Anatabine

Last Updated: September 28, 2022

Anatabine is an alkaloid compound found in tobacco and plants in the nightshade family, which includes eggplant and peppers. Anatabine possesses anti-inflammatory properties but further research is needed to determine if supplementation is practical.

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Anatabine is most often used for.


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1.

Sources and Structure

1.1

Sources

Anatabine is an alkaloid found in tobacco and the solanaceae family of plants. This alkaloid is structurally similar to nicotine, and is an analogue of both nornicotine and anabasine (other alkaloids in the same plant family).[1]

It is found in:

  • Tobacco in the range of 927-1390μg/g[2] or on average 554μg per cigarette (range of 130-1120μg; American cigarettes containing 500-550μg)[1]

Anatabine is a tobacco alkaloid similar to nicotine, and is found in the same plants

1.2

Structure and Properties

Anatabine is an alkaloid with structural similarity to nicotine, and closer structure similarity to anabasine (which is anatabine without the double bond in the right ring pictured below).

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2.

Neurology

2.1

Cholinergic Neurotransmission

In vitro, anatabine has been noted to have bind to the α3β4 receptor with similar affinity as nicotine.[3]

May interact with nicotinic cholinergic receptors, although this is not well researched

2.2

Alzheimer& #039;s Disease

Anatabine has been found to reduce Aβ production (both Aβ1–40 and Aβ1–42) with an IC50 of around 640µg/mL, and it appeared to mostly inhibit β-cleavage of APP.[4] As this is known to occur with NF-kB inhibition[5][6] anatabine was then tested on the protein and it was found to inhibit NF-kB activation from TNF-α with a similar IC50 value[4] and nicotine was found to be inactive at the same concentrations tested. It has been noted elsewhere that this inhibitory effect on NF-kB is secondary to inhibiting STAT3 phosphorylation at 600-800µg/mL[7] although concnetrations as low as 10µg/mL can inhibit LPS-induced NF-kB activity and 400µg/mL can fully abolish IL-1β secretion induced by LPS.[7]

Nicotine has been found to inhibit Aβ production by regulating BACE-1 transcription in cells that express its receptor (α4β2 nicotinic acetylcholine receptor)[8] and anatabine has also been found to downregulate BACE-1 mRNA, which was credited to NF-kB inhibition (known to regulate BACE-1[9]). Activation of the nicotinic receptors can inhibit NF-kB[10] via STAT3[11] but nicotine seems to require a cholinergic receptor whereas anatabine does not.[4]

When injected into mice at 0.5-2mg/kg, only the higher dose was able to reduce brain and plasma Aβ concentrations to near control levels (in plasma) and by about 25% (brain)[4] and this dose has been noted to exert anti-inflammatory effects by reducing C-reactive protein[4] as well as IL-1β, IL-6, and TNF-α.[7]

Anatabine is a STAT3 inhibitor, which then inhibits NF-kB and exerts an anti-inflammatory effect. This appears to be active following injections of anatabine and may be of therapeutic benefit to Alzheimer's Disease

3.

Cardiovascular Health

3.1

Blood Pressure

Anatabine has structural similarity to nicotine, and since nicotine is able to acutely increase heart rate and blood pressure[12] anatabine has been investigated for its ability to do the same; it has since failed to significantly influence blood pressure or heart rate.[13]

Currently no significant interactions between anatabine and cardiovascular function are known

4.

Inflammation and Immunology

4.1

Mechanisms

Incubation of macrophages with 250-350μM was able to inhibit an IFN-γ and LPS induced increases in iNOS and COX-2 mRNA levels, suggesting antiinflammatory effects.[14]

May have general antiinflammatory properties at moderately high concentrations

4.2

Autoimmune Diseases

Despite the large amount of adverse health effects associated with tobacco smoking, both ulcerative colitis[15][16] and autoimmune (Hashimoto's) thyroiditis[17][18] have noted benefits associated with smoking. This is currently thought to be due to the antiinflammatory properties of nicotine via the α7 nicotinic receptor[19] (inhibits STAT3 and then NF-kB), but anatabine is also being tested.

