テアクリン

テアクリン
	優先IUPAC名 1,3,7,9-Tetramethyl-7,9-dihydro-1H-purine-2,6,8(3H)-trione
	別称 1,3,7,9-Tetramethyluric acid; Temurin; Temorine; Tetramethyluric acid; Tetramethyl uric acid; TeaCrine (trade name)
識別情報
CAS登録番号	2309-49-1
PubChem	75324
ChemSpider	67862
UNII	EJ939L81MY
ChEBI	CHEBI:139388;
	SMILES CN1C2=C(N(C1=O)C)N(C(=O)N(C2=O)C)C;
	InChI 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;
特性
化学式	C9H12N4O3
モル質量	224.22 g mol−1
融点	226 °C, 499 K, 439 °F
	特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

テアクリン、または 1,3,7,9-テトラメチル尿酸とは、クプアス(テオブロマ・グランディフローラム)や苦茶として知られる中国茶(アッサムチャ)で発見されるプリンアルカロイドである^[1]^[2]。テアクリンは抗炎症薬や鎮痛剤としての作用とアデノシンシグナルへの効果をカフェインと似たような方法で発現させる^[2]^[3]。苦茶の葉ではテアクリンは、カフェインから3段階の過程を経て合成されると考えられている^[2]。また、テアクリンとカフェインはその構造がよく似ている。

安全性[編集]

テアクリンを習慣化して使用していない健康体の人間の、1日300mg8週間以上使用した際の日常的な使用の臨床安全性が証明されている^[4]。さらにその上、カフェインや他の刺激物のような典型的な神経賦活作用を待つものと比較してタキフィラキシーのエビデンスがない^[4]。

動物を用いた実験では、カフェインのLD50(半数致死量)が265 mg/kgであったのに対し、テアクリンのLD50は810 mg/kgであった^[5]^[4]^[6]。

脚注・文献[編集]

^ 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.
^ ^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.
^ 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.
^ ^a ^b ^c “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. (2016). doi:10.1186/s12970-016-0113-3. PMC 4711067. PMID 26766930. "
• 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."
^ “Theacrine, a purine alkaloid with anti-inflammatory and analgesic activities”. Fitoterapia 81 (6): 627–31. (2010). doi:10.1016/j.fitote.2010.03.008. PMID 20227468 2016年5月15日閲覧. "the result of the acute toxicity test showed that the LD(50) of theacrine was 810.6 mg/kg (769.5-858.0mg/kg)."
^ “Comparative toxicity of caffeine and aminophylline (theophylline ethylenediamine) in young and adult rats”. Biology of the Neonate 34 (1–2): 68–71. (1978). 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"

この項目は、薬学に関連した書きかけの項目です。この項目を加筆・訂正などしてくださる協力者を求めています（プロジェクト:薬学／Portal:医学と医療/Portal:化学）。

[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.

[:0-2] 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.

[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.

[pmid26766930-4] “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. (2016). doi:10.1186/s12970-016-0113-3. PMC 4711067. PMID 26766930. "
• 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."

[pmid20227468-5] “Theacrine, a purine alkaloid with anti-inflammatory and analgesic activities”. Fitoterapia 81 (6): 627–31. (2010). doi:10.1016/j.fitote.2010.03.008. PMID 20227468 2016年5月15日閲覧. "the result of the acute toxicity test showed that the LD(50) of theacrine was 810.6 mg/kg (769.5-858.0mg/kg)."

[pmid698326-6] “Comparative toxicity of caffeine and aminophylline (theophylline ethylenediamine) in young and adult rats”. Biology of the Neonate 34 (1–2): 68–71. (1978). 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"

[1]

[2]

[3]

[4]

[5]

[6]

安全性[編集]

関連項目[編集]

脚注・文献[編集]