| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 500mg |
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| Targets |
(S)-Nornicotine targets nicotinic acetylcholine receptors (nAChRs), which are ligand-gated ion channels that mediate the effects of acetylcholine in the central and peripheral nervous systems. As a nicotine metabolite, (S)-nornicotine acts as an agonist at nicotinic receptors, though with lower potency than nicotine. The compound binds to neuronal nicotinic receptors, particularly the alpha4beta2 and alpha7 subtypes, and can activate these receptors leading to ion flux and downstream signaling. (S)-Nornicotine also has effects on dopamine release in the brain, similar to nicotine, though its potency is reduced. The compound's activity at nicotinic receptors contributes to its pharmacological effects and its role in nicotine addiction.
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| ln Vitro |
In vitro studies have demonstrated that (S)-nornicotine acts as an agonist at nicotinic acetylcholine receptors, though with lower potency than nicotine. The compound binds to neuronal nicotinic receptors, including the alpha4beta2 and alpha7 subtypes, and activates these receptors leading to ion flux. In receptor binding assays, (S)-nornicotine competes with radiolabeled nicotine or other nicotinic ligands for binding to nicotinic receptors. In functional assays, the compound induces calcium influx or ion flux in cells expressing nicotinic receptors. The compound's activity at nicotinic receptors is stereoselective, with the (S)-enantiomer being more potent than the (R)-enantiomer. (S)-Nornicotine also inhibits monoamine oxidase (MAO) activity, similar to nicotine.
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| ln Vivo |
In vivo studies have shown that (S)-nornicotine produces effects similar to nicotine, though with lower potency. The compound is a major metabolite of nicotine and contributes to the pharmacological effects of nicotine exposure. In animal models, (S)-nornicotine has been shown to affect locomotor activity, body temperature, and pain perception. The compound also affects dopamine release in the brain, similar to nicotine, though its effects are less potent. (S)-Nornicotine has been detected in the brains of smokers and is believed to contribute to the overall effects of tobacco use. The compound's metabolism and pharmacokinetics are similar to those of nicotine.
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| Enzyme Assay |
The in vitro receptor binding assay for (S)-nornicotine typically involves competition binding studies using membrane preparations from cells or tissues expressing nicotinic acetylcholine receptors. Radiolabeled nicotinic ligand (e.g., 3H-nicotine, 3H-cytisine, or ¹2⁵I-alpha-bungarotoxin for alpha7 receptors) is incubated with membrane preparations and varying concentrations of (S)-nornicotine (typically 0.001 nM to 100 uM) in binding buffer (e.g., 50 mM Tris-HCl, pH 7.4) at room temperature or 4degC for 1-4 hours. Bound and free ligand are separated by filtration through glass fiber filters, and radioactivity is measured by scintillation counting. The inhibition constant (Ki) is calculated from IC50 values. Selectivity for different nicotinic receptor subtypes can be assessed using membranes from cells expressing individual subtypes or using subtype-selective ligands.
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| Cell Assay |
In vitro cellular assays for (S)-nornicotine are conducted using cell lines expressing nicotinic acetylcholine receptors, such as SH-SY5Y cells (which express alpha3beta4 and alpha7 receptors), or heterologous expression systems (e.g., HEK-293 or CHO cells transfected with specific nAChR subtypes). Cells are seeded in 96-well or 24-well plates and treated with varying concentrations of (S)-nornicotine (typically 0.001 nM to 100 uM) for 1-60 minutes. Receptor activation is assessed by measuring calcium influx using fluorescent calcium indicators (e.g., Fluo-4), by measuring ion flux using radioactive tracers (e.g., ⁸⁶Rb+ efflux), or by measuring membrane potential using fluorescent dyes. Dopamine release can be measured in cell lines or primary neuronal cultures by HPLC or ELISA. Cell viability is monitored to ensure that observed effects are not due to cytotoxicity.
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| Animal Protocol |
In vivo animal studies for (S)-nornicotine typically involve administration to rodents by intravenous, intraperitoneal, or subcutaneous injection, or by oral gavage. Doses typically range from 0.01-10 mg/kg. Behavioral effects including locomotor activity, body temperature, and pain perception are assessed using standard behavioral tests. Dopamine release in the brain can be measured using microdialysis in freely moving animals. The compound's effects on cardiovascular parameters such as heart rate and blood pressure may also be assessed. For metabolism studies, animals are administered (S)-nornicotine and blood and tissue samples are collected at various time points for analysis by LC-MS/MS. Pharmacokinetic parameters are determined from concentration-time data.
