Chemistry:Nicotyrine
From HandWiki
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| IUPAC name
3-(1-methylpyrrol-2-yl)pyridine
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Other names
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3D model (JSmol)
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| Properties | |
| C10H10N2 | |
| Molar mass | 158.204 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Nicotryine is lesser known and minor tobacco alkaloid. It inhibits metabolism of nicotine[2][3] through CYP2A6 enzyme inhibition (Ki = 7.5 ± 2.9).[2][4][5] It also inhibits CYP2A13 (Ki = 5.6 ± 0.86) which might play role in nicotine metabolism.[5][6] Nicotyrine is formed by gradual oxidation of nicotine in e-liquids and causes delayed nicotine clearance and attenuated withdrawal symptoms.[6]
It has insecticidal properties like nicotine and certain derivatives have been synthesized for that property.[7]
Chemistry
alpha-nicotyrine and beta-nicotyrine are positional isomers of each other.
Synthesis
Nicotyrine can be produced readily from nicotine by catalytic dehydrogenation[8] and from tobacco biomass by catalytic pyrolysis.[9]
See also
References
- ↑ "Alpha-nicotyrine - MeSH - NCBI". https://www.ncbi.nlm.nih.gov/mesh/67008615.
- ↑ 2.0 2.1 "Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6". Biochemical Pharmacology 67 (4): 751–6. February 2004. doi:10.1016/j.bcp.2003.10.022. PMID 14757175.
- ↑ "Nicotyrine inhibits in vivo metabolism of nicotine without increasing its toxicity". Toxicology and Applied Pharmacology 65 (3): 366–72. September 1982. doi:10.1016/0041-008x(82)90382-9. PMID 7157369.
- ↑ "Inhibition and inactivation of cytochrome P450 2A6 and cytochrome P450 2A13 by menthofuran, β-nicotyrine and menthol". Chemico-Biological Interactions 197 (2–3): 87–92. May 2012. doi:10.1016/j.cbi.2012.03.009. PMID 22486895.
- ↑ 5.0 5.1 "Evaluation of inhibition selectivity for human cytochrome P450 2A enzymes". Drug Metabolism and Disposition 40 (9): 1797–802. September 2012. doi:10.1124/dmd.112.045161. PMID 22696418.
- ↑ 6.0 6.1 "Electronic cigarettes: The nicotyrine hypothesis". Medical Hypotheses 85 (3): 305–10. September 2015. doi:10.1016/j.mehy.2015.06.002. PMID 26100465.
- ↑ Frank, Robert L.; Holley, Robert W.; Wikholm, Donald M. (2002). "3,2'-Nicotyrine. Insecticidal Properties of Certain Azo Derivatives1". Journal of the American Chemical Society 64 (12): 2835–2838. doi:10.1021/ja01264a033. ISSN 0002-7863. https://pubs.acs.org/doi/pdf/10.1021/ja01264a033.
- ↑ SHIBAGAKI, Makoto; TAKAHASHI, Kyoko; KUNO, Hideyuki; MATSUSHITA, Hajime (1988). "Preparation of nicotyrine via catalytic dehydrogenation of nicotine.". Agricultural and Biological Chemistry 52 (10): 2651–2652. doi:10.1271/bbb1961.52.2651. ISSN 0002-1369.
- ↑ Ye, Xiao-ning; Lu, Qiang; Li, Wen-tao; Gao, Pan; Hu, Bin; Zhang, Zhi-bo; Dong, Chang-qing (2016). "Selective production of nicotyrine from catalytic fast pyrolysis of tobacco biomass with Pd/C catalyst". Journal of Analytical and Applied Pyrolysis 117: 88–93. doi:10.1016/j.jaap.2015.12.012. ISSN 0165-2370.
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