Anatabine

Anatabine
Systematic (IUPAC) name
[2R,(+)]-1,2,3,6-Tetrahydro-2,3'-bipyridine
Identifiers
CAS Number 581-49-7 YesY
ChemSpider 10910 YesY
Chemical data
Formula C10H12N2
Molar mass 160.22 g/mol
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Anatabine (uh-nat-uh-been,-bin) is one of the minor alkaloids found in plants in the Solanaceae family, 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 anabatine, 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 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, thyroiditis, and multiple sclerosis.[2] On a biochemical level, it appears to be active against certain nicotinic acetylcholine receptors.[2]

Commercial development

Rock Creek Pharmaceuticals (formerly known as Star Scientific), headquartered in Florida and with offices in Virginia, has been developing anatabine as a dietary supplement and as a drug.[3][4][5] The dietary supplements are known as Anatabloc and CigRx; the company has also marketed cosmetics with the Anatabloc brand.[4] Rock Creek has been working on synthetic methods to scale up production of anatabine and has funded pre-clinical and clinical research in several indications.[4]

The FDA has warned the company for unlawfully promoting CigRx and Anatabloc before anatabine was proved to be safe.[6][7]

In 2013, the company 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 R. Williams Sr, the CEO of the company.[5] Williams resigned and the company changed its name at the end of 2013 due to the scandal.[4]

References

  1. 1 2 Dewey, RE; Xie, J (Oct 2013). "Molecular genetics of alkaloid biosynthesis in Nicotiana tabacum. Review". Phytochemistry 94: 10–27. doi:10.1016/j.phytochem.2013.06.002. PMID 23953973.
  2. 1 2 Mello, NK; et al. (Feb 2014). "Anatabine significantly decreases nicotine self-administration". Exp Clin Psychopharmacol 22 (1): 1–8. doi:10.1037/a0035409. PMID 24490707. Note: content is supported by discussion section which provides a brief review of research to date.
  3. ↑ Rock Creek Pharmaceuticals Official Website
  4. 1 2 3 4 David Kroll for Forbes. January 31, 2014 The McDonnell Scandal: What's The Dope Behind Star Scientific Supplement Products?
  5. 1 2 Trip Gabriel for the New York Times. January 21, 2014 Ex-Governor of Virginia Is Indicted on Charges Over Loans and Gifts
  6. ↑ "FDA Says Star Scientific Illegally Marketing Products". CBS News. December 31, 2013.
  7. ↑ FDA Warning Letter
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