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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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
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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
Bioactivity Comments
Data show a range of bioactivity levels at various heterologously expressed human nACh heteromeric ion channels. Kis as follows; α2β4=9900nM [6], α3β2=14nM [1], α3β4=187nM [1], α4β2=1nM [4,7]. Due to the heterogeneity of nACh channels we have not tagged a primary drug target for nicotine, although the α4β2 is reported to be the predominant high affinity subtype in the brain which mediates nicotine addiction [2-3].
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
nicotinic acetylcholine receptor α4 subunit Hs Agonist Agonist 8.7 pKi - 5
pKi 8.7 (Ki 2.2x10-9 M) α4β2 [5]
Description: In vitro affinity for recombinant human α4β2 receptors in membranes from transfected CHO-K1 cells, determined by displacement of [3H]-(−)-cytisine.
nicotinic acetylcholine receptor α3 subunit Hs Agonist Agonist 5.8 pKi - 5
pKi 5.8 (Ki 1.744x10-6 M) α3β4 [5]
TRPA1 Hs Activator Activation 4.8 pEC50 - 8
pEC50 4.8 (EC50 1.7x10-5 M) non-covalent [8]
Voltage: -75.0 mV
Description: Patch clamp
Conditions: CHO cells expressing mouse or human TRPA1
Kv4.3 Rn Channel blocker - 7.4 pIC50 - 9
pIC50 7.4 [9]
nicotinic acetylcholine receptor α9 subunit Hs Antagonist Antagonist - - -
nicotinic acetylcholine receptor α10 subunit Hs Antagonist Antagonist - - -
Ligand mentioned in the following text fields