新煙草鹼

新煙草鹼
識別資訊
	IUPAC命名法 [2R,(+)]-1,2,3,6-四氫-2,3'-聯吡啶; [2R,(+)]-1,2,3,6-Tetrahydro-2,3'-bipyridine; ;
CAS號	581-49-7
PubChem CID	11388;
ChemSpider	10910 ;
UNII	5PP654XB7D;
KEGG	C10126;
ChEBI	CHEBI:2705;
ChEMBL	ChEMBL3640772;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID901016110 ;
化學資訊
化學式	C10H12N2
摩爾質量	160.22 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像;
	SMILES c1cc(cnc1)[C@@H]2CC=CCN2;
	InChI InChI=1S/C10H12N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h1-4,6,8,10,12H,5,7H2/t10-/m0/s1 ; Key:SOPPBXUYQGUQHE-JTQLQIEISA-N ;

新煙草鹼（英語：Anatabine）又稱去氫毒藜鹼，是一種存在於茄科植物中的微量生物鹼。商用煙草中一般含有2-4%（乾重）的生物鹼^[1]，其中尼古丁占據其中90%，剩餘10%則包括新煙草鹼、降煙鹼和假木賊鹼（新煙鹼）等微量生物鹼，這類生物鹼是茄科植物用於防禦害蟲而產生^[2]。

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新煙草鹼在體內外可抑制STAT3蛋白磷酸化，並產生抗炎活性^[3]。同時似乎對煙鹼型乙酰膽鹼受體有活性作用^[4]。

美國Star Scientific煙草公司在2014年中之前開發了兩款含有新煙草鹼的膳食補充劑，並以CigRx和Anatabloc的商品名進行銷售。隨後旗下子公司Rock Creek製藥（Rock Creek Pharmaceuticals）開始將新煙草鹼開發為藥物^[5]^[6]^[7]，並研究擴大新煙草鹼產量的方法，此外還額外資助了其幾種適應症的臨床前和臨床研究^[5]。

直到2013年，FDA警告在證明兩款膳食補充劑是安全的之前，Star Scientific涉嫌非法推廣^[8]^[9]。受此影響，Rock Creek公司高層發生人員大幅度變更，新高層以及幾乎全新的董事會撤回了這兩款產品。同年Star Scientific公司陷入政治醜聞，有消息稱弗吉尼亞州州長鮑勃·麥克唐納和其妻子被指控從Star Scientific首席執行官喬尼·威廉姆斯（Jonnie Williams）收受大額賄賂，並反過來推介公司產品作為報答，包括如安排與高層官員會面，以及給予州政府特殊恩惠等^[6]。受此事件影響，威廉姆斯於2014年辭去CEO職務，Star Scientific公司於2013年底進行董事會和管理層重組並更名^[5]。

然而，威廉姆斯在此事件中辯護所產生的總法律費用超出了公司的財務承受能力，導致公司於2016年申請破產，新煙草鹼的研發和臨床試驗被無限期暫停^[10]。

人們已經在動物模型和細胞中研究新煙草鹼是否可能有助於治療尼古丁成癮和炎症。並且已對包括阿茲海默症^[11]、甲狀腺炎^[12]、多發性硬化症^[4] 在內的炎症特徵疾病模型中進行了研究。此外，新煙草鹼發現有助於治療輕中度酒渣鼻^[13]。一項基於互聯網的調查顯示，82% 的用戶報告稱補充新煙草鹼對一種或多種關節疼痛有一定改善作用^[14]。

