3-Quinuclidinyl benzilate

3-Quinuclidinyl benzilate
Names
	Preferred IUPAC name 1-Azabicyclo[2.2.2]octan-3-yl hydroxydi(phenyl)acetate
	Other names BZ; EA-2277; CS-4030; QNB
Identifiers
CAS Number	6581-06-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL12980 ;
ChemSpider	21577 ;
ECHA InfoCard	100.164.060
IUPHAR/BPS	3260;
MeSH	Quinuclidinyl+benzilate
PubChem CID	23056;
UNII	E69DLR7470 ;
CompTox Dashboard (EPA)	DTXSID00894168 ;
	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 Key: HGMITUYOCPPQLE-UHFFFAOYSA-N ; 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-UHFFFAOYAEb l;
	SMILES O=C(C(C1=CC=CC=C1)(C2=CC=CC=C2)O)OC3CN4CCC3CC4;
Properties
Chemical formula	C21H23NO3
Molar mass	337.419 g·mol−1
Appearance	White crystalline powder
Melting point	164 to 165 °C (327 to 329 °F; 437 to 438 K)
Boiling point	322 °C (612 °F; 595 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

3-Quinuclidinyl benzilate (QNB) (IUPAC name 1-azabicyclo[2.2.2]octan-3-yl hydroxy(diphenyl)acetate; US Army code EA-2277; NATO code BZ; Soviet code Substance 78) is an odorless and bitter-tasting military-grade incapacitating agent. It impairs muscle movement and causes delirium and hallucinations to the point of helplessness.

BZ was first synthesized by the Swiss pharmaceutical company Hoffman-LaRoche in 1951, which unsuccessfully tried to develop it into a treatment for gastrointestinal disease. Within a few years, the United States Army took it up as part of its chemical weapons program. Allegations have been made that the U.S. army used it in the Vietnam War. The army denies this; in 1969 it officially banned the compound due to its "wide range of variability of effects, long onset time, and inefficiency of existing munitions." There have also been numerous, unproven allegations of its use in Syria, Bosnia and Russia.