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=CN=CC=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 75 Target ID: CHEMBL1907589 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15528443	Agonist 2662	7.9 null [pKi]
Neuronal acetylcholine receptor; alpha3/beta4 39 Target ID: CHEMBL1907594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22148173	Agonist 2662	260.0 nM [Ki]
Neuronal acetylcholine receptor protein alpha-7 subunit 77 Target ID: CHEMBL2492 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15528443	Agonist 2662	3.0 µM [Ki]
Neuronal acetylcholine receptor; alpha9/alpha10 7 Target ID: CHEMBL2109238 Sources: http://www.guidetopharmacology.org/GRAC/FamilyIntroductionForward?familyId=76	Antagonist 2760
Target ID: Nicotinic acetylcholine receptors Sources: http://www.guidetopharmacology.org/GRAC/FamilyIntroductionForward?familyId=76	Agonist 2662

Conditions

Condition	Modality	Targets	Highest Phase	Product
Nicotine dependence 32 Sources: https://www.drugs.com/pro/equaline-nicotine-lozenge.html	Palliative		Approved 8360	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 1599

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 506 OCT2 638 OCT3 149 OCTN1 29 OCTN2 66	CYP2A6 523 UGT2B10 127 UGT2B17 213 UGT1A4 347 FMO3 66 CYP2A13 12 CYP2B6 660 OCT2 348 UGT1A9 380 MATE1 132	CYP1A2 689 CYP2E1 126

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1673	inducer 1542 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3243019/ Page: -	no
CYP2E1 964	inducer 1542 Sources: https://bpspubs.onlinelibrary.wiley.com/doi/full/10.1111/j.1365-2125.2009.03568.x Page: -	yes
OCT1 523	inhibitor 3240 Sources: https://www.sciencedirect.com/science/article/pii/S0197018612003877 Page: -	yes
OCT2 639	inhibitor 3240 Sources: https://www.sciencedirect.com/science/article/pii/S0197018612003877 Page: -	yes
OCT3 149	inhibitor 3240 Sources: https://www.sciencedirect.com/science/article/pii/S0197018612003877 Page: -	yes
OCTN1 29	inhibitor 3240 Sources: https://www.sciencedirect.com/science/article/pii/S0197018612003877 Page: -	yes
OCTN2 71	inhibitor 3240 Sources: https://www.sciencedirect.com/science/article/pii/S0197018612003877 Page: -	yes

Drug as victim

Target	Modality	Activity
CYP2A13 12	substrate 3326 Sources: https://link.springer.com/chapter/10.1007/978-3-540-69248-5_2 Page: 245.0	minor
CYP2B6 660	substrate 3326 Sources: https://link.springer.com/chapter/10.1007/978-3-540-69248-5_2 Page: 245.0	minor
UGT1A9 380	substrate 3326 Sources: https://molpharm.aspetjournals.org/content/72/3/761 Page: -	no
CYP2A6 523	substrate 3326 Sources: https://ascpt.onlinelibrary.wiley.com/doi/full/10.1016/j.clpt.2004.02.011 Page: -	yes
FMO3 66	substrate 3326 Sources: https://link.springer.com/chapter/10.1007/978-3-540-69248-5_2 Page: 245.0	yes
MATE1 132	substrate 3326 Sources: https://www.sciencedirect.com/science/article/pii/S0197018612003877 Page: -	yes
OCT2 348	substrate 3326 Sources: https://link.springer.com/chapter/10.1007/978-3-540-69248-5_2 Page: 60.0	yes
UGT1A4 347	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/17909004/ Page: -	yes
UGT2B10 127	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/20876810/ Page: -	yes
UGT2B17 213	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/20876810/ Page: -	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1632	inhibitor 1613 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
Cow's urine poisoning in Nigeria. Experimental observations in mice.	1975 Jun	1179485
Enhancement of haloperidol-induced catalepsy by nicotine: an investigation of possible mechanisms.	2000 Nov	11100936
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
Effects of nicotine on the intervertebral disc: an experimental study in rabbits.	2001	11484105
Chronic nicotine exposure reduces N-methyl-D-aspartate receptor-mediated damage in the hippocampus without altering calcium accumulation or extrusion: evidence of calbindin-D28K overexpression.	2001	11226671
Effect of nicotine on fibroblast beta 1 integrin expression and distribution in vitro.	2001 Apr	11338295
Variable CYP2A6-mediated nicotine metabolism alters smoking behavior and risk.	2001 Apr	11259349
Formation of the quaternary ammonium-linked glucuronide of nicotine in human liver microsomes: identification and stereoselectivity in the kinetics.	2001 Dec	11717169
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 induced changes in gene expression by human coronary artery endothelial cells.	2001 Feb 1	11166759
Nicotine self-administration and withdrawal: modulation of anxiety in the social interaction test in rats.	2001 Jan	11271403
Relationship between interindividual differences in nicotine metabolism and CYP2A6 genetic polymorphism in humans.	2001 Jan	11180041
Cardiovascular effects of transdermal nicotine in mildly hypertensive smokers.	2001 Jul	11465642
Nicotine produces selective degeneration in the medial habenula and fasciculus retroflexus.	2001 Jul 6	11430869
Nicotine metabolism and CYP2A6 allele frequencies in Koreans.	2001 Jun	11434509
Nicotinic regulation of c-fos and osteopontin expression in human-derived osteoblast-like cells and human trabecular bone organ culture.	2001 Jun	11425648
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
An immunotherapeutic program for the treatment of nicotine addiction: hapten design and synthesis.	2001 Jun 15	11397142
A novel single nucleotide polymorphism altering stability and activity of CYP2a6.	2001 Mar 2	11237731
Inhibition of nicotine-induced seizures in rats by combining vaccination against nicotine with chronic nicotine infusion.	2001 May	11518099
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
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
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
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
Effects of whole deletion of CYP2A6 on nicotine metabolism in humans.	2002 May	12024803
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
Lasting effects of adolescent nicotine exposure on the electroencephalogram, event related potentials, and locomotor activity in the rat.	2002 Sep 20	12234654
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 `Wed Jul 05 22:39:31 UTC 2023` Edited by `admin` on `Wed Jul 05 22:39:31 UTC 2023`
Record UNII	6M3C89ZY6R
Record Status	`Validated (UNII)`
Record Version

Download

Related Record	Type

Name

Type

Language

NICOTINE

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

NICOTINUM

Common Name

English

NICOTINE COMPONENT OF COMMIT

Brand 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

NICOTINE COMPONENT OF NICORETTE

Brand Name

English

β-Pyridyl-α-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