Nicotine

Identification

Summary

Nicotine is a stimulatory alkaloid found in tobacco products that is often used for the relief of nicotine withdrawal symptoms and as an aid to smoking cessation.

Brand Names
Habitrol, Nicoderm C-Q, Nicorelief, Nicorette, Nicotrol
Generic Name
Nicotine
DrugBank Accession Number
DB00184
Background

Nicotine is highly toxic alkaloid. It is the prototypical agonist at nicotinic cholinergic receptors where it dramatically stimulates neurons and ultimately blocks synaptic transmission. Nicotine is also important medically because of its presence in tobacco smoke.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 162.2316
Monoisotopic: 162.115698458
Chemical Formula
C10H14N2
Synonyms
  • (−)-nicotine
  • (S)-(−)-nicotine
  • (S)-3-(1-methylpyrrolidin-2-yl)pyridine
  • (S)-3-(N-methylpyrrolidin-2-yl)pyridine
  • (S)-Nicotine
  • 3-(2-(N-methylpyrrolidinyl))pyridine
  • 3-(N-methylpyrollidino)pyridine
  • L(−)-nicotine
  • Nicotina
  • Nicotine
  • Nicotine betadex
  • Nicotine polacrilex
  • Nikotin
  • Nikotyna

Pharmacology

Indication

For the relief of nicotine withdrawal symptoms and as an aid to smoking cessation.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofWithdrawal nicotine•••••••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Nicotine, the primary alkaloid in tobacco products binds stereo-selectively to nicotinic-cholinergic receptors on autonomic ganglia, the adrenal medulla, neuromuscular junctions and in the brain. Nicotine exerts two effects, a stimulant effect exerted at the locus ceruleus and a reward effect in the limbic system. Itranvenous administration of nicotine causes release of acetylcholine, norepinephrine, dopamine, serotonine, vasopressin, beta-endorphin and ACTH. Nicotine is a highly addictive substance. Nicotine also induces peripheral vasoconstriction, tachycardia and elevated blood pressure. Nicotine inhalers and patches are used to treat smoking withdrawl syndrome. Nicotine is classified as a stimulant of autonomic ganglia.

Mechanism of action

Nicotine is a stimulant drug that acts as an agonist at nicotinic acetylcholine receptors. These are ionotropic receptors composed up of five homomeric or heteromeric subunits. In the brain, nicotine binds to nicotinic acetylcholine receptors on dopaminergic neurons in the cortico-limbic pathways. This causes the channel to open and allow conductance of multiple cations including sodium, calcium, and potassium. This leads to depolarization, which activates voltage-gated calcium channels and allows more calcium to enter the axon terminal. Calcium stimulates vesicle trafficking towards the plasma membrane and the release of dopamine into the synapse. Dopamine binding to its receptors is responsible the euphoric and addictive properties of nicotine. Nicotine also binds to nicotinic acetylcholine receptors on the chromaffin cells in the adrenal medulla. Binding opens the ion channel allowing influx of sodium, causing depolarization of the cell, which activates voltage-gated calcium channels. Calcium triggers the release of epinephrine from intracellular vesicles into the bloodstream, which causes vasoconstriction, increased blood pressure, increased heart rate, and increased blood sugar.

TargetActionsOrganism
ANeuronal acetylcholine receptor subunit alpha-4
agonist
Humans
ANeuronal acetylcholine receptor subunit alpha-7
agonist
Humans
ANeuronal acetylcholine receptor subunit beta-2
agonist
Humans
UNeuronal acetylcholine receptor subunit alpha-2
agonist
Humans
UNeuronal acetylcholine receptor subunit alpha-3
agonist
Humans
UNeuronal acetylcholine receptor subunit alpha-5
agonist
Humans
UNeuronal acetylcholine receptor subunit alpha-6
agonist
Humans
UNeuronal acetylcholine receptor subunit alpha-9
agonist
Humans
UNeuronal acetylcholine receptor subunit alpha-10
agonist
Humans
UNeuronal acetylcholine receptor subunit beta-3
agonist
Humans
UNeuronal acetylcholine receptor subunit beta-4
agonist
Humans
UCytochrome P450 19A1
inhibitor
Humans
UCholine O-acetyltransferase
inhibitor
Humans
Absorption

Absorption of nicotine through the buccal mucosa is relatively slow and the high and rapid rise followed by the decline in nicotine arterial plasma concentrations seen with cigarette smoking are not achieved with the inhaler. About 10% of absorbed nicotine is excreted unchanged in urine.

Volume of distribution
  • 2 to 3 L/kg
Protein binding

Less than 5%

Metabolism

Primarily hepatic, cotinine is the primary metabolite.

Hover over products below to view reaction partners

Route of elimination

About 10% of the nicotine absorbed is excreted unchanged in the urine.

Half-life

Cotinine has a half life of 15-20 hours, while nicotine has a half life of 1-3 hours

Clearance
  • 1.2 L/min [healthy adult smoker]
Adverse Effects
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Toxicity

Symptoms of overdose include nausea, abdominal pain, vomiting, diarrhea, diaphoresis, flushing, dizziness, disturbed hearing and vision, confusion, weakness, palpitations, altered respiration and hypotension. LD50= 24 mg/kg (orally in mice).

