Anatabine

Anatabine
Systematic (IUPAC) name
[2R,(+)]-1,2,3,6-Tetrahydro-2,3'-bipyridine
Clinical data
Pregnancy cat.  ?
Legal status  ?
Identifiers
CAS number 581-49-7 Y
ATC code  ?
ChemSpider 10910 Y
Chemical data
Formula C10H12N2 
Mol. mass 160.22 g/mol
 Y(what is this?)  (verify)

Anatabine (uh-nat-uh-been,-bin) is one of the minor alkaloids found in plants in the Solanaceae family, which includes the tobacco plant, that has been shown to affect monoamine oxidase (MAO) activity.[1][2] Anatabine is found in cigarette tobacco and smoke, and is absorbed in the human body after tobacco use.[3]

There have been hypotheses that minor tobacco constituents and other non-nicotine therapies may be beneficial in fighting nicotine withdrawal.[4] Many studies have been conducted investigating the effects of smoking on MAO activity.[5][6][7][8]

Anatabine is one of the ingredients in the smoking alternative dietary supplement, CiGRX, developed by Rock Creek Pharmaceuticals.[9] The use of anatabine rather than nicotine replacement therapy is related to the half-lives of nicotine and anatabine. The latency of needing a cigarette (LTNC) among regular smokers was less than two hours[10] compared to the half-life of anatabine which is 10 hours.[3]

Rock Creek Pharmaceuticals has also developed Anatabloc, a product that targets inflammation.[11] The Roskamp Institute in Sarasota, Florida, has worked with Rock Creek Pharmaceuticals to study the effects of the anatabine compound on inflammatory diseases and disorders. Roskamp findings can be viewed at The Roskamp Institute Website.[12]

Anatabine's potential in fighting Alzheimer's disease and other inflammatory illnesses is being studied.[12]

References

  1. ^ Rose JE, Behm FM, Ramsey C, Ritchie JC (November 2001). "Platelet monoamine oxidase, smoking cessation, and tobacco withdrawal symptoms". Nicotine Tob. Res. 3 (4): 383–90. doi:10.1080/14622200110087277. PMID 11694206. 
  2. ^ Castagnoli K, Petzer JB, Steyn SJ, van der Schyf CJ, Castagnoli N (2003). "Inhibition of human MAO-A and MAO-B by a compound isolated from flue-cured tobacco leaves and its neuroprotective properties in the MPTP mouse model of neurodegeneration". Inflammopharmacology 11 (2): 183–8. doi:10.1163/156856003765764353. PMID 15035820. 
  3. ^ a b Jacob P, Yu L, Shulgin AT, Benowitz NL (May 1999). "Minor tobacco alkaloids as biomarkers for tobacco use: comparison of users of cigarettes, smokeless tobacco, cigars, and pipes". Am J Public Health 89 (5): 731–6. doi:10.2105/AJPH.89.5.731. PMC 1508721. PMID 10224986. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1508721. 
  4. ^ Mattioli L, Perfumi M (March 2011). "Evaluation of Rhodiola rosea L. extract on affective and physical signs of nicotine withdrawal in mice". J. Psychopharmacol. (Oxford) 25 (3): 402–10. doi:10.1177/0269881109348166. PMID 19939867. 
  5. ^ Fowler JS, Volkow ND, Wang GJ, Pappas N, Logan J, MacGregor R, Alexoff D, Shea C, Schlyer D, Wolf AP, Warner D, Zezulkova I, Cilento R (February 1996). "Inhibition of monoamine oxidase B in the brains of smokers". Nature 379 (6567): 733–6. doi:10.1038/379733a0. PMID 8602220. 
  6. ^ Fowler JS, Volkow ND, Wang GJ, Pappas N, Logan J, Shea C, Alexoff D, MacGregor RR, Schlyer DJ, Zezulkova I, Wolf AP (November 1996). "Brain monoamine oxidase A inhibition in cigarette smokers". Proc. Natl. Acad. Sci. U.S.A. 93 (24): 14065–9. PMC 19495. PMID 8943061. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=19495. 
  7. ^ van Amsterdam J, Talhout R, Vleeming W, Opperhuizen A (October 2006). "Contribution of monoamine oxidase (MAO) inhibition to tobacco and alcohol addiction". Life Sci. 79 (21): 1969–73. doi:10.1016/j.lfs.2006.06.010. PMID 16884739. 
  8. ^ Norman TR, Chamberlain KG, French MA (March 1987). "Platelet monoamine oxidase: low activity in cigarette smokers". Psychiatry Res 20 (3): 199–205. doi:10.1016/0165-1781(87)90079-5. PMID 3588781. 
  9. ^ "CiGRX". Star Scientific, Inc. http://www.cigrx.com. Retrieved 2011-09-06. 
  10. ^ Ursprung WW, Morello P, Gershenson B, DiFranza JR (April 2011). "Development of a measure of the latency to needing a cigarette". J Adolesc Health 48 (4): 338–43. doi:10.1016/j.jadohealth.2010.07.011. PMID 21402261. 
  11. ^ "Anatabloc". Star Scientific, Inc. http://www.anatabloc.com. Retrieved 2011-09-06. 
  12. ^ a b "Role of Anatabine as an anti-inflammatory agent". Roskamp Institute. http://www.rfdn.org/inflammaging.html. Retrieved 2011-09-06.