Cotinine

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of cotinine
General
Surname Cotinine
other names
  • ( S ) -1-methyl-5- (3-pyridinyl) -2-pyrrolidinone
  • ( S ) - (-) - cotinine
Molecular formula C 10 H 12 N 2 O
External identifiers / databases
CAS number 486-56-6
EC number 207-634-9
ECHA InfoCard 100.006.941
PubChem 854019
ChemSpider 746405
Wikidata Q421177
properties
Molar mass 176.22 g mol −1
Physical state

liquid

Melting point

41 ° C

boiling point

145–147 ° C (4 hPa)

Vapor pressure

11.4 m Pa (at 25 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302-315-319-335
P: 261-305 + 351 + 338
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cotinine is a occurring in various plant natural products and is one of the alkaloids of tobacco . In the human organism, nicotine is metabolized to cotinine. Due to its easier analytical accessibility and long-lasting traceability, it serves as a measure of tobacco consumption that has taken place.

The word cotinine is an anagram of nicotine .

Occurrence

Cotinine is found in tobacco leaves ( Nicotiana tabacum ) and in Duboisia hopwoodii . It is also produced by the oxidation of nicotine and can be detected in tobacco smoke.

Cotinin content in tobacco products
Tobacco product Cotinine µg / g tobacco
Cigarette tobacco 40-195
chewing tobacco 37-81
snuff 101-304

metabolism

Cotinine is found as a breakdown product of nicotine in smokers and passive smokers in blood , plasma , saliva and urine as N -glucuronide conjugate . It has a half-life of 16 to 22 hours. The half-life of nicotine is only about 30 minutes, so cotinine is suitable for differentiating between active and passive smoking. The determination of cotinine is also possible in hair .

Typical plasma cotinine values ​​in smokers are 100–300 ng · ml −1 and correlate with the number of cigarettes smoked daily. The following values ​​are found for non-smokers:

  • not exposed to secondhand smoke: 1.7 ng · ml −1
  • Exposed to secondhand smoke: 2.6 ng.ml −1
  • Restaurant staff: up to 5.6 ng.ml −1
  • Discotheque staff: up to 24 ng.ml −1
  • Staff in bars: up to 45 ng.ml −1

Smoking behavior marker

The determination of the cotinine content in urine or blood is well suited as a unit of measurement for tobacco consumption and thus enables a statement to be made about smoking behavior. Studies show that the level of the cotinine concentration makes it much easier to predict problems in the infant in the first year than information provided by parents on smoking behavior during pregnancy .

The cotinine concentration can also provide information about the amount of smoke inhaled by passive smoking in non-smokers who are exposed to the " sidestream smoke " of smokers.

Private health and life insurers who request a medical examination upon admission use the hair analysis, as cotinine - in contrast to nicotine itself - can still be detected after three to five days.

toxicology

In animal experiments with mice showed cotinine in peroral and intraperitoneal administration drowsiness and subdued behavior, strong at higher doses excitement and breathlessness . The toxicity found in mice ( LD 50 ) was between 930 mg kg −1 (intraperitoneal) and 1,604 mg kg −1 (oral).

Analytics

For a reliable qualitative and quantitative determination of the cotinine, the coupling of the HPLC with the mass spectrometry can be used after appropriate sample preparation . The coupling of gas chromatography and mass spectrometry is also suitable for the determination.

