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Cotinine
Systematic (IUPAC) name
(5S)-1-methyl-5-(3-pyridyl)pyrrolidin-2-one
Identifiers
CAS number 486-56-6
ATC code none
PubChem 854019
ChemSpider 746405
Chemical data
Formula C10H12N2O 
Mol. mass 176.22 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Half life 20 hours
Therapeutic considerations
Pregnancy cat.  ?
Legal status Prescription only
Routes Oral, Smoked

Cotinine is an alkaloid found in tobacco and is also a metabolite of nicotine.[1][2] The word "cotinine" is an anagram of "nicotine". Cotinine is used as a biomarker for exposure to tobacco smoke and has also been sold as an antidepressant under the brand name Scotine.[1]

Similarly to nicotine, cotinine binds to, activates, and desensitizes neuronal nicotinic acetylcholine receptors, though at much lower potency in comparison.[3][4][2][5] It has demonstrated nootropic and antipsychotic-like effects in scientific research.[6][7]

Measure of tobacco smoke exposure

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. The level of cotinine in the blood is proportionate to the amount of exposure to tobacco smoke, so it is a valuable indicator of tobacco smoke exposure, including secondary (passive) smoke.[8] People who smoke menthol cigarettes may retain cotinine in the blood for a longer period because menthol can compete with enzymatic metabolism of cotinine.[9] Genetic encoding of liver enzymes may also play a role, as African Americans routinely register higher blood cotinine levels than Caucasians.[10] Several variable factors (such as menthol cigarette preference and puff size) suggest that the explanation for this difference may be more complex than gender or race.[citation needed]

Drug tests can detect cotinine in the blood, urine, or saliva.

References

  1. ^ a b David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 0-412-46630-9. http://books.google.com/books?id=DeX7jgInYFMC&lpg=PA522&dq=scotine%20cotinine&as_brr=3&pg=PA522#v=onepage&q=&f=false. 
  2. ^ a b Dwoskin LP, Teng L, Buxton ST, Crooks PA (March 1999). "(S)-(-)-Cotinine, the major brain metabolite of nicotine, stimulates nicotinic receptors to evoke [3Hdopamine release from rat striatal slices in a calcium-dependent manner"]. The Journal of Pharmacology and Experimental Therapeutics 288 (3): 905–11. PMID 10027825. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=10027825. 
  3. ^ Anderson DJ, Arneric SP (March 1994). "Nicotinic receptor binding of [3Hcytisine, [3H]nicotine and [3H]methylcarbamylcholine in rat brain"]. European Journal of Pharmacology 253 (3): 261–7. PMID 8200419. http://linkinghub.elsevier.com/retrieve/pii/0014-2999(94)90200-3. 
  4. ^ Briggs CA, McKenna DG (September 1998). "Activation and inhibition of the human alpha7 nicotinic acetylcholine receptor by agonists". Neuropharmacology 37 (9): 1095–102. PMID 9833639. http://linkinghub.elsevier.com/retrieve/pii/S0028390898001105. 
  5. ^ Buccafusco JJ, Shuster LC, Terry AV (February 2007). "Disconnection between activation and desensitization of autonomic nicotinic receptors by nicotine and cotinine". Neuroscience Letters 413 (1): 68–71. doi:10.1016/j.neulet.2006.11.028. PMID 17157984. http://linkinghub.elsevier.com/retrieve/pii/S0304-3940(06)01232-8. 
  6. ^ Buccafusco JJ, Terry AV (October 2009). "A reversible model of the cognitive impairment associated with schizophrenia in monkeys: potential therapeutic effects of two nicotinic acetylcholine receptor agonists". Biochemical Pharmacology 78 (7): 852–62. doi:10.1016/j.bcp.2009.06.102. PMID 19577545. http://linkinghub.elsevier.com/retrieve/pii/S0006-2952(09)00498-5. 
  7. ^ Buccafusco JJ, Beach JW, Terry AV (February 2009). "Desensitization of nicotinic acetylcholine receptors as a strategy for drug development". The Journal of Pharmacology and Experimental Therapeutics 328 (2): 364–70. doi:10.1124/jpet.108.145292. PMID 19023041. PMC 2682277. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=19023041. 
  8. ^ Florescu A, Ferrence R, Einarson T, Selby P, Soldin O, Koren G (February 2009). "Methods for quantification of exposure to cigarette smoking and environmental tobacco smoke: focus on developmental toxicology". Therapeutic Drug Monitoring 31 (1): 14–30. doi:10.1097/FTD.0b013e3181957a3b. PMID 19125149. http://meta.wkhealth.com/pt/pt-core/template-journal/lwwgateway/media/landingpage.htm?issn=0163-4356&volume=31&issue=1&spage=14. 
  9. ^ Ham, Becky (December 2002). "Signs of smoking linger longer in menthol smokers". Center for the Advancement of Health. Science Blog. Archived from the original on 17 March 2010. http://www.webcitation.org/5oHyEmtc2. Retrieved 17 March 2010. 
  10. ^ News, BBC (2007-03-17). "'Race role' in tobacco smoke risk". BBC NEWS. http://news.bbc.co.uk/go/pr/fr/-/2/hi/health/6441267.stm. Retrieved 2007-03-18. 







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