In mice inflicted with experimental autoimmune thyroiditis and concurrently supplemented orally with approximately 12.5mg/kg anatabine, occurrence of thyroiditis and the antibody response were significantly reduced.[14] Autoimmune encephalomyelitis (research model for Multiple sclerosis) also sees clinical benefit in response to 20mg/kg anatabine in mice, although antibodies were not affected in this study.[20]

Appears to be beneficial for rodents with autoimmune diseases in high oral doses

5.

Physical Exercise and Skeletal Muscle

5.1

Muscle Soreness and Damage

Supplementation of 6-12mg anatabine (via lozenges that also conferred 834-1668IU vitamin A and 66-132IU Vitamin D) for ten days prior to physical exercise testing in otherwise healthy young men failed to outperform placebo (which contained the vitamins) in reducing muscle soreness or power output when measured over the next three days.[13]

The lone study in humans assessing the antiinflammatory properties of anatabine failed to find any significant influence of supplementation

References
4.^Paris D, Beaulieu-Abdelahad D, Bachmeier C, Reed J, Ait-Ghezala G, Bishop A, Chao J, Mathura V, Crawford F, Mullan MAnatabine lowers Alzheimer's Aβ production in vitro and in vivoEur J Pharmacol.(2011 Nov 30)
5.^Paris D, Patel N, Quadros A, Linan M, Bakshi P, Ait-Ghezala G, Mullan MInhibition of Abeta production by NF-kappaB inhibitorsNeurosci Lett.(2007 Mar 19)
6.^Paris D, Ganey NJ, Laporte V, Patel NS, Beaulieu-Abdelahad D, Bachmeier C, March A, Ait-Ghezala G, Mullan MJReduction of beta-amyloid pathology by celastrol in a transgenic mouse model of Alzheimer's diseaseJ Neuroinflammation.(2010 Mar 8)
7.^Paris D, Beaulieu-Abdelahad D, Abdullah L, Bachmeier C, Ait-Ghezala G, Reed J, Verma M, Crawford F, Mullan MAnti-inflammatory activity of anatabine via inhibition of STAT3 phosphorylationEur J Pharmacol.(2013 Jan 5)
9.^Buggia-Prevot V, Sevalle J, Rossner S, Checler FNFkappaB-dependent control of BACE1 promoter transactivation by Abeta42J Biol Chem.(2008 Apr 11)
11.^Peña G, Cai B, Liu J, van der Zanden EP, Deitch EA, de Jonge WJ, Ulloa LUnphosphorylated STAT3 modulates alpha 7 nicotinic receptor signaling and cytokine production in sepsisEur J Immunol.(2010 Sep)
12.^Haass M, Kübler WNicotine and sympathetic neurotransmissionCardiovasc Drugs Ther.(1997 Jan)
13.^Jenkins ND, Housh TJ, Johnson GO, Traylor DA, Bergstrom HC, Cochrane KC, Lewis RW Jr, Schmidt RJ, Cramer JTThe effects of anatabine on non-invasive indicators of muscle damage: a randomized, double-blind, placebo-controlled, crossover studyJ Int Soc Sports Nutr.(2013 Jul 22)
14.^Caturegli P, De Remigis A, Ferlito M, Landek-Salgado MA, Iwama S, Tzou SC, Ladenson PWAnatabine ameliorates experimental autoimmune thyroiditisEndocrinology.(2012 Sep)
15.^Boyko EJ, Perera DR, Koepsell TD, Keane EM, Inui TSEffects of cigarette smoking on the clinical course of ulcerative colitisScand J Gastroenterol.(1988 Nov)
16.^Calabrese E, Yanai H, Shuster D, Rubin DT, Hanauer SBLow-dose smoking resumption in ex-smokers with refractory ulcerative colitisJ Crohns Colitis.(2012 Aug)
19.^Bencherif M, Lippiello PM, Lucas R, Marrero MBAlpha7 nicotinic receptors as novel therapeutic targets for inflammation-based diseasesCell Mol Life Sci.(2011 Mar)
20.^Paris D, Beaulieu-Abdelahad D, Mullan M, Ait-Ghezala G, Mathura V, Bachmeier C, Crawford F, Mullan MJAmelioration of experimental autoimmune encephalomyelitis by anatabinePLoS One.(2013)