3-quinuclidinyl-benzilate   Click here for help

GtoPdb Ligand ID: 3260

Abbreviated name: QNB
Synonyms: Buzz | BZ | EA-2277 | Substance 78
Compound class: Synthetic organic
Comment: Quinuclidinyl benzilate is a anticholinergic glycolate that acts as a competitive, non-selective antagonist of muscarinic receptors in cardiac muscle, smooth muscle, exocrine glands and at postsynaptic receptors in neurons. It is a non-lethal incapacitating chemical warfare agent controlled under schedule 2 of the Chemical Weapons Convention of 1997.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 49.77
Molecular weight 337.17
XLogP 3.16
No. Lipinski's rules broken 0
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Canonical SMILES O=C(C(c1ccccc1)(c1ccccc1)O)OC1CN2CCC1CC2
Isomeric SMILES O=C(C(c1ccccc1)(c1ccccc1)O)OC1CN2CCC1CC2
InChI InChI=1S/C21H23NO3/c23-20(25-19-15-22-13-11-16(19)12-14-22)21(24,17-7-3-1-4-8-17)18-9-5-2-6-10-18/h1-10,16,19,24H,11-15H2
Bioactivity Comments
[3H]QNB binds to bovine brain preparations with a Kd of 0.24nM [2]. Physostigmine is a specific antidote for quinuclidinyl benzilate poisoning.
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
M4 receptor Hs Antagonist Antagonist 10.4 pKi - 1
pKi 10.4 (Ki 4x10-11 M) [1]