Myosmine

(±)-Nicotine (Item No. 16535) is the racemic mixture of the dominant alkaloid found in tobacco plants. It acts as an agonist at neuronal nicotinic acetylcholine receptors (K_is = 481 and 11.1 nM for α3β4 and α4β2 subtypes, respectively) and possesses addictive and teratogenic properties.¹ Myosmine is a minor tobacco alkaloid that is structurally related to nicotine. It can also be found in a variety of other plants that are commonly eaten, including maize, rice, and potato.² Myosmine weakly binds to neuronal acetylcholine receptors (K_i = 3.3 µM).³ However, it can be nitrosated, giving rise to a DNA adduct.^2,4,5

WARNING This product is not for human or veterinary use.

1. Zaveri, N., Jiang, F., Olsen, C., et al. Novel α3β4 nicotinic acetylcholine receptor-selective ligands. Discovery, structure-activity studies, and pharmacological evaluation. J. Med. Chem. 53(22), 8187-8191 (2010).

2. Tyroller, S., Zwickenpflung, W., and Richter, E. New sources of dietary myosmine uptake from cereals, fruits, vegetables, and milk. J. Agric. Food Chem. 50(17), 4909-4915 (2002).

3. Ferretti, G., Dukat, M., Giannella, M., et al. Binding of nicotine and homoazanicotine analogues at neuronal nicotinic acetylcholinergic (nACh) receptors. Bioorg. Med. Chem. Lett. 13(4), 733-735 (2003).

4. Zwickenpflung, W., Tyroller, S., and Richter, E. Metabolism of myosmine in wistar rats. Drug Metab. Dispos. 33(11), 1648-1656 (2005).

5. Hecht, S.S., Han, S., Kenney, P.M.J., et al. Investigation of the reaction of myosmine with sodium nitrite in vitro and in rats. Chem. Res. Toxicol. 20(3), 543-549 (2007).