Pathways
PathwayCategory
Nicotine Action PathwayDrug action
Nicotine Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Nicotine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Nicotine can be increased when combined with Abatacept.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Nicotine.
AcetaminophenNicotine may increase the hepatotoxic activities of Acetaminophen.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Nicotine.
Food Interactions
  • Take separate from meals. For nicotine gum, lozenges, and oral sprays, avoid eating and drinking for 15 minutes before and during its use.

Products

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dosage, form, labeller, route of administration, and marketing period.
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Product Ingredients
IngredientUNIICASInChI Key
Nicotine bitartrate7892ZN5G4165-31-6RFEJUZJILGIRHQ-OMDKHLBYSA-N
Nicotine bitartrate dihydrateR7M676M8YV6019-06-3LDMPZNTVIGIREC-ZGPNLCEMSA-N
Product Images
International/Other Brands
Habitrol / Nicoderm
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Nicorette InvisipatchPatch25 mg / 16 hourTransdermalMcneil Consumer Healthcare Division Of Johnson & Johnson IncNot applicableNot applicableCanada flag
Nicotine PolacrilexPowder200 g/1kgOralNicobrand Ltd.1994-02-012010-12-08US flag
Nicotine PolacrilexPowder150 g/1kgOralNicobrand Ltd.1994-02-012010-12-08US flag
Nicotine PolacrilexPowder180 g/1kgOralNicobrand Ltd.1994-02-012010-12-08US flag
Nicotine TartratePowder1 kg/1kgOralNicobrand Ltd.1997-07-11Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
American Fare Nicotine Transdermal SystemPatch, extended release14 mg/1TransdermalGlaxoSmithKline Consumer Healthcare Holdings (US) LLC2012-01-022014-12-29US flag
Basic Care NicotineGum, chewing4 mg/1OralL. Perrigo Company2019-01-23Not applicableUS flag
Basic Care NicotineLozenge2 mg/1OralL. Perrigo Company2018-10-11Not applicableUS flag
Basic Care NicotineGum, chewing2 mg/1OralL. Perrigo Company2018-12-12Not applicableUS flag
Basic Care NicotineLozenge4 mg/1OralL. Perrigo Company2018-10-16Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Basic Care NicotineNicotine (2 mg/1) + Nicotine (2 mg/1)KitOralL. Perrigo Company2019-01-16Not applicableUS flag
Basic Care NicotineNicotine (2 mg/1) + Nicotine (2 mg/1)KitOralL. Perrigo Company2019-01-16Not applicableUS flag
Nicorette and Aquafresh Fruit Chill and Extreme Clean WhiteningNicotine (4 mg/1) + Sodium fluoride (1.13 mg/1g)Gum, chewing; Kit; PasteDental; OralGlaxoSmithKline Consumer Healthcare Holdings (US) LLC2015-12-072018-06-30US flag
NicotineNicotine (4 mg/1) + Nicotine (4 mg/1)Kit; LozengeOralCVS PHARMACY2018-04-09Not applicableUS flag
NicotineNicotine (2 mg/1) + Nicotine (2 mg/1)Kit; LozengeOralCVS PHARMACY2018-04-09Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Nicotine PolacrilexNicotine (200 g/1kg)PowderOralNicobrand Ltd.1994-02-012010-12-08US flag
Nicotine PolacrilexNicotine (150 g/1kg)PowderOralNicobrand Ltd.1994-02-012010-12-08US flag
Nicotine PolacrilexNicotine (180 g/1kg)PowderOralNicobrand Ltd.1994-02-012010-12-08US flag
Nicotine TartrateNicotine bitartrate (1 kg/1kg)PowderOralNicobrand Ltd.1997-07-11Not applicableUS flag
Nicotine UN1654Nicotine (1 L/1L)LiquidOralNicobrand Ltd.1997-07-11Not applicableUS flag

Categories

ATC Codes
N07BA01 — Nicotine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyrrolidinylpyridines. These are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Pyrrolidinylpyridines
Direct Parent
Pyrrolidinylpyridines
Alternative Parents
Alkaloids and derivatives / Aralkylamines / N-alkylpyrrolidines / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Alkaloid or derivatives / Amine / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / N-alkylpyrrolidine / Organic nitrogen compound / Organonitrogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
nicotine (CHEBI:17688) / Pesticides, Pyridine alkaloids, Alkaloids (C00745)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
6M3C89ZY6R
CAS number
54-11-5
InChI Key
SNICXCGAKADSCV-JTQLQIEISA-N
InChI
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
IUPAC Name
3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
SMILES
CN1CCC[C@H]1C1=CN=CC=C1

References

Synthesis Reference

Charles G. Chavdarian, Edward B. Sanders, "Process for the preparation of optically active nicotine analogs." U.S. Patent US4321387, issued September, 1959.

