mecamylamine   

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
Click here for structure editor
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
SMILES / InChI / InChIKey
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
InChI Key IMYZQPCYWPFTAG-UHFFFAOYSA-N
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
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 - - - -