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Nicotine

This article is about the chemical. For other uses, see Nicotine (disambiguation).

Nicotine
Top: Concentrated nicotine liquid

Bottom left: Skeleton representation of a nicotine molecule

Bottom right: Ball-and-stick model of a nicotine molecule
Clinical data
Trade namesNicorette, Nicotrol
AHFS/Drugs.comMonograph
Pregnancy
category
  • AU: D
Dependence
liability		Physical: Low–moderate[1] Psychological: High[2][3]
Addiction
liability		Very high[4]
Routes of
administration		Inhalation; insufflation; oral – buccal, sublingual, and ingestion; transdermal; rectal
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding<5%
MetabolismPrimarily hepatic: CYP2A6, CYP2B6, FMO3, others
MetabolitesCotinine
Elimination half-life1–2 hours; 20 hours active metabolite
ExcretionRenal, urine pH-dependent;[8]
10–20% (gum), 30% (inhaled); 10–30% (intranasal)
Identifiers
  • 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.000.177 Edit this at Wikidata
Chemical and physical data
FormulaC10H14N2
Molar mass162.236 g·mol−1
3D model (JSmol)
ChiralityChiral
Density1.01 g/cm3
Melting point−79 °C (−110 °F)
Boiling point247 °C (477 °F)
  • c1ncccc1[C@@H]2CCCN2C
  • InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-/m0/s1 checkY
  • Key:SNICXCGAKADSCV-JTQLQIEISA-N checkY
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Nicotine is a naturally produced alkaloid in the nightshade family of plants (most predominantly in tobacco and Duboisia hopwoodii)[9] and is widely used recreationally as a stimulant and anxiolytic. As a pharmaceutical drug, it is used for smoking cessation to relieve withdrawal symptoms.[10][7][11][12] Nicotine acts as a receptor agonist at most nicotinic acetylcholine receptors (nAChRs),[13][14][15] except at two nicotinic receptor subunits (nAChRα9 and nAChRα10) where it acts as a receptor antagonist.[13]

Nicotine constitutes approximately 0.6–3.0% of the dry weight of tobacco.[16] Nicotine is also present at ppb-concentrations in edible plants in the family Solanaceae, including potatoes, tomatoes, and eggplants,[17] though sources disagree on whether this has any biological significance to human consumers.[17] It functions as an antiherbivore toxin; consequently, nicotine was widely used as an insecticide in the past,[18][19] and neonicotinoids (structurally similar to nicotine), such as imidacloprid, are some of the most effective and widely used insecticides.

Nicotine is highly addictive.[20][21][22] Slow-release forms (gums and patches, when used correctly) can be less addictive and help in quitting.[23][24][25][26] Animal research suggests that monoamine oxidase inhibitors present in tobacco smoke may enhance nicotine's addictive properties.[27][28] An average cigarette yields about 2 mg of absorbed nicotine.[29] The estimated lower dose limit for fatal outcomes is 500–1,000 mg of ingested nicotine for an adult (6.5–13 mg/kg).[27][29] Nicotine addiction involves drug-reinforced behavior, compulsive use, and relapse following abstinence.[30] Nicotine dependence involves tolerance, sensitization,[31] physical dependence, psychological dependence,[32] and can cause distress.[33][34] Nicotine withdrawal symptoms include depressed mood, stress, anxiety, irritability, difficulty concentrating, and sleep disturbances.[2] Mild nicotine withdrawal symptoms are measurable in unrestricted smokers, who experience normal moods only as their blood nicotine levels peak, with each cigarette.[35] On quitting, withdrawal symptoms worsen sharply, then gradually improve to a normal state.[35]

Nicotine use as a tool for quitting smoking has a good safety history.[36] Animal studies suggest that nicotine may adversely affect cognitive development in adolescence, but the relevance of these findings to human brain development is disputed.[37][27] At low amounts, it has a mild analgesic effect.[38] According to the International Agency for Research on Cancer, "nicotine is not generally considered to be a carcinogen."[39][40] The Surgeon General of the United States indicates that evidence is inadequate to infer the presence or absence of a causal relationship between exposure to nicotine and risk for cancer.[41] Nicotine has been shown to produce birth defects in humans and is considered a teratogen.[42][43] The median lethal dose of nicotine in humans is unknown.[44] High doses are known to cause nicotine poisoning, organ failure, and death through paralysis of respiratory muscles,[41][45] though serious or fatal overdoses are rare.[46]

