Lewisite 3 (L-3) is an

organoarsenic Organoarsenic chemistry is the chemistry of compounds containing a chemical bond between arsenic and carbon. A few organoarsenic compounds, also called "organoarsenicals," are produced industrially with uses as insecticides, herbicides, and fungic ...

chemical weapon like

lewisite 1 Lewisite (L) (A-243) is an organoarsenic compound. It was once manufactured in the United States, Japan, Germany and the Soviet Union for use as a chemical weapon, acting as a vesicant (blister agent) and lung irritant. Although the substance is c ...

and

lewisite 2 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.McNutt, Patrick M., and Tracey L. Hamilton. "Ocular toxi ...

first synthesized in 1904 by

Julius Arthur Nieuwland Julius Aloysius Arthur Nieuwland, CSC, (14 February 1878 – 11 June 1936) was a Belgian-born Holy Cross priest and professor of chemistry and botany at the University of Notre Dame, Indiana. He is known for his contributions to acetylene ...

.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. 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 ''Pelargonium'' () is a genus of flowering plants that includes about 280 species of perennials, succulents, and shrubs, commonly called geraniums, pelargoniums, or storksbills. ''Geranium'' is also the botanical name and common name of a separa ...

Synthesis

Lewisite 3 is made as a

byproduct A by-product or byproduct is a secondary product derived from a production process, manufacturing process or chemical reaction; it is not the primary product or service being produced. A by-product can be useful and marketable or it can be cons ...

along with lewisite 2 in the reaction that makes lewisite 1.Chemistry of Sulfur Mustard and Lewisite https://www.ncbi.nlm.nih.gov/books/NBK236079/

Acetylene Acetylene (Chemical nomenclature, systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is u ...

reacts with AsCl3 in

hydrochloric acid Hydrochloric acid, also known as muriatic acid or spirits of salt, is an aqueous solution of hydrogen chloride (HCl). It is a colorless solution with a distinctive pungency, pungent smell. It is classified as a acid strength, strong acid. It is ...

solution, with

mercuric chloride Mercury(II) chloride (mercury bichloride, mercury dichloride, mercuric chloride), historically also sulema or corrosive sublimate, is the inorganic chemical compound of mercury and chlorine with the formula HgCl2, used as a laboratory reagent. ...

as a

catalyst Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...

, to give lewisite in 80 to 85% yield. :AsCl₃ + C₂H₂ → (ClCH=CH)AsCl₂ Lewisite 3 is formed when there are three additions of

acetylene Acetylene (Chemical nomenclature, systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is u ...

to the

arsenic Arsenic is a chemical element; it has Symbol (chemistry), symbol As and atomic number 33. It is a metalloid and one of the pnictogens, and therefore shares many properties with its group 15 neighbors phosphorus and antimony. Arsenic is not ...

center instead of one.

Exposure

Adverse health effects caused by lewisite can vary and are dependent on the amount and duration of exposure. 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 A nosebleed, also known as epistaxis, is an instance of bleeding from the nose. Blood can flow down into the stomach, and cause nausea and vomiting. In more severe cases, blood may come out of both nostrils. Rarely, bleeding may be so significa ...

(epistaxis),

laryngitis Laryngitis is inflammation of the larynx (voice box). Symptoms often include a hoarse voice and may include fever, cough, pain in the front of the neck, and trouble swallowing. Typically, these last under 2 weeks. Causes Laryngitis is cat ...

sneezing A sneeze (also known as sternutation) is a semi-autonomous, convulsive expulsion of air from the lungs through the nose and mouth, usually caused by foreign particles irritating the nasal mucosa. A sneeze expels air forcibly from the mouth a ...

cough A cough is a sudden expulsion of air through the large breathing passages which can help clear them of fluids, irritants, foreign particles and Microorganism, microbes. As a protective reflex, coughing can be repetitive with the cough reflex fol ...

ing,

vomiting Vomiting (also known as emesis, puking and throwing up) is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose. Vomiting can be the result of ailments like food poisoning, gastroenteritis, pre ...

, difficult breathing (

dyspnea Shortness of breath (SOB), known as dyspnea (in AmE) or dyspnoea (in BrE), is an uncomfortable feeling of not being able to breathe well enough. The American Thoracic Society defines it as "a subjective experience of breathing discomfort that ...

