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 [ChemSpider];
3D model (JSmol)	Interactive image;
ChemSpider	43515875;
PubChem CID	15872156;
UNII	RY9AJC5PA7 ;
CompTox Dashboard (EPA)	DTXSID401045665 ;
	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

Methylliberine is an isolate of coffee beans, tea, cola nuts, guarana, cocoa, and yerba mate.^[1] It is structurally related to Liberine.

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 methyliberine have been conducted in rats and it is approved for use as a dietary supplement in the US.^[6]

References

^ "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.
^ 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.
^ 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.
^ 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.
^ ^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.
^ 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.

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[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.

[kinetics-5] 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.

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