Nicotine
Chemical stimulant produced by some plants / From Wikipedia, the free encyclopedia
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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]
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Trade names | Nicorette, Nicotrol | ||
AHFS/Drugs.com | Monograph | ||
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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 | ||
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Protein binding | <5% | ||
Metabolism | Primarily hepatic: CYP2A6, CYP2B6, FMO3, others | ||
Metabolites | Cotinine | ||
Elimination half-life | 1–2 hours; 20 hours active metabolite | ||
Excretion | Renal, urine pH-dependent;[8] 10–20% (gum), 30% (inhaled); 10–30% (intranasal) | ||
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ECHA InfoCard | 100.000.177 | ||
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Formula | C10H14N2 | ||
Molar mass | 162.236 g·mol−1 | ||
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Chirality | Chiral | ||
Density | 1.01 g/cm3 | ||
Melting point | −79 °C (−110 °F) | ||
Boiling point | 247 °C (477 °F) | ||
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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]