Methylliberine

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Methylliberine
Methylliberine.svg
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
PubChem CID
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.

Contents

Pharmacology

Pharmacodynamics

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 confirm this action. [2] There is no evidence that methylliberine augments dopamine receptors in a way that is distinct from caffeine, contrary to claims made by manufacturer. [3] [4]

Pharmacokinetics

Methylliberine has a short half-life of only 1.5 hours compared to the 5-7 hour half life of caffeine. [5] An interaction study showed concomitant administration of both caffeine and methylliberine increases the half-life of caffeine by about 2 fold. [5] This is likely due to inhibition of the CYP1A2 enzyme. [5] Safety studies of methylliberine have been conducted in rats. [6]

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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. Garrett, B. E.; Holtzman, S. G. (January 1994). "D1 and D2 dopamine receptor antagonists block caffeine-induced stimulation of locomotor activity in rats". Pharmacology, Biochemistry, and Behavior. 47 (1): 89–94. doi:10.1016/0091-3057(94)90115-5. ISSN   0091-3057. PMID   7906891. S2CID   23508010.
  4. 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. (2020-02-28). "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 . ISSN   2072-6643. PMC   7146520 . PMID   32121218.
  5. 1 2 3 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 .
  6. 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 . PMID   31911801.