| Size | Price | Stock | Qty |
|---|---|---|---|
| 100mg |
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| Other Sizes |
| Targets |
Human Endogenous Metabolite
(±)-Nornicotine targets neuronal nicotinic acetylcholine receptors (nAChRs). It acts as a partial agonist at nAChRs containing α7 and α6 subunits. It induces currents in Xenopus oocytes expressing human α7 nAChRs or α6 subunit-containing nAChRs with EC₅₀ values of 17 and 3.7 µM, respectively. |
|---|---|
| ln Vitro |
In vitro, (±)-nornicotine acts as a nicotinic acetylcholine receptor (nAChR) agonist. It induces currents in Xenopus oocytes expressing human α7 nAChRs (EC₅₀ = 17 µM) and α6 subunit-containing nAChRs (EC₅₀ = 3.7 µM). It is a partial agonist and is less potent than nicotine.
|
| ln Vivo |
In vivo, (±)-nornicotine is a metabolite of nicotine. It is found in tobacco products and is formed endogenously from nicotine. Its presence in the body contributes to the overall pharmacological profile of nicotine exposure. As an nAChR agonist, it may have effects on the central nervous system.
|
| Enzyme Assay |
In vitro receptor binding assays for (±)-nornicotine involve incubating the compound with membrane preparations expressing nAChRs or with Xenopus oocytes injected with nAChR subunit cRNAs. Receptor activation is measured by electrophysiology (two-electrode voltage clamp) to record currents. EC₅₀ values are determined from dose-response curves.
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| Cell Assay |
For in vitro cell assays, cell lines expressing nAChRs (e.g., SH-SY5Y, PC12) are cultured and treated with (±)-nornicotine. Receptor activation is assessed by measuring calcium influx using fluorescent dyes (e.g., Fluo-4) or by measuring downstream signaling pathways. Cell viability is assessed by MTT assay.
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| Animal Protocol |
For in vivo animal studies, (±)-nornicotine is typically administered to rodents to study its effects on the central nervous system. Behavioral tests are performed to assess its impact on locomotion, cognition, and reward. Its pharmacokinetics and metabolism are studied after nicotine administration.
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| ADME/Pharmacokinetics |
Metabolism/Metabolites
Norepinephrine is a known metabolite of nicotine in thirdhand smoke. (±)-Nornicotine has the molecular formula C₉H₁₂N₂ and a molecular weight of 148.20. It is a liquid at room temperature. The compound is stable under recommended storage conditions. It is soluble in organic solvents and water. It is a precursor to the carcinogenic nitrosamine NNN. |
| 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 (±)-Nornicotine is for research use only. As a tobacco alkaloid and precursor to a carcinogenic nitrosamine, it should be handled with appropriate safety precautions. Its toxicity profile is related to its nicotinic receptor activity and its role in tobacco-related carcinogenesis. |
| References | |
| Additional Infomation |
Nornicotine has been reported in Senegalese tobacco (Senegalia berlandieri), fragrant tobacco (Nicotiana suaveolens), and other organisms with relevant data. Nornicotine is the demethylated form of the plant alkaloid nicotine. It is present in tobacco and is a metabolite of nicotine, acting as a nicotine acetylcholine receptor agonist. Nornicotine can be metabolized to produce the carcinogen N-nitrosonornicotine (NNN).
(±)-Nornicotine (CAS# 5746-86-1) is the major metabolite of nicotine and a tobacco alkaloid. It has not been approved as a therapeutic drug. The compound is used in research on nicotine addiction, tobacco carcinogenesis, and as a reference standard for analytical methods. It is the precursor to the carcinogen NNN. |
| Molecular Formula |
C9H12N2
|
|---|---|
| Molecular Weight |
148.21
|
| Exact Mass |
148.1
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| CAS # |
5746-86-1
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| Related CAS # |
(±)-Nornicotine-d7; (±)-Nornicotine; 5746-86-1
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| PubChem CID |
412
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| Appearance |
Colorless to light yellow liquid
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| Density |
1,074 g/cm3
|
| Boiling Point |
107-108°C 2mm
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| Flash Point |
101°C
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| Index of Refraction |
1.54
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| Source |
Endogenously produced metabolite
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| LogP |
1.834
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| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
11
|
| Complexity |
125
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
N1CCCC1C1C=NC=CC=1
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| InChi Key |
MYKUKUCHPMASKF-UHFFFAOYSA-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
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| Chemical Name |
3-pyrrolidin-2-ylpyridine
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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 (~674.8 mM; with ultrasonication)
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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% Tween-80 + 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 DMSO stock solution (25.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and 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 DMSO stock solution (25.0 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. 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. 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. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (25.0 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| 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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