US4321387
General References
  1. Nolley EP, Kelley BM: Adolescent reward system perseveration due to nicotine: studies with methylphenidate. Neurotoxicol Teratol. 2007 Jan-Feb;29(1):47-56. Epub 2006 Oct 4. [Article]
  2. de Leon J, Tracy J, McCann E, McGrory A, Diaz FJ: Schizophrenia and tobacco smoking: a replication study in another US psychiatric hospital. Schizophr Res. 2002 Jul 1;56(1-2):55-65. [Article]
  3. de Leon J, Dadvand M, Canuso C, White AO, Stanilla JK, Simpson GM: Schizophrenia and smoking: an epidemiological survey in a state hospital. Am J Psychiatry. 1995 Mar;152(3):453-5. [Article]
  4. Aguilar MC, Gurpegui M, Diaz FJ, de Leon J: Nicotine dependence and symptoms in schizophrenia: naturalistic study of complex interactions. Br J Psychiatry. 2005 Mar;186:215-21. [Article]
Human Metabolome Database
HMDB0001934
KEGG Drug
D03365
KEGG Compound
C00745
PubChem Compound
89594
PubChem Substance
46506924
ChemSpider
80863
BindingDB
82070
RxNav
31765
ChEBI
17688
ChEMBL
CHEMBL3
ZINC
ZINC000000391812
Therapeutic Targets Database
DAP000175
PharmGKB
PA450626
PDBe Ligand
NCT
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Nicotine
PDB Entries
1p2y / 1p7r / 1uw6 / 2yk1 / 4ejg / 4ejj / 5kxi / 5o87 / 6c71 / 6cnj
show 10 more
FDA label
Download (11.2 MB)
MSDS
Download (77.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingBasic ScienceE Cigarette Use1
4Active Not RecruitingHealth Services ResearchSmoking, Cessation / Smoking, Cigarette1
4Active Not RecruitingPreventionSmoking, Cessation1
4Active Not RecruitingTreatmentCigarette Smokers / Tobacco Use Disorders1
4Active Not RecruitingTreatmentTobacco Smoking Behavior1

