3-Quinuclidinyl benzilate

Names

IUPAC name

1-azabicyclo[2.2.2]oct-3-yl 2-hydroxy-2,2-diphenylacetate

Identifiers

CAS Number

6581-06-2^N

3D model (Jmol)

ChEMBL12980^Y

21577^Y

Quinuclidinyl+benzilate

E69DLR7470^N

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^Y

Key: HGMITUYOCPPQLE-UHFFFAOYSA-N^Y
InChI=1/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

Key: HGMITUYOCPPQLE-UHFFFAOYAE

SMILES

O=C(OC2C1CCN(CC1)C2)C(O)(c3ccccc3)c4ccccc4

Properties

C₂₁H₂₃NO₃

337.41 g/mol

164-165 °C

322 °C

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

Infobox references

3-Quinuclidinyl benzilate (QNB) — IUPAC name 1-azabicyclo[2.2.2]oct-3-yl 2-hydroxy-2,2-diphenylacetate; US Army code EA-2277; NATO code BZ; Soviet code Substance 78 — is an odorless military incapacitating agent.

BZ is a glycolate anticholinergic compound related to atropine, scopolamine, hyoscyamine, and other deliriants. Dispersal would be as an aerosolized solid (primarily for inhalation) or as agent dissolved in one or more solvents for ingestion or percutaneous absorption.

Acting as a competitive non-selective blocker at postsynaptic and postjunctional muscarinic receptor sites in smooth muscle, exocrine glands, and the brain, BZ decreases the effective concentration of acetylcholine seen by receptors at these sites. Thus, BZ causes PNS effects that in general are the opposite of those seen in nerve agent poisoning. CNS effects include stupor, confusion, and confabulation with concrete and panoramic illusions and hallucinations, and with regression to primitive, involuntary behaviors such as floccillation and disrobing.

Physostigmine, which increases the concentration of acetylcholine in synapses and in neuromuscular and neuroglandular junctions, is a specific antidote.

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