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β-Nicotyrine (Synonyms: α-Nicotyrine,NSC 127943,NSC 407276)

Catalog No.GC15056

cytochrome P450 (CYP) isoforms, CYP2A6 and CYP2A13 inhibitor

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β-Nicotyrine Chemical Structure

Cas No.: 487-19-4

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1mg
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5mg
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10mg
$290.00
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25mg
$490.00
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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Background

β-Nicotyrine is an alkaloid metabolite of nicotine as well as a major product of its pyrolysis.[1],[2] It binds comparably to two cytochrome P450 (CYP) isoforms, CYP2A6 and CYP2A13 (Kis = 7.5 and 5.6 µM, respectively), which are prominently involved in the metabolism of xenobiotics in the airways.[3] However, β-nicotyrine appears to more effectively inactivate CYP2A6, leaving only 49% activity after a 10 minute exposure with 20 µM β-nicotyrine, as opposed to 87% remaining activity for CYP2A13 treated identically.[4] Presumably through this effect, β-nicotyrine inhibits DNA strand breaks induced by the genotoxic tobacco metabolite (4-(methylnitrosamino)-1-(2-pyridyl)-1-butanone), which is bioactivated by CYP2A isoforms.[5]

Reference:
[1]. Swain, M.L., Eisner, A., Woodward, C.F., et al. Ultraviolet absorption spectra of nicotine, nornicotine and some of their derivatives. Journal of the American Chemical Society 71(4), 1341-1345 (1949).
[2]. Clayton, P., Lu, A., and Bishop, L. The pyrolysis of (−)-(S)-nicotine: Racemization and decomposition. Chirality 22(4), 442-446 (2010).
[3]. Stephens, E.S., Walsh, A.A., and Scott, E.E. Evaluation of inhibition selectivity for human cytochrome P450 2A enzymes. Drug Metabolism and Disposition 40(9), 1797-1802 (2012).
[4]. Kramlinger, V.M., von Weymarn, L.B., and Murphy, S.E. 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 (2012).
[5]. Ordonez, P., Sierra, A.B., Camacho, O.M., et al. Nicotine, cotinine, and β-nicotyrine inhibit NNK-induced DNA-strand break in the hepatic cell line HepaRG. Toxicol.In Vitro 28(2014), 1329-1337 (2014).

Chemical Properties

Cas No. 487-19-4 SDF
Synonyms α-Nicotyrine,NSC 127943,NSC 407276
Chemical Name 3-(1-methyl-1H-pyrrol-2-yl)-pyridine
Canonical SMILES CN1C=CC=C1C2=CC=CN=C2
Formula C10H10N2 M.Wt 158.2
Solubility ≤50mg/ml in ethanol;30mg/ml in DMSO;50mg/ml in dimethyl formamide Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 6.3211 mL 31.6056 mL 63.2111 mL
5 mM 1.2642 mL 6.3211 mL 12.6422 mL
10 mM 0.6321 mL 3.1606 mL 6.3211 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 28 reference(s) in Google Scholar.)

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