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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 3 May 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 3 May 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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