假木賊鹼

假木賊鹼
臨床資料
ATC碼	未分配;
識別資訊
	IUPAC命名法 3-(2-哌啶基)吡啶; 3-(2-piperidyl)pyridine; ;
CAS號	494-52-0
ChemSpider	21106257 ;
UNII	LMS11II2LO;
KEGG	C06180 ;
ChEBI	CHEBI:28986 ;
ChEMBL	ChEMBL280963 ;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID9041607 ;
ECHA InfoCard	100.150.777、100.007.084
化學資訊
化學式	C10H14N2
摩爾質量	162.24 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像;
	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 ;

假木賊鹼（英語：Anabasine），又稱毒藜鹼，新煙鹼等，是一種含有吡啶和哌啶結構的茄科生物鹼，可見於光煙草等煙草植物中^[1]。其為尼古丁的同分異構體。干煙絲中一般含有2-4 %的生物鹼^[2]，其中90 %為尼古丁，假木賊鹼連同降煙鹼等則占據餘下的10%^[3]。自然環境下，這類生物鹼是茄科植物為了抵禦蟲害而產生，因此假木賊鹼在過去曾被作為殺蟲劑來使用。

香煙中存在痕量的假木賊鹼，因此假木賊鹼可用於檢測一個人是否接觸過香煙^[4]。

Anabasine不同中文名稱
領域	名稱
化學名	3-(2-哌啶基)吡啶
生物化學	毒藜鹼、假木賊鹼、新煙鹼^[5]^[6]
農學	滅蟲鹼^[7]
音譯名	安納巴松、阿那巴辛

藥理學

假木賊鹼和其他煙草生物鹼一樣是一種煙鹼型乙酰膽鹼受體激動劑。高劑量的假木賊鹼會對神經細胞造成去極化阻滯，產生類似尼古丁中毒的症狀，最終心臟驟停而死^[8]。在更大計量下對家豬展現出致畸作用^[9]。

假木賊鹼的小鼠靜脈注射LD₅₀為11-16 mg/kg,具體數值則取決於其對映體構型^[10]。

B. Bhatti等人以假木賊鹼為基礎合成了一些效果更強、環張力更大的雙環衍生物，包括 2-(3-哌啶基)吡啶基-1-氮雜雙環[3.2.2]壬烷（TC-1698（英語：TC-1698））、2-(3-哌啶基)吡啶基-1-氮雜雙環[3.2.2]辛烷和2-(3-哌啶基)吡啶基-1-氮雜雙環[3.2.1]辛烷^[11]。

參考文獻

^ 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 .
^ 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 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.
^ 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.
^ 中國食品發酵工業研究所 (編). 英汉食品工业词汇. 北京: 中國輕工業出版社. 1993.
^ 蘇子仁、賴小平 (編). 汉英、英汉中草药化学成分词汇. 北京: 中國中醫藥出版社. 2006. ISBN 9787801569103.
^ 詹英賢 (編). 英汉农学词典（上）. 北京: 農業出版社. 1989.
^ 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.
^ Notes on Poisoning: Nicotiana tabacum. Canadian Biodiversity Information Facility. 2008-03-18 [2008-05-01].
^ 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.
^ 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] 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 .

[Dewey-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] 中國食品發酵工業研究所 (編). 英汉食品工业词汇. 北京: 中國輕工業出版社. 1993.

[6] 蘇子仁、賴小平 (編). 汉英、英汉中草药化学成分词汇. 北京: 中國中醫藥出版社. 2006. ISBN 9787801569103.

[7] 詹英賢 (編). 英汉农学词典（上）. 北京: 農業出版社. 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].

[usda-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.

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