3-quinuclidinyl benzilate

Structural formula
General
Surname	3-quinuclidinyl benzilate
other names	Benzilic acid 3-quinuclidinyl ester; Benzilic acid ester; 1-Azabicyclo [2.2.2] oct-8-yl 2-hydroxy-2,2-diphenyl acetate; QNB (3-quinuclidinyl benzilate); BZ (NATO code); Agent 15; Buzz; EA 2277;
Molecular formula	C 21 H 23 NO 3
Brief description	colorless and odorless solid
External identifiers / databases
EC number	636-245-0
ECHA InfoCard	100.164.060
PubChem	23056
Wikidata	Q223068
properties
Molar mass	337.41 g mol −1
Physical state	firmly
density	1.33 g cm −3
Melting point	189 ° C (from 170 ° C partial decomposition)
boiling point	322 ° C (from 170 ° C partial decomposition)
solubility	very little soluble in water; soluble in acids, ethanol and diethyl ether ;
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 300
	P: 264-301 + 310
Toxicological data	103 mg kg −1 ( LD 50 , mouse , ip ) ; 25 mg kg −1 ( LD 50 , mouse , iv ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

3- Quinuclidinyl benzilate ( BZ , QNB , in a misleading abbreviation also benzilic acid ester ) is a chemical warfare agent . He belongs to the group of psychological warfare agents . Since 1997, BZ - like other chemical weapons - has been officially banned internationally by the Chemical Weapons Convention ; Development, manufacture and storage are also prohibited.

history

The US military conducted clinical studies . In the period from 1959 to 1975, around 2800 soldiers are said to have been contaminated with BZ. During this time, comparative tests with LSD were also carried out. It quickly became clear, however, that BZ, in contrast to LSD, can be used much better as a warfare agent.

Name and characteristics

The designation benzilic acid ester is ambiguous, as it is not clear with which alcohol the benzilic acid ( 2-hydroxy-2,2-diphenylacetic acid ) is esterified . BZ is the ester of benzilic acid and 3-quinuclidinol ( 1-azabicyclo [2.2.2] octan-3-ol ), which occurs as a substructure in quinine .

3-quinuclidinyl benzilate is not very soluble in water; The compound is more soluble in acids, ethanol and diethyl ether . Upon heating, the decomposition of the substance starts at about 170 ° C in carbon dioxide , water , nitrogen , nitrogen oxides , and trace amounts of hydrogen cyanide ( Hydrocyanic acid ).

effect

BZ has an anticholinergic and parasympatholytic effect . The symptoms of intoxication are therefore also similar to other anticholinergics such as scopolamine and atropine . The effective dose is given as 5 μg / kg; the dose necessary for incapacity to act is around 9 μg / kg, and the dose that is 50% lethal in animal experiments ( semi-lethal dose or LD ₅₀ ) is 25 to 100 mg / kg (mouse, ip ).

First headache , confusion, hallucinations , then anxiety, concentration disorders, general restlessness alternating with apathetic phases. After a short time, the person concerned is in a state of complete loss of reality. He no longer has any conscious contact with his environment.

Physically, dry mucous membranes, reddened skin and constipation as well as severe dilation of the pupil can be observed.

The average duration of action is three days. However, individual symptoms can relapse for up to six weeks. Affected soldiers reported that there were permanent changes in personality in individual cases.

The following is decisive for military significance:

Application as an aerosol .
Those affected are quickly unable to fight or act (onset of effects after about an hour).
The effect lasts for at least three days.
After recovery, those affected can only remember the time before the contamination ( amnesia ).
Only in rare cases does permanent damage remain.

Calls

According to the journalist Pierre Darcout , BZ was used in the Vietnam War . The Dutch writer Wil Ververy reports on five missions in Vietnam. The US stocks of benzilic acid ester were officially destroyed in 1990.

It is possible that the substance was used as "Agent 15" on December 23, 2012 by Syrian government troops against rebels, the reports being based only on eyewitness reports from local doctors. According to an article in Foreign Policy magazine about the use of chemical weapons, which quoted a cable from the US Consulate General in Istanbul to the US State Department, the US government officially refrained from this account.

The film Jacob's Ladder addresses this issue. The series Navy CIS deals with the topic in episode 13, season 4. The series Numbers deals with it in episode 1, season 4. The science fiction novel The Silicon Island (original title 荒潮) by the Chinese author Chen Qiufan also deals with "Benzilic acid ester or QNB".

