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Nicotine1
Nicotine
NicotineSystematic (IUPAC) name
3-[(2
S 
)-1-methylpyrrolidin-2-yl]pyridine
IdentifiersCAS number
54-11-5
 [1]
ATC code
N07 BA01
 [2] 
QP53 AX13
 [3]
PubChem
CID 942
 [4]
DrugBank
DB00184
 [5]
ChemSpider
80863
 [6] 
UNII
6M3C89ZY6R
 [7] 
Chemical dataFormulaC
10
H
14
N
2
Mol. mass
162.26 g/mol
SMILES
eMolecules
 [8]
& PubChem
 [9]
Physical dataDensity
1.01 g/cm³
Melt. point
-79 °C (-110 °F)
Boiling point
247 °C (477 °F)
Pharmacokinetic dataBioavailability
20 to 45% (oral)
Metabolism
hepatic
Half-life
2 hours
Therapeutic considerationsPregnancy cat.
D(US)
 
Nicotine2
Legal status
Unscheduled (AU) ? (UK) ? (US)
Dependenceliability
Medium to high
Routessmoked
(as smoking tobacco, mapacho, etc.),
insufflated
(as tobacco snuff or nicotine nasal spray),
chewed
(asnicotine gum, tobacco gum or chewing tobacco),
transdermal
(as nicotine patch, nicogel or topical tobaccopaste),
intrabuccal
(as dipping tobacco, snuffs, dissolvable tobacco or creamy snuff),
vaporized
(as electroniccigarette, etc.),
directly inhaled
(as nicotine inhaler),
oral
(as nicotini)
 
(what is this?)
 
(verify)
 [10]
Nicotine
is an alkaloid found in the nightshade family of plants (
Solanaceae
) that constitutes approximately0.6
 – 
3.0% of the dry weight of tobacco,
[11]
 
[12]
with biosynthesis taking place in the roots and accumulationoccurring in the leaves. It functions as an antiherbivore chemical with particular specificity to insects; thereforenicotine was widely used as an insecticide in the past,
[13]
 
[14]
and currently nicotine analogs such as imidaclopridcontinue to be widely used. Nicotine is also found in several other members of the Solanaceae family, with smallamounts being present in species such as the Eggplant and Tomato.In low concentrations (an average cigarette yields about 1 mg of absorbed nicotine), the substance acts as a stimulantin mammals and is the main factor responsible for the dependence-forming properties of tobacco smoking.According to the American Heart Association, nicotine addiction has historically been one of the hardest addictionsto break, while the pharmacological and behavioral characteristics that determine tobacco addiction are similar tothose that determine addiction to drugs such as heroin and cocaine.
[15]
Nicotine content in cigarettes has slowlyincreased over the years, and one study found that there was an average increase of 1.6% per year between the yearsof 1998 and 2005. This was found for all major market categories of cigarettes.
[16]
History and name
Nicotine is named after the tobacco plant
 Nicotiana tabacum,
which in turn is named after Jean Nicot de Villemain,French ambassador in Portugal, who sent tobacco and seeds from Brazil to Paris in 1560 and promoted theirmedicinal use. Nicotine was first isolated from the tobacco plant in 1828 by German chemists Posselt & Reimann,who considered it a poison.
[17]
Its chemical empirical formula was described by Melsens in 1843,
[18]
its structurewas discovered by Adolf Pinner and Richard Wolffenstein in 1893, and it was first synthesized by A. Pictet andCrepieux in 1904.
[19]
Chemistry
Nicotine is a hygroscopic, oily liquid that is miscible with water in its base form. As a nitrogenous base, nicotineforms salts with acids that are usually solid and water soluble. Nicotine easily penetrates the skin. As shown by thephysical data, free base nicotine will burn at a temperature below its boiling point, and its vapors will combust at308 K (35 °C; 95 °F) in air despite a low vapor pressure. Because of this, most of the nicotine is burned when acigarette is smoked; however, enough is inhaled to cause pharmacological effects.
 
Nicotine3
Optical activity
Nicotine is optically active, having two enantiomeric forms. The naturally occurring form of nicotine is levorotatory,with [α]
D
=
 – 
166.4°. The dextrorotatory form, (+)-nicotine, has only one-half the physiological activity of (
 – 
)-nicotine. It is therefore weaker in the sense that a higher dose is required to attain the same effects.
[20]
The saltsof (+)-nicotine are usually dextrorotatory.
Pharmacology
Pharmacokinetics
Side effects of nicotine.[21]
As nicotine enters the body, it is distributedquickly through the bloodstream and can crossthe blood-brain barrier. On average it takes aboutseven seconds for the substance to reach thebrain when inhaled. The half life of nicotine inthe body is around two hours.
[22]
The amount of nicotine absorbed by the bodyfrom smoking depends on many factors,including the type of tobacco, whether the smokeis inhaled, and whether a filter is used. Forchewing tobacco, dipping tobacco, snus andsnuff, which are held in the mouth between thelip and gum, or taken in the nose, the amountreleased into the body tends to be much greaterthan smoked tobacco. Nicotine is metabolized inthe liver by cytochrome P450 enzymes (mostlyCYP2A6, and also by CYP2B6). A majormetabolite is cotinine.Other primary metabolites include nicotine
 N 
'-oxide, nornicotine, nicotine isomethonium ion, 2-hydroxynicotine andnicotine glucuronide.
[23]
Glucuronidation and oxidative metabolism of nicotine to cotinine are both inhibited by menthol, an additive tomentholated cigarettes, thus increasing the half-life of nicotine
in vivo
.
[24]
Detection of use
Nicotine can be quantified in blood, plasma, or urine to confirm a diagnosis of poisoning or to facilitate amedicolegal death investigation. Urinary or salivary cotinine concentrations are frequently measured for thepurposes of pre-employment and health insurance medical screening programs. Careful interpretation of results isimportant, since passive exposure to cigarette smoke can result in significant accumulation of nicotine, followed bythe appearance of its metabolites in various body fluids.
[25]
 
[26]
Interestingly, nicotine use is not regulated incompetitive sports programs, yet the drug has been shown to have a significant beneficial effect on athleticperformance.
[27]
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