3-Quinuclidinyl benzilate

Source: Wikipedia, the free encyclopedia.
3-Quinuclidinyl benzilate
Bonding model
Bonding model
Ball and stick model
Ball and stick model
Names
IUPAC name
1-azabicyclo[2.2.2]octan-3-yl hydroxy(diphenyl)acetate
Other names
BZ
EA-2277
CS-4030
QNB
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
ECHA InfoCard
 100.164.060 Edit this at Wikidata
IUPHAR/BPS
MeSH Quinuclidinyl+benzilate
UNII
  • 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 checkY
    Key: HGMITUYOCPPQLE-UHFFFAOYSA-N checkY
  • 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
  • O=C(C(C1=CC=CC=C1)(C2=CC=CC=C2)O)OC3CN4CCC3CC4
Properties
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).
☒N verify (what is checkY☒N ?)

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[1]) is an odorless and bitter-tasting military incapacitating agent.[2] BZ is an antagonist of muscarinic acetylcholine receptors whose structure is the ester of benzilic acid with an alcohol derived from quinuclidine
.

Physiochemical characteristics

BZ is a white crystalline powder with a bitter taste. It is odorless and nonirritating with delayed symptoms several hours after contact.[2][3] It is stable in most solvents, with a half-life of three to four weeks in moist air; even heat-producing munitions can disperse it. It is extremely persistent in soil and water and on most surfaces. BZ is soluble in water, soluble in dilute acids, trichloroethylene, dimethylformamide, and most organic solvents, and insoluble with aqueous alkali.[3][4]

Effects

As a powerful

blindness), tachycardia, dermal vasodilation, xerostomia and hyperthermia.[5] The readily-observable symptoms of the anticholinergic toxidrome are famously characterized by the mnemonic "Mad as a hatter, red as a beet, dry as a bone and blind as a bat" (and variations thereof).[6]

Toxicity

Based on data from more than 500 reported cases of accidental atropine overdose and deliberate poisoning, the median lethal oral dose is estimated to be approximately 450 mg (with a shallow probit slope of 1.8). Some estimates of lethality with BZ have been grossly erroneous, and ultimately the safety margin for BZ is inconclusive due to lack of human data at higher dosage ranges, though some researchers have estimated it to be 0.5 to 3.0 mg/kg and an LD01 is 0.2 to 1.4 mg/kg (Rosenblatt, Dacre, Shiotsuka, & Rowlett, 1977).[7]

Treatment

Antidotes for BZ include 7-MEOTA, which can be administered in tablet or injection form. Atropine and tacrine (THA) have also been used as treatments, THA having been shown to reduce the effects of BZ within minutes.[8][9] Some military references suggest the use of physostigmine to temporarily increase synaptic acetylcholine concentrations.[2]

History

Invention and research

BZ was invented by the Swiss

M43 cluster bomb
, until all such stocks were destroyed in 1989 as part of a general downsizing of the US chemical warfare program.

In 2022 a documentary film, Dr Delirium and The Edgewood Experiments, was broadcast on Discovery+, featuring an interview with Ketchum not previously shown.[14]

Use and alleged use

In February 1998, the British

CIA concluded that Iraq had not stockpiled or weaponized Agent 15.[a][17]

According to Konstantin Anokhin, professor at the Institute of Normal Physiology in Moscow, BZ was the

2002 Nord-Ost siege, but at least 115 hostages perished due to overdose;[18]
but many other agents have also been proposed, and none definitively confirmed.

In January 2013, an unidentified U.S. administration official, referring to an undisclosed U.S. State Department cable, claimed that "Syrian contacts made a compelling case that Agent 15, a hallucinogenic chemical similar to BZ,

U.S. National Security Council
spokesman stated,

The reporting we have seen from media sources regarding alleged chemical weapons incidents in Syria has not been consistent with what we believe to be true about the Syrian chemical weapons program.[17][21]

Legality

BZ is listed as a Schedule 2 compound by the OPCW (Szinicz, 2005).[22]

See also

Footnotes

  1. ^ "We assess that Iraq never went beyond research with Agent 15 – a hallucinogenic chemical similar to BZ – or any other psychochemical. Agent 15 became an issue after a 9 February 1998 British press release claimed that the UK had information, thought to be reliable, that Iraq had large quantities of this chemical agent in the 1980s. UNSCOM and intelligence information indicated that Iraq researched a number of psychochemicals, including Agent 15, BZ, and PCP; however, UNSCOM indicated it saw no evidence of Iraqi importation of large quantities, weaponization, procurement of militarily significant quantities of precursors, or industrial production of these agents."[16]

References

  1. ^ Conant, Eve (22 November 2002). "More Questions Than Answers". Newsweek. Retrieved 15 April 2018.
  2. ^ a b c QNB: Incapacitating Agent. Emergency Response Safety and Health Database. National Institute for Occupational Safety and Health. Accessed April 20, 2009.
  3. ^
    OCLC 903965588
    .
  4. ^ US Army FM 3-9
  5. ^ Committee on Acute Exposure Guideline Levels; Committee on Toxicology; Board on Environmental Studies and Toxicology; Division on Earth and Life Studies; National Research Council. Washington (DC): National Academies Press (US); 2013 Apr 26.
  6. S2CID 37914161
    .
  7. ^
    OCLC 858939565
    .
  8. OCLC 903965588
    .
  9. OCLC 858939565
    .
  10. ^ a b c d e Kirby, Reid. "Paradise Lost: The Psycho Agents", The CBW Conventions Bulletin, May 2006, Issue no. 71, pp. 2-3, accessed December 11, 2008.
  11. ^ Possible Long-Term Health Effects of Short-Term Exposure To Chemical Agents, Volume 2: Cholinesterase Reactivators, Psychochemicals and Irritants and Vesicants. (1984)
  12. ^ Ketchum - Chemical Warfare: Secrets Almost Forgotten Archived 2022-10-22 at the Wayback Machine (2006)
  13. ^ "Army's Hallucinogenic Weapons Unveiled". Wired. April 2007. Archived from the original on 24 December 2016. Retrieved 22 August 2022.
  14. ^ Simonpillai, Radheyan (9 June 2022). "'It affected a great number of people': inside the world of shocking military drug experiments". The Guardian.
  15. ^ Colin Brown; Ian Burrel (10 February 1998). "Iraqi 'zombie gas' arsenal revealed". The Independent. UK. Archived from the original on 2011-05-13.
  16. U.S. Central Intelligence Agency. April 2002. Archived from the original
    on 14 April 2019. Retrieved 28 January 2013.
  17. ^ a b Lewis, Jeffrey (25 January 2013). "Why everyone's wrong about Assad's zombie gas". Foreign Policy. Retrieved 28 January 2013.
  18. ^ "Hostages given military's nerve gas antidote". The Guardian. 28 October 2002.
  19. U.S. Central Intelligence Agency. April 2002. Archived from the original on 2019-04-14. Retrieved 2013-01-19.[full citation needed
    ]
  20. ^ Rogin, Josh (15 January 2013). "Secret State Department cable: Chemical weapons used in Syria". Foreign Policy The Cable. Retrieved 16 January 2013.
  21. ^ a b "U.S. plays down media report that Syria used chemical weapons". Reuters. 16 January 2013. Retrieved 28 January 2013.
  22. S2CID 103245582
    .

External links

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