假木贼碱

假木贼碱
临床资料
ATC码	未分配;
识别信息
	IUPAC命名法 3-(2-哌啶基)吡啶; 3-(2-piperidyl)pyridine; ;
CAS号	494-52-0
ChemSpider	21106257 ;
UNII	LMS11II2LO;
KEGG	C06180 ;
ChEBI	CHEBI:28986 ;
ChEMBL	ChEMBL280963 ;
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID9041607 ;
ECHA InfoCard	100.150.777、100.007.084
化学信息
化学式	C10H14N2
摩尔质量	162.24 g·mol−1
3D模型（JSmol（英语：JSmol））	交互式图像;
	SMILES n1cc(ccc1)C2CCCCN2;
	InChI InChI=1S/C10H14N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h3-4,6,8,10,12H,1-2,5,7H2 ; Key:MTXSIJUGVMTTMU-UHFFFAOYSA-N ;

假木贼碱（英语：Anabasine），又称毒藜碱，新烟碱等，是一种含有吡啶和哌啶结构的茄科生物碱，可见于光烟草等烟草植物中^[1]。其为尼古丁的同分异构体。干烟丝中一般含有2-4 %的生物碱^[2]，其中90 %为尼古丁，假木贼碱连同降烟碱等则占据余下的10%^[3]。自然环境下，这类生物碱是茄科植物为了抵御虫害而产生，因此假木贼碱在过去曾被作为杀虫剂来使用。

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香烟中存在痕量的假木贼碱，因此假木贼碱可用于检测一个人是否接触过香烟^[4]。

More information 领域, 名称 ...

Anabasine不同中文名称
领域	名称
化学名	3-(2-哌啶基)吡啶
生物化学	毒藜碱、假木贼碱、新烟碱^[5]^[6]
农学	灭虫碱^[7]
音译名	安纳巴松、阿那巴辛

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药理学

假木贼碱和其他烟草生物碱一样是一种烟碱型乙酰胆碱受体激动剂。高剂量的假木贼碱会对神经细胞造成去极化阻滞，产生类似尼古丁中毒的症状，最终心脏骤停而死^[8]。在更大计量下对家猪展现出致畸作用^[9]。

假木贼碱的小鼠静脉注射LD₅₀为11-16 mg/kg,具体数值则取决于其对映体构型^[10]。

B. Bhatti等人以假木贼碱为基础合成了一些效果更强、环张力更大的双环衍生物，包括 2-(3-哌啶基)吡啶基-1-氮杂双环[3.2.2]壬烷（TC-1698（英语：TC-1698））、2-(3-哌啶基)吡啶基-1-氮杂双环[3.2.2]辛烷和2-(3-哌啶基)吡啶基-1-氮杂双环[3.2.1]辛烷^[11]。

参考文献

[1]
Laszlo C, Kaminski K, Guan H, Fatarova M, Wei J, Bergounioux A, et al. Fractionation and Extraction Optimization of Potentially Valuable Compounds and Their Profiling in Six Varieties of Two Nicotiana Species. Molecules. November 2022, 27 (22): 8105. PMC 9694777 . PMID 36432206. doi:10.3390/molecules27228105 .
[2]
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. Fractionation and Extraction Optimization of Potentially Valuable Compounds and Their Profiling in Six Varieties of Two Nicotiana Species. Molecules. November 2022, 27 (22): 8105. PMC 9694777 . PMID 36432206. doi:10.3390/molecules27228105 .
[3]
Dewey RE, Xie J. Molecular genetics of alkaloid biosynthesis in Nicotiana tabacum. Phytochemistry. October 2013, 94: 10–27. Bibcode:2013PChem..94...10D. PMID 23953973. doi:10.1016/j.phytochem.2013.06.002.
[4]
Jacob P, Yu L, Shulgin AT, Benowitz NL. Minor tobacco alkaloids as biomarkers for tobacco use: comparison of users of cigarettes, smokeless tobacco, cigars, and pipes. American Journal of Public Health. May 1999, 89 (5): 731–6. PMC 1508721 . PMID 10224986. doi:10.2105/AJPH.89.5.731.
[5]
中国食品发酵工业研究所 (编). 英汉食品工业词汇. 北京: 中国轻工业出版社. 1993.
[6]
苏子仁、赖小平 (编). 汉英、英汉中草药化学成分词汇. 北京: 中国中医药出版社. 2006. ISBN 9787801569103.
[7]
詹英贤 (编). 英汉农学词典（上）. 北京: 农业出版社. 1989.
[8]
Mizrachi N, Levy S, Goren ZQ. Fatal poisoning from Nicotiana glauca leaves: identification of anabasine by gas-chromatography/mass spectrometry. Journal of Forensic Sciences. May 2000, 45 (3): 736–41. PMID 10855991. doi:10.1520/JFS14761J.
[9]
Notes on Poisoning: Nicotiana tabacum. Canadian Biodiversity Information Facility. 2008-03-18 [2008-05-01].
[10]
Lee ST, Wildeboer K, Panter KE, Kem WR, Gardner DR, Molyneux RJ, et al. Relative toxicities and neuromuscular nicotinic receptor agonistic potencies of anabasine enantiomers and anabaseine. Neurotoxicology and Teratology. 2006, 28 (2): 220–8. PMID 16488116. doi:10.1016/j.ntt.2005.12.010.
[11]
Bhatti BS, Strachan JP, Breining SR, Miller CH, Tahiri P, Crooks PA, et al. Synthesis of 2-(pyridin-3-yl)-1-azabicyclo[3.2.2]nonane, 2-(pyridin-3-yl)-1-azabicyclo[2.2.2]octane, and 2-(pyridin-3-yl)-1-azabicyclo[3.2.1]octane, a class of potent nicotinic acetylcholine receptor-ligands. The Journal of Organic Chemistry. May 2008, 73 (9): 3497–507. PMID 18363376. doi:10.1021/jo800028q.

