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Nicotine

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 N07BA01 (WHO) QP53AX13 (WHO)
Legal status
Legal status
  • AU: Unscheduled
  • CA: Unscheduled
  • NZ: Unscheduled
  • UK: Unscheduled
  • US: Unscheduled
  • UN: Unscheduled
  • EU: Unscheduled
Pharmacokinetic data
Bioavailability 20 to 45% (oral), 53% (intranasal), 68% (transdermal)
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 54-11-5 YesY
PubChem (CID) 89594
IUPHAR/BPS 2585
DrugBank DB00184 YesY
ChemSpider 80863 YesY
UNII 6M3C89ZY6R YesY
KEGG D03365 YesY
ChEBI CHEBI:18723 N
ChEMBL CHEMBL3 YesY
PDB ligand ID NCT (PDBe, RCSB PDB)
ECHA InfoCard 100.000.177
Chemical and physical data
Formula C10H14N2
Molar mass 162.23 g/mol
3D model (Jmol) Interactive image
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 alkaloid found in the nightshade family of plants (Solanaceae) and is a stimulant drug. Nicotine is a nicotinic acetylcholine receptor (nAChR) agonist, except at nAChRα9 and nAChRα10 where it acts as an 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.

It constitutes approximately 0.6–3.0% of the dry weight of tobacco and is present in the range of 2–7 µg/kg of various edible plants. 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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