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| ADME/Pharmacokinetics |
Metabolism/Metabolites
Norenicotine is a known metabolite of nicotine in the human body. Pharmacokinetic properties of (S)-nornicotine are similar to those of nicotine. As a small, lipophilic amine, it is well absorbed and distributes widely in the body, including the brain. The compound has a molecular weight of 148.20 and a molecular formula of C9H12N2. It is metabolized primarily in the liver by cytochrome P450 enzymes, including CYP2A6, to various metabolites including cotinine and trans-3'-hydroxycotinine. The compound's half-life in plasma is shorter than that of nicotine. (S)-Nornicotine is a major metabolite of nicotine and is detected in the urine of smokers. Detailed pharmacokinetic parameters can be found in the literature on nicotine metabolism. |
| Toxicity/Toxicokinetics |
Interactions
...Norepinephrine causes abnormal protein glycosylation and catalyzes covalent modification of certain prescription drugs (e.g., the commonly used steroid prednisone). ... Non-human Toxicity Values Mouse intravenous LD50: 3409 μg/kg (3.409 mg/kg) Mouse intraperitoneal LD50: 14,660 μg/kg (14.66 mg/kg) Rabbit intravenous LD50: 3 mg/kg The toxicological profile of (S)-nornicotine is similar to that of nicotine. As a nicotinic agonist, the compound can cause adverse effects including nausea, vomiting, dizziness, tachycardia, and hypertension at high doses. In severe cases, nicotine toxicity can cause seizures, respiratory depression, and death. (S)-Nornicotine is a minor tobacco alkaloid and a metabolite of nicotine. It is for research use only and is not intended for human therapeutic use. The compound should be handled with appropriate safety precautions in a laboratory setting. The LD50 in rodents is expected to be similar to that of nicotine. |
| Additional Infomation |
(S)-Nornicotinic acid is a pyridine alkaloid, a compound of nicotine pyrrolidine lacking a methyl group on the nitrogen atom. It is a metabolite, a nicotine acetylcholine receptor agonist, and a plant-derived insecticide. It is both a pyridine alkaloid and a pyrrolidine alkaloid. It is the conjugate base of (S)-nornicotinic acid (1+) and the enantiomer of (+)-nornicotinic acid. It is derived from the hydride of nicotine. 3-[(2S)-pyrrolidine-2-yl]pyridine has been reported in tobacco (Nicotiana suaveolens), tobacco (Nicotiana tomentosa), and other organisms with relevant data.
(S)-Nornicotine (CAS 494-97-3) is a naturally occurring alkaloid found in tobacco (Nicotiana tabacum) and is a major metabolite of nicotine. It is the (S)-enantiomer of nornicotine, which is the demethylated derivative of nicotine. The compound acts as an agonist at nicotinic acetylcholine receptors, though with lower potency than nicotine, and also inhibits monoamine oxidase (MAO) activity. (S)-Nornicotine is a minor tobacco alkaloid and is also formed by the N-demethylation of nicotine in the body, primarily by CYP2A6. The compound is used in pharmacological research to study nicotinic receptor function, nicotine metabolism, and the pharmacology of tobacco alkaloids. It is available for research purposes only. |
| Molecular Formula |
C9H12N2
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| Molecular Weight |
148.2050
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| Exact Mass |
148.1
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| CAS # |
494-97-3
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| Related CAS # |
(S)-Nornicotine hydrochloride;101832-65-9
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| PubChem CID |
91462
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| Appearance |
Light yellow to brown liquid
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| Density |
1.043g/cm3
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| Boiling Point |
269.999ºC at 760 mmHg
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| Flash Point |
111.291ºC
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| Vapour Pressure |
0.007mmHg at 25°C
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| Index of Refraction |
1.536
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| LogP |
1.834
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
11
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| Complexity |
125
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| Defined Atom Stereocenter Count |
1
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| SMILES |
N1([H])C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C1=C([H])N=C([H])C([H])=C1[H]
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| InChi Key |
MYKUKUCHPMASKF-VIFPVBQESA-N
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| InChi Code |
InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2/t9-/m0/s1
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| Chemical Name |
3-[(2S)-pyrrolidin-2-yl]pyridine
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~674.72 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.87 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (16.87 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (16.87 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.7472 mL | 33.7359 mL | 67.4718 mL | |
| 5 mM | 1.3494 mL | 6.7472 mL | 13.4944 mL | |
| 10 mM | 0.6747 mL | 3.3736 mL | 6.7472 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution 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 stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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