Lewisite 3

Last updated
Lewisite 3 [1]
Lewisite 3.svg
Names
Preferred IUPAC name
Tris[(E)-2-chloroethen-1-yl]arsane
Other names
Tris((E)-2-chlorovinyl)arsine

(E,E,E)-Lewisite 3

L-3
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C6H6AsCl3/c8-4-1-7(2-5-9)3-6-10/h1-6H/b4-1+,5-2+,6-3+
    Key: AOAVIJUEFJPSAI-GZDDRBCLSA-N
  • C(=C[As](C=CCl)C=CCl)Cl
Properties
C6H6AsCl3
Molar mass 259.4 g mol−1
Hazards
NFPA 704 (fire diamond)
4
1
1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Lewisite 3(L-3) is an organoarsenic chemical weapon like lewisite 1 and lewisite 2 first synthesized in 1904 by Julius Arthur Nieuwland. [2] It is usually found as a mixture of 2-chlorovinylarsonous dichloride (lewisite 1) as well as bis(2-chloroethenyl) arsinous chloride (lewisite 2) and tris(2-chlorovinyl)arsine (lewisite 3). [2] Pure lewisite 1 is an oily, colorless liquid, however, the impure mixture can appear amber to black with an odor distinct to geraniums. [3] [4]

Contents

Synthesis

Lewisite 3 is made as a byproduct along with lewisite 2 in the reaction that makes lewisite 1. [5]

Acetylene reacts with AsCl3 in hydrochloric acid solution, with mercuric chloride as a catalyst, to give lewisite in 80 to 85% yield. [5]

AsCl3 + C2H2 → (ClCH=CH)AsCl2

Lewisite 3 is formed when there are three additions of acetylene to the arsenic center instead of one.

Exposure

Adverse health effects caused by lewisite can vary and are dependent on; the amount people are exposed to and, the amount of time someone is exposed to it. Lewisite immediately damages the skin, eyes, and respiratory tract and is a strong irritant and blistering agent. Due to its arsenic center, lewisite may also cause problems similar to arsenic poisonings like stomach ailments and low blood pressure.

Inhalation

Inhalation, the most common route of exposure, causes a burning pain and irritation throughout the respiratory tract, nosebleed (epistaxis), laryngitis, sneezing, coughing, vomiting, difficult breathing (dyspnea). From one acute exposure, someone who has inhaled lewisite can develop chronic respiratory disease. [4] In severe cases of exposure, can cause fatal pulmonary edema, pneumonitis, or respiratory failure.

Ingestion

Ingestion results in severe pain, nausea, vomiting, and tissue damage. [4] Those exposed to lewisite can develop refractory hypotension (low blood pressure) known as Lewisite shock, as well as some features of arsenic toxicity. [6] Lewisite causes physical damage to capillaries, which then become leaky, meaning that there is not enough blood volume to maintain blood pressure, a condition called hypovolemia. When the blood pressure is low, the kidneys may not receive enough oxygen and can be damaged. [4]

Eye Exposure

The results of eye exposure can range from stinging, burning pain and strong irritation to blistering and scarring of the cornea, along with blepharospasm, lacrimation, and edema of the eyelids and periorbital area. Eye exposure to lewisite can cause permanent visual impairment or blindness. [4] The eyes can swell shut, which can keep the eyes safe from further exposure. The most severe consequences of eye exposure to lewisite are globe perforation and blindness. [4] Generalised symptoms also include restlessness, weakness, hypothermia and low blood pressure.

Chronic Exposure

Chronic exposure to lewisite can cause arsenic poisoning and development of a lewisite allergy. It can also cause various long-term illnesses or permanent damage to organs, depending on where the exposure has occurred, including conjunctivitis, aversion to light (photophobia), visual impairment, double vision (diplopia), tearing (lacrimation), dry mucous membranes, garlic breath, burning pain in the nose and mouth, toxic encephalopathy, peripheral neuropathy, seizures, nausea, vomiting, chronic obstructive pulmonary disease (COPD), bronchitis, dermatitis, skin ulcers, basal cell carcinoma, and squamous cell carcinoma. [4]

Treatment

Basic first aid for lewisite exposure is decontamination and irrigation of any areas that have been exposed, and when necessary airway management, assisted ventilation, and monitoring of vital signs. [4] British anti-lewisite, also called dimercaprol, is the antidote for lewisite. It can be injected to prevent systemic toxicity, but will not prevent injury to the skin, eyes, or mucous membranes. Chemically, dimercaprol is a chelating agent that binds to the arsenic in lewisite. [7] It is contraindicated in those with peanut allergies. [4]

See also

Related Research Articles

Mustard gas or sulfur mustard is any of several chemical compounds that contain the chemical structure SCH2CH2Cl. In the wider sense, compounds with the substituent SCH2CH2X and NCH2CH2X are known as sulfur mustards and nitrogen mustards (X = Cl, Br), respectively. Such compounds are potent alkylating agents, which can interfere with several biological processes. Also known as mustard agents, this family of compounds are infamous cytotoxic and blister agents. The name mustard gas is technically incorrect: the substances, when dispersed, are often not gases but a fine mist of liquid droplets. Mustard gases form blisters on exposed skin and in the lungs, often resulting in prolonged illness ending in death. The typical mustard gas is the organosulfur compound called bis(2-chloroethyl) sulfide.