In the course of the Skripal poisoning case , the Russian Foreign Minister Lavrov alleged that the Swiss Spiez laboratory had detected BZ in the samples from the OPCW , thus refuting Russian authorship. In fact, the substance “Q3” (3-quinuclidinol), the (hydrolysis) decomposition product of BZ without the benzilic acid part, was found here. However, the Q3 was not part of the actual sample, but only contained in a control sample to which the OPCW added the Q3. Such control samples based on the principle of a blank sample are regularly sent by the OPCW together with the actual sample to the laboratories commissioned with the analysis, whereby it is not stated which is the correct, unchanged sample. This is a typical procedure as evidence of an uninfluenced, error-free implementation of the analysis.

Countermeasures

As with all chemical weapons , protection by appropriate clothing and a gas mask is crucial. After contamination, medicinal charcoal can help with oral poisoning , and physostigmine can also help as an antidote . For helpers, it should be noted that the contaminated because of the hallucinations that occur must be disarmed immediately and kept under constant control.

Web links

BZ . In: Erowid . (English)
CBRNE - Incapacitating Agents, 3-Quinuclidinyl Benzilate at eMedicin
nih.gov: Agent BZ (3-Quinuclidinyl Benzilate): Acute Exposure Guideline Levels

Individual evidence

↑ ^a ^b entry on BZ. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.
↑ ^a ^b ^c ^d Günter Hommel, Herbert F. Bender: Handbook of dangerous goods. Volume 6: Leaflets 2072-2502. 2nd edition, Springer, 2004, ISBN 978-3-540-20370-4 , leaflet 2288.
↑ ^a ^b Data sheet 3-quinuclidinyl benzilate from Sigma-Aldrich , accessed on May 14, 2015 ( PDF ).
↑ ^a ^b Entry on 3-quinuclidinyl benzilate in the ChemIDplus database of the United States National Library of Medicine (NLM)
^ US Army Armament Research & Development Command , Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX # 11998.
^ Günter Hommel: Handbook of dangerous goods. Transport - hazard classes , leaflet 2288, 2002, Springer-Verlag , ISBN 3-540-20348-6 .
↑ brainlogs.de: Neuro-weapons on the advance , August 24, 2009.
↑ Josh Rogin: Exclusive: Secret State Department cable: Chemical weapons used in Syria. Reported to Foreign Policy on January 15, 2013.
↑ Chemical weapons in Syria - The mystery about the use of Agent 15 in Homs , spiegel.de, January 16, 2013.
↑ Russian defeat in the Skripal case - OPCW exposes brazen disinformation , NZZ, April 19, 2018, page 1
^ The Guardian: OPCW rejects Russian claims of second Salisbury nerve agent. In: theguardian.com. April 18, 2018, accessed April 18, 2018 .
↑ Andreas Rüesch: Skripal: Russia pulls Switzerland into the case . 17th April 2018.

[roempp-1] try on BZ. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.

[hommel2004-2] Günter Hommel, Herbert F. Bender: Handbook of dangerous goods. Volume 6: Leaflets 2072-2502. 2nd edition, Springer, 2004, ISBN 978-3-540-20370-4 , leaflet 2288.

[Sigma-3] Data sheet 3-quinuclidinyl benzilate from Sigma-Aldrich , accessed on May 14, 2015 ( PDF ).

[ChemIDplus-4] Entry on 3-quinuclidinyl benzilate in the ChemIDplus database of the United States National Library of Medicine (NLM)

[5] US Army Armament Research & Development Command , Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX # 11998.

[hommel-6] Günter Hommel: Handbook of dangerous goods. Transport - hazard classes , leaflet 2288, 2002, Springer-Verlag , ISBN 3-540-20348-6 .

[7] rainlogs.de: Neuro-weapons on the advance , August 24, 2009.

[8] Josh Rogin: Exclusive: Secret State Department cable: Chemical weapons used in Syria. Reported to Foreign Policy on January 15, 2013.

[9] Chemical weapons in Syria - The mystery about the use of Agent 15 in Homs , spiegel.de, January 16, 2013.

[10] Russian defeat in the Skripal case - OPCW exposes brazen disinformation , NZZ, April 19, 2018, page 1

[guardian-11] The Guardian: OPCW rejects Russian claims of second Salisbury nerve agent. In: theguardian.com. April 18, 2018, accessed April 18, 2018 .

[12] Andreas Rüesch: Skripal: Russia pulls Switzerland into the case . 17th April 2018.