[1] [1]
Laszlo C, Kaminski K, Guan H, Fatarova M, Wei J, Bergounioux A, et al. Fractionation and Extraction Optimization of Potentially Valuable Compounds and Their Profiling in Six Varieties of Two Nicotiana Species. Molecules. November 2022, 27 (22): 8105. PMC 9694777 . PMID 36432206. doi:10.3390/molecules27228105 .

[2] [2]
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. Fractionation and Extraction Optimization of Potentially Valuable Compounds and Their Profiling in Six Varieties of Two Nicotiana Species. Molecules. November 2022, 27 (22): 8105. PMC 9694777 . PMID 36432206. doi:10.3390/molecules27228105 .

[Dewey-3] [3]
Dewey RE, Xie J. Molecular genetics of alkaloid biosynthesis in Nicotiana tabacum. Phytochemistry. October 2013, 94: 10–27. Bibcode:2013PChem..94...10D. PMID 23953973. doi:10.1016/j.phytochem.2013.06.002.

[4] [4]
Jacob P, Yu L, Shulgin AT, Benowitz NL. Minor tobacco alkaloids as biomarkers for tobacco use: comparison of users of cigarettes, smokeless tobacco, cigars, and pipes. American Journal of Public Health. May 1999, 89 (5): 731–6. PMC 1508721 . PMID 10224986. doi:10.2105/AJPH.89.5.731.

[5] [5]
中国食品发酵工业研究所 (编). 英汉食品工业词汇. 北京: 中国轻工业出版社. 1993.

[6] [6]
苏子仁、赖小平 (编). 汉英、英汉中草药化学成分词汇. 北京: 中国中医药出版社. 2006. ISBN 9787801569103.

[7] [7]
詹英贤 (编). 英汉农学词典（上）. 北京: 农业出版社. 1989.

[8] [8]
Mizrachi N, Levy S, Goren ZQ. Fatal poisoning from Nicotiana glauca leaves: identification of anabasine by gas-chromatography/mass spectrometry. Journal of Forensic Sciences. May 2000, 45 (3): 736–41. PMID 10855991. doi:10.1520/JFS14761J.

[9] [9]
Notes on Poisoning: Nicotiana tabacum. Canadian Biodiversity Information Facility. 2008-03-18 [2008-05-01].

[usda-10] [10]
Lee ST, Wildeboer K, Panter KE, Kem WR, Gardner DR, Molyneux RJ, et al. Relative toxicities and neuromuscular nicotinic receptor agonistic potencies of anabasine enantiomers and anabaseine. Neurotoxicology and Teratology. 2006, 28 (2): 220–8. PMID 16488116. doi:10.1016/j.ntt.2005.12.010.

[11] [11]
Bhatti BS, Strachan JP, Breining SR, Miller CH, Tahiri P, Crooks PA, et al. Synthesis of 2-(pyridin-3-yl)-1-azabicyclo[3.2.2]nonane, 2-(pyridin-3-yl)-1-azabicyclo[2.2.2]octane, and 2-(pyridin-3-yl)-1-azabicyclo[3.2.1]octane, a class of potent nicotinic acetylcholine receptor-ligands. The Journal of Organic Chemistry. May 2008, 73 (9): 3497–507. PMID 18363376. doi:10.1021/jo800028q.

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