Pharmacoeconomics

Manufacturers
  • Novartis consumer health inc
  • Sanofi aventis us llc
  • Aveva drug delivery systems inc
  • Mcneil consumer healthcare
  • Pharmacia and upjohn co
  • Pfizer inc
  • Glaxosmithkline
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Perrigo co
  • Perrigo r and d co
  • Watson laboratories inc
  • Glaxosmithkline consumer healthcare
Packagers
  • Aveva Drug Delivery Systems Inc.
  • Cardinal Health
  • CVS Pharmacy
  • Dispensing Solutions
  • Elan Pharmaceuticals Inc.
  • Gallipot
  • GlaxoSmithKline Inc.
  • LTS Lohmann Therapy Systems Corp.
  • Mckesson Corp.
  • McNeil Laboratories
  • Novartis AG
  • Perrigo Co.
  • Pfizer Inc.
  • Pharmacia Inc.
  • Physicians Total Care Inc.
Dosage Forms
FormRouteStrength
Patch, extended releaseTransdermal14 mg/1
KitOral
Patch, extended releaseTransdermal21 mg/1
Patch, extended releaseTransdermal7 mg/1
LozengeOral2 mg/1
LozengeOral4 mg/1
Patch, extended releaseTransdermal7 mg/24h
PatchTransdermal14 mg/1
PatchTransdermal21 mg/1
PatchTransdermal7 mg/1
Patch, extended releaseTopical21 mg/1
Patch, extended releaseTopical7 mg/1
PatchTransdermal114 mg / pad
PatchTransdermal36 mg / pad
PatchTransdermal78 mg / pad
PatchTransdermal31.5 mg
PatchTransdermal47.3 mg
PatchTransdermal15.8 mg
SprayOral1 mg
Gum, chewingOral
Gum, chewingOral2 G
PatchTransdermal
PatchTransdermal10 MG/16ORE
PatchTransdermal15 MG/16ORE
PatchTransdermal5 MG/16ORE
Solution
Solution10 MG
Tablet
PlasterTransdermal10 mg/16h
Aerosol, meteredRespiratory (inhalation)15 mg
PlasterTransdermal15 mg/16h
PlasterTransdermal25 mg/16h
Gum, chewing; kit; pasteDental; Oral
Gum, chewingBuccal2 mg
Gum, chewingBuccal4 mg
Gum, chewingOral2 mg / gum
AerosolRespiratory (inhalation)10 mg
PatchTransdermal10 mg/16hr
PatchTransdermal15 mg/16hr
PatchTransdermal25 mg/16hr
PatchTransdermal10 mg/16h
Patch, extended releaseTransdermal15.75 mg/9sq cm
PatchTransdermal15 mg/16h
Patch, extended releaseTransdermal23.62 mg/13.5sq cm
PatchTransdermal25 mg/16h
Patch, extended releaseTransdermal39.37 mg/22.5sq cm
PatchTransdermal25 mg / 16 hour
PatchTransdermal15.75 mg
PatchTransdermal23.62 mg
PatchTransdermal39.37 mg
PatchTransdermal25 mg
Gum, chewingOral4 mg / gum
PatchTransdermal10 mg/20sq cm
PatchTransdermal15 mg/30sq cm
PatchTransdermal5 mg/10sq cm
SprayTransmucosal
Kit; lozengeOral
PatchTransdermal14 mg/1d
PatchTransdermal14 mg/24h
PatchTransdermal21 mg/1d
PatchTransdermal21 mg/24h
PatchTransdermal7 mg/24h
PatchTransdermal7 mg/1d
Gum, chewingOral4 mg/1
PowderOral150 g/1kg
PowderOral180 g/1kg
PowderOral200 g/1kg
Gum, chewingBuccal2 mg/1
Gum, chewingBuccal4 mg/1
PowderNot applicable1 kg/1kg
PowderOral1 kg/1kg
PatchTopical
KitTransdermal
Patch, extended releaseTopical21 mg/24h
Patch, extended releaseTransdermal21 mg/24h
Patch, extended releaseTopical14 mg/24h
Patch, extended releaseTransdermal14 mg/24h
Patch, extended releaseTopical7 mg/24h
LiquidOral1 L/1L
Tablet, extended release2 mg
PatchTransdermal14 mg/24hr
PatchTransdermal21 mg/24hr
PatchTransdermal7 mg/24hr
GumOral2 mg
Gum, chewingOral2.0 mg
GumOral
Gum, chewingOral4.0 mg
TabletTransmucosal
LozengeOral1 mg
LozengeBuccal2 mg
PlasterTransdermal7 mg/24h
PatchTransdermal17.5 mg/10sq cm
PlasterTransdermal14 mg/24h
PatchTransdermal35 mg/20sq cm
PlasterTransdermal21 mg/24h
PatchTransdermal52.5 mg/30sq cm
Patch
InhalantRespiratory (inhalation)4 mg/1
Spray, meteredNasal10 mg/1mL
FilmOral2.5 MG
PatchCutaneous36.000 mg
PatchTransdermal14 mg/24ore
PatchTransdermal21 mg/24ore
PatchTransdermal7 mg/24ore
TabletTransmucosal1.5 MG
TabletTransmucosal2 MG
TabletTransmucosal4 MG
PatchTransdermal14 MG
PatchTransdermal21 MG
LozengeOral2 mg
LozengeOral4 mg
PatchTransdermal7 MG
PlasterTransdermal14 mg/24stunde
PlasterTransdermal21 mg/24stunde
PlasterTransdermal7 mg/24stunde
PatchTransdermal36 mg
PatchTransdermal78 mg
TabletBuccal; Oral2 mg
PatchTopical; Transdermal114 mg
Gum, chewingOral2 mg/1
Gum, chewingOral2 mg/2h
Gum, chewingOral4 mg/2h
Tablet, chewableOral2 mg
Tablet, chewableOral4 mg
Gum, chewingOral2 mg
Gum, chewingOral4 mg
Prices
Unit descriptionCostUnit
Nicotrol 168 10 mg Inhalant Inhaler223.5USD inhaler
Nicotine 30 21 mg/24hr Patches Box206.52USD box
Nicotine 30 14 mg/24hr Patches Box196.27USD box
Nicotrol NS 10 mg/ml Solution 10ml Bottle55.88USD bottle
Nicotine polacrilex powder11.25USD g
Nicotrol ns 10 mg/ml spray5.37USD ml
Nicoderm cq 21 mg/24hr patch4.08USD patch
Nicoderm cq 14 mg/24hr patch3.52USD patch
Nicoderm cq 7 mg/24hr patch3.52USD patch
Nicotine 11 mg/24hr patch3.14USD patch
Nicotine 22 mg/24hr patch3.14USD patch
Nicotine transdermal system1.83USD each
Nicotrol cartridge inhaler1.28USD each
Commit 2 mg lozenge0.55USD lozenge
Commit 4 mg lozenge0.55USD lozenge
Nicorette 4 mg chewing gum0.52USD each
Nicorette 2 mg chewing gum0.45USD each
Thrive nicotine 2 mg gum0.42USD each
Thrive nicotine 4 mg gum0.42USD each
CVS Pharmacy nicotine 4 mg chewing gum0.38USD each
CVS Pharmacy nicotine 2 mg chewing gum0.34USD each
Nicotine 4 mg chewing gum0.3USD each
Nicotine 2 mg chewing gum0.25USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5656255No1997-08-122014-08-12US flag
US5501236No1996-03-262010-06-08US flag
CA1333051No1994-11-152011-11-15Canada flag
US8323683No2012-12-042028-04-30US flag
US8999379No2015-04-072020-02-13US flag
US9205059No2015-12-082019-12-15US flag
US8075911No2011-12-132021-05-22US flag
US8663680No2014-03-042020-02-13US flag
US8501164No2013-08-062029-06-14US flag
US8940772No2015-01-272029-04-30US flag

