Nicotyrine

Nicotyrine
Names
	IUPAC name 3-(1-methylpyrrol-2-yl)pyridine
	Other names alpha-nicotyrine; beta-nicotyrine; ss-nicotyrine; 3,2'-nicotyrine;
Identifiers
CAS Number	487-19-4;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:7564;
ChEMBL	ChEMBL1522291;
ChemSpider	2282468;
ECHA InfoCard	100.006.956
EC Number	207-651-1;
KEGG	C10161;
PubChem CID	10249;
UNII	XN4R1LH79Y;
CompTox Dashboard (EPA)	DTXSID3075048 ;
	InChI InChI=1S/C10H10N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2-8H,1H3 Key: RYFOJXFXERAMLS-UHFFFAOYSA-N;
	SMILES CN1C=CC=C1C2=CN=CC=C2;
Properties
Chemical formula	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). Infobox references

Nicotryine is lesser known and minor tobacco alkaloid. It inhibits metabolism of nicotine^[2]^[3] through CYP2A6 enzyme inhibition (K_i = 7.5 ± 2.9).^[2]^[4]^[5] It also inhibits CYP2A13 (K_i = 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]

References

^ "Alpha-nicotyrine - MeSH - NCBI".
^ ^a ^b Denton TT, Zhang X, Cashman JR (February 2004). "Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6". Biochemical Pharmacology. 67 (4): 751–6. doi:10.1016/j.bcp.2003.10.022. PMID 14757175.
^ Stålhandske T, Slanina P (September 1982). "Nicotyrine inhibits in vivo metabolism of nicotine without increasing its toxicity". Toxicology and Applied Pharmacology. 65 (3): 366–72. doi:10.1016/0041-008x(82)90382-9. PMID 7157369.
^ Kramlinger VM, von Weymarn LB, Murphy SE (May 2012). "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. doi:10.1016/j.cbi.2012.03.009. PMC 3362486. PMID 22486895.
^ ^a ^b Stephens ES, Walsh AA, Scott EE (September 2012). "Evaluation of inhibition selectivity for human cytochrome P450 2A enzymes". Drug Metabolism and Disposition. 40 (9): 1797–802. doi:10.1124/dmd.112.045161. PMC 3422547. PMID 22696418.
^ ^a ^b Abramovitz A, McQueen A, Martinez RE, Williams BJ, Sumner W (September 2015). "Electronic cigarettes: The nicotyrine hypothesis". Medical Hypotheses. 85 (3): 305–10. 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.
^ 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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[1] "Alpha-nicotyrine - MeSH - NCBI".

[pmid14757175-2] Denton TT, Zhang X, Cashman JR (February 2004). "Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6". Biochemical Pharmacology. 67 (4): 751–6. doi:10.1016/j.bcp.2003.10.022. PMID 14757175.

[pmid7157369-3] Stålhandske T, Slanina P (September 1982). "Nicotyrine inhibits in vivo metabolism of nicotine without increasing its toxicity". Toxicology and Applied Pharmacology. 65 (3): 366–72. doi:10.1016/0041-008x(82)90382-9. PMID 7157369.

[pmid22486895-4] Kramlinger VM, von Weymarn LB, Murphy SE (May 2012). "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. doi:10.1016/j.cbi.2012.03.009. PMC 3362486. PMID 22486895.

[pmid22696418-5] Stephens ES, Walsh AA, Scott EE (September 2012). "Evaluation of inhibition selectivity for human cytochrome P450 2A enzymes". Drug Metabolism and Disposition. 40 (9): 1797–802. doi:10.1124/dmd.112.045161. PMC 3422547. PMID 22696418.

[pmid26100465-6] Abramovitz A, McQueen A, Martinez RE, Williams BJ, Sumner W (September 2015). "Electronic cigarettes: The nicotyrine hypothesis". Medical Hypotheses. 85 (3): 305–10. doi:10.1016/j.mehy.2015.06.002. PMID 26100465.

[FrankHolley2002-7] 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.

[SHIBAGAKITAKAHASHI1988-8] 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.

[YeLu2016-9] 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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Chemistry

Synthesis

See also

References