NICOTINE BITARTRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H14N2.2C4H6O6.2H2O
Molecular Weight	498.4358
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.O.O[C@H]([C@@H](O)C(O)=O)C(O)=O.O[C@H]([C@@H](O)C(O)=O)C(O)=O.CN1CCC[C@H]1C2=CN=CC=C2

InChI

InChIKey=LDMPZNTVIGIREC-ZGPNLCEMSA-N

InChI=1S/C10H14N2.2C4H6O6.2H2O/c1-12-7-3-5-10(12)9-4-2-6-11-8-9;2*5-1(3(7)8)2(6)4(9)10;;/h2,4,6,8,10H,3,5,7H2,1H3;2*1-2,5-6H,(H,7,8)(H,9,10);2*1H2/t10-;2*1-,2-;;/m011../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

Molecular Formula	C4H6O6
Molecular Weight	150.0868
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Nicotine potentiates sulpiride-induced catalepsy in mice.	1998	10958255
[Treatment outcome in tobacco dependence after nicotine replacement therapy and group therapy].	1999	10497441
Inducible, heterologous expression of human alpha7-nicotinic acetylcholine receptors in a native nicotinic receptor-null human clonal line.	1999 Apr 17	10216184
Pharmacological characterization of nicotine-induced seizures in mice.	1999 Dec	10565853
Gain of function mutation of the alpha7 nicotinic receptor: distinct pharmacology of the human alpha7V274T variant.	1999 Feb 5	10082212
Antioxidant role of oils isolated from garlic (Allium sativum Linn) and onion (Allium cepa Linn) on nicotine-induced lipid peroxidation.	1999 Oct	10509436
Chronic nicotine pretreatment protects the blood-brain barrier against nicotine-induced seizures in the rat.	1999 Sep	10479471
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
Potential role of the alpha4 and alpha6 nicotinic receptor subunits in regulating nicotine-induced seizures.	2000 Apr	10734154
Transdermal nicotine mimics the smoking-induced endothelial dysfunction.	2000 Aug	10976548
Genetic and pharmacological strategies identify a behavioral function of neuronal nicotinic receptors.	2000 Aug	10942032
Dermal exposure to pesticides modifies antioxidant enzymes in tissues of rats.	2000 Jul	10874619
Antioxidant effect of onion oil (Allium cepa. Linn) on the damages induced by nicotine in rats as compared to alpha-tocopherol.	2000 Jul 27	10906423
Nicotinic receptor function: new perspectives from knockout mice.	2000 Jun	10838608
Nicotine switches the form of H(2)O(2)-induced cell death from apoptosis to necrosis in U937 cells.	2000 Jun 1	10880836
An animal model of adolescent nicotine exposure: effects on gene expression and macromolecular constituents in rat brain regions.	2000 Jun 9	10837795
Neurobiological mechanisms by which nicotine mediates different types of anxiety.	2000 Mar 30	10771018
[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
Abstinence effects and reactivity to nicotine during 11 days of smoking deprivation.	2000 May	11072453
Enhancement of haloperidol-induced catalepsy by nicotine: an investigation of possible mechanisms.	2000 Nov	11100936
Involvement of 5-hydroxytryptamine(1A) receptors in nicotine-induced tail tremor in rats.	2000 Nov 10	11070179
Nicotine-induced nystagmus: three-dimensional analysis and dependence on head position.	2000 Nov 28	11094116
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
Nicotine is a potent blocker of the cardiac A-type K(+) channels. Effects on cloned Kv4.3 channels and native transient outward current.	2000 Sep 5	10973847
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
Variable CYP2A6-mediated nicotine metabolism alters smoking behavior and risk.	2001 Apr	11259349
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
Relationship between interindividual differences in nicotine metabolism and CYP2A6 genetic polymorphism in humans.	2001 Jan	11180041
A novel single nucleotide polymorphism altering stability and activity of CYP2a6.	2001 Mar 2	11237731
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
Nornicotine, a nicotine metabolite and tobacco alkaloid: desensitization of nicotinic receptor-stimulated dopamine release from rat striatum.	2001 Sep 28	11779039
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
Increased sensitivity to nicotine-induced seizures in mice heterozygous for the L250T mutation in the alpha7 nicotinic acetylcholine receptor.	2002 Feb 11	11893908
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
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
Lobeline attenuates locomotor stimulation induced by repeated nicotine administration in rats.	2003 Jan	12479946
A functional role for nicotine in Bcl2 phosphorylation and suppression of apoptosis.	2003 Jan 17	12421819

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 23:54:08 UTC 2023` Edited by `admin` on `Wed Jul 05 23:54:08 UTC 2023`
Record UNII	R7M676M8YV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NICOTINE BITARTRATE

Official Name

English

NICOTINE (AS BITARTRATE)

Common Name

English

Nicotine bitartrate dihydrate [WHO-DD]

Common Name

English

NICOTINE DITARTRATE DIHYDRATE

Systematic Name

English

NICOTINE BITARTRATE [USAN]

Common Name

English

3-((2S)-1-METHYL-2-PYRROLIDINYL)PYRIDINE, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE (1:2), DIHYDRATE

Common Name

English

NICOTINE BITARTRATE DIHYDRATE

Systematic Name

English

NICOTINE DITARTRATE DIHYDRATE [EP MONOGRAPH]

Common Name

English

Nicotine bitartrate [WHO-DD]

Common Name

English

NICOTINE DITARTRATE DIHYDRATE [EP IMPURITY]

Common Name

English

NICOTINE ACID TARTRATE DIHYDRATE

Common Name

English

PYRIDINE, 3-((2S)-1-METHYL-2-PYRROLIDINYL)-, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE, HYDRATE (1:2:2)

Systematic Name

English

Code System Code Type Description

NCI_THESAURUS

C170219