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{{short description|Chemical compound}}
{{cs1 config|name-list-style=vanc}}
{{Drugbox {{Drugbox
| Watchedfields = changed
| verifiedrevid = 451420793 | verifiedrevid = 451607368
| IUPAC_name = -1,2,3,6-Tetrahydro-2,3'-bipyridine | IUPAC_name = -1,2,3,6-Tetrahydro-2,3'-bipyridine
| image = Anatabine.svg | image = Anatabine.svg


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 581-49-7 | CAS_number = 581-49-7
| ChEBI = 2705
| ChEMBL = 3640772
| KEGG = C10126
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5PP654XB7D
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10910 | ChemSpiderID = 10910
| PubChem = 11388


<!--Chemical data--> <!--Chemical data-->
| C=10 | H=12 | N=2
| chemical_formula = C<sub>10</sub>H<sub>12</sub>N<sub>2</sub>

| molecular_weight = 160.22 g/mol
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SOPPBXUYQGUQHE-JTQLQIEISA-N | StdInChIKey = SOPPBXUYQGUQHE-JTQLQIEISA-N
| SMILES = c1cc(cnc1)2CC=CCN2
}} }}


'''Anatabine''' (uh-nat-uh-been,-bin) is one of the minor ] found in plants in the ] family, which includes the ], that has been shown to affect ].<ref name="pmid11694206">{{cite journal | author = Rose JE, Behm FM, Ramsey C, Ritchie JC | title = Platelet monoamine oxidase, smoking cessation, and tobacco withdrawal symptoms | journal = Nicotine Tob. Res. | volume = 3 | issue = 4 | pages = 383–90 | year = 2001 | month = November | pmid = 11694206 | doi = 10.1080/14622200110087277 }}</ref><ref name="pmid15035820">{{cite journal | author = Castagnoli K, Petzer JB, Steyn SJ, van der Schyf CJ, Castagnoli N | title = 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 | journal = Inflammopharmacology | volume = 11 | issue = 2 | pages = 183–8 | year = 2003 | pmid = 15035820 | doi = 10.1163/156856003765764353 }}</ref> Anatabine is found in cigarette tobacco and smoke, and is absorbed in the human body after tobacco use.<ref name="Payton1999">{{cite journal | author = Jacob P, Yu L, Shulgin AT, Benowitz NL | title = Minor tobacco alkaloids as biomarkers for tobacco use: comparison of users of cigarettes, smokeless tobacco, cigars, and pipes | journal = Am J Public Health | volume = 89 | issue = 5 | pages = 731–6 | year = 1999 | month = May | pmid = 10224986 | pmc = 1508721 | doi = 10.2105/AJPH.89.5.731 }}</ref> '''Anatabine''' (uh-nat-uh-been,-bin) is one of the minor ]s found in plants in the family ], which includes the ] and ]. Commercial tobacco plants typically produce alkaloids at levels between 2% and 4% of total dry weight,<ref>{{cite journal | vauthors = 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 | title = Fractionation and Extraction Optimization of Potentially Valuable Compounds and Their Profiling in Six Varieties of Two ''Nicotiana'' Species | journal = Molecules | volume = 27 | issue = 22 | page = 8105 | date = November 2022 | pmid = 36432206 | pmc = 9694777 | doi = 10.3390/molecules27228105 | doi-access = free }}</ref> with ] accounting for about 90% of the total alkaloid content, and the related compounds anatabine, ], and ] making up nearly all the rest.<ref name=Dewey>{{cite journal | vauthors = Dewey RE, Xie J | title = Molecular genetics of alkaloid biosynthesis in Nicotiana tabacum | journal = Phytochemistry | volume = 94 | pages = 10–27 | date = October 2013 | pmid = 23953973 | doi = 10.1016/j.phytochem.2013.06.002 | bibcode = 2013PChem..94...10D }}</ref> These compounds are thought to be biologically active, and part of plants' natural defense system against insects.<ref name=Dewey/>

Anatabine has ] activity partly through inhibition of ] phosphorylation in vitro and in vivo.<ref name="pmid23178521">{{cite journal |vauthors=Paris D, Beaulieu-Abdelahad D, Abdullah L, Bachmeier C, Ait-Ghezala G, Reed J, Verma M, Crawford F, Mullan M |title=Anti-inflammatory activity of anatabine via inhibition of STAT3 phosphorylation |journal=] |volume=698 |issue=1–3 |pages=145–53 |date=January 2013 |pmid=23178521 |doi=10.1016/j.ejphar.2012.11.017 |issn=}}</ref>

== Pharmacology ==
On a ] level, it appears to be active against certain ].<ref name=Mello/>

