(R,S)-Anatabine

(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

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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).