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)-79 °CPhysProp
boiling point (°C)247 °CPhysProp
water solubility1E+006 mg/LSEIDELL,A (1941)
logP1.17HANSCH,C ET AL. (1995)
logS0.79ADME Research, USCD
Caco2 permeability-4.71ADME Research, USCD
pKa8.5http://www.surgeongeneral.gov/library/reports/50-years-of-progress/sgr50-chap-5.pdf
Predicted Properties
PropertyValueSource
Water Solubility93.3 mg/mLALOGPS
logP0.87ALOGPS
logP1.16Chemaxon
logS-0.24ALOGPS
pKa (Strongest Basic)8.58Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area16.13 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity49.66 m3·mol-1Chemaxon
Polarizability18.59 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9748
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.8998
P-glycoprotein inhibitor IINon-inhibitor0.9368
Renal organic cation transporterInhibitor0.6868
CYP450 2C9 substrateNon-substrate0.7998
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.6347
CYP450 2C9 inhibitorNon-inhibitor0.8433
CYP450 2D6 inhibitorNon-inhibitor0.8838
CYP450 2C19 inhibitorNon-inhibitor0.8543
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7589
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9626
BiodegradationNot ready biodegradable0.9478
Rat acute toxicity3.4798 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8851
hERG inhibition (predictor II)Non-inhibitor0.7978
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (2.96 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-9500000000-f2d4835c504301f9410e
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-001i-4900000000-6d65165a4417a6129eeb
GC-MS Spectrum - EI-BGC-MSsplash10-01q9-7900000000-1e2c38b5e4e7aae10d37
GC-MS Spectrum - EI-BGC-MSsplash10-001i-9800000000-fe889308f7088d47c31d
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-9500000000-f2d4835c504301f9410e
Mass Spectrum (Electron Ionization)MSsplash10-001i-9400000000-47a036aa305825218fa2
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00di-0900000000-3e7377f36ca2547f4885
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-001i-2900000000-a505fff3a4028a6f0d52
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-00lr-7900000000-b91a12a16d7688e8679d
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-01q9-7900000000-10d401d7ffa1c2cdbd9f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-03di-0900000000-440798524836a27b78b4
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-01q9-0900000000-926940dd7f4851dbd73b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00lr-0900000000-6bccc06d40ab273cf972
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0159-2900000000-f7512c405bb662e040a6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-014i-7900000000-f1781566be5aee88f6ef
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-001i-0900000000-09e9b29571abf3a52e44
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0900000000-16cdb5f23105be4a892b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0900000000-720fe01876c739a30be0
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-85a813588b57acf531fe
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-93a3dae1577f4f2dda53
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-1900000000-cb6f8cec40dd9ed35d00
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00lr-1900000000-1443b1cf22d2de281898
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-0900000000-440798524836a27b78b4
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01q9-0900000000-926940dd7f4851dbd73b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00lr-0900000000-6bccc06d40ab273cf972
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0159-2900000000-1e50e1cd59e45e211535
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-7900000000-f1781566be5aee88f6ef
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0900000000-09e9b29571abf3a52e44
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-1900000000-5c94a5e0cae203f5cc0d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1900000000-7297d3409bafd5940f7b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-4900000000-6eb5eb6e8465f6bcc549
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01t9-8900000000-cb7d52fa096bf9026acc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-8900000000-fc9d44dfdbf638ced593
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-016r-9000000000-6a2a9d2fab1dd0ca25a5
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-137.2553359
predicted
DarkChem Lite v0.1.0
[M-H]-137.7063359
predicted
DarkChem Lite v0.1.0
[M-H]-137.6019359
predicted
DarkChem Lite v0.1.0
[M-H]-132.68898
predicted
DeepCCS 1.0 (2019)
[M+H]+138.5525359
predicted
DarkChem Lite v0.1.0
[M+H]+138.2663359
predicted
DarkChem Lite v0.1.0
[M+H]+138.6181359
predicted
DarkChem Lite v0.1.0
[M+H]+135.03639
predicted
DeepCCS 1.0 (2019)
[M+Na]+137.6425359
predicted
DarkChem Lite v0.1.0
[M+Na]+138.0374359
predicted
DarkChem Lite v0.1.0
[M+Na]+137.8634359
predicted
DarkChem Lite v0.1.0
[M+Na]+142.47316
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name
CHRNA4
Uniprot ID
P43681
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-4
Molecular Weight
69956.47 Da
References
  1. Espeseth T, Endestad T, Rootwelt H, Reinvang I: Nicotine receptor gene CHRNA4 modulates early event-related potentials in auditory and visual oddball target detection tasks. Neuroscience. 2007 Jul 29;147(4):974-85. Epub 2007 Jun 27. [Article]
  2. Winterer G, Musso F, Konrad A, Vucurevic G, Stoeter P, Sander T, Gallinat J: Association of attentional network function with exon 5 variations of the CHRNA4 gene. Hum Mol Genet. 2007 Sep 15;16(18):2165-74. Epub 2007 Jul 5. [Article]
