Chemistry:Anatabine
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| Formula | C10H12N2 |
| Molar mass | 160.220 g·mol−1 |
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Anatabine (uh-nat-uh-been,-bin) is one of the minor alkaloids found in plants in the family Solanaceae, which includes the tobacco plant and tomato. Commercial tobacco plants typically produce alkaloids at levels between 2% and 4% of total dry weight, with nicotine accounting for about 90% of the total alkaloid content, and the related compounds anatabine, nornicotine, and anabasine making up nearly all the rest.[1] These compounds are thought to be biologically active, and part of plants' natural defense system against insects.[1]
Anatabine has anti-inflammatory activity partly through inhibition of STAT3 phosphorylation in vitro and in vivo.[2]
Pharmacology
On a biochemical level, it appears to be active against certain nicotinic acetylcholine receptors.[3]
Commercial development
Star Scientific developed and sold the compound as a dietary supplement primarily through GNC up until mid 2014. Subsequently, Rock Creek Pharmaceuticals (formerly a subsidiary of Star Scientific), headquartered in Florida, began developing anatabine as a drug.[4][5] The dietary supplements were known as Anatabloc and CigRx; the company has also marketed cosmetics with the Anatabloc brand.[4] Rock Creek had been working on synthetic methods to scale up production of anatabine and has funded pre-clinical and clinical research in several indications.[4]
In 2013 the FDA warned Star Scientific for unlawfully promoting CigRx and Anatabloc before anatabine was proved to be safe.[6][7] Subsequently, new management and a mostly new board under the banner of Rock Creek Pharmaceuticals withdrew the dietary supplement because of the FDA's concerns.
In 2013, Star Scientific became embroiled in political scandal, when news broke that the governor of Virginia, Bob McDonnell, and his wife had received significant loans and gifts from Jonnie Williams Sr, the CEO of the company. They were found to have helped the company in several ways like arranging meetings with top officials and giving special favors from the state government.[5] Williams resigned in 2014 and the company changed its name and restructured its board and management at the end of 2013 due to the scandal.[4]
However, the accumulated legal costs from the defense of Jonnie Williams in the McDonnell scandal overwhelmed the company’s finances and it filed for bankruptcy in 2016.[8] As a consequence, the development and clinical trials of anatabine were halted indefinitely.
Research
Anatabine has been studied in animal models and in cells to see if it might be useful for treating nicotine addiction and inflammation, and has been studied in models of diseases characterized by inflammation, such as Alzheimer's disease,[9] thyroiditis,[10] and multiple sclerosis.[3] Anatabine cream was helpful in managing mild to moderate rosacea.[11] An internet based survey showed 82% users reported a benefit from anatabine supplementation for one or more joint pain conditions.[12]
See also
- Anatalline
- Anabaseine
- Myosmine
References
- ↑ 1.0 1.1 "Molecular genetics of alkaloid biosynthesis in Nicotiana tabacum". Phytochemistry 94: 10–27. October 2013. doi:10.1016/j.phytochem.2013.06.002. PMID 23953973. Bibcode: 2013PChem..94...10D.
- ↑ "Anti-inflammatory activity of anatabine via inhibition of STAT3 phosphorylation". European Journal of Pharmacology 698 (1–3): 145–53. January 2013. doi:10.1016/j.ejphar.2012.11.017. PMID 23178521.
- ↑ 3.0 3.1 "Anatabine significantly decreases nicotine self-administration". Experimental and Clinical Psychopharmacology 22 (1): 1–8. February 2014. doi:10.1037/a0035409. PMID 24490707. Note: content is supported by discussion section which provides a brief review of research to date.
- ↑ 4.0 4.1 4.2 4.3 Kroll, David (31 January 2014). "The McDonnell Scandal: What's The Dope Behind Star Scientific Supplement Products?". Forbes. https://www.forbes.com/sites/davidkroll/2014/01/31/whats-the-dope-on-anatabine-in-star-scientifics-anatabloc-and-cigrx/.
- ↑ 5.0 5.1 Gabriel, Trip (21 January 2014). "Ex-Governor of Virginia Is Indicted on Charges Over Loans and Gifts". New York Times. https://www.nytimes.com/2014/01/22/us/former-virginia-governor-and-his-wife-are-indicted.html.
- ↑ "FDA Says Star Scientific Illegally Marketing Products". CBS News. December 31, 2013. http://washington.cbslocal.com/2013/12/31/fda-says-star-scientific-illegally-marketing-products/.
- ↑ FDA Warning Letter
- ↑ "With a History of Political Corruption Rock Creek Pharma Files for Bankruptcy". http://www.biospace.com/News/with-a-history-of-political-corruption-rock-creek/434072.
- ↑ "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 10 (7): e0134776. 2015. doi:10.1371/journal.pone.0134776. PMID 26230317. Bibcode: 2015PLoSO..1034776V.
- ↑ "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 99 (1): E137-42. January 2014. doi:10.1210/jc.2013-2951. PMID 24178792.
- ↑ "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 5 (3): 347–56. 2013. doi:10.1159/000357019. PMID 24348385.
- ↑ "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 6: 73–84. 2013. doi:10.4137/CMAMD.S13001. PMID 24250235.
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