Nicotyrine Explained

Nicotryine is lesser known and minor tobacco alkaloid. It inhibits metabolism of nicotine^{[1] [2]} through CYP2A6 enzyme inhibition (K_i = 7.5 ± 2.9).^{[3] [4]} It also inhibits CYP2A13 (K_i = 5.6 ± 0.86) which might play role in nicotine metabolism.^[5] Nicotyrine is formed by gradual oxidation of nicotine in e-liquids and causes delayed nicotine clearance and attenuated withdrawal symptoms.^[5]

It has insecticidal properties like nicotine and certain derivatives have been synthesized for that property.^[6]

Chemistry

alpha-nicotyrine and beta-nicotyrine are positional isomers of each other.

Synthesis

Nicotyrine can be produced readily from nicotine by catalytic dehydrogenation^[7] and from tobacco biomass by catalytic pyrolysis.^[8]

See also

• Myosmine

Notes and References

1. Denton TT, Zhang X, Cashman JR . Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6 . . 67 . 4 . 751–6 . February 2004 . 14757175 . 10.1016/j.bcp.2003.10.022 .
2. Stålhandske T, Slanina P . Nicotyrine inhibits in vivo metabolism of nicotine without increasing its toxicity . . 65 . 3 . 366–72 . September 1982 . 7157369 . 10.1016/0041-008x(82)90382-9 .
3. Kramlinger VM, von Weymarn LB, Murphy SE . Inhibition and inactivation of cytochrome P450 2A6 and cytochrome P450 2A13 by menthofuran, β-nicotyrine and menthol . . 197 . 2–3 . 87–92 . May 2012 . 22486895 . 3362486 . 10.1016/j.cbi.2012.03.009 .
4. Stephens ES, Walsh AA, Scott EE . Evaluation of inhibition selectivity for human cytochrome P450 2A enzymes . . 40 . 9 . 1797–802 . September 2012 . 22696418 . 3422547 . 10.1124/dmd.112.045161 .
5. Abramovitz A, McQueen A, Martinez RE, Williams BJ, Sumner W . Electronic cigarettes: The nicotyrine hypothesis . . 85 . 3 . 305–10 . September 2015 . 26100465 . 10.1016/j.mehy.2015.06.002 . free .
6. Frank . Robert L. . Holley . Robert W. . Wikholm . Donald M. . 3,2'-Nicotyrine. Insecticidal Properties of Certain Azo Derivatives1 . Journal of the American Chemical Society . 64 . 12 . 2002 . 2835–2838 . 0002-7863 . 10.1021/ja01264a033.
7. SHIBAGAKI. Makoto. TAKAHASHI. Kyoko. KUNO. Hideyuki. MATSUSHITA. Hajime. Preparation of nicotyrine via catalytic dehydrogenation of nicotine.. Agricultural and Biological Chemistry. 52. 10. 1988. 2651–2652. 0002-1369. 10.1271/bbb1961.52.2651. free.
8. Ye . Xiao-ning . Lu . Qiang . Li . Wen-tao . Gao . Pan . Hu . Bin . Zhang . Zhi-bo . Dong . Chang-qing . Selective production of nicotyrine from catalytic fast pyrolysis of tobacco biomass with Pd/C catalyst . Journal of Analytical and Applied Pyrolysis . 117 . 2016 . 88–93 . 0165-2370 . 10.1016/j.jaap.2015.12.012.