  3. Ehringer MA, Clegg HV, Collins AC, Corley RP, Crowley T, Hewitt JK, Hopfer CJ, Krauter K, Lessem J, Rhee SH, Schlaepfer I, Smolen A, Stallings MC, Young SE, Zeiger JS: Association of the neuronal nicotinic receptor beta2 subunit gene (CHRNB2) with subjective responses to alcohol and nicotine. Am J Med Genet B Neuropsychiatr Genet. 2007 Jul 5;144B(5):596-604. [Article]
  4. Klaassen A, Glykys J, Maguire J, Labarca C, Mody I, Boulter J: Seizures and enhanced cortical GABAergic inhibition in two mouse models of human autosomal dominant nocturnal frontal lobe epilepsy. Proc Natl Acad Sci U S A. 2006 Dec 12;103(50):19152-7. Epub 2006 Dec 4. [Article]
  5. De Luca V, Voineskos S, Wong G, Kennedy JL: Genetic interaction between alpha4 and beta2 subunits of high affinity nicotinic receptor: analysis in schizophrenia. Exp Brain Res. 2006 Sep;174(2):292-6. Epub 2006 Apr 25. [Article]
  6. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [Article]
  7. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [Article]
  8. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [Article]
  9. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Toxic substance binding
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The cha...
Gene Name
CHRNA7
Uniprot ID
P36544
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-7
Molecular Weight
56448.925 Da
References
  1. Mexal S, Jenkins PM, Lautner MA, Iacob E, Crouch EL, Stitzel JA: alpha7 nicotinic receptor gene promoter polymorphisms in inbred mice affect expression in a cell type-specific fashion. J Biol Chem. 2007 May 4;282(18):13220-7. Epub 2007 Mar 14. [Article]
  2. Olincy A, Harris JG, Johnson LL, Pender V, Kongs S, Allensworth D, Ellis J, Zerbe GO, Leonard S, Stevens KE, Stevens JO, Martin L, Adler LE, Soti F, Kem WR, Freedman R: Proof-of-concept trial of an alpha7 nicotinic agonist in schizophrenia. Arch Gen Psychiatry. 2006 Jun;63(6):630-8. [Article]
  3. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [Article]
  4. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [Article]
  5. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [Article]
  6. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name
CHRNB2
Uniprot ID
P17787
Uniprot Name
Neuronal acetylcholine receptor subunit beta-2
Molecular Weight
57018.575 Da
References
  1. Ehringer MA, Clegg HV, Collins AC, Corley RP, Crowley T, Hewitt JK, Hopfer CJ, Krauter K, Lessem J, Rhee SH, Schlaepfer I, Smolen A, Stallings MC, Young SE, Zeiger JS: Association of the neuronal nicotinic receptor beta2 subunit gene (CHRNB2) with subjective responses to alcohol and nicotine. Am J Med Genet B Neuropsychiatr Genet. 2007 Jul 5;144B(5):596-604. [Article]
  2. De Luca V, Voineskos S, Wong G, Kennedy JL: Genetic interaction between alpha4 and beta2 subunits of high affinity nicotinic receptor: analysis in schizophrenia. Exp Brain Res. 2006 Sep;174(2):292-6. Epub 2006 Apr 25. [Article]
  3. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [Article]
  4. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [Article]
  5. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [Article]
  6. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Drug binding
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNA2
Uniprot ID
Q15822
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-2
Molecular Weight
59764.82 Da
References
  1. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [Article]
  2. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [Article]
  3. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [Article]
  4. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [Article]
  5. Sullivan PF, Neale BM, van den Oord E, Miles MF, Neale MC, Bulik CM, Joyce PR, Straub RE, Kendler KS: Candidate genes for nicotine dependence via linkage, epistasis, and bioinformatics. Am J Med Genet B Neuropsychiatr Genet. 2004 Apr 1;126B(1):23-36. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNA3
Uniprot ID
P32297
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-3
Molecular Weight
57479.54 Da
References
  1. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [Article]
  2. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [Article]
  3. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [Article]
  4. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNA5
Uniprot ID
P30532
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-5
Molecular Weight
53053.965 Da
References
  1. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [Article]
  2. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [Article]
  3. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [Article]
  4. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Acetylcholine-activated cation-selective channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNA6
Uniprot ID
Q15825
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-6
Molecular Weight
56897.745 Da
References
  1. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [Article]
  2. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [Article]
  3. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [Article]
  4. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Calcium channel activity
Specific Function
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding induces a conformation change that leads to the opening of an ion-conducting channel across the plasm...
Gene Name
CHRNA9
Uniprot ID
Q9UGM1
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-9
Molecular Weight
54806.63 Da
References
  1. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [Article]
  2. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [Article]
  3. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [Article]
  4. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Receptor binding
