Theacrine

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Contents

Theacrine
Theacrine.svg
Theacrine ball-and-stick.png
Names
Preferred IUPAC name
1,3,7,9-Tetramethyl-7,9-dihydro-1H-purine-2,6,8(3H)-trione
Other names
1,3,7,9-Tetramethyluric acid; Temurin; Temorine; Tetramethyluric acid; Tetramethyl uric acid; TeaCrine (trade name)
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.017.268 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C9H12N4O3/c1-10-5-6(11(2)8(10)15)12(3)9(16)13(4)7(5)14/h1-4H3
    Key: QGDOQULISIQFHQ-UHFFFAOYSA-N
  • InChI=1/C9H12N4O3/c1-10-5-6(11(2)8(10)15)12(3)9(16)13(4)7(5)14/h1-4H3
    Key: QGDOQULISIQFHQ-UHFFFAOYAN
  • CN1C2=C(N(C1=O)C)N(C(=O)N(C2=O)C)C
Properties
C9H12N4O3
Molar mass 224.220 g·mol−1
Melting point 226 °C (439 °F; 499 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Theacrine, also known as 1,3,7,9-tetramethyluric acid, is a purine alkaloid found in cupuaçu (Theobroma grandiflorum) and in a Chinese kucha tea (Chinese : 苦 茶 ; pinyin :kǔ chá; lit.'bitter tea') ( Camellia assamica var. kucha). [1] [2] It shows anti-inflammatory and analgesic effects and appears to affect adenosine signalling in a manner similar to caffeine. [2] [3] In kucha leaves, theacrine is synthesized from caffeine in what is thought to be a three-step pathway. [2] Theacrine and caffeine are structurally similar.

Caffeine vs Theacrine.png

Pharmacology

Pharmacodynamics

The exact mechanism of action of theacrine is uncertain, as no binding affinities have been published. However, animal research involving selective A1 and A2A adenosine agonists found theacrine pretreatment attenuated the expected motor depression induced by adenosine agonism, indicating that theacrine is likely an adenosine antagonist. [2]

Administration of selective dopamine D1 and D2 antagonists demonstrate that, similarly to caffeine, [4] the behavioural effects of theacrine are in part mediated by dopamine receptors. [2]

Pharmacokinetics

Theacrine has half-life of 30 to 33 hours. [5]

Safety

Theacrine has demonstrated clinical safety and non-habituating effects in healthy humans over eight weeks of daily use at up to 300 mg/day. [6] Moreover, there was no evidence of the tachyphylaxis typical of neuroactive agents like caffeine and other stimulants. [6]

In animal studies, theacrine has an LD50 of 810 mg/kg, [3] [6] compared to 265 mg/kg for caffeine. [7]

See also

References

  1. ↑ Zheng XQ, Ye CX, Kato M, Crozier A, Ashihara H (2002). "Theacrine (1,3,7,9-tetramethyluric acid) synthesis in leaves of a Chinese tea, kucha (Camellia assamica var. Kucha)". Phytochemistry. 60 (2): 129–34. Bibcode:2002PChem..60..129Z. doi:10.1016/s0031-9422(02)00086-9. PMID   12009315.
  2. 1 2 3 4 5 Feduccia AA, Wang Y, Simms JA, Yi HY, Li R, Bjeldanes L, Ye C, Bartlett SE (2012). "Locomotor activation by theacrine, a purine alkaloid structurally similar to caffeine: Involvement of adenosine and dopamine receptors". Pharmacology Biochemistry and Behavior. 102 (2): 241–248. doi:10.1016/j.pbb.2012.04.014. PMID   22579816. S2CID   31549989.
  3. 1 2 Wang Y, Yang X, Zheng X, Li J, Ye C, Song X (2010). "Theacrine, a purine alkaloid with anti-inflammatory and analgesic activities". Fitoterapia. 81 (6): 627–631. doi:10.1016/j.fitote.2010.03.008. PMID   20227468.
  4. ↑ Garrett BE, Holtzman SG (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.
  5. ↑ Mondal G, Wang YH, Butawan M, Bloomer RJ, Yates R (2021-01-06). Caffeine and Methylliberine: A Human Pharmacokinetic Interaction Study (Report). Pharmacology and Therapeutics. doi:10.1101/2021.01.05.21249234.
  6. 1 2 3 Taylor L, Mumford P, Roberts M, Hayward S, Mullins J, Urbina S, Wilborn C (2016). "Safety of TeaCrine®, a non-habituating, naturally-occurring purine alkaloid over eight weeks of continuous use". Journal of the International Society of Sports Nutrition. 13: 2. doi: 10.1186/s12970-016-0113-3 . PMC   4711067 . PMID   26766930.
  7. ↑ Warszawski D, Gorodischer R, Kaplanski J (1978). "Comparative toxicity of caffeine and aminophylline (theophylline ethylenediamine) in young and adult rats". Biology of the Neonate. 34 (1–2): 68–71. doi:10.1159/000241107. PMID   698326.
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