). From one acute exposure, someone who has inhaled lewisite can develop chronic respiratory disease. In severe cases of exposure, can cause fatal

pulmonary edema Pulmonary edema (British English: oedema), also known as pulmonary congestion, is excessive fluid accumulation in the tissue or air spaces (usually alveoli) of the lungs. This leads to impaired gas exchange, most often leading to shortness ...

pneumonitis Pneumonitis describes general inflammation of lung tissue. Possible causative agents include radiation therapy of the chest, exposure to medications used during chemo-therapy, the inhalation of debris (e.g., animal dander), aspiration, herbicide ...

, or

respiratory failure Respiratory failure results from inadequate gas exchange by the respiratory system, meaning that the arterial oxygen, carbon dioxide, or both cannot be kept at normal levels. A drop in the oxygen carried in the blood is known as hypoxemia; a r ...

Ingestion

Ingestion results in severe pain, nausea, vomiting, and tissue damage. Those exposed to lewisite can develop refractory

hypotension Hypotension, also known as low blood pressure, is a cardiovascular condition characterized by abnormally reduced blood pressure. Blood pressure is the force of blood pushing against the walls of the arteries as the heart pumps out blood and is ...

(low blood pressure) known as Lewisite shock, as well as some features of arsenic toxicity. Lewisite causes physical damage to

capillaries A capillary is a small blood vessel, from 5 to 10 micrometres in diameter, and is part of the microcirculation system. Capillaries are microvessels and the smallest blood vessels in the body. They are composed of only the tunica intima (the in ...

, which then become leaky, meaning that there is not enough blood volume to maintain blood pressure, a condition called

hypovolemia Hypovolemia, also known as volume depletion or volume contraction, is a state of abnormally low extracellular fluid in the body. This may be due to either a loss of both salt and water or a decrease in blood volume. Hypovolemia refers to the loss ...

. When the blood pressure is low, the kidneys may not receive enough oxygen and can be damaged.

Eye Exposure

The results of eye exposure can range from stinging, burning pain and strong irritation to

blister A blister is a small pocket of body fluid (lymph, serum, plasma, blood, or pus) within the upper layers of the skin, usually caused by forceful rubbing (friction), burning, freezing, chemical exposure or infection. Most blisters are filled ...

ing and scarring of the cornea, along with

blepharospasm Blepharospasm is a neurological disorder characterized by intermittent, involuntary spasms and contractions of the orbicularis oculi muscle, orbicularis oculi (eyelid) muscles around both eyes. These result in abnormal twitching or blinking, an ...

lacrimation Tears are a clear liquid secreted by the lacrimal glands (tear gland) found in the eyes of all land mammals. Tears are made up of water, electrolytes, proteins, lipids, and mucins that form layers on the surface of eyes. The different types of ...

, and edema of the eyelids and periorbital area. Eye exposure to lewisite can cause permanent visual impairment or blindness. 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 Visual or vision impairment (VI or VIP) is the partial or total inability of visual perception. In the absence of treatment such as corrective eyewear, assistive devices, and medical treatment, visual impairment may cause the individual difficul ...

. Generalised symptoms also include restlessness, weakness, hypothermia and low blood pressure.

Chronic Exposure

Chronic exposure to lewisite can cause

arsenic poisoning Arsenic poisoning (or arsenicosis) is a medical condition that occurs due to elevated levels of arsenic in the body. If arsenic poisoning occurs over a brief period of time, symptoms may include vomiting, abdominal pain, encephalopathy, and water ...

and development of a lewisite

allergy Allergies, also known as allergic diseases, are various conditions caused by hypersensitivity of the immune system to typically harmless substances in the environment. These diseases include Allergic rhinitis, hay fever, Food allergy, food al ...

. It can also cause various long-term illnesses or permanent damage to organs, depending on where the exposure has occurred, including

conjunctivitis Conjunctivitis, also known as pink eye or Madras eye, is inflammation of the conjunctiva, the thin, clear layer that covers the white surface of the eye and the inner eyelid. It makes the eye appear pink or reddish. Pain, burning, scratchiness ...

, aversion to light (

photophobia Photophobia is a medical symptom of abnormal intolerance to visual perception of light. As a medical symptom, photophobia is not a morbid fear or phobia, but an experience of discomfort or pain to the eyes due to light exposure or by presence o ...

), visual impairment, double vision (

diplopia Diplopia is the simultaneous perception of two images of a single object that may be displaced in relation to each other. Also called double vision, it is a loss of visual focus under regular conditions, and is often voluntary. However, when occ ...

