β-Nicotyrine
(Synonyms: 二烯烟碱,α-Nicotyrine,NSC 127943,NSC 407276) 目录号 : GC15056
β-Nicotyrine是一种尼古丁的热解产物，可与细胞色素P450 (CYP) isoforms CYP2A6和CYP2A13结合，并能更有效地抑制CYP2A6的活性
Cas No.:487-19-4
Sample solution is provided at 25 µL, 10mM.
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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.
β-Nicotyrine是一种尼古丁的热解产物，可与细胞色素P450 (CYP) isoforms CYP2A6和CYP2A13结合，并能更有效地抑制CYP2A6的活性[1-2]。β-Nicotyrine通过抑制CYP2A亚型，β-Nicotyrine能够抑制由基因毒性烟草代谢物诱导的DNA链断裂[3-4]。
在体外，β-Nicotyrine(5–50μM)与Tobacco Nitrosamine(NNK；100μM)共同处理代谢活性的人源肝细胞系HepaRG 12小时，能够显著抑制由NNK生物活化所诱导的DNA单链和双链断裂[5]。
在体内，β-Nicotyrine(0.05–1.0mg/kg)与尼古丁(0.0125–0.2mg/kg) 联合皮下注射，用于处理已建立尼古丁辨别训练的Sprague-Dawley大鼠10分钟或60分钟，能够显著增强和延长尼古丁的辨别刺激效应[6]。
| 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 | |
| 别名 | 二烯烟碱,α-Nicotyrine,NSC 127943,NSC 407276 | ||
| 化学名 | 3-(1-methyl-1H-pyrrol-2-yl)-pyridine | ||
| Canonical SMILES | CN1C=CC=C1C2=CC=CN=C2 | ||
| 分子式 | C10H10N2 | 分子量 | 158.2 |
| 溶解度 | ≤50mg/ml in ethanol;30mg/ml in DMSO;50mg/ml in dimethyl formamide | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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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 | 632.1 μL | 3.1606 mL | 6.3211 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Quality Control & SDS
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- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet