NICOTINE

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 Search

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.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Neuronal acetylcholine receptor; alpha4/beta2 77 Target ID: CHEMBL1907589 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15528443	Agonist 2752	7.9 null [pKi]
Neuronal acetylcholine receptor; alpha3/beta4 40 Target ID: CHEMBL1907594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22148173	Agonist 2752	260.0 nM [Ki]
Neuronal acetylcholine receptor protein alpha-7 subunit 78 Target ID: CHEMBL2492 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15528443	Agonist 2752	3.0 µM [Ki]
Neuronal acetylcholine receptor; alpha9/alpha10 7 Target ID: CHEMBL2109238 Sources: http://www.guidetopharmacology.org/GRAC/FamilyIntroductionForward?familyId=76	Antagonist 2849
Nicotinic acetylcholine receptors 17 Target ID: Nicotinic acetylcholine receptors Sources: http://www.guidetopharmacology.org/GRAC/FamilyIntroductionForward?familyId=76	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Nicotine dependence 33 Sources: https://www.drugs.com/pro/equaline-nicotine-lozenge.html	Palliative		Approved 8583	NICORETTE Approved Use Reduces withdrawal symptoms, including nicotine craving associated with quitting smoking Launch Date 1984

C_max

Value	Dose	Co-administered	Analyte	Population
12 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020385s011lbl.pdf	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

Value	Dose	Co-administered	Analyte	Population
6 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020385s011lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 min DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020385s011lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
95% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020385s011lbl.pdf	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

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 620 OCT2 779 OCT3 159 OCTN1 32 OCTN2 71	CYP2A6 626 UGT2B10 131 UGT2B17 237 UGT1A4 399 FMO3 77 CYP2A13 12 CYP2B6 776 OCT2 434 UGT1A9 423 MATE1 182	CYP1A2 832 CYP2E1 131

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inducer 1966 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3243019/ Page: -	no
CYP2E1 1146	inducer 1966 Sources: https://bpspubs.onlinelibrary.wiley.com/doi/full/10.1111/j.1365-2125.2009.03568.x Page: -	yes
OCT1 656	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/pii/S0197018612003877 Page: -	yes
OCT2 782	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/pii/S0197018612003877 Page: -	yes
OCT3 161	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/pii/S0197018612003877 Page: -	yes
OCTN1 32	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/pii/S0197018612003877 Page: -	yes
OCTN2 71	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/pii/S0197018612003877 Page: -	yes

Drug as victim

Target	Modality	Activity
CYP2A13 12	substrate 4014 Sources: https://link.springer.com/chapter/10.1007/978-3-540-69248-5_2 Page: 245.0	minor
CYP2B6 776	substrate 4014 Sources: https://link.springer.com/chapter/10.1007/978-3-540-69248-5_2 Page: 245.0	minor
UGT1A9 423	substrate 4014 Sources: https://molpharm.aspetjournals.org/content/72/3/761 Page: -	no
CYP2A6 626	substrate 4014 Sources: https://ascpt.onlinelibrary.wiley.com/doi/full/10.1016/j.clpt.2004.02.011 Page: -	yes
FMO3 77	substrate 4014 Sources: https://link.springer.com/chapter/10.1007/978-3-540-69248-5_2 Page: 245.0	yes
MATE1 182	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S0197018612003877 Page: -	yes
OCT2 434	substrate 4014 Sources: https://link.springer.com/chapter/10.1007/978-3-540-69248-5_2 Page: 60.0	yes
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17909004/ Page: -	yes
UGT2B10 131	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20876810/ Page: -	yes
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20876810/ Page: -	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://journals.physiology.org/doi/full/10.1152/ajpheart.1999.277.3.H1081 Page: -