Individual evidence

  1. ↑ a b c Entry on cotinine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  2. ↑ Data sheet cotinine from AlfaAesar, accessed on March 17, 2010 ( PDF )(JavaScript required) .
  3. ↑ a b data sheet (-) - cotinine from Sigma-Aldrich , accessed on March 23, 2011 ( PDF ).
  4. ↑ a b c J. F. BORZELLECA, ER BOWMAN, H. McKENNIS: Studies on the respiratory and cardiovascular effects of (-) - cotinine. In: The Journal of pharmacology and experimental therapeutics. Volume 137, September 1962, pp. 313-318, PMID 13871520 .
  5. ↑ a b entry on cotinine. In: Römpp Online . Georg Thieme Verlag, accessed on October 24, 2016.
  6. ↑ CI Vardavas, MN Tzatzarakis, AM Tsatsakis, D. Athanasopoulos, E. Balomenaki, MK Linardakis, AG Kafatos: Biomarkers of passive smoking among Greek preschool children. In: European Journal of Pediatrics. Volume 165, Number 12, December 2006, pp. 891-896, doi: 10.1007 / s00431-006-0196-y , PMID 16874499 .
  7. ↑ B. Madea: Hair analysis: technology and interpretation in medicine and law. Deutscher Ärzteverlag, 2003, ISBN 3-7691-0437-4 .
  8. ^ H. Zuo et al .: Smoking, plasma cotinine and risk of atrial fibrillation: the Hordaland Health Study . In: Journal of Internal Medicine . 2017, doi : 10.1111 / joim.12689 (English, full text ).
  9. ^ Peter H Whincup et al .: Passive smoking and risk of coronary heart disease and stroke: prospective study with cotinine measurement. In: BMJ. 329 (7459), 2004, p. 200 (24 July) full text (PDF) , doi: 10.1136 / bmj.38146.427188.55 .
  10. ↑ FY Wu, HT Chiu, HD Wu, CJ Lin, JS Lai, HW Kuo: Comparison of urinary and plasma cotinine levels during the three trimesters of pregnancy. In: Pediatr Perinat Epidemiol . 22 (3), May 2008, pp. 296-301. PMID 18426525 .
  11. ↑ DV Joseph, JA Jackson, J. Westaway, NA Taub, SA Petersen, MP Wailoo: Effect of parental smoking on cotinine levels in newborns. In: Arch Dis Child Fetal Neonatal Ed. 92 (6), Nov 2007, pp. F484-F488. PMID 17580319 .
  12. ↑ CI Vardavas, MN Tzatzarakis, AM Tsatsakis, D. Athanasopoulos, E. Balomenaki, MK Linardakis, AG Kafatos: Biomarkers of passive smoking among Greek preschool children. PMID 16874499 .
  13. ↑ M. Simoni, S. Baldacci, R. Puntoni, F. Pistelli, S. Farchi, E. Lo Presti, R. Pistelli, G. Corbo, N. Agabiti, S. Basso, G. Matteelli, F. Di Pede , L. Carrozzi, F. Forastiere, G. Viegi: Plasma, salivary and urinary cotinine in non-smoker Italian women exposed and unexposed to environmental tobacco smoking (SEASD study). In: Clin Chem Lab Med. 44 (5), 2006, pp. 632-638. PMID 16681437 .
  14. ↑ A. Thaqi, K. Franke, G. Merkel, HE Wichmann, J. Heinrich: Biomarkers of exposure to passive smoking of school children: frequency and determinants. In: Indoor Air. 15 (5), Oct 2005, pp. 302-310. PMID 16108902 .
  15. ↑ V. Kurzendörfer: Introduction to life insurance. Verlag Versicherungswirtsch., 2000, ISBN 3-88487-859-X .
  16. ↑ Inukai T, Kaji S, Kataoka H .: Analysis of nicotine and cotinine in hair by on-line in-tube solid-phase microextraction coupled with liquid chromatography-tandem mass spectrometry as biomarkers of exposure to tobacco smoke. , J Pharm Biomed Anal. 2018 Jul 15; 156: 272-277, PMID 29729641
  17. ↑ Mohammadi S, Domeno C, Nerin I, Aznar M, Samper P, Khayatian G, Nerin C .: Toxic compounds from tobacco in placenta samples analyzed by UPLC-QTOF-MS , J Pharm Biomed Anal. 2017 Oct 25; 145: 331-338, PMID 28710994
  18. ↑ Li Y, Li Y, Zhu J, Lei L, Zheng QY, Zou XL .: Determination of Nicotine and Cotinine in Urine by Dispersive Liquid-Liquid Microextraction Combined with Gas Chromatography-Mass Spectrometry]. , Sichuan Da Xue Xue Bao Yi Xue Ban. 2016 May; 47 (3): 416-9. Chinese, PMID 27468492
  19. ↑ Wang Y, Huang Z, Ye Y, Zhang Y, Xiao S .: Determination of urinary cotinine of children exposed to passive smoking by stable isotope dilution gas chromatography-triple quadrupole mass spectrometry. , Se Pooh. 2014 Jun; 32 (6): 658-61. Chinese, PMID 25269267
  20. ↑ Iwai M, Ogawa T, Hattori H, Zaitsu K, Ishii A, Suzuki O, Seno H .: Simple and rapid assay method for simultaneous quantification of urinary nicotine and cotinine using micro-extraction by packed sorbent and gas chromatography-mass spectrometry. , Nagoya J Med Sci. 2013 Aug; 75 (3-4): 255-61, PMID 24640182

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