  1. ^ McLaughlin I, Dani JA, De Biasi M (2015). "Nicotine Withdrawal". The Neuropharmacology of Nicotine Dependence. Current Topics in Behavioral Neurosciences. Vol. 24. pp. 99–123. doi:10.1007/978-3-319-13482-6_4. ISBN 978-3-319-13481-9. PMC 4542051. PMID 25638335.
  2. ^ a b Cite error: The named reference Dependence-withdrawal was invoked but never defined (see the help page).
  3. ^ Cosci F, Pistelli F, Lazzarini N, Carrozzi L (2011). "Nicotine dependence and psychological distress: outcomes and clinical implications in smoking cessation". Psychology Research and Behavior Management. 4: 119–28. doi:10.2147/prbm.s14243. PMC 3218785. PMID 22114542.
  4. ^ Hollinger MA (19 October 2007). Introduction to Pharmacology (Third ed.). Abingdon: CRC Press. pp. 222–223. ISBN 978-1-4200-4742-4.
  5. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  6. ^ "The Medicines (Products Other Than Veterinary Drugs) (General Sale List) Amendment Order 2001". legislation.gov.uk. Retrieved 2 August 2022.
  7. ^ a b Nicotine. PubChem Compound Database. United States National Library of Medicine – National Center for Biotechnology Information. 16 February 2019. Retrieved 29 April 2024.
  8. ^ Landoni JH. "Nicotine (PIM)". INCHEM. International Programme on Chemical Safety. Retrieved 29 January 2019.
  9. ^ Fagerström K (December 2014). "Nicotine: Pharmacology, Toxicity and Therapeutic use". Journal of Smoking Cessation. 9 (2): 53–59. doi:10.1017/jsc.2014.27.
  10. ^ Sajja RK, Rahman S, Cucullo L (March 2016). "Drugs of abuse and blood-brain barrier endothelial dysfunction: A focus on the role of oxidative stress". Journal of Cerebral Blood Flow and Metabolism. 36 (3): 539–54. doi:10.1177/0271678X15616978. PMC 4794105. PMID 26661236.
  11. ^ "Nicotine: Clinical data". IUPHAR/BPS Guide to Pharmacology. International Union of Basic and Clinical Pharmacology. Retrieved 29 April 2024. Used as an aid to smoking cessation and for the relief of nicotine withdrawal symptoms.
  12. ^ Abou-Donia M (5 February 2015). Mammalian Toxicology. John Wiley & Sons. pp. 587–. ISBN 978-1-118-68285-2.
  13. ^ a b Cite error: The named reference IUPHAR was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference MalenkaNicotine was invoked but never defined (see the help page).
  15. ^ Kishioka S, Kiguchi N, Kobayashi Y, Saika F (2014). "Nicotine effects and the endogenous opioid system". Journal of Pharmacological Sciences. 125 (2): 117–24. doi:10.1254/jphs.14R03CP. PMID 24882143.
  16. ^ "Smoking and Tobacco Control Monograph No. 9" (PDF). Archived (PDF) from the original on 9 October 2022. Retrieved 19 December 2012.
  17. ^ a b Cite error: The named reference SiegmundLeitner1999 was invoked but never defined (see the help page).
  18. ^ Rodgman A, Perfetti TA (2009). The chemical components of tobacco and tobacco smoke. Boca Raton, FL: CRC Press. ISBN 978-1-4200-7883-1. LCCN 2008018913.[page needed]
  19. ^ Ujváry I (1999). "Nicotine and Other Insecticidal Alkaloids". In Yamamoto I, Casida J (eds.). Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor. Tokyo: Springer-Verlag. pp. 29–69.
  20. ^ Perkins KA, Karelitz JL (August 2013). "Reinforcement enhancing effects of nicotine via smoking". Psychopharmacology. 228 (3): 479–86. doi:10.1007/s00213-013-3054-4. PMC 3707934. PMID 23494236.
  21. ^ Cite error: The named reference Grana2014 was invoked but never defined (see the help page).
  22. ^ Cite error: The named reference Siqueira2016 was invoked but never defined (see the help page).
  23. ^ Etter JF (July 2007). "Addiction to the nicotine gum in never smokers". BMC Public Health. 7: 159. doi:10.1186/1471-2458-7-159. PMC 1939993. PMID 17640334.
  24. ^ Olausson P, Jentsch JD, Taylor JR (January 2004). "Nicotine enhances responding with conditioned reinforcement". Psychopharmacology. 171 (2): 173–178. doi:10.1007/s00213-003-1575-y. PMID 13680077. S2CID 11855403.
  25. ^ "Evidence Review of E-Cigarettes and Heated Tobacco Products" (PDF). Public Health England. 2018.
  26. ^ "Tobacco more addictive than Nicotine". Archived from the original on 20 April 2023.
