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Nicotine addiction

Nicotine
Nicotine.svg
Nicotine-3D-vdW.png
Clinical data
Trade names Nicorette, Nicotrol
AHFS/Drugs.com Monograph
Pregnancy
category
  • AU: D
  • US: D (Evidence of risk)
Dependence
liability		 Physical: low–moderate
Psychological: moderate–high
Addiction
liability		 High
Routes of
administration		 Inhalation; insufflation; oral – buccal, sublingual, and ingestion; transdermal; rectal
ATC code
Legal status
Legal status
  • AU: Unscheduled
  • CA: Unscheduled
  • DE: Unscheduled
  • NZ: Unscheduled
  • UK: Unscheduled
  • US: Unscheduled
  • UN: Unscheduled
Pharmacokinetic data
Protein binding <5%
Metabolism Primarily hepatic: CYP2A6, CYP2B6, FMO3, others
Metabolites Cotinine
Biological half-life 1-2 hours; 20 hours active metabolite
Excretion Urine (10-20% (gum), pH-dependent; 30% (inhaled); 10-30% (intranasal))
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
ECHA InfoCard 100.000.177
Chemical and physical data
Formula C10H14N2
Molar mass 162.23 g/mol
3D model (Jmol)
Chirality Chiral
Density 1.01 g/cm3
Melting point −79 °C (−110 °F)
Boiling point 247 °C (477 °F)
 NYesY (what is this?)  
NFPA 704
"fire diamond"
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
The fire diamond hazard sign for nicotine.

Nicotine is a potent parasympathomimetic stimulant and an alkaloid found in the nightshade family of plants. Nicotine acts as a receptor agonist at most nicotinic acetylcholine receptors (nAChRs), except at two nicotinic receptor subunits (nAChRα9 and nAChRα10) where it acts as an receptor antagonist. Nicotine is found in the leaves of Nicotiana rustica in amounts of 2–14%, the tobacco plant Nicotiana tabacum, Duboisia hopwoodii and Asclepias syriaca.

Nicotine constitutes approximately 0.6–3.0% of the dry weight of tobacco. Less than one millionth of that concentration (2–7 µg/kg) is found in edible Solanaceae such as eggplants and tomatoes. It functions as an antiherbivore chemical; consequently, nicotine was widely used as an insecticide in the past and neonicotinoids such as imidacloprid are currently widely used.

Nicotine is highly addictive. An average cigarette yields about 2 mg of absorbed nicotine, and in lesser doses of that order, the substance acts as a stimulant in mammals, while high amounts (50–100 mg) can be harmful. This stimulant effect is a contributing factor to the addictive properties of tobacco smoking. Nicotine's addictive nature includes psychoactive effects, drug-reinforced behavior, compulsive use, relapse after abstinence, physical dependence and tolerance.


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