Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 17:44:35 UTC |
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Update Date | 2023-02-21 17:21:05 UTC |
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HMDB ID | HMDB0031642 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | N-Nitroso-pyrrolidine |
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Description | N-Nitroso-pyrrolidine belongs to the class of organic compounds known as pyrrolidines. Pyrrolidines are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. N-Nitroso-pyrrolidine has been detected, but not quantified, in several different foods, such as green bell peppers, orange bell peppers, pepper (c. annuum), red bell peppers, and yellow bell peppers. This could make N-nitroso-pyrrolidine a potential biomarker for the consumption of these foods. |
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Structure | InChI=1S/C4H8N2O/c7-5-6-3-1-2-4-6/h1-4H2 |
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Synonyms | Value | Source |
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N-Nitrosopyrrolidine | MeSH | N Nitrosopyrrolidine | MeSH | 1-Nitrosopyrrolidine | ChEMBL, HMDB | 1-nitroso-Pyrrolidine | ChEMBL, HMDB | N-nitroso-1-Pyrrolidinamine | HMDB | nitroso-Pyrrolidine | HMDB | Nitrosopyrrolidine | HMDB | tetrahydro-N-nitroso-Pyrrole | HMDB |
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Chemical Formula | C4H8N2O |
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Average Molecular Weight | 100.1191 |
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Monoisotopic Molecular Weight | 100.063662888 |
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IUPAC Name | 1-nitrosopyrrolidine |
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Traditional Name | N-nitrosopyrrolidine |
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CAS Registry Number | 930-55-2 |
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SMILES | O=NN1CCCC1 |
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InChI Identifier | InChI=1S/C4H8N2O/c7-5-6-3-1-2-4-6/h1-4H2 |
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InChI Key | WNYADZVDBIBLJJ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as pyrrolidines. Pyrrolidines are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pyrrolidines |
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Sub Class | Not Available |
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Direct Parent | Pyrrolidines |
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Alternative Parents | |
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Substituents | - Pyrrolidine
- Organic n-nitroso compound
- Organic nitroso compound
- Azacycle
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organonitrogen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 1000000 mg/L @ 24C (exp) | The Good Scents Company Information System | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - N-Nitroso-pyrrolidine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0g2c-9000000000-25d8797fa4ff751a2d70 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Nitroso-pyrrolidine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0f6x-9300000000-c9950fc76ef0705da573 | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Nitroso-pyrrolidine LC-ESI-QFT , positive-QTOF | splash10-0udi-1900000000-85f43e28b348aeb93404 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Nitroso-pyrrolidine LC-ESI-QFT , positive-QTOF | splash10-0udi-1900000000-85f43e28b348aeb93404 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Nitroso-pyrrolidine LC-ESI-QFT , positive-QTOF | splash10-0udi-1900000000-85f43e28b348aeb93404 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Nitroso-pyrrolidine LC-ESI-QFT , positive-QTOF | splash10-0udi-3900000000-79fa9d8de9566bec999e | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Nitroso-pyrrolidine LC-ESI-QFT , positive-QTOF | splash10-0zfr-7900000000-0a674ea8d4b2d3f65b02 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Nitroso-pyrrolidine LC-ESI-QFT , positive-QTOF | splash10-0pb9-9500000000-98bb6cb1fe4c3f9a5bc7 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 30V, Positive-QTOF | splash10-0udi-1900000000-84056e4af9b3004d1162 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 75V, Positive-QTOF | splash10-0zfr-7900000000-fda6e8cba67fb1021878 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 