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Anatabine

Anatabine
Identifiers
  • [2R,(+)]-1,2,3,6-Tetrahydro-2,3'-bipyridine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H12N2
Molar mass160.220 g·mol−1
3D model (JSmol)
  • c1cc(cnc1)[C@@H]2CC=CCN2
  • 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 checkY
  • Key:SOPPBXUYQGUQHE-JTQLQIEISA-N checkY
  (verify)

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,[1] 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.[2] These compounds are thought to be biologically active, and part of plants' natural defense system against insects.[2]

Anatabine has anti-inflammatory activity partly through inhibition of STAT3 phosphorylation in vitro and in vivo.[3]

Pharmacology

On a biochemical level, it appears to be active against certain nicotinic acetylcholine receptors.[4]

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.[5][6] The dietary supplements were known as Anatabloc and CigRx; the company has also marketed cosmetics with the Anatabloc brand.[5] 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.[5]

In 2013 the FDA warned Star Scientific for unlawfully promoting CigRx and Anatabloc before anatabine was proved to be safe.[7][8] 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.[6] 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.[5]

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.[9] 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,[10] thyroiditis,[11] and multiple sclerosis.[4] Anatabine cream was helpful in managing mild to moderate rosacea.[12] An internet based survey showed 82% users reported a benefit from anatabine supplementation for one or more joint pain conditions.[13]

See also

References

  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 (November 2022). "Fractionation and Extraction Optimization of Potentially Valuable Compounds and Their Profiling in Six Varieties of Two Nicotiana Species". Molecules. 27 (22): 8105. doi:10.3390/molecules27228105. PMC 9694777. PMID 36432206.
  2. ^ a b Dewey RE, Xie J (October 2013). "Molecular genetics of alkaloid biosynthesis in Nicotiana tabacum". Phytochemistry. 94: 10–27. Bibcode:2013PChem..94...10D. doi:10.1016/j.phytochem.2013.06.002. PMID 23953973.
  3. ^ Paris D, Beaulieu-Abdelahad D, Abdullah L, Bachmeier C, Ait-Ghezala G, Reed J, Verma M, Crawford F, Mullan M (January 2013). "Anti-inflammatory activity of anatabine via inhibition of STAT3 phosphorylation". European Journal of Pharmacology. 698 (1–3): 145–53. doi:10.1016/j.ejphar.2012.11.017. PMID 23178521.
  4. ^ a b Mello NK, Fivel PA, Kohut SJ, Caine SB (February 2014). "Anatabine significantly decreases nicotine self-administration". Experimental and Clinical Psychopharmacology. 22 (1): 1–8. doi:10.1037/a0035409. PMID 24490707. S2CID 15879738. Note: content is supported by discussion section which provides a brief review of research to date.
  5. ^ a b c d Kroll D (31 January 2014). "The McDonnell Scandal: What's The Dope Behind Star Scientific Supplement Products?". Forbes.
  6. ^ a b Gabriel T (21 January 2014). "Ex-Governor of Virginia Is Indicted on Charges Over Loans and Gifts". New York Times.
  7. ^ "FDA Says Star Scientific Illegally Marketing Products". CBS News. December 31, 2013.
  8. ^ FDA Warning Letter
  9. ^ "With a History of Political Corruption Rock Creek Pharma Files for Bankruptcy". www.biospace.com. Retrieved 2017-08-17.
  10. ^ Verma M, Beaulieu-Abdelahad D, Ait-Ghezala G, Li R, Crawford F, Mullan M, Paris D (2015). "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. Bibcode:2015PLoSO..1034776V. doi:10.1371/journal.pone.0134776. PMC 4521847. PMID 26230317.
  11. ^ Schmeltz LR, Blevins TC, Aronoff SL, Ozer K, Leffert JD, Goldberg MA, et al. (January 2014). "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. doi:10.1210/jc.2013-2951. PMC 3928963. PMID 24178792.
  12. ^ Lanier RK, Cohen AE, Weinkle SH (2013). "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. doi:10.1159/000357019. PMC 3861860. PMID 24348385.
  13. ^ Lanier RK, Gibson KD, Cohen AE, Varga M (2013). "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. doi:10.4137/CMAMD.S13001. PMC 3825642. PMID 24250235.
Quelle: https://en.wikipedia.org/wiki/Anatabloc