NICOTINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H14N2
Molecular Weight	162.2319
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCC[C@@]1([H])c2cccnc2

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	162.2319
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 63 Target ID: CHEMBL1907589 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15528443	Agonist 2451	7.9 null [pKi]
Neuronal acetylcholine receptor; alpha3/beta4 38 Target ID: CHEMBL1907594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22148173	Agonist 2451	260.0 nM [Ki]
Neuronal acetylcholine receptor protein alpha-7 subunit 68 Target ID: CHEMBL2492 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15528443	Agonist 2451	3.0 µM [Ki]
Neuronal acetylcholine receptor; alpha9/alpha10 8 Target ID: CHEMBL2109238 Sources: http://www.guidetopharmacology.org/GRAC/FamilyIntroductionForward?familyId=76	Antagonist 2575
Target ID: Nicotinic acetylcholine receptors Sources: http://www.guidetopharmacology.org/GRAC/FamilyIntroductionForward?familyId=76	Agonist 2451

Conditions

Condition	Modality	Targets	Highest Phase	Product
Nicotine dependence 24 Sources: https://www.drugs.com/pro/equaline-nicotine-lozenge.html	Palliative		Approved 7968	NICORETTE Approved Use Reduces withdrawal symptoms, including nicotine craving associated with quitting smoking Launch Date 4.42713604E11

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

Doses

Dose	Population	Adverse events
6 mg single, oral Highest studied dose Dose: 6 mg Route: oral Route: single Dose: 6 mg Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/	healthy, 19 - 49 years n = 44 Health Status: healthy Condition: adult smokers Age Group: 19 - 49 years Sex: M+F Population Size: 44 Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/	Disc. AE: Bradycardia... AEs leading to discontinuation/dose reduction: Bradycardia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/
4 mg single, oral Studied dose Dose: 4 mg Route: oral Route: single Dose: 4 mg Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/	healthy, 19 - 49 years n = 44 Health Status: healthy Condition: adult smokers Age Group: 19 - 49 years Sex: M+F Population Size: 44 Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/	Disc. AE: Allergic dermatitis... AEs leading to discontinuation/dose reduction: Allergic dermatitis (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/
6 mg 1 times / hour steady, oral Highest studied dose Dose: 6 mg, 1 times / hour Route: oral Route: steady Dose: 6 mg, 1 times / hour Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/	healthy, 19 - 50 years n = 50 Health Status: healthy Condition: adult smokers Age Group: 19 - 50 years Sex: M+F Population Size: 50 Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/	Disc. AE: Hypersensitivity, Nausea... AEs leading to discontinuation/dose reduction: Hypersensitivity (1 patient) Nausea (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/
8 mg 1 times / hour steady, oral Highest studied dose Dose: 8 mg, 1 times / hour Route: oral Route: steady Dose: 8 mg, 1 times / hour Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/	healthy, 19 - 50 years n = 50 Health Status: healthy Condition: adult smokers Age Group: 19 - 50 years Sex: M+F Population Size: 50 Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/	Disc. AE: Depression, Nausea... AEs leading to discontinuation/dose reduction: Depression (1 patient) Nausea (grade 2-3, 2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/
111 mg single, transdermal Overdose Dose: 111 mg Route: transdermal Route: single Dose: 111 mg Sources: https://pubmed.ncbi.nlm.nih.gov/32146302/	healthy, 41 years n = 1 Health Status: healthy Condition: adult smoker Age Group: 41 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/32146302/	Disc. AE: Death... AEs leading to discontinuation/dose reduction: Death (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/32146302/
84 mg 1 times / day steady, transdermal Highest studied dose Dose: 84 mg, 1 times / day Route: transdermal Route: steady Dose: 84 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30370685/	healthy, adult n = 36 Health Status: healthy Condition: adult smokers Age Group: adult Sex: unknown Population Size: 36 Sources: https://pubmed.ncbi.nlm.nih.gov/30370685/	Other AEs: Nausea... Other AEs: Nausea Sources: https://pubmed.ncbi.nlm.nih.gov/30370685/

AEs

AE	Significance	Dose	Population
Bradycardia	1 patient Disc. AE	6 mg single, oral Highest studied dose Dose: 6 mg Route: oral Route: single Dose: 6 mg Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/	healthy, 19 - 49 years n = 44 Health Status: healthy Condition: adult smokers Age Group: 19 - 49 years Sex: M+F Population Size: 44 Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/
Allergic dermatitis	1 patient Disc. AE	4 mg single, oral Studied dose Dose: 4 mg Route: oral Route: single Dose: 4 mg Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/	healthy, 19 - 49 years n = 44 Health Status: healthy Condition: adult smokers Age Group: 19 - 49 years Sex: M+F Population Size: 44 Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/
Hypersensitivity	1 patient Disc. AE	6 mg 1 times / hour steady, oral Highest studied dose Dose: 6 mg, 1 times / hour Route: oral Route: steady Dose: 6 mg, 1 times / hour Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/	healthy, 19 - 50 years n = 50 Health Status: healthy Condition: adult smokers Age Group: 19 - 50 years Sex: M+F Population Size: 50 Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/
Nausea	1 patient Disc. AE	6 mg 1 times / hour steady, oral Highest studied dose Dose: 6 mg, 1 times / hour Route: oral Route: steady Dose: 6 mg, 1 times / hour Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/	healthy, 19 - 50 years n = 50 Health Status: healthy Condition: adult smokers Age Group: 19 - 50 years Sex: M+F Population Size: 50 Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/
Depression	1 patient Disc. AE	8 mg 1 times / hour steady, oral Highest studied dose Dose: 8 mg, 1 times / hour Route: oral Route: steady Dose: 8 mg, 1 times / hour Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/	healthy, 19 - 50 years n = 50 Health Status: healthy Condition: adult smokers Age Group: 19 - 50 years Sex: M+F Population Size: 50 Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/
Nausea	grade 2-3, 2 patients Disc. AE	8 mg 1 times / hour steady, oral Highest studied dose Dose: 8 mg, 1 times / hour Route: oral Route: steady Dose: 8 mg, 1 times / hour Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/	healthy, 19 - 50 years n = 50 Health Status: healthy Condition: adult smokers Age Group: 19 - 50 years Sex: M+F Population Size: 50 Sources: https://pubmed.ncbi.nlm.nih.gov/27613939/
Death	grade 5, 1 patient Disc. AE	111 mg single, transdermal Overdose Dose: 111 mg Route: transdermal Route: single Dose: 111 mg Sources: https://pubmed.ncbi.nlm.nih.gov/32146302/	healthy, 41 years n = 1 Health Status: healthy Condition: adult smoker Age Group: 41 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/32146302/
Nausea		84 mg 1 times / day steady, transdermal Highest studied dose Dose: 84 mg, 1 times / day Route: transdermal Route: steady Dose: 84 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30370685/	healthy, adult n = 36 Health Status: healthy Condition: adult smokers Age Group: adult Sex: unknown Population Size: 36 Sources: https://pubmed.ncbi.nlm.nih.gov/30370685/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1359

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 473 OCT2 582 OCT3 139 OCTN1 28 OCTN2 66	CYP2A6 452 UGT2B10 111 UGT2B17 184 UGT1A4 294 FMO3 49 CYP2A13 11 CYP2B6 575 OCT2 304 UGT1A9 327 MATE1 123	CYP1A2 618 CYP2E1 116

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1406	inducer 1333 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3243019/ Page: -	no
CYP2E1 841	inducer 1333 Sources: https://bpspubs.onlinelibrary.wiley.com/doi/full/10.1111/j.1365-2125.2009.03568.x Page: -	yes
OCT1 488	inhibitor 2612 Sources: https://www.sciencedirect.com/science/article/pii/S0197018612003877 Page: -	yes
OCT2 583	inhibitor 2612 Sources: https://www.sciencedirect.com/science/article/pii/S0197018612003877 Page: -	yes
OCT3 139	inhibitor 2612 Sources: https://www.sciencedirect.com/science/article/pii/S0197018612003877 Page: -	yes
OCTN1 28	inhibitor 2612 Sources: https://www.sciencedirect.com/science/article/pii/S0197018612003877 Page: -	yes
OCTN2 71	inhibitor 2612 Sources: https://www.sciencedirect.com/science/article/pii/S0197018612003877 Page: -	yes

Drug as victim

Target	Modality	Activity
CYP2A13 11	substrate 2751 Sources: https://link.springer.com/chapter/10.1007/978-3-540-69248-5_2 Page: 245.0	minor
CYP2B6 575	substrate 2751 Sources: https://link.springer.com/chapter/10.1007/978-3-540-69248-5_2 Page: 245.0	minor
UGT1A9 327	substrate 2751 Sources: https://molpharm.aspetjournals.org/content/72/3/761 Page: -	no
CYP2A6 452	substrate 2751 Sources: https://ascpt.onlinelibrary.wiley.com/doi/full/10.1016/j.clpt.2004.02.011 Page: -	yes
FMO3 49	substrate 2751 Sources: https://link.springer.com/chapter/10.1007/978-3-540-69248-5_2 Page: 245.0	yes
MATE1 123	substrate 2751 Sources: https://www.sciencedirect.com/science/article/pii/S0197018612003877 Page: -	yes
OCT2 304	substrate 2751 Sources: https://link.springer.com/chapter/10.1007/978-3-540-69248-5_2 Page: 60.0	yes
UGT1A4 294	substrate 2751 Sources: https://pubmed.ncbi.nlm.nih.gov/17909004/ Page: -	yes
UGT2B10 111	substrate 2751 Sources: https://pubmed.ncbi.nlm.nih.gov/20876810/ Page: -	yes
UGT2B17 184	substrate 2751 Sources: https://pubmed.ncbi.nlm.nih.gov/20876810/ Page: -	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1391	inhibitor 1373 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
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
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	AC181425000	https://www.fishersci.com/shop/products/l-nicotine-99-acros-organics-3/AC181425000
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
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	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
Avantor Inc	75835-322	https://us.vwr.com/store/product/21998648/exempted-drug-of-abuse-reference-standards-restek
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
BLD Pharm	BD01315752	http://www.bldpharm.com/products/104062-50-2.html
BioSynth	J-500021	https://www.biosynth.com/en/products/all-products/products/J-500021.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
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
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
OChem	4370	http://www.ocheminc.com/index.php?act=psearch&pid=006N369
Oakwood	241305	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=122304&ExtHyperLink=1
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	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	N5511_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/n5511?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
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
abcr GmbH	AB118155	http://www.abcr.com/shop/en/AB118155
eNovation Chemicals	D659532	https://www.enovationchem.com/ProductDetails.asp?ProductID=D659532
mcule	MCULE-8728421654	https://mcule.com/MCULE-8728421654/

PubMed

Title	Date	PubMed
Modulation of phosphatidylinositol turnover on central nicotinic receptors.	1997 Jul	10072918
Nicotine potentiates sulpiride-induced catalepsy in mice.	1998	10958255
Ginseng total saponin inhibits nicotine-induced hyperactivity and conditioned place preference in mice.	1999 Jul	10432212
Predictors and timing of adverse experiences during trandsdermal nicotine therapy.	1999 Jun	10392670
Selective alpha 7 nicotinic receptor stimulation normalizes chronic cocaine-induced loss of hippocampal sensory inhibition in C3H mice.	1999 Nov 15	10578459
Mimicking gene defects to treat drug dependence.	2000	10911933
Analgesic and toxic effects of ABT-594 resemble epibatidine and nicotine in rats.	2000 Apr	10781917
Transdermal nicotine mimics the smoking-induced endothelial dysfunction.	2000 Aug	10976548
Deficient cotinine formation from nicotine is attributed to the whole deletion of the CYP2A6 gene in humans.	2000 Jan	10668854
Regional and cellular induction of nicotine-metabolizing CYP2B1 in rat brain by chronic nicotine treatment.	2000 Jun 15	10799646
[A comparative study of the central H-cholinergic-blocking and NMDA-blocking actions of MK-801, memantin, amantadine, pyrilen and IEM-1754 in experiments on intact rats].	2000 Mar-Apr	10834088
Kynurenic acid does not protect against nicotine-induced seizures in mice.	2000 Nov-Dec	11334243
Prenatal nicotine exposure is associated with an increase in [125I]epibatidine binding in discrete cortical regions in rats.	2000 Oct	11124396
Duplications and defects in the CYP2A6 gene: identification, genotyping, and in vivo effects on smoking.	2000 Oct	10999944
Evidence that nicotinic alpha(7) receptors are not involved in the hyperlocomotor and rewarding effects of nicotine.	2000 Sep	10945867
Effect of nicotine on fibroblast beta 1 integrin expression and distribution in vitro.	2001 Apr	11338295
Nicotine inhibits UV-induced activation of the apoptotic pathway.	2001 Dec 15	11701223
Tolerance to nicotine's effects in the elevated plus-maze and increased anxiety during withdrawal.	2001 Feb	11267637
Nicotine self-administration and withdrawal: modulation of anxiety in the social interaction test in rats.	2001 Jan	11271403
Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro.	2001 Jun	11353760
Reversal of diminished inhibitory sensory gating in cocaine addicts by a nicotinic cholinergic mechanism.	2001 Jun	11331147
Smoking and balance: correlation of nicotine-induced nystagmus and postural body sway.	2001 May 8	11338195
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
Activation of 5-HT(2C) receptors reduces the locomotor and rewarding effects of nicotine.	2001 Sep	11605085
Microsomal N-glucuronidation of nicotine and cotinine: human hepatic interindividual, human intertissue, and interspecies hepatic variation.	2002 Dec	12433822
Increased sensitivity to nicotine-induced seizures in mice heterozygous for the L250T mutation in the alpha7 nicotinic acetylcholine receptor.	2002 Feb 11	11893908
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
Nicotine potentiation of morphine-induced catalepsy in mice.	2002 May	11900788
Genetic polymorphisms in human CYP2A6 gene causing impaired nicotine metabolism.	2002 Nov	12445030
CYP2A6 genetic variation and potential consequences.	2002 Nov 18	12406643
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
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
Oral caffeine maintenance potentiates the reinforcing and stimulant subjective effects of intravenous nicotine in cigarette smokers.	2003 Jan	12434259
Nicotinic acetylcholine receptors and the regulation of neuronal signalling.	2004 Jun	15165747
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 `Fri Jun 25 20:58:06 UTC 2021` Edited by `admin` on `Fri Jun 25 20:58:06 UTC 2021`
Record UNII	6M3C89ZY6R
Record Status	`Validated (UNII)`
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Systematic Name

