β-Nicotyrine (Synonyms: α-Nicotyrine,NSC 127943,NSC 407276) |
رقم الكتالوجGC15056
One-Click Copy Product Info
|
β-Nicotyrine is a pyrolysis product of nicotine that can bind to cytochrome P450 (CYP) isoforms CYP2A6 and CYP2A13, and more effectively inhibit the activity of CYP2A6.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 487-19-4
Sample solution is provided at 25 µL, 10mM.
_1-3.$$$39978408@51.jpg');)
_1-9.$$$38538795@65.jpg');)
_1-9.$$$39112701@51.jpg');)
_1-7.$$$37316672@70.jpg');)
_366-372.$$$36198801@70.jpg');)
.$$$38565142@65.jpg');)
_1867-1883.$$$33248023@67.jpg');)
_eads6055.$$$39977546@45.jpg');)
_eadm9805.$$$40080571@45.jpg');)
_eadj3020.$$$39666821@45.jpg');)
_1-20.$$$39757301@28.jpg');)
_1-24.$$$38898113@28.jpg');)
_273-287.$$$36806353@46.jpg');)
_1-16.$$$37156877@44.jpg');)
_1-19.$$$37460805@44.jpg');)
_1291-1307.$$$34518654@46.jpg');)
β-Nicotyrine is a pyrolysis product of nicotine that can bind to cytochrome P450 (CYP) isoforms CYP2A6 and CYP2A13, and more effectively inhibit the activity of CYP2A6[1-2]. By inhibiting CYP2A subtypes, β-Nicotyrine is able to suppress DNA strand breaks induced by genotoxic tobacco metabolites[3-4].
In vitro, β-Nicotyrine (5–50μM) and Tobacco Nitrosamine (NNK; 100μM) were co-administered to metabolically active human hepatocyte cell line HepaRG for 12 hours, significantly inhibiting DNA single-strand and double-strand breaks induced by NNK bioactivation[5].
In vivo, β-Nicotyrine (0.05–1.0mg/kg) and nicotine (0.0125–0.2mg/kg) were co-administered subcutaneously to Sprague-Dawley rats that had undergone nicotine discrimination training, with testing conducted at 10- and 60-minute pretreatment intervals. This treatment significantly enhanced and prolonged the discriminative stimulus effects of nicotine[6].
References:
[1] Kramlinger VM, von Weymarn LB, Murphy SE. Inhibition and inactivation of cytochrome P450 2A6 and cytochrome P450 2A13 by menthofuran, β-nicotyrine and menthol. Chem Biol Interact. 2012 May 30;197(2-3):87-92.
[2] Denton TT, Zhang X, Cashman JR. Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6. Biochem Pharmacol. 2004 Feb 15;67(4):751-6.
[3] Shigenaga MK, Kim BH, Caldera-Munoz P, et al. Liver and lung microsomal metabolism of the tobacco alkaloid beta-nicotyrine. Chem Res Toxicol. 1989 Sep-Oct;2(5):282-7.
[4] Kurgat C, Kibet J, Cheplogoi P. Molecular modeling of major tobacco alkaloids in mainstream cigarette smoke. Chem Cent J. 2016 Jul 15;10:43.
[5] Ordonez P, Sierra AB, Camacho OM, et al. Nicotine, cotinine, and β-nicotyrine inhibit NNK-induced DNA-strand break in the hepatic cell line HepaRG. Toxicol In Vitro. 2014 Jul 15:S0887-2333(14)00135-0.
[6] Smethells JR, Wilde S, Muelken P, et al. β-Nicotyrine and e-cigarette abuse liability I: Pharmacodynamics and interaction with pharmacokinetics and discriminative stimulus effects of nicotine in rats. Drug Alcohol Depend. 2025 Dec 1;277:112949.
| Cell experiment [1]: | |
Cell lines | Human HepaRG cells (metabolically competent hepatocyte cell line) |
Preparation Method | HepaRG cells were treated with β-Nicotyrine (5–50μM) and the tobacco-specific nitrosamine NNK (100μM) for 12 hours. |
Reaction Conditions | 5-50µM; 12h |
Applications | β-Nicotyrine significantly inhibited NNK bioactivation-induced DNA single-strand and double-strand breaks in HepaRG cells. The protective effect was comparable to the known CYP inhibitor PPITC. β-Nicotyrine achieved this by inhibiting the activity of cytochrome P450 (CYP) enzymes, particularly CYP2A6 and CYP2A13, thereby interfering with the metabolic activation of NNK. |
| Animal experiment [2]: | |
Animal models | Sprague-Dawley rats |
Preparation Method | Rats were administered β-Nicotyrine (0.05-1.0mg/kg) and nicotine (0.0125-0.2mg/kg) subcutaneously either alone or in combination, with behavioral testing conducted at 10- and 60-minute pretreatment intervals using drug discrimination paradigms. |
Dosage form | 0.05-1.0mg/kg; s.c.; Single injection. |
Applications | β-Nicotyrine significantly slowed nicotine clearance by approximately 50% and prolonged nicotine's half-life from 68 to 125 minutes when administered at clinically relevant doses (25% of nicotine dose). β-Nicotyrine enhanced and prolonged the discriminative stimulus effects of nicotine, particularly at the 60-minute pretreatment interval, indicating increased nicotine discriminability. Unlike nicotine and nornicotine, β-Nicotyrine showed no binding affinity to nicotinic acetylcholine receptors (α2β2, α3β4, α4β2) or other noncholinergic targets, and produced only weak nicotine-like subjective effects in female rats with no effects in males. |
References: | |
| Cas No. | 487-19-4 | SDF | |
| المرادفات | 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 |
| الذوبان | ≤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. | ||
| Prepare stock solution | |||
|
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 | 632.1 μL | 3.1606 mL | 6.3211 mL |
Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
g
μL
Step 2: Enter the in vivo formulation (This is only the calculator, not formulation. Please contact us first if there is no in vivo formulation at the solubility Section.)
Calculation results:
Working concentration: mg/ml;
Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )
Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL saline, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
- View current batch:
- Purity: >98.00% Appearance: A liquid
- COA (Certificate of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 28 reference(s) in Google Scholar.)