  27. ^ a b c Royal College of Physicians (28 April 2016). "Nicotine without smoke: Tobacco harm reduction". Retrieved 16 September 2020.
  28. ^ Smith TT, Rupprecht LE, Cwalina SN, Onimus MJ, Murphy SE, Donny EC, et al. (August 2016). "Effects of Monoamine Oxidase Inhibition on the Reinforcing Properties of Low-Dose Nicotine". Neuropsychopharmacology. 41 (9): 2335–2343. doi:10.1038/npp.2016.36. PMC 4946064. PMID 26955970.
  29. ^ a b Cite error: The named reference MayerNewLethalDose2013 was invoked but never defined (see the help page).
  30. ^ Caponnetto P, Campagna D, Papale G, Russo C, Polosa R (February 2012). "The emerging phenomenon of electronic cigarettes". Expert Review of Respiratory Medicine. 6 (1): 63–74. doi:10.1586/ers.11.92. PMID 22283580. S2CID 207223131.
  31. ^ Jain R, Mukherjee K, Balhara YP (April 2008). "The role of NMDA receptor antagonists in nicotine tolerance, sensitization, and physical dependence: a preclinical review". Yonsei Medical Journal. 49 (2): 175–88. doi:10.3349/ymj.2008.49.2.175. PMC 2615322. PMID 18452252.
  32. ^ Miyasato K (March 2013). "[Psychiatric and psychological features of nicotine dependence]". Nihon Rinsho. Japanese Journal of Clinical Medicine. 71 (3): 477–81. PMID 23631239.
  33. ^ Cite error: The named reference Parrott2015 was invoked but never defined (see the help page).
  34. ^ Parrott AC (March 2006). "Nicotine psychobiology: how chronic-dose prospective studies can illuminate some of the theoretical issues from acute-dose research" (PDF). Psychopharmacology. 184 (3–4): 567–76. doi:10.1007/s00213-005-0294-y. PMID 16463194. S2CID 11356233.
  35. ^ a b Cite error: The named reference Parrott2003 was invoked but never defined (see the help page).
  36. ^ Schraufnagel DE, Blasi F, Drummond MB, Lam DC, Latif E, Rosen MJ, et al. (September 2014). "Electronic cigarettes. A position statement of the forum of international respiratory societies". American Journal of Respiratory and Critical Care Medicine. 190 (6): 611–8. doi:10.1164/rccm.201407-1198PP. PMID 25006874. S2CID 43763340.
  37. ^ "E-Cigarette Use Among Youth and Young Adults. 2016 Surgeon General's report.lts" (PDF). surgeongeneral.gov. Archived (PDF) from the original on 9 October 2022.
  38. ^ Schraufnagel DE (March 2015). "Electronic Cigarettes: Vulnerability of Youth". Pediatric Allergy, Immunology, and Pulmonology. 28 (1): 2–6. doi:10.1089/ped.2015.0490. PMC 4359356. PMID 25830075.
  39. ^ IARC Working Group on the Evaluation of Carcinogenic Risks to Humans. Personal Habits and Indoor Combustions. Lyon (FR): International Agency for Research on Cancer; 2012. (IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, No. 100E.) TOBACCO SMOKING. Available from: https://www.ncbi.nlm.nih.gov/books/NBK304395/
  40. ^ Cite error: The named reference IARCCancerStatement was invoked but never defined (see the help page).
  41. ^ a b Cite error: The named reference SGUS2014 was invoked but never defined (see the help page).
  42. ^ Kohlmeier KA (June 2015). "Nicotine during pregnancy: changes induced in neurotransmission, which could heighten proclivity to addict and induce maladaptive control of attention". Journal of Developmental Origins of Health and Disease. 6 (3): 169–81. doi:10.1017/S2040174414000531. PMID 25385318. S2CID 29298949.
  43. ^ "Nicotine". United States National Library of Medicine – Toxicology Data Network. Hazardous Substances Data Bank. 20 August 2009.
  44. ^ Cite error: The named reference ECHA nicotine monograph was invoked but never defined (see the help page).
  45. ^ Effah F, Taiwo B, Baines D, Bailey A, Marczylo T (October 2022). "Pulmonary effects of e-liquid flavors: a systematic review". Journal of Toxicology and Environmental Health Part B: Critical Reviews. 25 (7): 343–371. Bibcode:2022JTEHB..25..343E. doi:10.1080/10937404.2022.2124563. PMC 9590402. PMID 36154615.
  46. ^ Lavoie FW, Harris TM (1991). "Fatal nicotine ingestion". The Journal of Emergency Medicine. 9 (3): 133–136. doi:10.1016/0736-4679(91)90318-a. PMID 2050970.

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