A minor tobacco alkaloid
Related Products
Alternative(s)
15132(R,S)-Anatabine (tartrate)
Labeled Version(s)
37198(R,S)-Anatabine-d4
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(R,S)-Anatabine

Item No. 11001

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,2,3,6-tetrahydro-2,3'-bipyridine
CAS Number
2743-90-0
Synonyms
  • (±)-Anatabine
Molecular Formula
C10H12N2
Formula Weight
160.2
Purity
≥95%
Formulation (Request formulation change)
A 50 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMSO: 15 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 0.3 mg/ml
λmax
261 nm
SMILES
[C@@H]1(C2=CN=CC=C2)CC=CCN1
InChi Code
InChI=1S/C10H12N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h1-4,6,8,10,12H,5,7H2
InChi Key
SOPPBXUYQGUQHE-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $41

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    10 mg

    $69

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    50 mg

    $266

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    100 mg

    $469

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    Product Description

    (R,S)-Anatabine is an alkaloid that has been found as a minor component in tobacco (Nicotiana).1 It is an agonist of α4β2 and α6/α3β2β4 subunit-containing nicotinic acetylcholine receptors (nAChRs; EC50s = 6.1 and 3.6 µM, respectively). It is selective for α4β2 and α6/α3β2β4 subunit-containing nAChRs over α3β4 subunit-containing nAChRs and α7 nAChRs (EC50s = 70.6 and 158.5 µM, respectively).2 (R,S)-Anatabine stimulates dopamine, but not norepinephrine, release from isolated rat brain synaptosomes (EC50s = 1.76 and >100 µM, respectively). It increases the time spent at the top of the tank in a novel tank test, indicating anxiolytic-like activity, in zebrafish when used at a concentration of 10 mg/L. (R,S)-Anatabine (0.05 mg/ml in the drinking water) decreases disease severity in a mouse model of moderate, but not low or severe, experimental autoimmune thyroiditis induced by immunization with thyroglobulin, complete Freund's adjuvant (CFA), and M. tuberculosis.3 It decreases food and nicotine self-administration in monkeys (ED50s = 2.085 and 0.854 mg/kg, respectively).4 (R,S)-Anatabine has been used as a biomarker of tobacco use.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Weeks, W.W., and Bush, L.P. Alkaloid changes in tobacco seeds during germination. Plant Physiol. 53(1), 73-75 (1974).

    2. Alijevic, O., Jaka, O., Alzualde, A., et al. Differentiating the neuropharmacological properties of nicotinic acetylcholine receptor-activating alkaloids. Front. Pharmacol. 13, 668065 (2022).

    3. Caturegli , P., De Remigis, A., Ferlito, M., et al. Anatabine ameliorates experimental autoimmune thyroiditis. Endocrinology 153(9), 4580-4587 (2012).

    4. Mello, N.K., Fivel, P.A., Kohut, S.J., et al. Anatabine significantly decreases nicotine self-administration. Exp. Clin. Psychopharmacol. 22(1), 1-8 (2014).

    5. Jacob, P., III, Yu, L., Shulgin, A.T., et al. Minor tobacco alkaloids as biomarkers for tobacco use: Comparison of users of cigarettes, smokeless tobacco, cigars, and pipes. Am. J. Public Health 89(5), 731-736 (1999).

    6. Murphy, S.E., Link, C.A., Jensen, J., et al. A comparison of urinary biomarkers of tobacco and carcinogen exposure in smokers. Cancer Epidemiol. Biomarkers Prev. 13(10), 1617-1623 (2004).