90V, Positive-QTOF | splash10-0pb9-9500000000-84c6d034657142a09d21 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 60V, Positive-QTOF | splash10-0udi-3900000000-e01767039cac569f296c | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 10V, Negative-QTOF | splash10-0002-9000000000-4f72e350127fc271c203 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 20V, Negative-QTOF | splash10-001j-9000000000-370f605a1fa54cb29bff | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 40V, Negative-QTOF | splash10-0aor-9000000000-e5d77a59e81129df0a5c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 10V, Negative-QTOF | splash10-0002-9000000000-0b57691aff180313e37a | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 20V, Negative-QTOF | splash10-0002-9000000000-67edf338cfba7b6ef1e3 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 40V, Negative-QTOF | splash10-00kb-9000000000-4c1cf43c5f1ce342a8ec | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 10V, Positive-QTOF | splash10-0udi-2900000000-954c68340e2ec5c96773 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 20V, Positive-QTOF | splash10-0uk9-9400000000-b485c8519f27b43bd31e | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 40V, Positive-QTOF | splash10-006x-9000000000-c7530b5d976c4a448753 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 10V, Positive-QTOF | splash10-0udi-3900000000-9fcafc467833636e9b20 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 20V, Positive-QTOF | splash10-0uk9-9600000000-6331dff30f7d5884aa62 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Nitroso-pyrrolidine 40V, Positive-QTOF | splash10-0abc-9000000000-080a502c75e912983699 | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
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General References | - Tatematsu K, Koide A, Morimura K, Fukushima S, Mori Y: The enhancing effect of ethanol on the mutagenic activation of N-nitrosomethylbenzylamine by cytochrome P450 2A in the rat oesophagus. Mutagenesis. 2013 Mar;28(2):161-9. doi: 10.1093/mutage/ges066. Epub 2013 Jan 15. [PubMed:23325793 ]
- Li L, Wang P, Xu X, Zhou G: Influence of various cooking methods on the concentrations of volatile N-nitrosamines and biogenic amines in dry-cured sausages. J Food Sci. 2012 May;77(5):C560-5. doi: 10.1111/j.1750-3841.2012.02667.x. [PubMed:23163937 ]
- Pozzi R, Bocchini P, Pinelli F, Galletti GC: Determination of nitrosamines in water by gas chromatography/chemical ionization/selective ion trapping mass spectrometry. J Chromatogr A. 2011 Apr 8;1218(14):1808-14. doi: 10.1016/j.chroma.2011.02.009. Epub 2011 Feb 13. [PubMed:21377686 ]
- Authors unspecified: N-Nitrosamines (15 listings): N-Nitrosopyrrolidine. Rep Carcinog. 2011;12:323-4. [PubMed:21860516 ]
- Wagner ED, Hsu KM, Lagunas A, Mitch WA, Plewa MJ: Comparative genotoxicity of nitrosamine drinking water disinfection byproducts in Salmonella and mammalian cells. Mutat Res. 2012 Jan 24;741(1-2):109-15. doi: 10.1016/j.mrgentox.2011.11.006. Epub 2011 Nov 18. [PubMed:22108029 ]
- Hecht SS, Upadhyaya P, Wang M: Evolution of research on the DNA adduct chemistry of N-nitrosopyrrolidine and related aldehydes. Chem Res Toxicol. 2011 Jun 20;24(6):781-90. doi: 10.1021/tx200064a. Epub 2011 Apr 21. [PubMed:21480629 ]
- Tezel U, Padhye LP, Huang CH, Pavlostathis SG: Biotransformation of nitrosamines and precursor secondary amines under methanogenic conditions. Environ Sci Technol. 2011 Oct 1;45(19):8290-7. doi: 10.1021/es2005557. Epub 2011 Sep 2. [PubMed:21863807 ]
- Ma F, Wan Y, Yuan G, Meng L, Dong Z, Hu J: Occurrence and source of nitrosamines and secondary amines in groundwater and its adjacent Jialu River basin, China. Environ Sci Technol. 2012 Mar 20;46(6):3236-43. doi: 10.1021/es204520b. Epub 2012 Mar 1. [PubMed:22352424 ]
- Engemann A, Focke C, Humpf HU: Intestinal formation of N-nitroso compounds in the pig cecum model. J Agric Food Chem. 2013 Jan 30;61(4):998-1005. doi: 10.1021/jf305040e. Epub 2013 Jan 22. [PubMed:23297847 ]
- McDonald JA, Harden NB, Nghiem LD, Khan SJ: Analysis of N-nitrosamines in water by isotope dilution gas chromatography-electron ionisation tandem mass spectrometry. Talanta. 2012 Sep 15;99:146-54. doi: 10.1016/j.talanta.2012.05.032. Epub 2012 May 25. [PubMed:22967534 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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