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MedKoo Cat#: 573151 | Name: Anatabine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Anatabine is one of the minor alkaloids found in plants in the Solanaceae family, which includes the tobacco plant and tomato. Anatabine may be useful for treating nicotine addiction and inflammation, Alzheimer's Disease, thyroiditis, and multiple sclerosis.

Chemical Structure

Anatabine
Anatabine
CAS#581-49-7

Theoretical Analysis

MedKoo Cat#: 573151

Name: Anatabine

CAS#: 581-49-7

Chemical Formula: C10H12N2

Exact Mass: 160.1000

Molecular Weight: 160.22

Elemental Analysis: C, 74.97; H, 7.55; N, 17.48

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Synonym
Anatabine, (-)-Anatabine
IUPAC/Chemical Name
(S)-1,2,3,6-tetrahydro-2,3'-bipyridine
InChi Key
SOPPBXUYQGUQHE-JTQLQIEISA-N
InChi Code
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
SMILES Code
c1([C@@H]2CC=CCN2)cccnc1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
TBD
In vitro activity:
Macrophages were first activated with interferon-γ to induce the expression of iNOS and COX2 and then incubated with anatabine at concentrations of 250 or 350 μM. These concentrations were chosen based on a dose-response curve ranging from 250 to 2000 μM (Supplemental Fig. 1). Anatabine suppressed in a dose-dependent manner the increase of iNOS and COX2 induced by interferon-γ (Fig. 4), confirming in vitro its antiinflammatory properties. The effect seen with interferon-γ was also seen when macrophages were stimulated with lipopolysaccharide (Supplemental Fig. 1). Reference: Endocrinology. 2012 Sep;153(9):4580-7. https://pubmed.ncbi.nlm.nih.gov/22807490/
In vivo activity:
24r-mTBI-anatabine mice had a 65% decrease in cumulative distance compared to 24r-mTBI-vehicle group (p < 0.05, MANOVA). For distance traveled, 24r-mTBI-anatabine mice exhibited a 30% decrease compared to 24r-mTBI-vehicle. Treatment with anatabine significantly reduced latency to enter the box in the injured mice starting on day 2 of the acquisition trial (24r-mTBI-anatabine vs 24r-mTBI-vehicle: day 2 p < 0.01, day 3 p < 0.01, day 4 p < 0.001, day 5 p < 0.01, day 6 p < 0.01, one-way ANOVA). During the probe trial, 24r-mTBI-vehicle mice spent 90% longer to locate the target hole compared to the 24r-sham-vehicle (Fig. 4D; 24r-mTBI-vehicle vs 24r-sham-vehicle: 28.3 ± 21 s vs 2.6 ± 1.2 s; p < 0.05, one-way ANOVA). In the 24r-mTBI-anatabine mice, mean time was 82.3% decreased compared to 24r-mTBI-vehicle (24r-mTBI-anatabine vs 24r-mTBI-vehicle: 4.9 ± 4.2 s vs 28.3 ± 21 s; p < 0.05, one-way ANOVA). Reference: Sci Rep. 2021; 11: 7900. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8041866/

