Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2023-02-21 17:15:24 UTC |
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HMDB ID | HMDB0001046 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Cotinine |
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Description | Cotinine is an alkaloid found in tobacco (Nicotiana tabacum). Cotinine belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring. It is also the predominant human metabolite of nicotine (when nicotine is inhaled or absorbed). In humans, about 70 to 80% of nicotine that is inhaled or absorbed is converted to cotinine. This transformation involves two steps. The first is mediated by a cytochrome P450 system (mainly CYP2A6 and CYP2B6) to produce nicotine iminium ion. The second step is catalyzed by aldehyde oxidase (AOX). A number of cotinine metabolites have also been structurally characterized. Indeed, it appears that most of the reported urinary metabolites of nicotine are derived from cotinine. Cotinine is widely used as a biomarker for exposure to tobacco smoke. Cotinine has an in vivo half-life of approximately 20 hours, and is typically detectable for several days (up to one week) after the use of tobacco. Similar to nicotine, cotinine binds to, activates, and desensitizes neuronal nicotinic acetylcholine receptors, though at much lower potency in comparison. It has demonstrated nootropic and antipsychotic-like effects in animal models. Cotinine treatment has also been shown to reduce depression, anxiety, and fear-related behavior as well as memory impairment in animal models of depression, PTSD, and Alzheimer's disease. |
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Structure | InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3 |
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Synonyms | Value | Source |
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Cotinine(15% OF the dose) | HMDB | (-)-Cotinine | HMDB | (S)-(-)-Cotinine | HMDB | (S)-Cotinine | HMDB | Cotinina | HMDB | Cotininum | HMDB | S-(-)-Cotinine | HMDB |
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Chemical Formula | C10H12N2O |
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Average Molecular Weight | 176.2151 |
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Monoisotopic Molecular Weight | 176.094963016 |
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IUPAC Name | 1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one |
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Traditional Name | (-)-cotinine |
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CAS Registry Number | 486-56-6 |
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SMILES | CN1C(CCC1=O)C1=CN=CC=C1 |
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InChI Identifier | InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3 |
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InChI Key | UIKROCXWUNQSPJ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pyridines and derivatives |
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Sub Class | Pyrrolidinylpyridines |
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Direct Parent | Pyrrolidinylpyridines |
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Alternative Parents | |
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Substituents | - Pyrrolidinylpyridine
- Alkaloid or derivatives
- Pyrrolidone
- 2-pyrrolidone
- N-alkylpyrrolidine
- Pyrrolidine
- Tertiary carboxylic acid amide
- Heteroaromatic compound
- Lactam
- Carboxamide group
- Carboxylic acid derivative
- Azacycle
- Organic oxide
- Carbonyl group
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic 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 | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 41 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | 0.07 | LI,NY & GORROD,JW (1992) |
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Experimental Chromatographic Properties | Experimental Collision Cross SectionsAdduct Type | Data Source | CCS Value (Å2) | Reference |
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[M+H]+ | CBM | 140.7 | 30932474 |
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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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Experimental GC-MS | GC-MS Spectrum - Cotinine EI-B (Non-derivatized) | splash10-0002-9500000000-f031a7d223ea527c7a80 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Cotinine CI-B (Non-derivatized) | splash10-004i-0900000000-61e8e1349a9d42866260 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Cotinine EI-B (Non-derivatized) | splash10-0002-9500000000-f031a7d223ea527c7a80 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Cotinine CI-B (Non-derivatized) | splash10-004i-0900000000-61e8e1349a9d42866260 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cotinine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0gdl-6900000000-7eb4053aab6127e95391 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cotinine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Cotinine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-002b-9600000000-0cc3afdaebb529092e24 | 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 - Cotinine Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-004i-2900000000-7f61a2f6f72860e4c6e1 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cotinine Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-001i-9100000000-3a5b30b90a390122b868 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cotinine Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-001i-9000000000-b82772b6f28d39966cd1 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cotinine EI-B (HITACHI M-60) , Positive-QTOF | splash10-0002-9500000000-e8a00bc1cf980c18ed06 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cotinine CI-B (HITACHI M-60) , Positive-QTOF | splash10-004i-0900000000-61e8e1349a9d42866260 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cotinine LC-ESI-QTOF , positive-QTOF | splash10-004i-0900000000-16fb662f236943b7061e | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cotinine LC-ESI-QTOF , positive-QTOF | splash10-004i-0900000000-bb6734f53ed607f8551f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cotinine LC-ESI-QFT , positive-QTOF | splash10-004i-3900000000-b7fe72bb7584aa19a736 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cotinine LC-ESI-QFT , positive-QTOF | splash10-004i-2900000000-bb9334268373122b4f81 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cotinine 20V, Positive-QTOF | splash10-004i-0900000000-bb6734f53ed607f8551f | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cotinine 35V, Positive-QTOF | splash10-004i-3900000000-617e9ef99f5ff220e7f9 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cotinine 35V, Positive-QTOF | splash10-004i-3900000000-1ad4398aa27830eabbbd | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cotinine 40V, Positive-QTOF | splash10-001i-9000000000-3210604d5a8368e435a0 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cotinine 10V, Positive-QTOF | splash10-004i-0900000000-785e2933ae8dc3d4b297 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cotinine 20V, Positive-QTOF | splash10-001i-9000000000-4be8a9d2dee773690bd3 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Cotinine 10V, Positive-QTOF | splash10-001j-9100000000-8081f3e6f95787810baa | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cotinine 10V, Positive-QTOF | splash10-004i-0900000000-a4a59884dbcf842f195a | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cotinine 20V, Positive-QTOF | splash10-004i-1900000000-0cfe8e8d340c82c8fd11 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cotinine 40V, Positive-QTOF | splash10-0k9y-9500000000-e18e0cea3d758c6ff768 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cotinine 10V, Negative-QTOF | splash10-004i-0900000000-6fcf3e50bea7e8c25008 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cotinine 20V, Negative-QTOF | splash10-004i-0900000000-dad0516bb0862355ae61 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cotinine 40V, Negative-QTOF | splash10-05r4-9700000000-36486e0d1769fb592c7a | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cotinine 10V, Positive-QTOF | splash10-004i-0900000000-55ef895c84a338046aba | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cotinine 20V, Positive-QTOF | splash10-004i-1900000000-72acff4eea7467f91613 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cotinine 40V, Positive-QTOF | splash10-0006-9800000000-8b60e7a4fd9931166f14 | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | 2021-10-10 | Wishart Lab | View Spectrum | Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | 2021-10-10 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | 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]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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General References | - Bentley MC, Abrar M, Kelk M, Cook J, Phillips K: Validation of an assay for the determination of cotinine and 3-hydroxycotinine in human saliva using automated solid-phase extraction and liquid chromatography with tandem mass spectrometric detection. J Chromatogr B Biomed Sci Appl. 1999 Feb 19;723(1-2):185-94. [PubMed:10080645 ]
