9-甲基-β-咔啉

9-甲基-β-咔啉
	IUPAC名; 5-Methyl-5H-pyrido[3,4-b]indole; 5-甲基-5H-吡啶并[3,4-b]吲哚
别名	9-Me-BC; 9-甲基-9H-β-咔啉; 9-甲基去甲哈尔满; 9-MBC; N-甲基-β-咔啉
识别
CAS号	2521-07-5
PubChem	164979
ChemSpider	144638
SMILES	CN1C2=CC=CC=C2C3=C1C=NC=C3;
MeSH	C529608
性质
化学式	C12H10N2
摩尔质量	182.22 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

9-甲基-β-咔啉（英语：9-Methyl-β-carboline，简称9-Me-BC）是β-咔啉家族的杂环胺，是一种研究性化学物质。^[1]

化学

9-Me-BC是β-咔啉的甲基化衍生物，分子式为C₁₂H₁₀N₂。

它可以通过对游离碱β-咔啉（去甲哈尔满）进行埃施魏勒-克拉克反应来制备^{[来源请求]}

生物效应

多巴胺能神经元细胞培养物的体外研究表明，在长期给予鱼藤酮后，酪氨酸羟化酶和相关转录因子的表达增加，神经突生长增加，神经元再生，炎症细胞因子的表达减少。^[2]在原代中脑多巴胺能神经元细胞培养物的研究中，该物质增加了分化的多巴胺能神经元的数量，并产生了更高水平的与多巴胺能分化相关的转录因子。^[3]9-甲基-β-咔啉还在体外抑制神经毒素前体 MPTP向多巴胺能神经毒素MPP⁺的氧化过程。^[4]

啮齿动物体内研究表明，海马体多巴胺水平升高，径向臂迷宫（英语：Radial arm maze）测试中的空间学习表现得到改善，并且海马齿状回的树突生长增加，^[5]在帕金森病动物模型中，左侧表达酪氨酸羟化酶的神经元数量恢复，而注射MPP⁺后纹状体中此类细胞的数量减少了50%。^[6]

9-甲基-β-咔啉是一种已知的单胺氧化酶A和单胺氧化酶B 抑制剂，并已被提议在帕金森病的治疗中进行进一步研究。^[7]

它可能具有光敏作用。^[8]

参见

参考资料

^ Polanski, W; Enzensperger, C; Reichmann, H; Gille, G. The exceptional properties of 9-methyl-β-carboline: Stimulation, protection and regeneration of dopaminergic neurons coupled with anti-inflammatory effects.. J Neurochem. 2010, 113 (6): 1659–1675. PMID 20374418. doi:10.1111/j.1471-4159.2010.06725.x .
^ Polanski, W; Enzensperger, C; Reichmann, H; Gille, G. The exceptional properties of 9-methyl-β-carboline: Stimulation, protection and regeneration of dopaminergic neurons coupled with anti-inflammatory effects.. J Neurochem. 2010, 113 (6): 1659–1675. PMID 20374418. doi:10.1111/j.1471-4159.2010.06725.x .
^ Hamann, J; Wernicke, C; Lehmann, J; Reichmann, H; Rommelspacher, H; Gille, G. 9-Methyl-β-carboline up-regulates the appearance of differentiated dopaminergic neurones in primary mesencephalic culture.. Neurochem. Int. 2008, 52 (4–5): 688–700. PMID 17913302. S2CID 24226033. doi:10.1016/j.neuint.2007.08.018.
^ Herraiz, T; Guillén, H. Inhibition of the bioactivation of the neurotoxin MPTP by antioxidants, redox agents and monoamine oxidase inhibitors.. Food Chem. Toxicol. 2011, 49 (8): 1773–1781. PMID 21554916. doi:10.1016/j.fct.2011.04.026. hdl:10261/63126.
^ Gruss, M; Appenroth, D; Flubacher, A; Enzersperger, C; Bock, J; Fleck, C; Gille, G; Braun, K. 9-Methyl-β-carboline-induced cognitive enhancement is associated with elevated hippocampal dopamine levels and dendritic and synaptic proliferation.. J Neurochem. 2012, 121 (6): 924–931. PMID 22380576. doi:10.1111/j.1471-4159.2012.07713.x .
^ Wernicke, C; Hellmann, J; Zieba, B; Kuter, K; Ossowska, K; Frenzel, M; Bencher, NA; Rommelspacher, H. 9-Methyl-beta-carboline has restorative effects in an animal model of Parkinson's disease.. Pharmacol Rep. 2010, 62 (1): 35–53. PMID 20360614. doi:10.1016/s1734-1140(10)70241-3.
^ Polanski, W; Reichmann, H; Gille, G. Stimulation, protection and regeneration of dopaminergic neurons by 9-methyl-β-carboline: a new anti-Parkinson drug?. Expert Rev Neurother. 2011, 11 (6): 845–860. PMID 21651332. S2CID 24899640. doi:10.1586/ern.11.1.
^ Vignoni M, Rasse-Suriani FA, Butzbach K, Erra-Balsells R, Epe B, Cabrerizo FM. Mechanisms of DNA damage by photoexcited 9-methyl-β-carbolines. Org Biomol Chem. 2013, 11 (32): 5300–9. PMID 23842892. doi:10.1039/c3ob40344k.