Preparing Stock Solutions

The following data is based on the product molecular weight 160.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Caturegli P, De Remigis A, Ferlito M, Landek-Salgado MA, Iwama S, Tzou SC, Ladenson PW. Anatabine ameliorates experimental autoimmune thyroiditis. Endocrinology. 2012 Sep;153(9):4580-7. doi: 10.1210/en.2012-1452. Epub 2012 Jul 17. PMID: 22807490. 2. Paris D, Beaulieu-Abdelahad D, Bachmeier C, Reed J, Ait-Ghezala G, Bishop A, Chao J, Mathura V, Crawford F, Mullan M. Anatabine lowers Alzheimer's Aβ production in vitro and in vivo. Eur J Pharmacol. 2011 Nov 30;670(2-3):384-91. doi: 10.1016/j.ejphar.2011.09.019. Epub 2011 Sep 19. PMID: 21958873. 3. Morin A, Mouzon B, Ferguson S, Paris D, Saltiel N, Browning M, Mullan M, Crawford F. A 3-month-delayed treatment with anatabine improves chronic outcomes in two different models of repetitive mild traumatic brain injury in hTau mice. Sci Rep. 2021 Apr 12;11(1):7900. doi: 10.1038/s41598-021-87161-7. PMID: 33846461; PMCID: PMC8041866. 4. Ruiz Castro PA, Kogel U, Lo Sasso G, Phillips BW, Sewer A, Titz B, Garcia L, Kondylis A, Guedj E, Peric D, Bornand D, Dulize R, Merg C, Corciulo M, Ivanov NV, Peitsch MC, Hoeng J. Anatabine ameliorates intestinal inflammation and reduces the production of pro-inflammatory factors in a dextran sulfate sodium mouse model of colitis. J Inflamm (Lond). 2020 Aug 24;17:29. doi: 10.1186/s12950-020-00260-6. PMID: 32855621; PMCID: PMC7446176.
In vitro protocol:
1. Caturegli P, De Remigis A, Ferlito M, Landek-Salgado MA, Iwama S, Tzou SC, Ladenson PW. Anatabine ameliorates experimental autoimmune thyroiditis. Endocrinology. 2012 Sep;153(9):4580-7. doi: 10.1210/en.2012-1452. Epub 2012 Jul 17. PMID: 22807490. 2. Paris D, Beaulieu-Abdelahad D, Bachmeier C, Reed J, Ait-Ghezala G, Bishop A, Chao J, Mathura V, Crawford F, Mullan M. Anatabine lowers Alzheimer's Aβ production in vitro and in vivo. Eur J Pharmacol. 2011 Nov 30;670(2-3):384-91. doi: 10.1016/j.ejphar.2011.09.019. Epub 2011 Sep 19. PMID: 21958873.
In vivo protocol:
1. Morin A, Mouzon B, Ferguson S, Paris D, Saltiel N, Browning M, Mullan M, Crawford F. A 3-month-delayed treatment with anatabine improves chronic outcomes in two different models of repetitive mild traumatic brain injury in hTau mice. Sci Rep. 2021 Apr 12;11(1):7900. doi: 10.1038/s41598-021-87161-7. PMID: 33846461; PMCID: PMC8041866. 2. Ruiz Castro PA, Kogel U, Lo Sasso G, Phillips BW, Sewer A, Titz B, Garcia L, Kondylis A, Guedj E, Peric D, Bornand D, Dulize R, Merg C, Corciulo M, Ivanov NV, Peitsch MC, Hoeng J. Anatabine ameliorates intestinal inflammation and reduces the production of pro-inflammatory factors in a dextran sulfate sodium mouse model of colitis. J Inflamm (Lond). 2020 Aug 24;17:29. doi: 10.1186/s12950-020-00260-6. PMID: 32855621; PMCID: PMC7446176.
1: Ferguson S, Mouzon B, Paris D, Aponte D, Abdullah L, Stewart W, Mullan M, Crawford F. Acute or Delayed Treatment with Anatabine Improves Spatial Memory and Reduces Pathological Sequelae at Late Time-Points after Repetitive Mild Traumatic Brain Injury. J Neurotrauma. 2017 Apr 15;34(8):1676-1691. doi: 10.1089/neu.2016.4636. Epub 2017 Jan 20. PubMed PMID: 27889957; PubMed Central PMCID: PMC5749608. 2: Verma M, Beaulieu-Abdelahad D, Ait-Ghezala G, Li R, Crawford F, Mullan M, Paris D. Chronic Anatabine Treatment Reduces Alzheimer's Disease (AD)-Like Pathology and Improves Socio-Behavioral Deficits in a Transgenic Mouse Model of AD. PLoS One. 2015 May 26;10(5):e0128224. doi: 10.1371/journal.pone.0128224. eCollection 2015. Erratum in: PLoS One. 2015;10(7):e0134776. PubMed PMID: 26010758; PubMed Central PMCID: PMC4444019. 3: Levin ED, Hao I, Burke DA, Cauley M, Hall BJ, Rezvani AH. Effects of tobacco smoke constituents, anabasine and anatabine, on memory and attention in female rats. J Psychopharmacol. 2014 Oct;28(10):915-22. doi: 10.1177/0269881114543721. Epub 2014 Aug 13. PubMed PMID: 25122040; PubMed Central PMCID: PMC4305443. 4: Schmeltz LR, Blevins TC, Aronoff SL, Ozer K, Leffert JD, Goldberg MA, Horowitz BS, Bertenshaw RH, Troya P, Cohen AE, Lanier RK, Wright C 4th. Anatabine supplementation decreases thyroglobulin antibodies in patients with chronic lymphocytic autoimmune (Hashimoto's) thyroiditis: a randomized controlled clinical trial. J Clin Endocrinol Metab. 2014 Jan;99(1):E137-42. doi: 10.1210/jc.2013-2951. Epub 2013 Dec 20. PubMed PMID: 24178792; PubMed Central PMCID: PMC3928963. 5: Paris D, Beaulieu-Abdelahad D, Mullan M, Ait-Ghezala G, Mathura V, Bachmeier C, Crawford F, Mullan MJ. Amelioration of experimental autoimmune encephalomyelitis by anatabine. PLoS One. 2013;8(1):e55392. doi: 10.1371/journal.pone.0055392. Epub 2013 Jan 30. PubMed PMID: 23383175; PubMed Central PMCID: PMC3559544. 6: Paris D, Beaulieu-Abdelahad D, Abdullah L, Bachmeier C, Ait-Ghezala G, Reed J, Verma M, Crawford F, Mullan M. Anti-inflammatory activity of anatabine via inhibition of STAT3 phosphorylation. Eur J Pharmacol. 2013 Jan 5;698(1-3):145-53. doi: 10.1016/j.ejphar.2012.11.017. Epub 2012 Nov 21. PubMed PMID: 23178521. 7: Caturegli P, De Remigis A, Ferlito M, Landek-Salgado MA, Iwama S, Tzou SC, Ladenson PW. Anatabine ameliorates experimental autoimmune thyroiditis. Endocrinology. 2012 Sep;153(9):4580-7. doi: 10.1210/en.2012-1452. Epub 2012 Jul 17. PubMed PMID: 22807490.