Theacrine
Chemical structure of theacrine.
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 Edit this at Wikidata
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 tea known as kucha (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

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 antagonists indicates that theacrine is likely an adenosine antagonist.[2]

Administration of selective dopamine D1 and D2 antagonists demonstrate that, similarly to caffeine,[4] theacrine's actions are in part mediated by dopamine receptors.[2] This should not be taken as evidence that theacrine directly interacts with dopamine receptors, as some marketers have misleadingly claimed.[citation needed]

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. doi:10.1016/s0031-9422(02)00086-9. PMID 12009315.
  2. ^ a b c d e Feduccia, Allison A.; Wang, Yuanyuan; Simms, Jeffrey A.; Yi, Henry Y.; Li, Rui; Bjeldanes, Leonard; Ye, Chuangxing; Bartlett, Selena E. (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. ^ a b Wang, Yuanyuan; Yang, Xiaorong; Zheng, Xinqiang; Li, Jing; Ye, Chuangxing; Song, Xiaohong (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, 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.
  5. ^ Mondal, Goutam; Wang, Yan-Hong; Butawan, Matthew; Bloomer, Richard J; Yates, Ryan (2021-01-06). Caffeine and Methylliberine: A Human Pharmacokinetic Interaction Study (Report). Pharmacology and Therapeutics. doi:10.1101/2021.01.05.21249234.
  6. ^ a b c 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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