[pmid20374418-1] Polanski, W; Enzensperger, C; Reichmann, H; Gille, G. The exceptional properties of 9-methyl-β-carboline: Stimulation, protection and regeneration of dopaminergic neurons coupled with anti-inflammatory effects.. J Neurochem. 2010, 113 (6): 1659–1675. PMID 20374418. doi:10.1111/j.1471-4159.2010.06725.x .

[pmid203744182-2] Polanski, W; Enzensperger, C; Reichmann, H; Gille, G. The exceptional properties of 9-methyl-β-carboline: Stimulation, protection and regeneration of dopaminergic neurons coupled with anti-inflammatory effects.. J Neurochem. 2010, 113 (6): 1659–1675. PMID 20374418. doi:10.1111/j.1471-4159.2010.06725.x .

[pmid17913302-3] Hamann, J; Wernicke, C; Lehmann, J; Reichmann, H; Rommelspacher, H; Gille, G. 9-Methyl-β-carboline up-regulates the appearance of differentiated dopaminergic neurones in primary mesencephalic culture.. Neurochem. Int. 2008, 52 (4–5): 688–700. PMID 17913302. S2CID 24226033. doi:10.1016/j.neuint.2007.08.018.

[pmid21554916-4] Herraiz, T; Guillén, H. Inhibition of the bioactivation of the neurotoxin MPTP by antioxidants, redox agents and monoamine oxidase inhibitors.. Food Chem. Toxicol. 2011, 49 (8): 1773–1781. PMID 21554916. doi:10.1016/j.fct.2011.04.026. hdl:10261/63126.

[pmid22380576-5] Gruss, M; Appenroth, D; Flubacher, A; Enzersperger, C; Bock, J; Fleck, C; Gille, G; Braun, K. 9-Methyl-β-carboline-induced cognitive enhancement is associated with elevated hippocampal dopamine levels and dendritic and synaptic proliferation.. J Neurochem. 2012, 121 (6): 924–931. PMID 22380576. doi:10.1111/j.1471-4159.2012.07713.x .

[pmid20360614-6] Wernicke, C; Hellmann, J; Zieba, B; Kuter, K; Ossowska, K; Frenzel, M; Bencher, NA; Rommelspacher, H. 9-Methyl-beta-carboline has restorative effects in an animal model of Parkinson's disease.. Pharmacol Rep. 2010, 62 (1): 35–53. PMID 20360614. doi:10.1016/s1734-1140(10)70241-3.

[pmid21651332-7] Polanski, W; Reichmann, H; Gille, G. Stimulation, protection and regeneration of dopaminergic neurons by 9-methyl-β-carboline: a new anti-Parkinson drug?. Expert Rev Neurother. 2011, 11 (6): 845–860. PMID 21651332. S2CID 24899640. doi:10.1586/ern.11.1.

[pmid23842892-8] Vignoni M, Rasse-Suriani FA, Butzbach K, Erra-Balsells R, Epe B, Cabrerizo FM. Mechanisms of DNA damage by photoexcited 9-methyl-β-carbolines. Org Biomol Chem. 2013, 11 (32): 5300–9. PMID 23842892. doi:10.1039/c3ob40344k.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]