), tearing (

), dry mucous membranes,

garlic breath Garlic breath is halitosis (bad breath) resulting from the consumption of garlic. Causes The major volatile compounds responsible for garlic breath are allyl methyl sulfide, allyl methyl disulfide, allyl mercaptan, diallyl disulfide, dimeth ...

, burning pain in the nose and mouth,

toxic encephalopathy Toxic encephalopathy is a neurologic disorder caused by exposure to neurotoxic organic solvents such as toluene, following exposure to heavy metals such as manganese, as a side effect of melarsoprol treatment for African trypanosomiasis, adverse e ...

peripheral neuropathy Peripheral neuropathy, often shortened to neuropathy, refers to damage or disease affecting the nerves. Damage to nerves may impair sensation, movement, gland function, and/or organ function depending on which nerve fibers are affected. Neuropa ...

seizures A seizure is a sudden, brief disruption of brain activity caused by abnormal, excessive, or synchronous neuronal firing. Depending on the regions of the brain involved, seizures can lead to changes in movement, sensation, behavior, awareness, o ...

nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. It can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the throat. Over 30 d ...

chronic obstructive pulmonary disease Chronic obstructive pulmonary disease (COPD) is a type of progressive lung disease characterized by chronic respiratory symptoms and airflow limitation. GOLD defines COPD as a heterogeneous lung condition characterized by chronic respiratory s ...

(COPD),

bronchitis Bronchitis is inflammation of the bronchi (large and medium-sized airways) in the lungs that causes coughing. Bronchitis usually begins as an infection in the nose, ears, throat, or sinuses. The infection then makes its way down to the bronchi. ...

dermatitis Dermatitis is a term used for different types of skin inflammation, typically characterized by itchiness, redness and a rash. In cases of short duration, there may be small blisters, while in long-term cases the skin may become thickened ...

skin ulcers An ulcer is a sore on the skin or a mucous membrane, accompanied by the disintegration of tissue. Ulcers can result in complete loss of the epidermis and often portions of the dermis and even subcutaneous fat. Ulcers are most common on the skin o ...

basal cell carcinoma Basal-cell carcinoma (BCC), also known as basal-cell cancer, basalioma, or rodent ulcer, is the most common type of skin cancer. It often appears as a painless, raised area of skin, which may be shiny with Telangiectasia, small blood vessels ru ...

, and

squamous cell carcinoma Squamous-cell carcinoma (SCC), also known as epidermoid carcinoma, comprises a number of different types of cancer that begin in squamous cells. These cells form on the surface of the skin, on the lining of hollow organs in the body, and on the ...

Treatment

Basic first aid for lewisite exposure is

decontamination Decontamination (sometimes abbreviated as decon, dcon, or decontam) is the process of removing contaminants on an object or area, including chemicals, micro-organisms, and/or radioactive substances. This may be achieved by chemical reaction, dis ...

and

irrigation Irrigation (also referred to as watering of plants) is the practice of applying controlled amounts of water to land to help grow crops, landscape plants, and lawns. Irrigation has been a key aspect of agriculture for over 5,000 years and has bee ...

of any areas that have been exposed, and when necessary

airway management Airway management includes a set of maneuvers and medical procedures performed to prevent and relieve an airway obstruction. This ensures an open pathway for gas exchange between a patient's lungs and the atmosphere. This is accomplished by either ...

assisted ventilation Mechanical ventilation or assisted ventilation is the medical term for using a ventilator machine to fully or partially provide artificial ventilation. Mechanical ventilation helps move air into and out of the lungs, with the main goal of he ...

, and monitoring of vital signs. British anti-lewisite, also called

dimercaprol 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 n ...

, 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 Chelation () is a type of bonding of ions and their molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These l ...

that binds to the

in lewisite.Vilensky, Joel A., and Kent Redman. "British anti-Lewisite (dimercaprol): an amazing history." Annals of emergency medicine 41.3 (2003): 378-383. It is

contraindicated In medicine, a contraindication is a condition (a situation or factor) that serves as a reason not to take a certain medical treatment due to the harm that it would cause the patient. Contraindication is the opposite of indication, which is a rea ...

in those with peanut allergies.

References

{{reflist Alkene derivatives Arsenical vesicants Organochlorides Arsenic(III) compounds