四甲基吡嗪

四甲基吡嗪
	IUPAC名; Tetramethylpyrazine; 四甲基吡嗪
别名	2,3,5,6-四甲基吡嗪、川芎嗪
识别
CAS号	1124-11-4
PubChem	14296
ChemSpider	13658
SMILES	CC1=C(N=C(C(=N1)C)C)C;
InChI	1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3;
InChIKey	FINHMKGKINIASC-UHFFFAOYSA-N
EINECS	214-391-2
ChEBI	133246
性质
化学式	C8H12N2
摩尔质量	136.19 g·mol−1
熔点	84-86 °C（271 K）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

四甲基吡嗪（英語：tetramethylpyrazine），又称为川芎嗪（ligustrazine，chuanxiongzine），是一种发现于纳豆和发酵可可豆的化学物质^[1]。纯化后为无色固体，属于烷基吡嗪。一项研究表明，四甲基吡嗪是酸酵头中主要挥发性有机物^[2]。四甲基吡嗪的生物合成涉及源自丙酮酸的3-羟基丁酮的胺化过程^[3]。在小鼠研究中，四甲基吡嗪展示出益智药特性和消炎活性^[4]^[5]。

川芎嗪名字来自北京制药工业研究所1972-1977年期间在川穹提取的生物碱中分离得到^[6]。

参考文献

^ Effect of mass and turning time on free amino acid, peptide-N, sugar and pyrazine concentration during cocoa fermentation. P Hashim, J Selamat, S Muhammad, S Kharidah and A Ali, Journal of the Science of Food and Agriculture, 1998, Volume 78, pages 543–550. doi:10.1002/(SICI)1097-0010(199812)78:4<543::AID-JSFA152>3.0.CO;2-2
^ Landis, Elizabeth A.; Oliverio, Angela M. The diversity and function of sourdough starter microbiomes. eLife. January 26, 2021, 10: e61644. PMC 7837699  . PMID 33496265. doi:10.7554/eLife.61644  .
^ Takuo Kosuge, Tahei Adachi & Hiroko Kamiya "Isolation Of Tetramethylpyrazine From Culture Of Bacillus Natto, And Biosynthetic Pathways Of Tetramethylpyrazine" Nature 1962, volume 195, 1103 .doi:10.1038/1951103a0
^ Wu, W; Yu, X; Luo, XP; Yang, SH; Zheng, D. Tetramethylpyrazine protects against scopolamine-induced memory impairments in rats by reversing the cAMP/PKA/CREB pathway. Behavioural Brain Research. 2013, 253: 212–6. PMID 23916742. S2CID 9100537. doi:10.1016/j.bbr.2013.07.052.
^ Kao, TK; Chang, CY; Ou, YC; Chen, WY; Kuan, YH; Pan, HC; Liao, SL; Li, GZ; Chen, CJ. Tetramethylpyrazine reduces cellular inflammatory response following permanent focal cerebral ischemia in rats. Experimental Neurology. 2013, 247: 188–201. PMID 23644042. S2CID 20967364. doi:10.1016/j.expneurol.2013.04.010.
^ 川芎嗪的实验研究与临床观察. 新医药学杂志. 1977, (04): 45.

[1] Effect of mass and turning time on free amino acid, peptide-N, sugar and pyrazine concentration during cocoa fermentation. P Hashim, J Selamat, S Muhammad, S Kharidah and A Ali, Journal of the Science of Food and Agriculture, 1998, Volume 78, pages 543–550. doi:10.1002/(SICI)1097-0010(199812)78:4<543::AID-JSFA152>3.0.CO;2-2

[2] Landis, Elizabeth A.; Oliverio, Angela M. The diversity and function of sourdough starter microbiomes. eLife. January 26, 2021, 10: e61644. PMC 7837699  . PMID 33496265. doi:10.7554/eLife.61644  .

[3] Takuo Kosuge, Tahei Adachi & Hiroko Kamiya "Isolation Of Tetramethylpyrazine From Culture Of Bacillus Natto, And Biosynthetic Pathways Of Tetramethylpyrazine" Nature 1962, volume 195, 1103 .doi:10.1038/1951103a0

[4] Wu, W; Yu, X; Luo, XP; Yang, SH; Zheng, D. Tetramethylpyrazine protects against scopolamine-induced memory impairments in rats by reversing the cAMP/PKA/CREB pathway. Behavioural Brain Research. 2013, 253: 212–6. PMID 23916742. S2CID 9100537. doi:10.1016/j.bbr.2013.07.052.

[Missingor-5] Kao, TK; Chang, CY; Ou, YC; Chen, WY; Kuan, YH; Pan, HC; Liao, SL; Li, GZ; Chen, CJ. Tetramethylpyrazine reduces cellular inflammatory response following permanent focal cerebral ischemia in rats. Experimental Neurology. 2013, 247: 188–201. PMID 23644042. S2CID 20967364. doi:10.1016/j.expneurol.2013.04.010.

[6] 川芎嗪的实验研究与临床观察. 新医药学杂志. 1977, (04): 45.

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四甲基吡嗪

IUPAC名 Tetramethylpyrazine 四甲基吡嗪
别名	2,3,5,6-四甲基吡嗪、川芎嗪
识别
CAS号	1124-11-4
PubChem	14296
ChemSpider	13658
SMILES	CC1=C(N=C(C(=N1)C)C)C
InChI	1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3
InChIKey	FINHMKGKINIASC-UHFFFAOYSA-N
EINECS	214-391-2
ChEBI	133246
性质
化学式	C₈H₁₂N₂
摩尔质量	136.19 g·mol⁻¹
熔点	84-86 °C（271 K）
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。