(±)-Anabasine (hydrochloride)

(±)-Anabasine is an alkaloid that has been found as a minor component in tobacco (Nicotiana).¹ It is a full agonist of nicotinic acetylcholine receptors (nAChRs) that induces depolarization of TE 671 cells endogenously expressing human fetal muscle-type nAChRs (EC₅₀ = 10.1 µM) but not SH-SY5Y cells that primarily express autonomic nAChRs.² It binds to α4β2 subunit-containing nAChRs in K177 cells (K_i = 37.63 nM in a radioligand binding assay).³ (±)-Anabasine is teratogenic in vivo, inducing congenital defects, including cleft palate and severe fixed excessive flexure of carpal joints, in piglets when administered to pregnant dams during gestation days 43 through 53 at a dose of 2.6 mg/kg twice per day.⁴

WARNING This product is not for human or veterinary use.

1. Kisaki, T., and Tamaki, E. Phytochemical studies on the tobacco alkaloids—x. : Degradation of the tobacco alkaloids and their optical rotatory changes in tobacco plants. Phytochemistry 5(3), 293-300 (1966).

2. Green, B.T., Lee, S.T., Panter, K.E., et al. Actions of piperidine alkaloid teratogens at fetal nicotinic acetylcholine receptors. Neurotoxicol. Teratol. 32(3), 383-390 (2010).

3. Gopalakrishnan, M., Monteggia, L.M., Anderson, D.J., et al. Stable expression, pharmacologic properties and regulation of the human neuronal nicotinic acetylcholine α4β₂ receptor. J. Pharmacol. Exp. Ther. 276(1), 289-297 (1996).

4. Keeler, R.F., Crowe, M.W., and Lambert, E.A. Teratogenicity in swine of the tobacco alkaloid anabasine isolated from Nicotiana glauca. Teratology 30(1), 61-69 (1984).