- Urakawa N, Nagata T, Kudo K, Kimura K, Imamura T: Simultaneous determination of nicotine and cotinine in various human tissues using capillary gas chromatography/mass spectrometry. Int J Legal Med. 1994;106(5):232-6. [PubMed:8068568 ]
- Poppe WA, Peeters R, Drijkoningen M, Ide PS, Daenens P, Lauweryns JM, Van Assche FA: Cervical cotinine and macrophage-Langerhans cell density in the normal human uterine cervix. Gynecol Obstet Invest. 1996;41(4):253-9. [PubMed:8793496 ]
- Jacqz-Aigrain E, Zhang D, Maillard G, Luton D, Andre J, Oury JF: Maternal smoking during pregnancy and nicotine and cotinine concentrations in maternal and neonatal hair. BJOG. 2002 Aug;109(8):909-11. [PubMed:12197371 ]
- Gwent SH, Wilson JF, Tsanaclis LM, Wicks JF: Time course of appearance of cotinine in human beard hair after a single dose of nicotine. Ther Drug Monit. 1995 Apr;17(2):195-8. [PubMed:7624910 ]
- Dobek D, Karmowski A, Sobiech KA, Terpilowski L, Mis-Michalek M: Average quantitative concentration of cotinine within the system pregnant woman-baby. Arch Immunol Ther Exp (Warsz). 1998;46(1):59-61. [PubMed:9510948 ]
- Torano JS, van Kan HJ: Simultaneous determination of the tobacco smoke uptake parameters nicotine, cotinine and thiocyanate in urine, saliva and hair, using gas chromatography-mass spectrometry for characterisation of smoking status of recently exposed subjects. Analyst. 2003 Jul;128(7):838-43. [PubMed:12894819 ]
- Knight JM, Eliopoulos C, Klein J, Greenwald M, Koren G: Passive smoking in children. Racial differences in systemic exposure to cotinine by hair and urine analysis. Chest. 1996 Feb;109(2):446-50. [PubMed:8620720 ]
- Hatsukami DK, Jensen J, Brauer LH, Mooney M, Schulte S, Sofuoglu M, Pentel PR: Lack of effect of 5HT3 antagonist in mediating subjective and behavioral responses to cotinine. Pharmacol Biochem Behav. 2003 Apr;75(1):1-7. [PubMed:12759107 ]
- Laskowska-Klita T, Chelchowska M, Leibschang J: [Concentrations of cotinine in serum and urine of smoking pregnant women and in placenta and umbilical cord blood]. Przegl Lek. 2005;62(10):1007-9. [PubMed:16521941 ]
- Authors unspecified: Nicotine absorption by workers harvesting green tobacco. Lancet. 1975 Mar 1;1(7905):478-80. [PubMed:46956 ]
- Tutka P, Wielosz M, Zatonski W: Exposure to environmental tobacco smoke and children health. Int J Occup Med Environ Health. 2002;15(4):325-35. [PubMed:12608620 ]
- Paszkowski T: [Concentration gradient of cotinine between blood serum and preovulatory follicular fluid]. Ginekol Pol. 1998 Dec;69(12):1131-6. [PubMed:10224789 ]
- Poppe WA, Peeters R, Daenens P, Ide PS, Van Assche FA: Tobacco smoking and the uterine cervix: cotinine in blood, urine and cervical fluid. Gynecol Obstet Invest. 1995;39(2):110-4. [PubMed:7737579 ]
- Istvan JA, Lee WW, Buist AS, Connett JE: Relation of salivary cotinine to blood pressure in middle-aged cigarette smokers. Am Heart J. 1999 May;137(5):928-31. [PubMed:10220643 ]
- Nafstad P, Botten G, Hagen JA, Zahlsen K, Nilsen OG, Silsand T, Kongerud J: Comparison of three methods for estimating environmental tobacco smoke exposure among children aged between 12 and 36 months. Int J Epidemiol. 1995 Feb;24(1):88-94. [PubMed:7797361 ]
- Eliopoulos C, Klein J, Chitayat D, Greenwald M, Koren G: Nicotine and cotinine in maternal and neonatal hair as markers of gestational smoking. Clin Invest Med. 1996 Aug;19(4):231-42. [PubMed:8853571 ]
- Eliopoulos C, Klein J, Koren G: Validation of self-reported smoking by analysis of hair for nicotine and cotinine. Ther Drug Monit. 1996 Oct;18(5):532-6. [PubMed:8885115 ]
- Wilson SE, Kahn RS, Khoury J, Lanphear BP: Racial differences in exposure to environmental tobacco smoke among children. Environ Health Perspect. 2005 Mar;113(3):362-7. [PubMed:15743729 ]
- Kintz P: Gas chromatographic analysis of nicotine and cotinine in hair. J Chromatogr. 1992 Sep 16;580(1-2):347-53. [PubMed:1400830 ]
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