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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H14N2
Molecular Weight 162.2316
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NICOTINE

SMILES

CN1CCC[C@H]1C2=CC=CN=C2

InChI

InChIKey=SNICXCGAKADSCV-JTQLQIEISA-N
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

HIDE SMILES / InChI

Molecular Formula C10H14N2
Molecular Weight 162.2316
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Sources: www.inchem.org/documents/pims/chemical/nicotine.htm
Curator's Comment: description was created based on several sources, including https://cancercontrol.cancer.gov/brp/tcrb/monographs/1/index.html https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2928221/

Nicotine is a natural alkaloid obtained from the dried leaves and stems of the nightshade family of pants, such as Nicotiana tabacum and Nicotiana rustica, where it occurs in concentrations of 0.5-8%. Cigarette tobacco varies in its nicotine content, but common blends contain 15-25 mg per cigarette, with a current trend towards lower levels. Nicotine is highly addictive substance, it exhibits a stimulant effect when adsorbed at 2 mg. Administration of higher doses could be harmful. Action of nicotine is mediated by nicotinic cholinergic receptors. Nicotine binds to the interface between two subunits of the receptors, opens the channel and allows the entry of sodium or calcium. The principal mediator of nicotine dependence is α4β2 nicotine receptor.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
NICORETTE

Approved Use

Reduces withdrawal symptoms, including nicotine craving associated with quitting smoking

Launch Date

1984
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
12 ng/mL
1 mg single, nasal
dose: 1 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NICOTINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
6 ng × h/mL
1 mg single, nasal
dose: 1 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NICOTINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3 min
1 mg single, nasal
dose: 1 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NICOTINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
95%
1 mg single, nasal
dose: 1 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
NICOTINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

