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-吡啶並[3,4-b]吲哚
別名	9-Me-BC; 9-甲基-9H-β-咔啉; 9-甲基去甲哈爾滿; 9-MBC; N-甲基-β-咔啉
識別
CAS號	2521-07-5
PubChem	164979
ChemSpider	144638
SMILES	CN1C2=CC=CC=C2C3=C1C=NC=C3;
MeSH	C529608
性質
化學式	C12H10N2
摩爾質量	182.22 g·mol−1
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

9-甲基-β-咔啉（英語：9-Methyl-β-carboline，簡稱9-Me-BC）是β-咔啉家族的雜環胺，是一種研究性化學物質。^[1]

化學

9-Me-BC是β-咔啉的甲基化衍生物，分子式為C₁₂H₁₀N₂。

它可以通過對游離鹼β-咔啉（去甲哈爾滿）進行埃施魏勒-克拉克反應來製備^{[來源請求]}

生物效應

多巴胺能神經元細胞培養物的體外研究表明，在長期給予魚藤酮後，酪氨酸羥化酶和相關轉錄因子的表達增加，神經突生長增加，神經元再生，炎症細胞因子的表達減少。^[2]在原代中腦多巴胺能神經元細胞培養物的研究中，該物質增加了分化的多巴胺能神經元的數量，並產生了更高水平的與多巴胺能分化相關的轉錄因子。^[3]9-甲基-β-咔啉還在體外抑制神經毒素前體 MPTP向多巴胺能神經毒素MPP⁺的氧化過程。^[4]

齧齒動物體內研究表明，海馬體多巴胺水平升高，徑向臂迷宮（英語：Radial arm maze）測試中的空間學習表現得到改善，並且海馬齒狀回的樹突生長增加，^[5]在帕金森病動物模型中，左側表達酪氨酸羥化酶的神經元數量恢復，而注射MPP⁺後紋狀體中此類細胞的數量減少了50%。^[6]

9-甲基-β-咔啉是一種已知的單胺氧化酶A和單胺氧化酶B 抑制劑，並已被提議在帕金森病的治療中進行進一步研究。^[7]

它可能具有光敏作用。^[8]

參見

參考資料

^ 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]