English

3-((2S)-1-METHYL-2-PYRROLIDINYL)PYRIDINE

Systematic Name

English

HABITROL

Brand Name

English

NICOTINUM

Common Name

English

NICOTINE COMPONENT OF COMMIT

Brand Name

English

NICOTINE [EP MONOGRAPH]

Common Name

English

NICOTINE [USP MONOGRAPH]

Common Name

English

NICOTINE [WHO-DD]

Common Name

English

NICOTINUM [HPUS]

Common Name

English

NICOTINE [ORANGE BOOK]

Common Name

English

NICOTINE COMPONENT OF NICORETTE

Brand Name

English

.BETA.-PYRIDYL-.ALPHA.-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 Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

LIVERTOX

683

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

WHO-ATC

N07BA01

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

NDF-RT

N0000175706

Created by admin on Fri Jun 25 20:58:07 UTC 2021 , Edited by admin on Fri Jun 25 20:58:07 UTC 2021

WHO-VATC

QP53AX13

Created by admin on Fri Jun 25 20:58:07 UTC 2021 , Edited by admin on Fri Jun 25 20:58:07 UTC 2021

WHO-VATC

QN07BA01

Created by admin on Fri Jun 25 20:58:07 UTC 2021 , Edited by admin on Fri Jun 25 20:58:07 UTC 2021

EPA PESTICIDE CODE

56702

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

NDF-RT

N0000006496

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

NCI_THESAURUS

C73579

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

NDF-RT

N0000006496

Created by admin on Fri Jun 25 20:58:07 UTC 2021 , Edited by admin on Fri Jun 25 20:58:07 UTC 2021

Code System Code Type Description

MESH

D009538

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

PRIMARY

RXCUI

7407

Created by admin on Fri Jun 25 20:58:07 UTC 2021 , Edited by admin on Fri Jun 25 20:58:07 UTC 2021

PRIMARY

IUPHAR

2585

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

PRIMARY

NCI_THESAURUS

C691

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

PRIMARY

PUBCHEM

89594

Created by admin on Fri Jun 25 20:58:07 UTC 2021 , Edited by admin on Fri Jun 25 20:58:07 UTC 2021

PRIMARY

HSDB

1107

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

PRIMARY

WIKIPEDIA

NICOTINE

Created by admin on Fri Jun 25 20:58:07 UTC 2021 , Edited by admin on Fri Jun 25 20:58:07 UTC 2021

PRIMARY

ChEMBL

CHEMBL3

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

PRIMARY

DRUG BANK

DB00184

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

PRIMARY

EPA CompTox

54-11-5

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

PRIMARY

EVMPD

SUB14645MIG

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

PRIMARY

LACTMED

Nicotine

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

PRIMARY

CAS

54-11-5

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

PRIMARY

EVMPD

SUB30160

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

PRIMARY

DRUG CENTRAL

1920

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

PRIMARY

MERCK INDEX

M7879

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

PRIMARY

Merck Index

FDA UNII

6M3C89ZY6R

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

PRIMARY

ECHA (EC/EINECS)

200-193-3

Created by admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021

PRIMARY

Related Record Type Details


					6M3C89ZY6R

NICOTINE

BASIS OF STRENGTH->SUBSTANCE

Interaction Type:

ASSAY (TITRATION)

Qualification:

EP

Amount:


					P4J1I8C6CX

NEURONAL ACETYLCHOLINE RECEPTOR SUBUNIT ALPHA-7

TARGET -> AGONIST

Comments:

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.


