(R,S)-Anatabine-d4

(R,S)-Anatabine-d₄ is intended for use as an internal standard for the quantification of (R,S)-anatabine by GC- or LC-MS. (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 or 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

1.Weeks, W.W., and Bush, L.P.Alkaloid changes in tobacco seeds during germinationPlant Physiol.53(1)73-75(1974) 2.Alijevic, O., Jaka, O., Alzualde, A., et al.Differentiating the neuropharmacological properties of nicotinic acetylcholine receptor-activating alkaloidsFront. Pharmacol.13668065(2022) 3.Caturegli , P., De Remigis, A., Ferlito, M., et al.Anatabine ameliorates experimental autoimmune thyroiditisEndocrinology153(9)4580-4587(2012) 4.Mello, N.K., Fivel, P.A., Kohut, S.J., et al.Anatabine significantly decreases nicotine self-administrationExp. 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 pipesAm. J. Public Health89(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 smokersCancer Epidemiol. Biomarkers Prev.13(10)1617-1623(2004)