nicotine   Click here for help

GtoPdb Ligand ID: 2585

Synonyms: Nicorette® | Nicotrol®
Approved drug PDB Ligand
nicotine is an approved drug (FDA (1984))
Compound class: Synthetic organic
Comment: Nicotine is a natural alkaloid of the tobacco plant. It is an addictive stimulant, which is an agonist of most nicotinic acetylcholine receptors (nAChRs) (it is an antagonist of the nAChRα9 and nAChRα10 receptor subtypes).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: nicotine

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 1
Topological polar surface area 16.13
Molecular weight 162.12
XLogP 1.13
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CN1CCCC1c1cccnc1
Isomeric SMILES CN1CCC[C@H]1c1cccnc1
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
InChI Key SNICXCGAKADSCV-JTQLQIEISA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Cohen C, Bergis OE, Galli F, Lochead AW, Jegham S, Biton B, Leonardon J, Avenet P, Sgard F, Besnard F et al.. (2003)
SSR591813, a novel selective and partial alpha4beta2 nicotinic receptor agonist with potential as an aid to smoking cessation.
J Pharmacol Exp Ther, 306 (1): 407-20. [PMID:12682217]
2. Cordero-Erausquin M, Marubio LM, Klink R, Changeux JP. (2000)
Nicotinic receptor function: new perspectives from knockout mice.
Trends Pharmacol Sci, 21 (6): 211-7. [PMID:10838608]
3. Flores CM, Rogers SW, Pabreza LA, Wolfe BB, Kellar KJ. (1992)
A subtype of nicotinic cholinergic receptor in rat brain is composed of alpha 4 and beta 2 subunits and is up-regulated by chronic nicotine treatment.
Mol Pharmacol, 41 (1): 31-7. [PMID:1732720]
4. Gopalakrishnan M, Monteggia LM, Anderson DJ, Molinari EJ, Piattoni-Kaplan M, Donnelly-Roberts D, Arneric SP, Sullivan JP. (1996)
Stable expression, pharmacologic properties and regulation of the human neuronal nicotinic acetylcholine alpha 4 beta 2 receptor.
J Pharmacol Exp Ther, 276 (1): 289-97. [PMID:8558445]
5. Nirogi R, Mohammed AR, Shinde AK, Ravella SR, Bogaraju N, Subramanian R, Mekala VR, Palacharla RC, Muddana N, Thentu JB et al.. (2020)
Discovery and Development of 3-(6-Chloropyridine-3-yloxymethyl)-2-azabicyclo[3.1.0]hexane Hydrochloride (SUVN-911): A Novel, Potent, Selective, and Orally Active Neuronal Nicotinic Acetylcholine α4β2 Receptor Antagonist for the Treatment of Depression.
J Med Chem, 63 (6): 2833-2853. [PMID:32026697]
6. Stauderman KA, Mahaffy LS, Akong M, Veliçelebi G, Chavez-Noriega LE, Crona JH, Johnson EC, Elliott KJ, Gillespie A, Reid RT et al.. (1998)
Characterization of human recombinant neuronal nicotinic acetylcholine receptor subunit combinations alpha2beta4, alpha3beta4 and alpha4beta4 stably expressed in HEK293 cells.
J Pharmacol Exp Ther, 284 (2): 777-89. [PMID:9454827]
7. Sullivan JP, Donnelly-Roberts D, Briggs CA, Anderson DJ, Gopalakrishnan M, Piattoni-Kaplan M, Campbell JE, McKenna DG, Molinari E, Hettinger AM et al.. (1996)
A-85380 [3-(2(S)-azetidinylmethoxy) pyridine]: in vitro pharmacological properties of a novel, high affinity alpha 4 beta 2 nicotinic acetylcholine receptor ligand.
Neuropharmacology, 35 (6): 725-34. [PMID:8887981]
8. Talavera K, Gees M, Karashima Y, Meseguer VM, Vanoirbeek JA, Damann N, Everaerts W, Benoit M, Janssens A, Vennekens R et al.. (2009)
Nicotine activates the chemosensory cation channel TRPA1.
Nat Neurosci, 12 (10): 1293-9. [PMID:19749751]
9. Wang H, Shi H, Zhang L, Pourrier M, Yang B, Nattel S, Wang Z. (2000)
Nicotine is a potent blocker of the cardiac A-type K(+) channels. Effects on cloned Kv4.3 channels and native transient outward current.
Circulation, 102 (10): 1165-71. [PMID:10973847]