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-1634	http://www.3bsc.com/index/pro_info.php?id=55353
AA Blocks	AA018PRG	https://www.aablocks.com/goods/Goods/detail?id=AA018PRG
abcr GmbH	AB118155	http://www.abcr.com/shop/en/AB118155
AbMole Bioscience	M5749	http://www.abmole.com/products/l-nicotine.html
Achemtek	0102-025835	http://www.achemtek.com/54-11-5
Acorn PharmaTech	ACN-047159	http://www.acornpharmatech.com/
Acros Organics	AC181420050	https://www.fishersci.com/shop/products/l-nicotine-99-acros-organics/AC181420050
Acros Organics	AC181420250	https://www.fishersci.com/shop/products/l-nicotine-99-acros-organics/AC181420250
Acros Organics	AC181421000	https://www.fishersci.com/shop/products/l-nicotine-99-acros-organics/AC181421000
Acros Organics	AC181425000	https://www.fishersci.com/shop/products/l-nicotine-99-acros-organics-3/AC181425000
AHH Chemical co.,ltd	MT-00062	http://www.ahhchemical.com/product/MT-00062.html
AHH Chemical co.,ltd	NP-1207	http://www.ahhchemical.com/product/NP-1207.html
Alfa Aesar	A12398	https://www.alfa.com/en/catalog/A12398/
Alfa Chemistry	284685-07-0	https://www.alfa-chemistry.com/cas_284685-07-0.htm
Alfa Chemistry	ACM54115	https://www.alfa-chemistry.com/nicotine-cas-54-11-5-item-1430.htm
Angene	AGN-PC-0JKDO3	http://www.angenechemical.com/productshow/AGN-PC-0JKDO3.html
Angene	AGN-PC-0O89FM	http://www.angenechemical.com/productshow/AGN-PC-0O89FM.html
ApexBio Technology	A8482	http://www.apexbt.com/nicotine-difartrate.html
Aurora Fine Chemicals LLC	A13.139.618	http://online.aurorafinechemicals.com/info?ID=A13.139.618
Avantor Inc	200006-856	https://us.vwr.com/store/product/7516631/s-nicotine
Avantor Inc	200006-858	https://us.vwr.com/store/product/7516631/s-nicotine
Avantor Inc	75835-322	https://us.vwr.com/store/product/21998648/exempted-drug-of-abuse-reference-standards-restek
Avantor Inc	BT130705-100G	https://us.vwr.com/store/product/16900436/s-nicotine-99
Avantor Inc	BT130705-25G	https://us.vwr.com/store/product/16900436/s-nicotine-99
BioSynth	J-500021	https://www.biosynth.com/en/products/all-products/products/J-500021.html
BLD Pharm	BD01315752	http://www.bldpharm.com/products/104062-50-2.html
Chem Scene	CS-3999	http://www.chemscene.com/54-11-5.html
ChemFaces	CFN99512	http://www.chemfaces.com/natural/L-Nicotine-CFN99512.html
ChemMol	97600113	http://www.chemmol.com/chemmol/97600113.html
ChemMol	99102363	http://www.chemmol.com/chemmol/99102363.html
Chemspace	CSSS00015193816	https://chem-space.com/CSSS00015193816
DC Chemicals	DCY-181	http://www.dcchemicals.com//product_show-L_Nicotine.html
Enamine	Z1954805269	https://www.enaminestore.com/catalog/Z1954805269
eNovation Chemicals	D659532	https://www.enovationchem.com/ProductDetails.asp?ProductID=D659532
Glentham Life Sciences	GK9991	http://www.glentham.com/products/product/GK9991/
Hairui	HR132183	http://www.hairuichem.com/en/product/25013-16-5.html
LGC Standards	DRE-A15520000ME-1000	https://www.lgcstandards.com/US/en/p/DRE-A15520000ME-1000
LGC Standards	DRE-CA15520000	https://www.lgcstandards.com/US/en/p/DRE-CA15520000
LGC Standards	DRE-CR15520000	https://www.lgcstandards.com/US/en/p/DRE-CR15520000
LGC Standards	DRE-L15520000ME	https://www.lgcstandards.com/US/en/p/DRE-L15520000ME
LGC Standards	DRE-XA15520000ME	https://www.lgcstandards.com/US/en/p/DRE-XA15520000ME
Matrix Scientific	153938	https://www.matrixscientific.com/153938.html
mcule	MCULE-8728421654	https://mcule.com/MCULE-8728421654/
MedChem Express	HY-B0638	http://www.medchemexpress.com/L-Nicotine.html
MuseChem	I000016	https://www.musechem.com/product/I000016.html
MuseChem	M122880	https://www.musechem.com/product/M122880.html
Oakwood	241305	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=122304&ExtHyperLink=1
OChem	4370	http://www.ocheminc.com/index.php?act=psearch&pid=006N369
Sigma-Aldrich	36733_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/36733?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	46343_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/46343?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	N-008_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/n008?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	N3876_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/n3876?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	N5511_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/n5511?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S537179	http://www.smolecule.com/products/s537179
Smolecule	S750181	https://www.smolecule.com/products/s750181
Synblock Inc	SB12751	http://www.synblock.com/product/54-11-5.html
TCI (Tokyo Chemical Industry)	N0079	http://www.tcichemicals.com/eshop/en/us/commodity/N0079/index.html
THE BioTek	bt-277084	https://www.thebiotek.com/product/inhibitors/bt-277084
VladaChem	VL143555	https://www.vladachem.com/product.php?products=54-11-5
Yuhao Chemical	LQ0003	http://www.chemyuhao.com/54-11-5.html