Specific Function
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an i...
Gene Name
CHRNA10
Uniprot ID
Q9GZZ6
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-10
Molecular Weight
49704.295 Da
References
  1. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [Article]
  2. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [Article]
  3. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [Article]
  4. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Drug binding
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNB3
Uniprot ID
Q05901
Uniprot Name
Neuronal acetylcholine receptor subunit beta-3
Molecular Weight
52728.215 Da
References
  1. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [Article]
  2. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [Article]
  3. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [Article]
  4. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNB4
Uniprot ID
P30926
Uniprot Name
Neuronal acetylcholine receptor subunit beta-4
Molecular Weight
56378.985 Da
References
  1. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [Article]
  2. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [Article]
  3. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [Article]
  4. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. Barbieri RL, Gochberg J, Ryan KJ: Nicotine, cotinine, and anabasine inhibit aromatase in human trophoblast in vitro. J Clin Invest. 1986 Jun;77(6):1727-33. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Choline o-acetyltransferase activity
Specific Function
Catalyzes the reversible synthesis of acetylcholine (ACh) from acetyl CoA and choline at cholinergic synapses.
Gene Name
CHAT
Uniprot ID
P28329
Uniprot Name
Choline O-acetyltransferase
Molecular Weight
82535.025 Da
References
  1. FAHMY AR, RYMAN BE, WALSH EO: The inhibition of choline acetylase by nicotine. J Pharm Pharmacol. 1954 Sep;6(9):607-9. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Wei C, Caccavale RJ, Weyand EH, Chen S, Iba MM: Induction of CYP1A1 and CYP1A2 expressions by prototypic and atypical inducers in the human lung. Cancer Lett. 2002 Apr 8;178(1):25-36. [Article]
  2. Zevin S, Benowitz NL: Drug interactions with tobacco smoking. An update. Clin Pharmacokinet. 1999 Jun;36(6):425-38. doi: 10.2165/00003088-199936060-00004. [Article]
  3. Yamazaki H, Inoue K, Hashimoto M, Shimada T: Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70. [Article]
Details
2. Cytochrome P450 1A2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
Curator comments
Nicotine has been shown to be a CYP1A2 substrate when it is present in high concentrations.
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Hukkanen J, Jacob P 3rd, Peng M, Dempsey D, Benowitz NL: Effect of nicotine on cytochrome P450 1A2 activity. Br J Clin Pharmacol. 2011 Nov;72(5):836-8. doi: 10.1111/j.1365-2125.2011.04023.x. [Article]
  2. Zevin S, Benowitz NL: Drug interactions with tobacco smoking. An update. Clin Pharmacokinet. 1999 Jun;36(6):425-38. doi: 10.2165/00003088-199936060-00004. [Article]
  3. Yamazaki H, Inoue K, Hashimoto M, Shimada T: Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70. [Article]
  4. Pal D, Kwatra D, Minocha M, Paturi DK, Budda B, Mitra AK: Efflux transporters- and cytochrome P-450-mediated interactions between drugs of abuse and antiretrovirals. Life Sci. 2011 May 23;88(21-22):959-71. doi: 10.1016/j.lfs.2010.09.012. Epub 2010 Nov 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Yamazaki H, Inoue K, Hashimoto M, Shimada T: Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Yamazaki H, Inoue K, Hashimoto M, Shimada T: Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
Nicotine has been shown to be a substrate of CYP2C9 when it is present in high concentrations. Clinical correlation is unknown.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Yamazaki H, Inoue K, Hashimoto M, Shimada T: Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Yamazaki H, Inoue K, Hashimoto M, Shimada T: Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70. [Article]
  2. Benowitz NL, Jacob P 3rd, Perez-Stable E: CYP2D6 phenotype and the metabolism of nicotine and cotinine. Pharmacogenetics. 1996 Jun;6(3):239-42. [Article]
  3. Tiili EM, Antikainen MS, Mitiushkina NV, Sukhovskaya OA, Imyanitov EN, Hirvonen AP: Effect of genotype and methylation of CYP2D6 on smoking behaviour. Pharmacogenet Genomics. 2015 Nov;25(11):531-40. doi: 10.1097/FPC.0000000000000166. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Yamazaki H, Inoue K, Hashimoto M, Shimada T: Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Serotonin binding
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
References
  1. Lewis AJ, Truman P, Hosking MR, Miller JH: Monoamine oxidase inhibitory activity in tobacco smoke varies with tobacco type. Tob Control. 2012 Jan;21(1):39-43. doi: 10.1136/tc.2010.040287. Epub 2011 Jun 2. [Article]
  2. Leroy C, Bragulat V, Berlin I, Gregoire MC, Bottlaender M, Roumenov D, Dolle F, Bourgeois S, Penttila J, Artiges E, Martinot JL, Trichard C: Cerebral monoamine oxidase A inhibition in tobacco smokers confirmed with PET and [11C]befloxatone. J Clin Psychopharmacol. 2009 Feb;29(1):86-8. doi: 10.1097/JCP.0b013e31819e98f. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Primary amine oxidase activity
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. Lewis AJ, Truman P, Hosking MR, Miller JH: Monoamine oxidase inhibitory activity in tobacco smoke varies with tobacco type. Tob Control. 2012 Jan;21(1):39-43. doi: 10.1136/tc.2010.040287. Epub 2011 Jun 2. [Article]
Details
10. Cytochrome P450 2A6