					6M3C89ZY6R

NICOTINE

BASIS OF STRENGTH->SUBSTANCE

Interaction Type:

ASSAY (TITRATION)

Qualification:

USP

Amount:


					7892ZN5G41

NICOTINE BITARTRATE ANHYDROUS

SALT/SOLVATE -> PARENT


					744Q1CL77H

NICOTINE SALICYLATE

SALT/SOLVATE -> PARENT


					LSV6GBW93D

NICOTINE HEMICITRATE

SALT/SOLVATE -> PARENT


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:


					JZ7JBT2MTT

URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 2B10

METABOLIC ENZYME -> SUBSTRATE


					8E4LAA4357

CYTOCHROME P450 2D6

METABOLIC ENZYME -> SUBSTRATE

NICOTINE BETADEX

SUB_CONCEPT->SUBSTANCE


					F0PHZ04D78

NICOTINE DICITRATE

SALT/SOLVATE -> PARENT


					6YR2608RSU

TOBACCO LEAF

PARENT -> CONSTITUENT ALWAYS PRESENT

Comments:

Nicotine (mg/cigarette) Domestic = 12.6 SD(1.6) Imported = 11.1 SD(2.2)


					UX4GTH155W

NICOTINE SULFATE

SALT/SOLVATE -> PARENT


					I16I55623S

NICOTINE DIHYDROCHLORIDE

SALT/SOLVATE -> PARENT


					246D9TQ2XG

CYTOCHROME P450 2A6

METABOLIC ENZYME -> SUBSTRATE


					R7M676M8YV

NICOTINE BITARTRATE

SALT/SOLVATE -> PARENT


					T397A2CQJ9

NICOTINE C-11

LABELED -> NON-LABELED

NICOTINE POLACRILEX

SUB_CONCEPT->SUBSTANCE

Related Record Type Details


					6V35J35GP5

NICOTINE N'-OXIDE, (1'S,2'S)-

METABOLITE LESS ACTIVE -> PARENT

Comments:

75% is converted into cotintine which is further metabolized.

Interaction Type:

MAJOR

Qualification:

PLASMA; URINE

Amount:


					K5161X06LL

COTININE

METABOLITE -> PARENT

Comments:

circulating nicotine is metabolized to cotinine by cytochrome P450 and aldehyde oxidase

Interaction Type:

MAJOR


					6V35J35GP5

NICOTINE N'-OXIDE, (1'S,2'S)-

METABOLITE -> PARENT

Comments:

in animals both N-oxide isomers form, in humans only the transisomers form.

Interaction Type:

MAJOR

Qualification:

URINE

Amount:


					CB9VB3OLM0

NICOTINE N-GLUCURONIDE

METABOLITE -> PARENT

Comments:

The extent of nicotine N-glucuronidation by African Americans is significantly lower than by Whites.


					H7LH47Y29A

3'-HYDROXYCOTININE, TRANS-

METABOLITE -> PARENT

Qualification:

PLASMA; URINE


					E3PE1559SW

COTININE N-GLUCURONIDE

METABOLITE -> PARENT

Comments:

The extent of Cotinine N-glucuronidation by African Americans is significantly lower than by Whites.


					OL86R2ULD8

BA-2702

METABOLITE INACTIVE -> PARENT

Related Record Type Details


					9O0A545W4L

MYOSMINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					83H6L5QD8Z

NORNICOTINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					K5161X06LL

COTININE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					XN4R1LH79Y

NICOTYRINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					5PP654XB7D

ANATABINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					LMS11II2LO

ANABASINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					9R173T257I

NICOTINE N'-OXIDE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

Related Record Type Details


					6M3C89ZY6R

NICOTINE

ACTIVE MOIETY

Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Biological Half-life	PHARMACOKINETIC

Volume of Distribution	PHARMACOKINETIC

Details

SMILES

InChI

DescriptionSources: www.inchem.org/documents/pims/chemical/nicotine.htmCurator'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/

CNS Activity

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

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/

C_max

T_1/2

F_unbound

Drug as perpetrator