==Commercial development==

] developed and sold the compound as a ] primarily through GNC up until mid 2014. Subsequently, Rock Creek Pharmaceuticals (formerly a subsidiary of ]), headquartered in Florida, began developing anatabine as a ].<ref name=Forbes>{{cite web | first = David | last = Kroll | work = Forbes | date = 31 January 2014 | url = https://www.forbes.com/sites/davidkroll/2014/01/31/whats-the-dope-on-anatabine-in-star-scientifics-anatabloc-and-cigrx/ | title = The McDonnell Scandal: What's The Dope Behind Star Scientific Supplement Products? }}</ref><ref name=Gabriel>{{cite web | first = Trip | last = Gabriel | work = New York Times | date = 21 January 2014 | url = https://www.nytimes.com/2014/01/22/us/former-virginia-governor-and-his-wife-are-indicted.html | title = Ex-Governor of Virginia Is Indicted on Charges Over Loans and Gifts }}</ref> The dietary supplements were known as Anatabloc and CigRx; the company has also marketed cosmetics with the Anatabloc brand.<ref name=Forbes/> Rock Creek had been working on synthetic methods to scale up production of anatabine and has funded ] and ] research in several ].<ref name=Forbes/>

In 2013 the FDA warned Star Scientific for unlawfully promoting CigRx and Anatabloc before anatabine was proved to be safe.<ref>{{cite news | url = http://washington.cbslocal.com/2013/12/31/fda-says-star-scientific-illegally-marketing-products/ | title = FDA Says Star Scientific Illegally Marketing Products | work = CBS News | date = December 31, 2013}}</ref><ref></ref> 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, ], and his wife had received significant loans and gifts from ] 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.<ref name=Gabriel/> 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.<ref name=Forbes/>
There have been hypotheses that minor tobacco constituents and other non-nicotine therapies may be beneficial in fighting nicotine withdrawal.<ref name="pmid19939867">{{cite journal | author = Mattioli L, Perfumi M | title = Evaluation of Rhodiola rosea L. extract on affective and physical signs of nicotine withdrawal in mice | journal = J. Psychopharmacol. (Oxford) | volume = 25 | issue = 3 | pages = 402–10 | year = 2011 | month = March | pmid = 19939867 | doi = 10.1177/0269881109348166 }}</ref> Many studies have been conducted investigating the effects of smoking on MAO activity.<ref name="pmid8602220">{{cite journal | author = 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 | title = Inhibition of monoamine oxidase B in the brains of smokers | journal = Nature | volume = 379 | issue = 6567 | pages = 733–6 | year = 1996 | month = February | pmid = 8602220 | doi = 10.1038/379733a0 }}</ref><ref name="pmid8943061">{{cite journal | author = Fowler JS, Volkow ND, Wang GJ, Pappas N, Logan J, Shea C, Alexoff D, MacGregor RR, Schlyer DJ, Zezulkova I, Wolf AP | title = Brain monoamine oxidase A inhibition in cigarette smokers | journal = Proc. Natl. Acad. Sci. U.S.A. | volume = 93 | issue = 24 | pages = 14065–9 | year = 1996 | month = November | pmid = 8943061 | pmc = 19495 | doi = }}</ref><ref name="pmid16884739">{{cite journal | author = van Amsterdam J, Talhout R, Vleeming W, Opperhuizen A | title = Contribution of monoamine oxidase (MAO) inhibition to tobacco and alcohol addiction | journal = Life Sci. | volume = 79 | issue = 21 | pages = 1969–73 | year = 2006 | month = October | pmid = 16884739 | doi = 10.1016/j.lfs.2006.06.010 }}</ref><ref name="pmid3588781">{{cite journal | author = Norman TR, Chamberlain KG, French MA | title = Platelet monoamine oxidase: low activity in cigarette smokers | journal = Psychiatry Res | volume = 20 | issue = 3 | pages = 199–205 | year = 1987 | month = March | pmid = 3588781 | doi = 10.1016/0165-1781(87)90079-5 }}</ref>