[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. 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]
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.
[3]
Paris D, Beaulieu-Abdelahad D, Abdullah L, Bachmeier C, Ait-Ghezala G, Reed J, Verma M, Crawford F, Mullan M. Anti-inflammatory activity of anatabine via inhibition of STAT3 phosphorylation. European Journal of Pharmacology. January 2013, 698 (1–3): 145–53. PMID 23178521. doi:10.1016/j.ejphar.2012.11.017.
[4]
Mello NK, Fivel PA, Kohut SJ, Caine SB. Anatabine significantly decreases nicotine self-administration. Experimental and Clinical Psychopharmacology. February 2014, 22 (1): 1–8. PMID 24490707. S2CID 15879738. doi:10.1037/a0035409. 注意: 源自原文討論部分中對已有研究的簡短評述性內容
[5]
Kroll, David. The McDonnell Scandal: What's The Dope Behind Star Scientific Supplement Products?. Forbes. 31 January 2014 [2024-07-29]. （原始內容存檔於2024-07-29）.
[6]
Gabriel, Trip. Ex-Governor of Virginia Is Indicted on Charges Over Loans and Gifts. New York Times. 21 January 2014 [2024-07-29]. （原始內容存檔於2024-07-29）.
[7]
Star Scientific, Inc. Star Scientific 推出 Anatabloc(TM) 膳食补充剂. 美通社. [2024-07-29]. （原始內容存檔於2024-07-29）（中文（簡體））.
[8]
FDA Says Star Scientific Illegally Marketing Products. CBS News. December 31, 2013 [2024-07-29]. （原始內容存檔於2014-01-27）.
[9]
FDA Warning Letter. [2024-07-29]. （原始內容存檔於2019-04-23）.
[10]
With a History of Political Corruption Rock Creek Pharma Files for Bankruptcy. www.biospace.com. [2017-08-17]. （原始內容存檔於2017-08-18）.
[11]
Verma M, Beaulieu-Abdelahad D, Ait-Ghezala G, Li R, Crawford F, Mullan M, Paris D. Correction: Chronic Anatabine Treatment Reduces Alzheimer's Disease (AD)-Like Pathology and Improves Socio-Behavioral Deficits in a Transgenic Mouse Model of AD. PLOS One. 2015, 10 (7): e0134776. Bibcode:2015PLoSO..1034776V. PMC 4521847 . PMID 26230317. doi:10.1371/journal.pone.0134776 .
[12]
Schmeltz LR, Blevins TC, Aronoff SL, Ozer K, Leffert JD, Goldberg MA, et al. Anatabine supplementation decreases thyroglobulin antibodies in patients with chronic lymphocytic autoimmune (Hashimoto's) thyroiditis: a randomized controlled clinical trial. The Journal of Clinical Endocrinology and Metabolism. January 2014, 99 (1): E137–42. PMC 3928963 . PMID 24178792. doi:10.1210/jc.2013-2951.
[13]
Lanier RK, Cohen AE, Weinkle SH. Effects of a facial cream containing the minor alkaloid anatabine on improving the appearance of the skin in mild to moderate rosacea: an open-label case series study. Case Reports in Dermatology. 2013, 5 (3): 347–56. PMC 3861860 . PMID 24348385. doi:10.1159/000357019.
[14]
Lanier RK, Gibson KD, Cohen AE, Varga M. Effects of dietary supplementation with the solanaceae plant alkaloid anatabine on joint pain and stiffness: results from an internet-based survey study. Clinical Medicine Insights. Arthritis and Musculoskeletal Disorders. 2013, 6: 73–84. PMC 3825642 . PMID 24250235. doi:10.4137/CMAMD.S13001.

[1] [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. 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-2] [2]
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.

[pmid23178521-3] [3]
Paris D, Beaulieu-Abdelahad D, Abdullah L, Bachmeier C, Ait-Ghezala G, Reed J, Verma M, Crawford F, Mullan M. Anti-inflammatory activity of anatabine via inhibition of STAT3 phosphorylation. European Journal of Pharmacology. January 2013, 698 (1–3): 145–53. PMID 23178521. doi:10.1016/j.ejphar.2012.11.017.

[Mello-4] [4]
Mello NK, Fivel PA, Kohut SJ, Caine SB. Anatabine significantly decreases nicotine self-administration. Experimental and Clinical Psychopharmacology. February 2014, 22 (1): 1–8. PMID 24490707. S2CID 15879738. doi:10.1037/a0035409. 注意: 源自原文討論部分中對已有研究的簡短評述性內容

[Forbes-5] [5]
Kroll, David. The McDonnell Scandal: What's The Dope Behind Star Scientific Supplement Products?. Forbes. 31 January 2014 [2024-07-29]. （原始內容存檔於2024-07-29）.

