GtoPdb Ligand ID: 3990

mecamylamine is an approved drug (FDA (2013))
Compound class: Synthetic organic
Comment: Mecamylamine is a non-selective, non-competitive antagonist of nicotinic acetylcholine receptors (nAChRs). It is often used as a research tool for its action as a ganglionic blocker (or ganglioplegic).
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 12.03
Molecular weight 167.17
XLogP 2.66
No. Lipinski's rules broken 0
Canonical SMILES CNC1(C)C2CCC(C1(C)C)C2
Isomeric SMILES CNC1(C)C2CCC(C1(C)C)C2
InChI InChI=1S/C11H21N/c1-10(2)8-5-6-9(7-8)11(10,3)12-4/h8-9,12H,5-7H2,1-4H3
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
nicotinic acetylcholine receptor α4 subunit Hs Channel blocker - 5.3 – 6.5 pIC50 -
pIC50 5.3 – 6.5 (IC50 4.9x10-6 – 3.3x10-7 M) α4β4
pIC50 5.4 – 5.4 (IC50 4.1x10-6 – 3.6x10-6 M) α4β2
nicotinic acetylcholine receptor α1 subunit Hs Channel blocker - ~5.8 pIC50 -
pIC50 ~5.8 (IC50 ~1.5x10-6 M) (α1)2β1δε
nicotinic acetylcholine receptor α3 subunit Hs Channel blocker - 5.1 – 6.4 pIC50 -
pIC50 6.4 (IC50 3.9x10-7 M) α3β4
pIC50 5.1 (IC50 7.6x10-6 M) α3β2
nicotinic acetylcholine receptor α6 subunit Hs Channel blocker - 5.0 pIC50 -
pIC50 5.0 (IC50 1.1x10-5 M) α6/α3β2β3 chimera
nicotinic acetylcholine receptor α7 subunit Hs Channel blocker - 4.8 pIC50 -
pIC50 4.8 (IC50 1.56x10-5 M) (α7)5
nicotinic acetylcholine receptor α2 subunit Hs Channel blocker - - - -