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.<ref>{{Cite web|url=http://www.biospace.com/News/with-a-history-of-political-corruption-rock-creek/434072|title=With a History of Political Corruption Rock Creek Pharma Files for Bankruptcy|website=www.biospace.com|access-date=2017-08-17}}</ref> As a consequence, the development and clinical trials of anatabine were halted indefinitely.
Anatabine is one of the ingredients in the smoking alternative dietary supplement, CiGRX, developed by Rock Creek Pharmaceuticals.<ref name="urlCiGRX">{{cite web | url = http://www.cigrx.com | title = CiGRX | publisher = Star Scientific, Inc | accessdate = 2011-09-06 }}</ref> 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<ref name="pmid21402261">{{cite journal | author = Ursprung WW, Morello P, Gershenson B, DiFranza JR | title = Development of a measure of the latency to needing a cigarette | journal = J Adolesc Health | volume = 48 | issue = 4 | pages = 338–43 | year = 2011 | month = April | pmid = 21402261 | doi = 10.1016/j.jadohealth.2010.07.011 | url = }}</ref> compared to the half-life of anatabine which is 10 hours.<ref name="Payton1999" />


== Research ==
Rock Creek Pharmaceuticals has also developed Anatabloc, a product that targets inflammation.<ref name="urlAnatabloc">{{cite web | url = http://www.anatabloc.com | title = Anatabloc | publisher = Star Scientific, Inc | accessdate = 2011-09-06 }}</ref> ] 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.<ref name="urlRoskamp Institute | Role of Anatabine as an anti-inflammatory agent">{{cite web | url = http://www.rfdn.org/inflammaging.html | title = Role of Anatabine as an anti-inflammatory agent | date = | work = | publisher = Roskamp Institute | quote = | accessdate = 2011-09-06 }}</ref>
Anatabine has been studied in animal models and in cells to see if it might be useful for treating ] and ], and has been studied in models of diseases characterized by inflammation, such as ],<ref name="pmid26230317">{{cite journal |vauthors=Verma M, Beaulieu-Abdelahad D, Ait-Ghezala G, Li R, Crawford F, Mullan M, Paris D |title=Correction: Chronic Anatabine Treatment Reduces Alzheimer's Disease (AD)-Like Pathology and Improves Socio-Behavioral Deficits in a Transgenic Mouse Model of AD |journal=] |volume=10 |issue=7 |pages=e0134776 |date=2015 |pmid=26230317 |pmc=4521847 |doi=10.1371/journal.pone.0134776 |issn=|doi-access=free |bibcode=2015PLoSO..1034776V }}</ref> ],<ref>{{cite journal | vauthors = Schmeltz LR, Blevins TC, Aronoff SL, Ozer K, Leffert JD, Goldberg MA, Horowitz BS, Bertenshaw RH, Troya P, Cohen AE, Lanier RK, Wright C | display-authors = 6 | title = Anatabine supplementation decreases thyroglobulin antibodies in patients with chronic lymphocytic autoimmune (Hashimoto's) thyroiditis: a randomized controlled clinical trial | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 99 | issue = 1 | pages = E137-42 | date = January 2014 | pmid = 24178792 | pmc = 3928963 | doi = 10.1210/jc.2013-2951 }}</ref> and ].<ref name=Mello>{{cite journal | vauthors = Mello NK, Fivel PA, Kohut SJ, Caine SB | title = Anatabine significantly decreases nicotine self-administration | journal = Experimental and Clinical Psychopharmacology | volume = 22 | issue = 1 | pages = 1–8 | date = February 2014 | pmid = 24490707 | doi = 10.1037/a0035409 | s2cid = 15879738 }} Note: content is supported by discussion section which provides a brief review of research to date.</ref> Anatabine cream was helpful in managing mild to moderate ].<ref name="pmid24348385">{{cite journal |vauthors=Lanier RK, Cohen AE, Weinkle SH |title=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 |journal=] |volume=5 |issue=3 |pages=347–56 |date=2013 |pmid=24348385 |pmc=3861860 |doi=10.1159/000357019|issn=}}</ref> An internet based survey showed 82% users reported a benefit from anatabine supplementation for one or more joint pain conditions.<ref name="pmid24250235">{{cite journal |vauthors=Lanier RK, Gibson KD, Cohen AE, Varga M |title=Effects of dietary supplementation with the solanaceae plant alkaloid anatabine on joint pain and stiffness: results from an internet-based survey study |journal=] |volume=6 |issue= |pages=73–84 |date=2013 |pmid=24250235 |pmc=3825642 |doi=10.4137/CMAMD.S13001 |issn=}}</ref>


== See also ==
Anatabine's potential in fighting Alzheimer's disease and other anti-inflammatory illnesses is being studied.<ref name="urlRoskamp Institute | Role of Anatabine as an anti-inflammatory agent">{{cite web | url = http://www.rfdn.org/inflammaging.html | title = Role of Anatabine as an anti-inflammatory agent | date = | work = | publisher = Roskamp Institute | quote = | accessdate = 2011-09-06 }}</ref>
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== References == == References ==
{{Reflist|2}} {{Reflist|2}}


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