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Yamazaki H, Inoue K, Hashimoto M, Shimada T: Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70. [Article]
  2. von Weymarn LB, Retzlaff C, Murphy SE: CYP2A6- and CYP2A13-catalyzed metabolism of the nicotine Delta5'(1')iminium ion. J Pharmacol Exp Ther. 2012 Nov;343(2):307-15. doi: 10.1124/jpet.112.195255. Epub 2012 Aug 6. [Article]
  3. Raunio H, Rautio A, Gullsten H, Pelkonen O: Polymorphisms of CYP2A6 and its practical consequences. Br J Clin Pharmacol. 2001 Oct;52(4):357-63. [Article]
  4. Denton TT, Zhang X, Cashman JR: Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6. Biochem Pharmacol. 2004 Feb 15;67(4):751-6. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
Curator comments
References provide evidence mainly through in vitro tests. The actual role and strength of the interaction of nicotine on CYP2E1 is unclear.
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Howard LA, Miksys S, Hoffmann E, Mash D, Tyndale RF: Brain CYP2E1 is induced by nicotine and ethanol in rat and is higher in smokers and alcoholics. Br J Pharmacol. 2003 Apr;138(7):1376-86. doi: 10.1038/sj.bjp.0705146. [Article]
  2. Van Vleet TR, Bombick DW, Coulombe RA Jr: Inhibition of human cytochrome P450 2E1 by nicotine, cotinine, and aqueous cigarette tar extract in vitro. Toxicol Sci. 2001 Dec;64(2):185-91. [Article]
  3. Yamazaki H, Inoue K, Hashimoto M, Shimada T: Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70. [Article]
  4. Micu AL, Miksys S, Sellers EM, Koop DR, Tyndale RF: Rat hepatic CYP2E1 is induced by very low nicotine doses: an investigation of induction, time course, dose response, and mechanism. J Pharmacol Exp Ther. 2003 Sep;306(3):941-7. doi: 10.1124/jpet.103.052183. Epub 2003 May 15. [Article]
  5. Hukkanen J, Jacob Iii P, Peng M, Dempsey D, Benowitz NL: Effects of nicotine on cytochrome P450 2A6 and 2E1 activities. Br J Clin Pharmacol. 2010 Feb;69(2):152-9. doi: 10.1111/j.1365-2125.2009.03568.x. [Article]
  6. Nakayama H, Okuda H, Nakashima T, Imaoka S, Funae Y: Nicotine metabolism by rat hepatic cytochrome P450s. Biochem Pharmacol. 1993 Jun 22;45(12):2554-6. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a coumarin 7-hydroxylase activity. Active in the metabolic activation of hexamethylphosphoramide, N,N-dimethylaniline, 2'-methoxyacetophenone, N-nitrosomethylphenylamine, and the tobacco-s...
Gene Name
CYP2A13
Uniprot ID
Q16696
Uniprot Name
Cytochrome P450 2A13
Molecular Weight
56687.095 Da
References
  1. von Weymarn LB, Brown KM, Murphy SE: Inactivation of CYP2A6 and CYP2A13 during nicotine metabolism. J Pharmacol Exp Ther. 2006 Jan;316(1):295-303. doi: 10.1124/jpet.105.091306. Epub 2005 Sep 27. [Article]
  2. He XY, Shen J, Hu WY, Ding X, Lu AY, Hong JY: Identification of Val117 and Arg372 as critical amino acid residues for the activity difference between human CYP2A6 and CYP2A13 in coumarin 7-hydroxylation. Arch Biochem Biophys. 2004 Jul 15;427(2):143-53. doi: 10.1016/j.abb.2004.03.016. [Article]
  3. Bao Z, He XY, Ding X, Prabhu S, Hong JY: Metabolism of nicotine and cotinine by human cytochrome P450 2A13. Drug Metab Dispos. 2005 Feb;33(2):258-61. doi: 10.1124/dmd.104.002105. Epub 2004 Nov 4. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Yamazaki H, Inoue K, Hashimoto M, Shimada T: Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70. [Article]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [Article]
  2. Urakami Y, Okuda M, Masuda S, Saito H, Inui KI: Functional characteristics and membrane localization of rat multispecific organic cation transporters, OCT1 and OCT2, mediating tubular secretion of cationic drugs. J Pharmacol Exp Ther. 1998 Nov;287(2):800-5. [Article]
  3. Okuda M, Urakami Y, Saito H, Inui K: Molecular mechanisms of organic cation transport in OCT2-expressing Xenopus oocytes. Biochim Biophys Acta. 1999 Mar 4;1417(2):224-31. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. [Article]
  2. Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [Article]
  3. Urakami Y, Okuda M, Masuda S, Saito H, Inui KI: Functional characteristics and membrane localization of rat multispecific organic cation transporters, OCT1 and OCT2, mediating tubular secretion of cationic drugs. J Pharmacol Exp Ther. 1998 Nov;287(2):800-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Toxin transporter activity
Specific Function
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name
SLC22A3
Uniprot ID
O75751
Uniprot Name
Solute carrier family 22 member 3
Molecular Weight
61279.485 Da
References
  1. Kekuda R, Prasad PD, Wu X, Wang H, Fei YJ, Leibach FH, Ganapathy V: Cloning and functional characterization of a potential-sensitive, polyspecific organic cation transporter (OCT3) most abundantly expressed in placenta. J Biol Chem. 1998 Jun 26;273(26):15971-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
References
  1. Wu X, Prasad PD, Leibach FH, Ganapathy V: cDNA sequence, transport function, and genomic organization of human OCTN2, a new member of the organic cation transporter family. Biochem Biophys Res Commun. 1998 May 29;246(3):589-95. [Article]
  2. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [Article]
  3. Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
Gene Name
SLC22A4
Uniprot ID
Q9H015
Uniprot Name
Solute carrier family 22 member 4
Molecular Weight
62154.48 Da
References
  1. Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [Article]
  2. Wu X, George RL, Huang W, Wang H, Conway SJ, Leibach FH, Ganapathy V: Structural and functional characteristics and tissue distribution pattern of rat OCTN1, an organic cation transporter, cloned from placenta. Biochim Biophys Acta. 2000 Jun 1;1466(1-2):315-27. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48