<span class="mw-page-title-main">Lewisite</span> Chemical compound

Lewisite (L) (A-243) is an organoarsenic compound. It was once manufactured in the U.S., Japan, Germany and the Soviet Union for use as a chemical weapon, acting as a vesicant and lung irritant. Although the substance is colorless and odorless in its pure form, impure samples of lewisite are a yellow, brown, violet-black, green, or amber oily liquid with a distinctive odor that has been described as similar to geraniums.

<span class="mw-page-title-main">Blister agent</span> Chemicals that result in blistering and skin irritation and damaging

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Cyanogen chloride is a highly toxic chemical compound with the formula CNCl. This linear, triatomic pseudohalogen is an easily condensed colorless gas. More commonly encountered in the laboratory is the related compound cyanogen bromide, a room-temperature solid that is widely used in biochemical analysis and preparation.

A blood agent is a toxic chemical agent that affects the body by being absorbed into the blood. Blood agents are fast-acting, potentially lethal poisons that typically manifest at room temperature as volatile colorless gases with a faint odor. They are either cyanide- or arsenic-based.

<span class="mw-page-title-main">Dimercaprol</span> Chemical compound

Dimercaprol, also called British anti-Lewisite (BAL), is a medication used to treat acute poisoning by arsenic, mercury, gold, and lead. It may also be used for antimony, thallium, or bismuth poisoning, although the evidence for those uses is not very strong. It is given by injection into a muscle.

<span class="mw-page-title-main">Chlormethine</span> Chemical compound

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<span class="mw-page-title-main">Abrin</span> Chemical compound

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<span class="mw-page-title-main">Adamsite</span> Chemical compound

Adamsite or DM is an organic compound; technically, an arsenical diphenylaminechlorarsine, that can be used as a riot control agent. DM belongs to the group of chemical warfare agents known as vomiting agents or sneeze gases. First synthesized in Germany by Heinrich Otto Wieland in 1915, it was independently developed by the US chemist Roger Adams at the University of Illinois in 1918.

<span class="mw-page-title-main">HN1 (nitrogen mustard)</span> Chemical compound

Bis(2-chloroethyl)ethylamine is the organic compound with the formula C2H5N(CH2CH2Cl)2. Often abbreviated HN1, it is a powerful vesicant and a nitrogen mustard gas used for chemical warfare. HN1 was developed in the 1920s and 1930s to remove warts and later as a military agent. Because of the latter use, it is a Schedule 1 chemical within the Chemical Weapons Convention and therefore use and production is strongly restricted. It has never been used in warfare.

Potassium nitrate is an oxidizer so storing it near fire hazards or reducing agents should be avoided to minimise risk in case of a fire.

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<span class="mw-page-title-main">Malaoxon</span> Chemical compound

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<span class="mw-page-title-main">Methyldichloroarsine</span> Chemical compound

Methyldichloroarsine, sometimes abbreviated "MD" and also known as methyl Dick, is an organoarsenic compound with the formula CH3AsCl2. This colourless volatile liquid is a highly toxic vesicant that has been used in chemical warfare.

<span class="mw-page-title-main">Phenyldichloroarsine</span> Chemical compound

Phenyldichloroarsine, also known by its wartime name phenyl Dick and its NATO abbreviation PD, is an organic arsenical vesicant and vomiting agent developed by Germany and France for use as a chemical warfare agent during World War I. The agent is known by multiple synonyms and is technically classified as a vesicant, or blister agent.

Chlorine gas poisoning is an illness resulting from the effects of exposure to chlorine beyond the threshold limit value.

<span class="mw-page-title-main">Lewisite 2</span> Chemical compound

Lewisite 2(L-2) is an organoarsenic chemical weapon with the formula AsCl(CH=CHCl)2. It is similar to lewisite 1 and lewisite 3 and was first synthesized in 1904 by Julius Arthur Nieuwland. It is usually found as a mixture of 2-chlorovinylarsonous dichloride (lewisite 1) as well as bis(2-chloroethenyl) arsinous chloride (lewisite 2) and tris(2-chlorovinyl)arsine (lewisite 3). Pure lewisite 1 is an oily, colorless liquid, however, the impure mixture can appear amber to black with an odor distinct to geraniums.

References

  1. ↑ National Center for Biotechnology Information. PubChem Database. Lewisite 3, CID=5352143, https://pubchem.ncbi.nlm.nih.gov/compound/Lewisite-3 (accessed on Apr. 19, 2020)
  2. 1 2 McNutt, Patrick M., and Tracey L. Hamilton. "Ocular toxicity of chemical warfare agents." Handbook of Toxicology of Chemical Warfare Agents. Academic Press, 2015. 535-555.
  3. ↑ "CDC - Facts about Lewisite". www.cdc.gov. Retrieved 2020-04-15.
  4. 1 2 3 4 5 6 7 8 9 "CDC - The Emergency Response Safety and Health Database: Blister Agent: LEWISITE (L) - NIOSH". www.cdc.gov. Retrieved 2016-01-14.
  5. 1 2 Chemistry of Sulfur Mustard and Lewisite https://www.ncbi.nlm.nih.gov/books/NBK236079/
  6. ↑ Chauhan, S.; Chauhan, S.; D’Cruz, R.; Faruqi, S.; Singh, K. K.; Varma, S.; Singh, M.; Karthik, V. Chemical warfare agents. Environ. Toxicol. Pharmacol. 2008, 26, 113-122
  7. ↑ Vilensky, Joel A., and Kent Redman. "British anti-Lewisite (dimercaprol): an amazing history." Annals of emergency medicine 41.3 (2003): 378-383.
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