[Gabriel-6] [6]
Gabriel, Trip. Ex-Governor of Virginia Is Indicted on Charges Over Loans and Gifts. New York Times. 21 January 2014 [2024-07-29]. （原始內容存檔於2024-07-29）.

[7] [7]
Star Scientific, Inc. Star Scientific 推出 Anatabloc(TM) 膳食补充剂. 美通社. [2024-07-29]. （原始內容存檔於2024-07-29）（中文（簡體））.

[8] [8]
FDA Says Star Scientific Illegally Marketing Products. CBS News. December 31, 2013 [2024-07-29]. （原始內容存檔於2014-01-27）.

[9] [9]
FDA Warning Letter. [2024-07-29]. （原始內容存檔於2019-04-23）.

[10] [10]
With a History of Political Corruption Rock Creek Pharma Files for Bankruptcy. www.biospace.com. [2017-08-17]. （原始內容存檔於2017-08-18）.

[pmid26230317-11] [11]
Verma M, Beaulieu-Abdelahad D, Ait-Ghezala G, Li R, Crawford F, Mullan M, Paris D. Correction: Chronic Anatabine Treatment Reduces Alzheimer's Disease (AD)-Like Pathology and Improves Socio-Behavioral Deficits in a Transgenic Mouse Model of AD. PLOS One. 2015, 10 (7): e0134776. Bibcode:2015PLoSO..1034776V. PMC 4521847 . PMID 26230317. doi:10.1371/journal.pone.0134776 .

[12] [12]
Schmeltz LR, Blevins TC, Aronoff SL, Ozer K, Leffert JD, Goldberg MA, et al. Anatabine supplementation decreases thyroglobulin antibodies in patients with chronic lymphocytic autoimmune (Hashimoto's) thyroiditis: a randomized controlled clinical trial. The Journal of Clinical Endocrinology and Metabolism. January 2014, 99 (1): E137–42. PMC 3928963 . PMID 24178792. doi:10.1210/jc.2013-2951.

[pmid24348385-13] [13]
Lanier RK, Cohen AE, Weinkle SH. Effects of a facial cream containing the minor alkaloid anatabine on improving the appearance of the skin in mild to moderate rosacea: an open-label case series study. Case Reports in Dermatology. 2013, 5 (3): 347–56. PMC 3861860 . PMID 24348385. doi:10.1159/000357019.

[pmid24250235-14] [14]
Lanier RK, Gibson KD, Cohen AE, Varga M. Effects of dietary supplementation with the solanaceae plant alkaloid anatabine on joint pain and stiffness: results from an internet-based survey study. Clinical Medicine Insights. Arthritis and Musculoskeletal Disorders. 2013, 6: 73–84. PMC 3825642 . PMID 24250235. doi:10.4137/CMAMD.S13001.

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[14]

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新煙草鹼

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參考文獻

識別資訊

IUPAC命名法 [2R,(+)]-1,2,3,6-四氫-2,3'-聯吡啶 [2R,(+)]-1,2,3,6-Tetrahydro-2,3'-bipyridine
CAS號	581-49-7 ^Y
PubChem CID	11388
ChemSpider	10910^Y
UNII	5PP654XB7D
KEGG	C10126
ChEBI	CHEBI:2705
ChEMBL	ChEMBL3640772
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID901016110
化學資訊
化學式	C₁₀H₁₂N₂
摩爾質量	160.22 g·mol⁻¹
3D模型（JSmol（英語：JSmol））	交互式圖像
SMILES c1cc(cnc1)[C@@H]2CC=CCN2
InChI InChI=1S/C10H12N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h1-4,6,8,10,12H,5,7H2/t10-/m0/s1^Y Key:SOPPBXUYQGUQHE-JTQLQIEISA-N^Y