nicotine   Click here for help

GtoPdb Ligand ID: 2585

Synonyms: Nicorette® | Nicotrol®
Approved drug PDB Ligand
nicotine is an approved drug (FDA (1984))
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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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
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]