Cayman (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 Freunds 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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