Drug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Cow's urine poisoning in Nigeria. Experimental observations in mice.
1975 Jun
Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior.
2000 Oct
Effects of nicotine on the intervertebral disc: an experimental study in rabbits.
2001
Formation of the quaternary ammonium-linked glucuronide of nicotine in human liver microsomes: identification and stereoselectivity in the kinetics.
2001 Dec
Contributory role for nornicotine in nicotine neuropharmacology: nornicotine-evoked [3H]dopamine overflow from rat nucleus accumbens slices.
2001 Dec 15
Nicotine inhibits UV-induced activation of the apoptotic pathway.
2001 Dec 15
Inhibition of nicotine-induced seizures in rats by combining vaccination against nicotine with chronic nicotine infusion.
2001 May
Comparison of cytochrome P450 2A6 polymorphism frequencies in Caucasians and African-Americans using a new one-step PCR-RFLP genotyping method.
2001 Nov 30
Chronic ethanol and nicotine interaction on rat tissue antioxidant defense system.
2001 Oct
Nicotine affects the signaling of the death pathway, reducing the response of head and neck cancer cell lines to DNA damaging agents.
2001 Oct
Nicotine induced seizures blocked by mecamylamine and its stereoisomers.
2001 Oct 19
Activation of 5-HT(2C) receptors reduces the locomotor and rewarding effects of nicotine.
2001 Sep
Acute myocardial infarction soon after nicotine replacement therapy.
2001 Sep
Efficient enantiomeric synthesis of pyrrolidine and piperidine alkaloids from tobacco.
2001 Sep 21
Nornicotine, a nicotine metabolite and tobacco alkaloid: desensitization of nicotinic receptor-stimulated dopamine release from rat striatum.
2001 Sep 28
Fetal and adolescent nicotine administration: effects on CNS serotonergic systems.
2001 Sep 28
[Acute confusional syndrome due to acute nicotine withdrawal].
2002
Molecular orbital calculations and nicotine metabolism: a rationale for experimentally observed metabolite ratios.
2002
Induction of CYP1A1 and CYP1A2 expressions by prototypic and atypical inducers in the human lung.
2002 Apr 8
Mechanisms of cytotoxicity of nicotine in human periodontal ligament fibroblast cultures in vitro.
2002 Aug
The relationship between hippocampal acetylcholine release and cholinergic convulsant sensitivity in withdrawal seizure-prone and withdrawal seizure-resistant selected mouse lines.
2002 Aug
Alcohol and nicotine reduce cell proliferation and enhance apoptosis in dentate gyrus.
2002 Aug 27
Microsomal N-glucuronidation of nicotine and cotinine: human hepatic interindividual, human intertissue, and interspecies hepatic variation.
2002 Dec
Genetic variation in CYP2A6-mediated nicotine metabolism alters smoking behavior.
2002 Feb
Increased sensitivity to nicotine-induced seizures in mice heterozygous for the L250T mutation in the alpha7 nicotinic acetylcholine receptor.
2002 Feb 11
An in vivo pilot study characterizing the new CYP2A6*7, *8, and *10 alleles.
2002 Jan 11
Absence of alpha7-containing neuronal nicotinic acetylcholine receptors does not prevent nicotine-induced seizures.
2002 Jan 31
Enhancement of cocaine-seeking behavior by repeated nicotine exposure in rats.
2002 Jul
Involvement of human heat shock protein 90 alpha in nicotine-induced apoptosis.
2002 Jul 1
The selectively bred high alcohol sensitivity (HAS) and low alcohol sensitivity (LAS) rats differ in sensitivity to nicotine.
2002 Jun
N-n-alkylnicotinium analogs, a novel class of nicotinic receptor antagonist: inhibition of S(-)-nicotine-evoked [(3)H]dopamine overflow from superfused rat striatal slices.
2002 Jun
Increased sensitivity to nicotine-induced seizures in mice expressing the L250T alpha 7 nicotinic acetylcholine receptor mutation.
2002 Mar
Up-regulation of L-type voltage-dependent calcium channels after long term exposure to nicotine in cerebral cortical neurons.
2002 Mar 8
Effects of whole deletion of CYP2A6 on nicotine metabolism in humans.
2002 May
Nicotine potentiation of morphine-induced catalepsy in mice.
2002 May
Genetic polymorphisms in human CYP2A6 gene causing impaired nicotine metabolism.
2002 Nov
Nicotine's oxidative and antioxidant properties in CNS.
2002 Nov 1
CYP2A6 genetic variation and potential consequences.
2002 Nov 18
Lack of CB1 cannabinoid receptors modifies nicotine behavioural responses, but not nicotine abstinence.
2002 Oct
beta 2 nicotinic acetylcholine receptor subunit modulates protective responses to stress: A receptor basis for sleep-disordered breathing after nicotine exposure.
2002 Oct 1
[Review of current etiopathogenic data of Buerger disease].
2002 Sep
N-glucuronidation of nicotine and cotinine in human: formation of cotinine glucuronide in liver microsomes and lack of catalysis by 10 examined UDP-glucuronosyltransferases.
2002 Sep
Lasting effects of adolescent nicotine exposure on the electroencephalogram, event related potentials, and locomotor activity in the rat.
2002 Sep 20
Lobeline attenuates locomotor stimulation induced by repeated nicotine administration in rats.
2003 Jan
Oral caffeine maintenance potentiates the reinforcing and stimulant subjective effects of intravenous nicotine in cigarette smokers.
2003 Jan
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.
2003 Jan 1
A functional role for nicotine in Bcl2 phosphorylation and suppression of apoptosis.
2003 Jan 17
Nicotinic acetylcholine receptors and the regulation of neuronal signalling.
2004 Jun
Nicotine addiction.
2010 Jun 17
How much nicotine kills a human? Tracing back the generally accepted lethal dose to dubious self-experiments in the nineteenth century.
2014 Jan
Patents

