Young Adults". Nutrients. 12 (3): 654. doi:10.3390/nu12030654. PMC 7146520. PMID 32121218.
  3. ^ a b c Mondal, Goutam; Wang, Yan-Hong; Yates, Ryan; Bloomer, Richard; Butawan, Matthew (9 August 2022). "Caffeine and Methylliberine: A Human Pharmacokinetic Interaction Study: Original Research". Journal of Exercise and Nutrition. 5 (3). doi:10.53520/jen2022.103124.
  4. ^ Murbach, Timothy S.; Glávits, Róbert; Endres, John R.; Clewell, Amy E.; Hirka, Gábor; Vértesi, Adél; Béres, Erzsébet; Szakonyiné, Ilona Pasics (27 October 2019). "A Toxicological Evaluation of Methylliberine (Dynamine®)". Journal of Toxicology. 2019: 1–25. doi:10.1155/2019/4981420. PMC 6930730.
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