| Size | Price | Stock | Qty |
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| 25mg |
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| Other Sizes |
| Targets |
3-(1-Nitrosopyrrolidin-2-yl)pyridine is a major tobacco-specific nitrosamine. It is a potent carcinogen found in tobacco products. It targets DNA by forming DNA adducts, leading to mutations and cancer. It is classified as a carcinogen and is a significant risk factor for tobacco-related cancers.
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| ln Vitro |
In vitro, 3-(1-Nitrosopyrrolidin-2-yl)pyridine is studied as a major tobacco-specific nitrosamine. It is used as a reference standard for the detection and quantification of nitrosamines in tobacco products and biological samples. Its genotoxicity and carcinogenicity are studied in cell-based assays.
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| ln Vivo |
In vivo, 3-(1-Nitrosopyrrolidin-2-yl)pyridine is a major tobacco-specific nitrosamine and a potent carcinogen. It is formed from nicotine during the curing and processing of tobacco. It is a significant risk factor for tobacco-related cancers, including lung, esophageal, and oral cancers.
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| Enzyme Assay |
In vitro assays for 3-(1-Nitrosopyrrolidin-2-yl)pyridine typically involve its detection and quantification in tobacco products and biological samples. The compound is extracted and analyzed by GC-MS or LC-MS. It is used as a reference standard for nitrosamine analysis. Genotoxicity assays are performed using the Ames test or comet assay.
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| Cell Assay |
For in vitro cell assays, cells are cultured and treated with 3-(1-Nitrosopyrrolidin-2-yl)pyridine at various concentrations. DNA damage is assessed by comet assay or γ-H2AX staining. Mutagenicity is evaluated using the Ames test. Cell viability is assessed by MTT assay. The compound's carcinogenic potential is studied in cell transformation assays.
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| Animal Protocol |
For in vivo animal studies, 3-(1-Nitrosopyrrolidin-2-yl)pyridine is administered to rodents to study its carcinogenicity. Animals are treated with the compound, and tumor formation is monitored. DNA adduct formation is assessed in tissues. The compound's role in tobacco-related carcinogenesis is studied.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
N'-nitrosonornicotinic acid (NNN) is a known third-hand smoke metabolite of N'-nitrosonornicotinic acid (NNN). Known metabolites of Np-nitrosonornicotinic acid include Np-nitrosonornicotinic acid and N-glucuronide. 3-(1-Nitrosopyrrolidin-2-yl)pyridine (MW 147.18) has the molecular formula C₉H₁₁N₃O. It is a yellow, oily liquid that solidifies at cold temperatures. It emits toxic fumes of nitrogen oxides when heated to decomposition. The compound is stable under recommended storage conditions. |
| Toxicity/Toxicokinetics |
The compound is for research use only. 3-(1-Nitrosopyrrolidin-2-yl)pyridine is a potent carcinogen and should be handled with extreme caution. Appropriate safety precautions should be followed, including the use of personal protective equipment and working in a fume hood. It emits toxic fumes when heated.
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| References |
[1]. Gao Y, Miksys S, Palmour RM, Tyndale RF. The Influence of Tobacco Smoke/Nicotine on CYP2A Expression in Human and African Green Monkey Lungs. Mol Pharmacol. 2020;98(6):658-668.
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| Additional Infomation |
N'-Nitrosaminoglycans belong to the pyrrolidine and pyridine classes of compounds. It has been reported that tobacco (Nicotiana tabacum) contains 3-(1-nitrosopyrrolidine-2-yl)pyridine, and related data have been reported. Nitrosaminoglycans are a yellow, oily liquid nitrosamine that solidifies at low temperatures and releases toxic nitrogen oxide fumes upon heating. The presence of nitrosaminoglycans in tobacco products is likely due to the nitrosation reaction of nicotine during the manufacturing and consumption of tobacco products. This substance is currently only used in research on inducing tumors in experimental animals. Exposure to nitrosaminoglycans can affect the liver, therefore there is reason to suspect its carcinogenicity in humans. (NCI05) N'-Nitrosaminoglycans belong to the pyrrolidine pyridine class of compounds. These compounds contain a pyrrolidine pyridine ring system, which consists of a pyrrolidine ring and a pyridine ring linked together.
3-(1-Nitrosopyrrolidin-2-yl)pyridine (CAS# 80508-23-2) is a major tobacco-specific nitrosamine and potent carcinogen. It has not been approved as a therapeutic agent. The compound is used as a reference standard in research on tobacco carcinogenesis, nitrosamine analysis, and cancer prevention. It is also known as nitrosonornicotine (NNN). |
| Molecular Formula |
C9H11N3O
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|---|---|
| Molecular Weight |
177.20
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| Exact Mass |
177.09
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| CAS # |
80508-23-2
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| PubChem CID |
27919
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| Appearance |
Typically exists as solid at room temperature
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| Boiling Point |
154ºC at 0.2 MM HG
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| Melting Point |
47 °C
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| Flash Point |
9℃
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| LogP |
1.837
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
13
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| Complexity |
186
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=NN1C(C2C=CC=NC=2)CCC1
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| InChi Key |
XKABJYQDMJTNGQ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H11N3O/c13-11-12-6-2-4-9(12)8-3-1-5-10-7-8/h1,3,5,7,9H,2,4,6H2
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| Chemical Name |
3-(1-nitrosopyrrolidin-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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.6433 mL | 28.2167 mL | 56.4334 mL | |
| 5 mM | 1.1287 mL | 5.6433 mL | 11.2867 mL | |
| 10 mM | 0.5643 mL | 2.8217 mL | 5.6433 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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