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Theacrine

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Theacrine
Chemical structure of theacrine.
Names
IUPAC name
1,3,7,9-Tetramethylpurine-2,6,8-trione
Other names
1,3,7,9-Tetramethyluric acid; Temurin; Temorine; Tetramethyluric acid; Tetramethyl uric acid
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
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]

Similarity to caffeine

Theacrine is similar to caffeine with an additional methyl group in the 9-position, and a carbamide as a result of an additional carbonyl group at the 8-position.

Caffeine vs theacrine

Safety

Theacrine has demonstrated clinical safety and non-habituating effects in healthy humans over 8 weeks of daily use at up to 300 mg/day.[4] Moreover, there was no evidence of tachyphylaxis that is typical of neuroactive agents such as caffeine and other stimulants.[4]

In animal studies, theacrine has an LD50 of 810 mg/kg,[5][4] compared to 265 mg/kg for caffeine.[6]

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 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): 241–8. doi:10.1016/j.pbb.2012.04.014. PMID 22579816. S2CID 31549989.
  3. ^ 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): 627–31. doi:10.1016/j.fitote.2010.03.008. PMID 20227468.
  4. ^ 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. Retrieved 2016-05-14.
    • These findings support the clinical safety and non-habituating neuro-energetic effects of TeaCrine® supplementation over 8 weeks of daily use (up to 300 mg/day). Moreover, there was no evidence of a tachyphylactic response that is typical of neuroactive agents such as caffeine and other stimulants.
    • Specifically, the acute toxicity for theacrine ingestion in mice has been previously reported [4] to be an LD50 of 810.6 mg/kg, which would equate to roughly 4.0 g for an individual weighing 76 kg.    {{cite journal}}: CS1 maint: unflagged free DOI (link)
  5. ^ 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): 627–31. doi:10.1016/j.fitote.2010.03.008. PMID 20227468. Retrieved 2016-05-15. the result of the acute toxicity test showed that the LD(50) of theacrine was 810.6 mg/kg (769.5-858.0mg/kg).
  6. ^ 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. In adult rats, the LD50 of caffeine and aminophylline was the same after 24 h and after 1 week of observation: caffeine 265 mg/kg
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