PubMed

Title	Date	PubMed
Cow's urine poisoning in Nigeria. Experimental observations in mice.	1975 Jun	1179485
Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior.	2000 Oct	11006350
Effects of nicotine on the intervertebral disc: an experimental study in rabbits.	2001	11484105
Formation of the quaternary ammonium-linked glucuronide of nicotine in human liver microsomes: identification and stereoselectivity in the kinetics.	2001 Dec	11717169
Contributory role for nornicotine in nicotine neuropharmacology: nornicotine-evoked [3H]dopamine overflow from rat nucleus accumbens slices.	2001 Dec 15	11755112
Nicotine inhibits UV-induced activation of the apoptotic pathway.	2001 Dec 15	11701223
Inhibition of nicotine-induced seizures in rats by combining vaccination against nicotine with chronic nicotine infusion.	2001 May	11518099
Comparison of cytochrome P450 2A6 polymorphism frequencies in Caucasians and African-Americans using a new one-step PCR-RFLP genotyping method.	2001 Nov 30	11684323
Chronic ethanol and nicotine interaction on rat tissue antioxidant defense system.	2001 Oct	11747978
Nicotine affects the signaling of the death pathway, reducing the response of head and neck cancer cell lines to DNA damaging agents.	2001 Oct	11592233
Nicotine induced seizures blocked by mecamylamine and its stereoisomers.	2001 Oct 19	11712662
Activation of 5-HT(2C) receptors reduces the locomotor and rewarding effects of nicotine.	2001 Sep	11605085
Acute myocardial infarction soon after nicotine replacement therapy.	2001 Sep	11528015
Efficient enantiomeric synthesis of pyrrolidine and piperidine alkaloids from tobacco.	2001 Sep 21	11559179
Nornicotine, a nicotine metabolite and tobacco alkaloid: desensitization of nicotinic receptor-stimulated dopamine release from rat striatum.	2001 Sep 28	11779039
Fetal and adolescent nicotine administration: effects on CNS serotonergic systems.	2001 Sep 28	11578609
[Acute confusional syndrome due to acute nicotine withdrawal].	2002	12325491
Molecular orbital calculations and nicotine metabolism: a rationale for experimentally observed metabolite ratios.	2002	12222752
Induction of CYP1A1 and CYP1A2 expressions by prototypic and atypical inducers in the human lung.	2002 Apr 8	11849738
Mechanisms of cytotoxicity of nicotine in human periodontal ligament fibroblast cultures in vitro.	2002 Aug	12200972
The relationship between hippocampal acetylcholine release and cholinergic convulsant sensitivity in withdrawal seizure-prone and withdrawal seizure-resistant selected mouse lines.	2002 Aug	12198388
Alcohol and nicotine reduce cell proliferation and enhance apoptosis in dentate gyrus.	2002 Aug 27	12218695
Microsomal N-glucuronidation of nicotine and cotinine: human hepatic interindividual, human intertissue, and interspecies hepatic variation.	2002 Dec	12433822
Genetic variation in CYP2A6-mediated nicotine metabolism alters smoking behavior.	2002 Feb	11805739
Increased sensitivity to nicotine-induced seizures in mice heterozygous for the L250T mutation in the alpha7 nicotinic acetylcholine receptor.	2002 Feb 11	11893908
An in vivo pilot study characterizing the new CYP2A67, 8, and *10 alleles.	2002 Jan 11	11779172
Absence of alpha7-containing neuronal nicotinic acetylcholine receptors does not prevent nicotine-induced seizures.	2002 Jan 31	11834293
Enhancement of cocaine-seeking behavior by repeated nicotine exposure in rats.	2002 Jul	12110995
Involvement of human heat shock protein 90 alpha in nicotine-induced apoptosis.	2002 Jul 1	12115584
The selectively bred high alcohol sensitivity (HAS) and low alcohol sensitivity (LAS) rats differ in sensitivity to nicotine.	2002 Jun	12068243
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	12023541
Increased sensitivity to nicotine-induced seizures in mice expressing the L250T alpha 7 nicotinic acetylcholine receptor mutation.	2002 Mar	11854451
Up-regulation of L-type voltage-dependent calcium channels after long term exposure to nicotine in cerebral cortical neurons.	2002 Mar 8	11756415
Effects of whole deletion of CYP2A6 on nicotine metabolism in humans.	2002 May	12024803
Nicotine potentiation of morphine-induced catalepsy in mice.	2002 May	11900788
Genetic polymorphisms in human CYP2A6 gene causing impaired nicotine metabolism.	2002 Nov	12445030
Nicotine's oxidative and antioxidant properties in CNS.	2002 Nov 1	12377264
CYP2A6 genetic variation and potential consequences.	2002 Nov 18	12406643
Lack of CB1 cannabinoid receptors modifies nicotine behavioural responses, but not nicotine abstinence.	2002 Oct	12384171
beta 2 nicotinic acetylcholine receptor subunit modulates protective responses to stress: A receptor basis for sleep-disordered breathing after nicotine exposure.	2002 Oct 1	12228730
[Review of current etiopathogenic data of Buerger disease].	2002 Sep	12474585
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	12167564
Lasting effects of adolescent nicotine exposure on the electroencephalogram, event related potentials, and locomotor activity in the rat.	2002 Sep 20	12234654
Lobeline attenuates locomotor stimulation induced by repeated nicotine administration in rats.	2003 Jan	12479946
Oral caffeine maintenance potentiates the reinforcing and stimulant subjective effects of intravenous nicotine in cigarette smokers.	2003 Jan	12434259
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.	2003 Jan 1	12464242
A functional role for nicotine in Bcl2 phosphorylation and suppression of apoptosis.	2003 Jan 17	12421819
Nicotinic acetylcholine receptors and the regulation of neuronal signalling.	2004 Jun	15165747
Nicotine addiction.	2010 Jun 17	20554984
How much nicotine kills a human? Tracing back the generally accepted lethal dose to dubious self-experiments in the nineteenth century.	2014 Jan	24091634

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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

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Classification Tree Code System Code

NCI_THESAURUS

C221