降烟碱

降烟碱
	IUPAC名; 3-[(2S)-2-Pyrrolidinyl]pyridine
别名	去甲烟碱
识别
CAS号	494-97-3
PubChem	91462
ChemSpider	82588
SMILES	n1cccc(c1)[C@H]2NCCC2;
InChI	1/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2/t9-/m0/s1;
InChIKey	MYKUKUCHPMASKF-VIFPVBQEBM
性质
化学式	C9H12N2
摩尔质量	148.2 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

降烟碱是存在于烟草等植物的生物碱，化学式为C₉H₁₂N₂。[1]它的结构与烟碱相似，但少了一个甲基，因此又称去甲烟碱。

降烟碱在腌制、加工烟草时会变为1类致癌物[2]N-亚硝基降烟碱。[3]降烟碱与口水反应也会产生N-亚硝基降烟碱。[4]

合成

降烟碱可通过用氧化银将烟碱去甲基化而成。[5]

\mathrm {\xrightarrow[{H_{2}O}]{Ag_{2}O}}

它也可由麦斯明的催化氢化[6]或被硼氢化钠还原产生。[7]

\mathrm {\xrightarrow[{H_{2}}]{Pd/C}}

药学作用

降烟碱与烟碱型乙酰胆碱受体的亲和力高[8]，会以此抑制大鼠纹状体的多巴胺转运体，释放多巴胺。[9][10][11]

参考资料

Laszlo C, Kaminski K, Guan H, Fatarova M, Wei J, Bergounioux A, Schlage WK, Schorderet-Weber S, Guy PA, Ivanov NV, Lamottke K, Hoeng J. . Molecules. November 2022, 27 (22): 8105. PMC 9694777 . PMID 36432206. doi:10.3390/molecules27228105 .
. monographs.iarc.fr. [2020-07-22].
Siminszky, B. . Proceedings of the National Academy of Sciences. 2005, 102 (41): 14919–24. PMC 1253577 . PMID 16192354. doi:10.1073/pnas.0506581102 .
Knezevich A, Muzic J, Hatsukami DK, Hecht SS, Stepanov I. . Nicotine & Tobacco Research. February 2013, 15 (2): 591–5. PMC 3611998 . PMID 22923602. doi:10.1093/ntr/nts172.
Spaeth. . Chem. Ber. 1936, 69 (2): 250–251. doi:10.1002/cber.19360690207.
Haines. . J. Am. Chem. Soc. 1945, 67 (8): 1258–1260. doi:10.1021/ja01224a011.
Dickerson, TJ; Janda, KD. . J. Am. Chem. Soc. 2002, 124 (13): 3220–1. PMID 11916401. doi:10.1021/ja017774f..
Papke RL, Dwoskin LP, Crooks PA. . Journal of Neurochemistry. April 2007, 101 (1): 160–7. PMID 17241116. doi:10.1111/j.1471-4159.2006.04355.x .
Middleton LS, Crooks PA, Wedlund PJ, Cass WA, Dwoskin LP. . Synapse. March 2007, 61 (3): 157–65. PMID 17146768. S2CID 35071082. doi:10.1002/syn.20351.
Dwoskin LP, Teng LH, Crooks PA. . European Journal of Pharmacology. September 2001, 428 (1): 69–79. PMID 11779039. doi:10.1016/s0014-2999(01)01283-3.
Dwoskin LP, Buxton ST, Jewell AL, Crooks PA. . Journal of Neurochemistry. June 1993, 60 (6): 2167–74. PMID 8492124. S2CID 25622404. doi:10.1111/j.1471-4159.1993.tb03502.x.

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[1] Laszlo C, Kaminski K, Guan H, Fatarova M, Wei J, Bergounioux A, Schlage WK, Schorderet-Weber S, Guy PA, Ivanov NV, Lamottke K, Hoeng J. . Molecules. November 2022, 27 (22): 8105. PMC 9694777 . PMID 36432206. doi:10.3390/molecules27228105 .

[:2-2] . monographs.iarc.fr. [2020-07-22].

[3] Siminszky, B. . Proceedings of the National Academy of Sciences. 2005, 102 (41): 14919–24. PMC 1253577 . PMID 16192354. doi:10.1073/pnas.0506581102 .

[:1-4] Knezevich A, Muzic J, Hatsukami DK, Hecht SS, Stepanov I. . Nicotine & Tobacco Research. February 2013, 15 (2): 591–5. PMC 3611998 . PMID 22923602. doi:10.1093/ntr/nts172.

[späth-5] Spaeth. . Chem. Ber. 1936, 69 (2): 250–251. doi:10.1002/cber.19360690207.

[6] Haines. . J. Am. Chem. Soc. 1945, 67 (8): 1258–1260. doi:10.1021/ja01224a011.

[7] Dickerson, TJ; Janda, KD. . J. Am. Chem. Soc. 2002, 124 (13): 3220–1. PMID 11916401. doi:10.1021/ja017774f..

[pmid17241116-8] Papke RL, Dwoskin LP, Crooks PA. . Journal of Neurochemistry. April 2007, 101 (1): 160–7. PMID 17241116. doi:10.1111/j.1471-4159.2006.04355.x .

[pmid17146768-9] Middleton LS, Crooks PA, Wedlund PJ, Cass WA, Dwoskin LP. . Synapse. March 2007, 61 (3): 157–65. PMID 17146768. S2CID 35071082. doi:10.1002/syn.20351.

[pmid11779039-10] Dwoskin LP, Teng LH, Crooks PA. . European Journal of Pharmacology. September 2001, 428 (1): 69–79. PMID 11779039. doi:10.1016/s0014-2999(01)01283-3.

[pmid8492124-11] Dwoskin LP, Buxton ST, Jewell AL, Crooks PA. . Journal of Neurochemistry. June 1993, 60 (6): 2167–74. PMID 8492124. S2CID 25622404. doi:10.1111/j.1471-4159.1993.tb03502.x.