Compound: 3-Quinuclidinyl benzilate
SMILES: O=C(OC1C2CCN(C1)CC2)C(O)(c3ccccc3)c4ccccc4
InChIKey: HGMITUYOCPPQLE-UHFFFAOYSA-N
Synonyms: 3-Quinuclidinyl benzilate, 6581-06-2, DTXSID00894168, NSC-173698, Benzeneacetic acid, alpha-hydroxy-alpha-phenyl-, 1-azabicyclo(2.2.2)oct-3-yl ester, Benzeneacetic acid, alpha-hydroxy-alpha-phenyl-, 1-azabicyclo[2.2.2]oct-3-yl ester, Benzilate, Quinuclidinyl, RO-2-3308, RefChem:872080, DTXCID701526727, E69DLR7470, Quinuclidinyl Benzilate, 3-Quinuclidyl benzilate, 3-quinuclidinyl-benzilate, [3H]QNB, 1-azabicyclo[2.2.2]octan-3-yl 2-hydroxy-2,2-diphenylacetate, (R)-(-)-3-Quinuclidinyl benzilate, Ro 2-3308, CHEMBL12980, (+-)-3-Quinuclidyl benzilate, (+-)-Oxyquinuclidine benzilate, NIOSH/DD4639000, (+-)-3-Quinuclidinol benzilate, (+-)-3-Quinuclidinyl benzilate, (+-)-beta-Quinuclidinyl benzilate, (+-)-3-Hydroxyquinuclidine benzilate, 3-Chinuclidylbenzilate, BZ, 3-Quinuclidinol benzilate, DD46390000, (+-)-Ro 2-3308, Benzilic acid, 3-quinuclidinyl ester, (+-)-, Buzz, QNB, Agent BZ, NSC 173698, CS 4030, EA 2277, Benzeneacetic acid, alpha-hydroxy-alpha-phenyl-, 1-azabicyclo(2.2.2)oct-3-yl ester, (+-)-, 1-Azabicyclo(2.2.2)octan-3-ol, benzilate, NSC170423, 3-Oxyquinuclidine benzilate, 3-quinuclidinylbenzilate, .beta.-Quinuclidinyl benzilate, 3-Hydroxyquinuclidine benzilate, [3H]quinuclidinylbenzilate, 3-Quinuclidinol, benzilate (ester), (+/-)-Quinuclidinyl benzilate, Benzeneacetic acid, .alpha.-hydroxy-.alpha.-phenyl-, 1-azabicyclo(2.2.2)oct-3-yl ester, Benzeneacetic acid, .alpha.-hydroxy-.alpha.-phenyl-, 1-azabicyclo[2.2.2]oct-3-yl ester, Substance 78, (+/-)-QNB, SCHEMBL59698, GTPL318, GTPL3260, R-(-)-3-Quinuclidinyl benzilate, BDBM50010096, NSC168347, NSC173698, AKOS027321160, (+/-)-Quinuclidinyl benzilate, powder, EA-2277, NSC-168347, NCGC00485298-01, DB-073210, NS00121904, quinuclidin-3-yl 2-hydroxy-2,2-diphenyl-acetate, L001186, Q223068, 1-Azabicyclo[2.2.2]octan-3-yl hydroxydi(phenyl)acetate, Benzeneacetic acid, 1-azabicyclo[2.2.2]oct-3-yl ester, 1-Azabicyclo[2.2.2]oct-3-yl hydroxy(diphenyl)acetate #, Hydroxy-diphenyl-acetic acid 1-aza-bicyclo[2.2.2]oct-3-yl ester, 1-AZABICYCLO[2.2.2]OCTAN-8-YL 2-HYDROXY-2,2-DI(PHENYL)ACETATE, Hydroxy-diphenyl-acetic acid 1-aza-bicyclo[2.2.2]oct-3-yl ester(QNB), Hydroxy-diphenyl-acetic acid 1-aza-bicyclo[2.2.2]oct-3-yl ester(R)-(-)-(QNB)
Theoretical properties:
molecular_formula: C21H23NO3
molecular_weight: 337.4 g/mol
exact_mass: 337.16779360 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 5
heavy_atom_count: 25
topological_polar_surface_area: 49.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystalline solid
color: Crystalline solid
odor: Slight benzene smell
melting_point: 164 °C
density: Decomposition point begins at 170 °C. Complete in 2 hours at 200 °C. Rate of hydrolysis: 25 °C at pH 7.0, about 4 weeks; at pH 9, 16 days, 16 hours; at pH 13, 1.8 minutes. Solid bulk density: 0.51 g/cu cm
solubility: Stable in most solvents ... soluble in propylene glycol, DMSO, and other solvents.
Descriptions:
chembl: QUINUCLIDINYL BENZILATE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 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.