CAS Number64091-91-4
Synonyms4-[Methyl(nitroso)amino]-1-(3-pyridinyl)-1-butanone; Nicotine-derived nitrosamine ketone; 4-(n-nitrosomethylamino)-1-(3-pyridyl)-1-butanone; 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone; N-Nitrosonornicotine ketone; NNK; Ozone/NNK; MFCD00274580; N-methyl-N-(4-oxo-4-pyridin-3-ylbutyl)nitrous amide; 4-[Methyl(nitroso)amino]-1-(pyridin-3-yl)butan-1-one
Molecular FormulaC10H13N3O2
Molecular Weight207.23
Purity98%
Density1.2±0.1 g/cm3
Boiling Point423.9±25.0 °C at 760 mmHg
Melting Point63-65ºC
Appearanceliquid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 64091-91-4 |
| Catalog No. | 2A-9092245 |
| Chinese Name | 4-甲基亚硝胺基-1-3-吡啶基-1-丁酮 |
| Synonyms | 4-[Methyl(nitroso)amino]-1-(3-pyridinyl)-1-butanone; Nicotine-derived nitrosamine ketone; 4-(n-nitrosomethylamino)-1-(3-pyridyl)-1-butanone; 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone; N-Nitrosonornicotine ketone; NNK; Ozone/NNK; MFCD00274580; N-methyl-N-(4-oxo-4-pyridin-3-ylbutyl)nitrous amide; 4-[Methyl(nitroso)amino]-1-(pyridin-3-yl)butan-1-one |
| Molecular Formula | C10H13N3O2 |
| Molecular Weight | 207.23 |
| Purity | 98 |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 423.9±25.0 °C at 760 mmHg |
| Melting Point | 63-65ºC |
| Appearance | liquid |
| Storage Condition | Store in an airtight container in a cool, dry plac |
| Packaging | II |
| Application | NNK is a nitrosated derivative of nicotine. NNK activates ERK1/2 and PKCα, while stimulating Bcl2 phosphorylation only at c-Myc at Ser70, Thr58 and Ser62 [1]. NNK induces survival and proliferation of |
| PubChem ID | 329818458 |
| MDL Number | MFCD00274580 |
| SMILES | CN(CCCC(=O)c1cccnc1)N=O |
| InChI | 1S/C10H13N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8H,3,5,7H2,1H3 |
| InChI Key | FLAQQSHRLBFIEZ-UHFFFAOYSA-N |
| NACRES Code | NA.24 |
| UNSPSC | 41116107 |
| Hazard Symbols | 6.1 |
| MSDS | msds/92245_1_64091_91_4.pdf |
| Bioactivity | NNK is a nicotine-nitrosated derivative. NNK simultaneously stimulates Bcl2 phosphorylation exclusively at Ser70 and c-Myc at Thr58 and Ser62 through activation of both ERK1/2 and PKCα[1]. NNK induces survival and proliferation of human lung cancer cells. NNK can be used for lung cancer mice model structure[2]. Related Catalog Research Areas >> Cancer Target Human Endogenous Metabolite In Vitro NNK (100 pM; 0-60 min) stimulates activation of PKCα and MAPKs ERK1/2 that directly induce c-Myc phosphorylation[1]. NNK (100 pM; 96 hours) enhances proliferation of cells expressing WT but not AA c-Myc mutant[1]. Western Blot Analysis Cell Line: NCI-H82 cells[1] Concentration: 100 pM Incubation Time: 0-60 min Result: Stimulated activation of PKCα and MAPKs ERK1/2 that directly induced c-Myc phosphorylation. Apoptosis Analysis Cell Line: H1299 lung cancer cells[1] Concentration: 100 pM Incubation Time: 96 hours Result: Enhanced proliferation of cells expressing WT but not T58A/S62A c-Myc mutant. References [1]. Jin Z, Gao F, Flagg T, Deng X. Tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone promotes functional cooperation of Bcl2 and c-Myc through phosphorylation in regulating cell survival and proliferation. J Biol Chem. 2004;279(38):40209-40219. [2]. Castonguay A, Pepin P, Stoner GD. Lung tumorigenicity of NNK given orally to A/J mice: its application to chemopreventive efficacy studies. Exp Lung Res. 1991;17(2):485-499. Chemical & Physical Properties Density 1.2±0.1 g/cm3 Boiling Point 423.9±25.0 °C at 760 mmHg Melting Point 63-65ºC Molecular Formula C10H13N3O2 Molecular Weight 207.229 Flash Point 210.2±23.2 °C Exact Mass 207.100784 PSA 62.63000 LogP 0.09 Vapour Pressure 0.0±1.0 mmHg at 25°C Index of Refraction 1.557 InChIKey FLAQQSHRLBFIEZ-UHFFFAOYSA-N SMILES CN(CCCC(=O)c1cccnc1)N=O Storage condition Amber Vial, -20°C Freezer Stability Stable. Incompatible with strong oxidizing agents. |
| Use of | Properties Articles42 Name 4-(N-nitrosomethylamino)-1-(3-pyridyl)butan-1-one Synonym More Synonyms nnk Biological Activity Related Catalog Research Areas >> Cancer Human Endogenous Metabolite References [1]. Jin Z, Gao F, Flagg T, Deng X. Tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone promotes functional cooperation of Bcl2 and c-Myc through phosphorylation in regulating cell survival and proliferation. J Biol Chem. 2004;279(38):40209-40219. [2]. Castonguay A, Pepin P, Stoner GD. Lung tumorigenicity of NNK given orally to A/J mice: its application to chemopreventive efficacy studies. Exp Lung Res. 1991;17(2):485-499. Chemical & Physical Properties Molecular Formula C10H13N3O2 Exact Mass 207.100784 PSA 62.63000 Index of Refraction 1.557 InChIKey FLAQQSHRLBFIEZ-UHFFFAOYSA-N Stability Stable. Incompatible with strong oxidizing agents. |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Danger Regulations: 1230 International Maritime Transport Danger Regulations: 1230 International Air Transport Danger Regulations: 1230 14.2 United Nations shipping name European Land Transport Dangerous Regulations: METHANOL, solution IMDG Code: METHANOL, solution IFRS: Methanol, solution 14.3 Transport hazard categories European land transport risk code: 3 (6.1) International sea transport risk code: 3 (6.1) International air transport risk code: 3 (6.1) 14.4 Package group European Dangerous Regulations for land transport: II International Dangerous Regulations for sea transport: II International Dangerous Regulations for air transport: II 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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