Sample Use Guides

Reduces withdrawal symptoms, including nicotine craving associated with quitting smoking, nicotine is available as a chewing gum, and is administered according to a schedule at doses 2-4 mg once every 2-4 hours. Nicotine is also available as a transdermal patch.
Route of Administration: Other
Functional activity of nicotine against hα4β2 nicotinic receptors was evaluated using the 86Rb+ ion flux assay in SH-EP1 cells, expressing hα4β2. The 86Rb+ efflux was measured using the “flip-plate” technique. Nicotine activated 86Rb+ efflux with EC50 of 290 nM.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:47:24 GMT 2025
Edited
by admin
on Mon Mar 31 17:47:24 GMT 2025
Record UNII
6M3C89ZY6R
Record Status Validated (UNII)
Record Version
  • Download
Related Record Type
Name Type Language
NICOTINUM
HPUS  
Preferred Name English
NICOTINE
EP   HSDB   ISO   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
Systematic Name English
NICOTINE [HSDB]
Common Name English
NSC-5065
Code English
Nicotine [WHO-DD]
Common Name English
NICODERM CQ
Brand Name English
NICOTINE [ISO]
Common Name English
NICOTINE [MI]
Common Name English
PYRIDINE, 3-((2S)-1-METHYL-2-PYRROLIDINYL)-
Systematic Name English
NICOTINE [VANDF]
Common Name English
PROSTEP
Brand Name English
3-((2S)-1-METHYLPYRROLIDIN-2-YL)PYRIDINE
Systematic Name English
3-((2S)-1-METHYL-2-PYRROLIDINYL)PYRIDINE
Systematic Name English
HABITROL
Brand Name English
NICOTINE (TPD)
Common Name English
NICOTINE [EP MONOGRAPH]
Common Name English
NICOTINE [USP MONOGRAPH]
Common Name English
NICOTINUM [HPUS]
Common Name English
NICOTINE [ORANGE BOOK]
Common Name English
?-Pyridyl-?-N-methyl pyrrolidine
Common Name English
NICOTINE S(-)
Common Name English
NICOTROL
Brand Name English
NICOTINE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C221
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
LIVERTOX NBK548698
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
WHO-ATC N07BA01
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
NDF-RT N0000175706
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
WHO-VATC QP53AX13
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
WHO-VATC QN07BA01
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
EPA PESTICIDE CODE 56702
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
NDF-RT N0000006496
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
NCI_THESAURUS C73579
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
NDF-RT N0000006496
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
Code System Code Type Description
MESH
D009538
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
RXCUI
7407
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
SMS_ID
100000079991
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
IUPHAR
2585
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
NCI_THESAURUS
C691
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
WIKIPEDIA
Nicotine replacement therapy
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
CHEBI
17688
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
PUBCHEM
89594
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
HSDB
1107
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
WIKIPEDIA
NICOTINE
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
ChEMBL
CHEMBL3
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
DRUG BANK
DB00184
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
EPA CompTox
DTXSID1020930
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
EVMPD
SUB14645MIG
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
LACTMED
Nicotine
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
CAS
54-11-5
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
ALANWOOD
nicotine
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
EVMPD
SUB30160
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
DRUG CENTRAL
1920
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
MERCK INDEX
m7879
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY Merck Index
NSC
5065
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
FDA UNII
6M3C89ZY6R
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-193-3
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
DAILYMED
6M3C89ZY6R
Created by admin on Mon Mar 31 17:47:24 GMT 2025 , Edited by admin on Mon Mar 31 17:47:24 GMT 2025
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
METABOLIC ENZYME -> INHIBITOR
TARGET -> AGONIST
NICOTINE IS AN ANTIHERBIVORY ALKALOID AND POTENT PARASYMPATHOMIMETIC STIMULANT AND FOUND IN PLANTS, MOSTLY THOSE IN THE NIGHTSHADE FAMILY. NICOTINE ACTS AS A RECEPTOR AGONIST AT MOST NICOTINIC ACETYLCHOLINE RECEPTORS (NACHRS), EXCEPT AT TWO NICOTINIC RECEPTOR SUBUNITS (NACHR.ALPHA.9 AND NACHR.ALPHA.10) WHERE IT ACTS AS A RECEPTOR ANTAGONIST.
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
SALT/SOLVATE -> PARENT
DERIVATIVE -> PARENT
Carcinogenic substance present in cigarette smoke
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
VACCINE ANTIGEN->TARGET
TARGET -> INHIBITOR
BINDING
IC50
METABOLIC ENZYME -> SUBSTRATE
SUB_CONCEPT->SUBSTANCE
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
PARENT -> CONSTITUENT ALWAYS PRESENT
Nicotine (mg/cigarette) Domestic = 12.6 SD(1.6) Imported = 11.1 SD(2.2)
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LABELED -> NON-LABELED
INHIBITOR -> TARGET
BINDS TO NICOTINE PREVENTS ACTION
SUB_CONCEPT->SUBSTANCE
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE LESS ACTIVE -> PARENT
75% is converted into cotintine which is further metabolized.
MAJOR
PLASMA; URINE
METABOLITE -> PARENT
circulating nicotine is metabolized to cotinine by cytochrome P450 and aldehyde oxidase
MAJOR
METABOLITE -> PARENT
in animals both N-oxide isomers form, in humans only the transisomers form.
MAJOR
URINE
METABOLITE -> PARENT
The extent of nicotine N-glucuronidation by African Americans is significantly lower than by Whites.
METABOLITE -> PARENT
PLASMA; URINE
METABOLITE -> PARENT
The extent of Cotinine N-glucuronidation by African Americans is significantly lower than by Whites.
METABOLITE INACTIVE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC