Mustard gas: Difference between revisions

Revision as of 11:20, 25 April 2005

Latest revision as of 03:22, 21 August 2025

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{{Short description|Chemical warfare agent}}

[[Image:Mustard_gas.png|frame|right|Chemical Structure of Mustard Gas Compound]]

{{Use American English|date=October 2024}}

'''Mustard gas''' (HD) is a [[chemical compound]] that was first used as a [[chemical weapon]] in [[World War I]]. In pure form, it is a colourless, odourless, viscous liquid at room temperature and causes blistering of the skin. The name comes from impure mustard gas, which is usually yellow-brown in colour and has an odour resembling [[mustard]], [[garlic]] or [[horseradish]]. It is otherwise not related to mustard in any way.

{{Use mdy dates|date=October 2024}}

{{cs1 config|name-list-style=vanc|display-authors=3}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477002998

| Name = Mustard gas

| ImageFile = Sulfur-mustard-2D-skeletal.svg

| ImageFile1 = Sulfur-mustard-3D-balls.png

| ImageFile2 = Sulfur-mustard-3D-vdW.png

| PIN = 1-Chloro-2-[(2-chloroethyl)sulfanyl]ethane

| OtherNames = Bis(2-chloroethyl) sulfide<br />HD <br />Iprit<br />Schwefel-LOST<br />Lost<br />Sulfur mustard<br />Senfgas<br />Yellow cross liquid<br />Yperite<br />Distilled mustard<br />Mustard T- mixture<br />1,1'-thiobis[2-chloroethane]<br />Dichlorodiethyl sulfide

| Section1 = {{Chembox Identifiers

| Beilstein = 1733595

| PubChem = 10461

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 21106142

| EC_number = 684-527-7

| InChI = 1/C4H8Cl2S/c5-1-3-7-4-2-6/h1-4H2

| InChIKey = QKSKPIVNLNLAAV-UHFFFAOYAK

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 455341

| Gmelin = 324535

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C4H8Cl2S/c5-1-3-7-4-2-6/h1-4H2

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = QKSKPIVNLNLAAV-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 505-60-2

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = T8KEC9FH9P

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C19164

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 25434

| SMILES = ClCCSCCCl

}}

| Section2 = {{Chembox Properties

| C=4 | H=8 | Cl=2 | S=1

| Appearance = Colorless if pure. Normally ranges from pale yellow to dark brown. Slight garlic or horseradish type odor.<ref name="FM 3-8">FM 3–8 Chemical Reference handbook, US Army, 1967</ref>

| Density = 1.27 g/mL, liquid

| Solubility = 7.6 mg/L at 20°C<ref name="opcw.org">[http://www.opcw.org/about-chemical-weapons/types-of-chemical-agent/mustard-agents/ Mustard agents: description, physical and chemical properties, mechanism of action, symptoms, antidotes and methods of treatment]. Organisation for the Prohibition of Chemical Weapons. Accessed June 8, 2010.</ref>

| SolubleOther = [[Alcohol (chemistry)|Alcohols]], [[ether]]s, [[hydrocarbon]]s, [[lipid]]s, [[tetrahydrofuran|THF]]

| MeltingPtC = 14.45

| BoilingPtC = 217

| BoilingPt_notes = begins to decompose at {{convert|217|C|F}} and boils at {{convert|218|C|F}}

}}

| Section7 = {{Chembox Hazards

| ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics0418.htm External MSDS]

| MainHazards = Flammable, toxic, vesicant, carcinogenic, mutagenic

| GHS_ref = <ref name=pubchem/>

| GHSPictograms = {{GHS06}}

| GHSSignalWord = Danger

| PPhrases = {{P-phrases|P260|P261|P262|P264|P270|P271|P280|P284|P301+P310|P302+P350|P302+P352|P304+P340|P305+P351+P338|P310|P312|P320|P321|P322|P330|P332+P313|P337+P313|P361|P362|P363|P403+P233|P405|P501}}

| HPhrases = {{H-phrases|H300|H310|H315|H319|H330|H335}}

| NFPA-H = 4

| NFPA-F = 1

| NFPA-R = 1

| FlashPtC = 105

}}

| Section8 = {{Chembox Related

| OtherCompounds = [[Nitrogen mustard]], [[Bis(chloroethyl) ether]], [[Chloromethyl methyl sulfide]]

}}

}}

'''Mustard gas''' or '''sulfur mustard''' are names commonly used for the [[organosulfur compound|organosulfur]] [[chemical compound]] [[bis(2-chloroethyl) sulfide]], which has the chemical structure S(CH₂CH₂Cl)₂, as well as other [[Chemical species|species]]. In the wider sense, compounds with the substituents {{chem2|\sSCH2CH2X or \sN(CH2CH2X)2}} are known as ''sulfur mustards'' or ''[[nitrogen mustards]]'', respectively, where X = Cl or Br. Such compounds are potent [[alkylating agent]]s, making mustard gas acutely and severely toxic.<ref name="pubchem">{{cite web |title=Mustard gas |url=https://pubchem.ncbi.nlm.nih.gov/compound/10461 |publisher=PubChem, US National Library of Medicine |access-date=4 October 2024 |date=28 September 2024}}</ref> Mustard gas is a [[carcinogen]].<ref name=pubchem/> There is no preventative agent against mustard gas, with protection depending entirely on skin and airways protection, and no [[antidote]] exists for mustard poisoning.<ref name=who/>

Also known as mustard agents, this family of compounds comprises infamous [[cytotoxicity|cytotoxins]] and [[blister agent]]s with a long history of use as [[chemical weapons]].<ref name="who">{{cite web |title=Mustard gas fact sheet |url=https://www.emro.who.int/ceha/information-resources/mustard-gas-fact-sheet.html |publisher=World Health Organization, Eastern Mediterranean Region, Regional Centre for Environmental Health Action |access-date=4 October 2024 |date=2024}}</ref> The name ''mustard gas'' is technically incorrect; the substances, when [[Dispersion (chemistry)|dispersed]], are often not gases but a fine mist of liquid droplets that can be readily absorbed through the skin and by inhalation.<ref name=pubchem/> The skin can be affected by contact with either the liquid or vapor. The rate of penetration into skin is proportional to dose, temperature and humidity.<ref name=pubchem/>

It was first synthesised by [[Frederick Guthrie]] in [[1860]], though it is possible that it was developed as early as [[1822]] by M. Depretz. V. Meyer would publish a paper in [[1886]] describing a synthesis which produced good yields. The abbreviation LOST comes from [[Lommel and Steinkopf|LOmmel and STeinkopf]] who developed a process for mass-producing the gas for war use at the [[Germany|German]] company [[Bayer AG]].

Sulfur mustards are viscous liquids at room temperature and have an odor resembling [[mustard plant]]s, [[garlic]], or [[horseradish]], hence the name.<ref name=pubchem/><ref name=who/> When pure, they are colorless, but when used in impure forms, such as in warfare, they are usually [[tawny (color)|yellow-brown]]. Mustard gases form [[blister]]s on exposed skin and in the lungs, often resulting in prolonged illness ending in death.<ref name=who/>

Other names for mustard gas include ''HD'', ''senfgas'', ''sulfur mustard'', ''blister gas'', ''S-LOST'', and ''Kampfstoff LOST'' or ''Yperite'' or ''Yperiet''.

"mustine" as shown in older medical dictionaries a substance used in chemotherapy to treat/cure cancer.The use of mustard gas in chemotherapy has ceased in most countries in recent years.

==Chemistry==

{{WMD/Chemical}}

Chemically, it is a [[thioether]] with the formula [[carbon|C]]₄[[hydrogen|H]]₈[[chlorine|Cl]]₂[[sulfur|S]]. Its structure can be described as 1,1-thio-''bis''-[2-chloroethane], (ClCH₂CH₂)₂S, 2,2&prime;-dichlorodiethyl sulfide or ''bis''-(2-chloroethyl)-sulfide. Mustard gas can be synthesized by reacting sulfur dichloride (SCl₂) with two moles of ethylene (C₂H₄).

==Etymology==

The compound readily eliminates chloride ion by intramolecular nucleophilic substitution to form a cyclic sulfonium ion. This very reactive intermediate is particularly detrimental to cellular health as it has a strong tendency to bond to the [[guanine]] nitrogen in [[DNA]] strands. This leads to either immediate cellular death or, as recent research has found, [[cancer]]. Mustard gas is not very soluble in water but is very soluble in fat, contributing to its rapid absorption into the skin.

The name of mustard gas derived from its yellow color, [[odor|smell]] of mustard, and burning sensation on eyes.<ref name="oed">{{cite web |title=Mustard gas |url=https://www.etymonline.com/search?q=mustard%20gas |publisher=Online Etymology Dictionary |access-date=3 July 2025 |date=2025}}</ref> The term was first used in 1917 during [[World War I]] when Germans used the poison in combat.<ref name=oed/>

==History as chemical weapons==

In the wider sense, compounds with the structural element BCH₂CH₂X, where ''X'' is any [[leaving group]] and ''B'' is a [[Lewis base]] are known as ''mustards''. Such compounds can form cyclic onium ions that readily react with [[nucleophile]]s. Examples are ''bis''-(2-chloroethyl)ether or the (2-haloethyl)amines.

Sulfur mustard is a type of chemical warfare agent.<ref>{{Cite web |title=What is a Chemical Weapon? |url=https://www.opcw.org/our-work/what-chemical-weapon |access-date=2023-09-15 |website=OPCW |language=en}}</ref> As a chemical weapon, mustard gas has been used in several armed conflicts since World War I, including the [[Iran–Iraq War]], resulting in more than 100,000 casualties.<ref>{{Cite journal|last1=Salouti|first1=Ramin|last2=Ghazavi|first2=Roghayeh|last3=Rajabi|first3=Sattar|last4=Zare|first4=Mohammad|last5=Talebnejad|first5=Mohammadreza|last6=Abtahi|first6=Mohammad Bagher|last7=Parvizi|first7=Maryam|last8=Madani|first8=Sedigheh|last9=Asadi-Amoli|first9=Fahimeh|last10=Mirsharif|first10=Ensieh-Sadat|last11=Gharebaghi|first11=Reza|date=2020|title=Sulfur Mustard and Immunology; Trends of 20 Years Research in the Web of Science Core Collection: A Scientometric Review|journal=Iranian Journal of Public Health|volume=49|issue=7|pages=1202–1210|doi=10.18502/ijph.v49i7.3573|issn=2251-6085|pmc=7548481|pmid=33083286}}</ref><ref>{{Cite journal|last1=Watson|first1=A. P.|last2=Griffin|first2=G. D.|date=1992|title=Toxicity of vesicant agents scheduled for destruction by the Chemical Stockpile Disposal Program|journal=Environmental Health Perspectives|volume=98|pages=259–280|doi=10.1289/ehp.9298259|issn=0091-6765|pmc=1519623|pmid=1486858|bibcode=1992EnvHP..98..259W }}</ref> Sulfur-based and [[nitrogen mustard|nitrogen-based]] mustard agents are regulated under [[List of Schedule 1 substances (CWC)|Schedule 1]] of the 1993 [[Chemical Weapons Convention]], as substances with few uses other than in [[chemical warfare]].<ref name=who/><ref>{{cite journal |last1=Smith |first1=Susan L. |title=War! What is it good for? Mustard gas medicine |journal=CMAJ |date=27 February 2017 |volume=189 |issue=8 |pages=E321–E322 |doi=10.1503/cmaj.161032 |pmid=28246228 |pmc=5325736 }}</ref> Mustard agents can be deployed by means of [[artillery shell]]s, [[aerial bomb]]s, [[rocket]]s, or by spraying from aircraft.

==PhysiologicalAdverse health effects==

[[File:Mustard gas burns.jpg|thumb|Soldier with moderate mustard agent burns sustained during [[World War I]] showing characteristic [[Bulla (dermatology)|bullae]] on the neck, armpit, and hands]]

Mustard gas is a strong [[vesicant]] (a compound that causes [[blister]]s). Those exposed usually suffer no immediate symptoms. The exposure develops (in 4 to 24 hours) into deep, itching or burning blisters wherever the mustard contacted the skin; the eyes (if exposed) become sore and the eyelids swollen, possibly leading to [[conjunctivitis]] and blindness. At very high concentrations, if inhaled, it causes bleeding and blistering within the [[respiration|respiratory system]], damaging the [[mucous membrane]] and leading to pulmonary [[edema]]. Blister agent exposure over more than 50% body surface area is usually fatal.

Mustard gases have powerful [[vesicant|blistering]] effects on victims. They are also [[carcinogen]]ic and [[mutagen]]ic [[alkylating agents]].<ref name=pubchem/> Their high [[lipophilic]]ity accelerates their absorption into the body.<ref name="opcw.org" /> Because mustard agents often do not elicit immediate symptoms, contaminated areas may appear normal.<ref name=who/> Within 24 hours of exposure, victims experience intense [[itch]]ing and skin irritation. If this irritation goes untreated, blisters filled with [[pus]] can form wherever the agent contacted the skin.<ref name=who/> As [[chemical burn]]s, these are severely debilitating.<ref name=pubchem/> Mustard gas can have the effect of turning a patient's skin different colors due to melanogenesis.<ref name=":0" /><ref name=who/>

Skin damage can be reduced if [[povidone]] [[iodine]] in a base of glycofurol is rapidly applied, but since mustard initially has no symptoms, the exposure is usually not identified until the blisters rise. The vesicant property can be neutralised by [[oxidation]] or chlorination, common bleach (NaOCl-) can be used or decontamination solution "DS2" (2% NaOH, 70% diethylenetriamine, 28% ethylene glycol monomethyl ether). Mustard gas is also [[carcinogen]]ic (cancer causing) and [[mutagen]]ic (causing damage to DNA of exposed cells).

If the victim's eyes were exposed, then they become sore, starting with [[conjunctivitis]] (also known as pink eye), after which the eyelids swell, resulting in temporary blindness. Extreme ocular exposure to mustard gas vapors may result in [[corneal ulcer]]ation, anterior chamber scarring, and [[neovascularization]].<ref>{{Cite journal|last1=Ghasemi|first1=Hassan|last2=Javadi|first2=Mohammad Ali|last3=Ardestani|first3=Sussan K.|last4=Mahmoudi|first4=Mahmoud|last5=Pourfarzam|first5=Shahryar|last6=Mahdavi|first6=Mohammad Reza Vaez|last7=Yarmohammadi|first7=Mohammad Ebrahim|last8=Baradaran-Rafii|first8=Alireza|last9=Jadidi|first9=Khosro|last10=Shariatpanahi|first10=Shamsa|last11=Rastin|first11=Maryam|date=2020|title=Alteration in inflammatory mediators in seriously eye-injured war veterans, long-term after sulfur mustard exposure|journal=International Immunopharmacology|volume=80|article-number=105897|doi=10.1016/j.intimp.2019.105897|issn=1878-1705|pmid=31685435|s2cid=207899509}}</ref><ref>{{Cite journal|last1=Ghazanfari|first1=Tooba|last2=Ghasemi|first2=Hassan|last3=Yaraee|first3=Roya|last4=Mahmoudi|first4=Mahmoud|last5=Javadi|first5=Mohammad Ali|last6=Soroush|first6=Mohammad Reza|last7=Faghihzadeh|first7=Soghrat|last8=Majd|first8=Ali Mohammad Mohseni|last9=Shakeri|first9=Raheleh|last10=Babaei|first10=Mahmoud|last11=Heidary|first11=Fatemeh|date=2019|title=Tear and serum interleukin-8 and serum CX3CL1, CCL2 and CCL5 in sulfur mustard eye-exposed patients|journal=International Immunopharmacology|volume=77|article-number=105844|doi=10.1016/j.intimp.2019.105844|issn=1878-1705|pmid=31669888|s2cid=204967476}}</ref><ref>{{Cite journal|last1=Heidary|first1=Fatemeh|last2=Gharebaghi|first2=Reza|last3=Ghasemi|first3=Hassan|last4=Mahdavi|first4=Mohammad Reza Vaez|last5=Ghaffarpour|first5=Sara|last6=Naghizadeh|first6=Mohammad Mehdi|last7=Ghazanfari|first7=Tooba|date=2019|title=Angiogenesis modulatory factors in subjects with chronic ocular complications of Sulfur Mustard exposure: A case-control study|journal=International Immunopharmacology|volume=76|article-number=105843|doi=10.1016/j.intimp.2019.105843|issn=1878-1705|pmid=31629219|s2cid=204799405}}</ref><ref>{{Cite journal|last1=Heidary|first1=Fatemeh|last2=Ardestani|first2=Sussan K.|last3=Ghasemi|first3=Hassan|last4=Javadi|first4=Mohammad Ali|last5=Mahmoudi|first5=Mahmoud|last6=Yaraee|first6=Roya|last7=Shams|first7=Jalaledin|last8=Falahi|first8=Faramarz|last9=Sedighi Moghadam|first9=Mohamad Reza|last10=Shariatpanahi|first10=Shamsa|last11=Shakeri|first11=Raheleh|date=2019|title=Alteration in serum levels of ICAM-1 and P-, E- and L-selectins in seriously eye-injured long-term following sulfur-mustard exposure|journal=International Immunopharmacology|volume=76|article-number=105820|doi=10.1016/j.intimp.2019.105820|issn=1878-1705|pmid=31480003|s2cid=201831881}}</ref> In these severe and infrequent cases, [[corneal transplantation]] has been used as a treatment.<ref>{{cite journal |title=Ocular injuries caused by mustard gas: diagnosis, treatment, and medical defense|journal= Military Medicine|volume=166|issue=1|pages=67–70|pmid=11197102|year=2001|last1=Safarinejad|first1=M. R.|last2=Moosavi|first2=S. A.|last3=Montazeri|first3=B|doi=10.1093/milmed/166.1.67|doi-access=free}}</ref> [[Miosis]], when the pupil constricts more than usual, may also occur, which may be the result of the cholinomimetic activity of mustard.<ref>[http://www.brooksidepress.org/Products/OperationalMedicine/DATA/operationalmed/Manuals/RedHandbook/004Vesicants.htm Vesicants]. brooksidepress.org</ref> If inhaled in high concentrations, mustard agents cause bleeding and blistering within the [[respiratory system]], damaging [[mucous membrane]]s and causing [[pulmonary edema]].<ref name=who/> Depending on the level of contamination, mustard agent burns can vary between [[first degree burn|first]] and [[second degree burn]]s. They can also be as severe, disfiguring, and dangerous as [[third degree burn]]s. Some 80% of sulfur mustard in contact with the skin evaporates, while 10% stays in the skin and 10% is absorbed and circulated in the blood.<ref name=pubchem/>

The carcinogenic and mutagenic effects of exposure to mustard gas increase the risk of developing [[cancer]] later in life.<ref name=pubchem/> In a study of patients 25 years after wartime exposure to chemical weaponry, c-DNA microarray profiling indicated that 122 genes were significantly mutated in the lungs and airways of mustard gas victims. Those genes all correspond to functions commonly affected by mustard gas exposure, including [[apoptosis]], inflammation, and stress responses.<ref>{{cite journal |doi=10.3109/10799893.2014.896379 |pmid=24823320 |url= https://www.researchgate.net/publication/262303374 |title=Microarray gene expression analysis of the human airway in patients exposed to sulfur mustard|journal= Journal of Receptors and Signal Transduction|volume=34|issue=4|pages=283–9|year=2014|last1=Najafi|first1=Ali|last2=Masoudi-Nejad|first2=Ali|last3=Imani Fooladi|first3=Abbas Ali|last4=Ghanei|first4=Mostafa|last5=Nourani|first5=Mohamad Reza|s2cid=41665583 }}</ref> The long-term ocular complications include burning, tearing, itching, [[photophobia]], [[presbyopia]], pain, and foreign-body sensations.<ref name=who/><ref>{{Cite journal|last1=Ghasemi|first1=Hassan|last2=Javadi|first2=Mohammad Ali|last3=Ardestani|first3=Sussan K.|last4=Mahmoudi|first4=Mahmoud|last5=Pourfarzam|first5=Shahryar|last6=Mahdavi|first6=Mohammad Reza Vaez|last7=Yarmohammadi|first7=Mohammad Ebrahim|last8=Baradaran-Rafii|first8=Alireza|last9=Jadidi|first9=Khosro|last10=Shariatpanahi|first10=Shamsa|last11=Rastin|first11=Maryam|date=2020|title=Alteration in inflammatory mediators in seriously eye-injured war veterans, long-term after sulfur mustard exposure|url=https://linkinghub.elsevier.com/retrieve/pii/S1567576919311853|journal=International Immunopharmacology|language=en|volume=80|article-number=105897|doi=10.1016/j.intimp.2019.105897|pmid=31685435|s2cid=207899509|url-access=subscription}}</ref><ref>{{Cite journal|last=Geraci|first=Matthew J.|date=2008|title=Mustard gas: imminent danger or eminent threat?|journal=The Annals of Pharmacotherapy|volume=42|issue=2|pages=237–246|doi=10.1345/aph.1K445|issn=1542-6270|pmid=18212254|s2cid=207263000}}</ref>

[[File:blister-arm.jpg|right|thumb|Typical appearance of [[Bulla (dermatology)|bullae]] on an arm caused by vesicant burns]]

===Medical management===

In a rinse-wipe-rinse sequence, skin is decontaminated of mustard gas by washing with liquid soap and water, or an absorbent powder.<ref name=who/> The eyes should be thoroughly rinsed using saline or clean water. A topical analgesic is used to relieve skin pain during decontamination.<ref name=who/> For skin lesions, topical treatments, such as [[calamine|calamine lotion]], steroids, and oral [[antihistamine]]s are used to relieve itching.<ref name="who" /> Larger blisters are irrigated repeatedly with saline or soapy water, then treated with an antibiotic and petroleum gauze.<ref name="who" />

Mustard agent burns do not heal quickly and (as with other types of burns) present a risk of [[sepsis]] caused by [[pathogen]]s such as ''[[Staphylococcus aureus]]'' and ''[[Pseudomonas aeruginosa]]''. The mechanisms behind mustard gas's effect on endothelial cells are still being studied, but recent studies have shown that high levels of exposure can induce high rates of both [[necrosis]] and [[apoptosis]]. In vitro tests have shown that at low concentrations of mustard gas, where apoptosis is the predominant result of exposure, pretreatment with 50 mM [[Acetylcysteine|N-acetyl-L-cysteine]] (NAC) was able to decrease the rate of apoptosis. NAC protects [[actin]] filaments from reorganization by mustard gas, demonstrating that actin filaments play a large role in the severe burns observed in victims.<ref>{{cite journal |doi=10.1006/taap.1996.0324 |pmid=8975783 |title=Sulfur Mustard Induces Apoptosis and Necrosis in Endothelial Cells |journal= Toxicology and Applied Pharmacology|volume=141 |issue=2 |pages=568–83 |year=1996 |last1=Dabrowska |first1=Milena I. |last2=Becks |first2=Lauren L. |last3=Lelli |first3=Joseph L. Jr. |last4=Levee |first4=Minette G. |last5=Hinshaw |first5=Daniel B. |bibcode=1996ToxAP.141..568D }}</ref>

A British nurse treating soldiers with mustard agent burns during [[World War I]] commented:<ref>{{cite book|author=Van Bergen, Leo |title=Before My Helpless Sight: Suffering, Dying and Military Medicine on the Western Front, 1914–1918|url=https://books.google.com/books?id=qR-mzZkvaMoC&pg=PA184|year=2009|publisher=Ashgate Publishing, Ltd.|isbn=978-0-7546-5853-5|page=184}}</ref>

{{Blockquote|They cannot be bandaged or touched. We cover them with a tent of propped-up sheets. Gas burns must be agonizing because usually the other cases do not complain, even with the worst wounds, but gas cases are invariably beyond endurance and they cannot help crying out.}}

===Mechanism of cellular toxicity===

[[File:Mustard-dna.svg|thumb|upright=1.8|Mustard gas alkylating an amino group via conversion to a sulfonium ion (2-chloroethylthiiranium)]]

Sulfur mustards readily eliminate [[chloride]] ions by intramolecular [[nucleophilic substitution]] to form cyclic [[sulfonium]] ions. These very reactive intermediates tend to permanently [[alkylation|alkylate]] [[nucleotide]]s in [[DNA]] strands, which can prevent cellular division, leading to [[apoptosis|programmed cell death]].<ref name="opcw.org">[http://www.opcw.org/about-chemical-weapons/types-of-chemical-agent/mustard-agents/ Mustard agents: description, physical and chemical properties, mechanism of action, symptoms, antidotes and methods of treatment]. Organisation for the Prohibition of Chemical Weapons. Accessed June 8, 2010.</ref> Alternatively, if cell death is not immediate, the damaged DNA can lead to the development of cancer.<ref name="opcw.org" /> [[Oxidative stress]] is another pathology involved in mustard gas toxicity.<ref>{{Cite journal |last1=Ghabili |first1=Kamyar |last2=Agutter |first2=Paul S. |last3=Ghanei |first3=Mostafa |last4=Ansarin |first4=Khalil |last5=Shoja |first5=Mohammadali M. |date=October 2010 |title=Mustard gas toxicity: the acute and chronic pathological effects |url=https://analyticalsciencejournals.onlinelibrary.wiley.com/doi/10.1002/jat.1581 |journal=Journal of Applied Toxicology |language=en |volume=30 |issue=7 |pages=627–643 |doi=10.1002/jat.1581 |pmid=20836142 |issn=0260-437X|url-access=subscription }}</ref>

Various compounds with the structural subgroup BC₂H₄X, where X is any [[leaving group]] and B is a [[Lewis base]], have a common name of mustard. Such compounds can form cyclic [[onium ion|"onium" ions]] (sulfonium, [[ammonium]], etc.) that are good [[alkylating agent]]s. These compounds include bis(2-haloethyl)ethers ([[Bis(chloroethyl) ether|oxygen mustards]]), the (2-haloethyl)amines ([[nitrogen mustard]]s), and [[sesquimustard]], which has two α-chloroethyl thioether groups (ClC₂H₄S−) connected by an ethylene bridge (−C₂H₄−). These compounds have a similar ability to alkylate DNA, but their physical properties vary.

==Formulations==

[[File:TestYperite4030618980 242ab5c81d b.jpg|thumb|262x262px|[[Lewisite]] (top row) and mustard gas (bottom row) test with [[concentration]]s from 0.01% to 0.06%]]

In its history, various types and mixtures of mustard gas have been employed. These include:

* '''H'''&nbsp;– Also known as '''HS''' ("Hun Stuff") or ''Levinstein mustard''. This is named after the inventor of the "quick but dirty" '''Levinstein Process''' for manufacture,<ref name="Stewart, Charles D. 2006 47">{{Cite book|author=Stewart, Charles D. |title=Weapons of mass casualties and terrorism response handbook |publisher=Jones and Bartlett |___location=Boston |year=2006 |page=47 |isbn=0-7637-2425-4 |url=https://books.google.com/books?id=7ZnXZfwWwgcC&q=levinstein+inventor+mustard&pg=PA46}}</ref><ref name="Federation of American Scientists">{{cite web|url=https://fas.org/programs/ssp/bio/chemweapons/production.html |title=Chemical Weapons Production and Storage |publisher=Federation of American Scientists |url-status=dead|archive-url=https://web.archive.org/web/20140811100809/http://fas.org/programs/ssp/bio/chemweapons/production.html |archive-date=August 11, 2014 }}</ref> reacting dry [[ethylene]] with [[disulfur dichloride]] under controlled conditions. Undistilled mustard gas contains 20–30% impurities, which means it does not store as well as HD. Also, as it decomposes, it increases in [[vapor pressure]], making the munition it is contained in likely to split, especially along a seam, releasing the agent to the atmosphere.<ref name="FM 3-8">FM 3–8 Chemical Reference handbook, US Army, 1967</ref>

* '''HD'''&nbsp;– Codenamed '''Pyro''' by the British, and '''Distilled Mustard''' by the US.<ref name="FM 3-8" /> [[distillation|Distilled]] mustard of 95% or higher purity. The term "mustard gas" usually refers to this variety of mustard.

* '''HT'''&nbsp;– Codenamed '''Runcol''' by the British, and '''Mustard T- mixture''' by the US.<ref name="FM 3-8" /> A mixture of 60% HD mustard and 40% [[O-mustard]], a related vesicant with lower [[freezing point]], lower [[Volatility (chemistry)|volatility]] and similar vesicant characteristics.

* '''HL'''&nbsp;– A blend of distilled mustard (HD) and [[lewisite]] (L), originally intended for use in winter conditions due to its lower freezing point compared to the pure substances. The lewisite component of HL was used as a form of [[antifreeze]].<ref>[https://www.cdc.gov/niosh/ershdb/EmergencyResponseCard_29750007.html The Emergency Response Safety and Health Database: Mustard-Lewisite Mixture (HL)]. National Institute for Occupational Safety and Health. Accessed March 19, 2009.</ref>

* '''HQ'''&nbsp;– A blend of distilled mustard (HD) and sesquimustard (Q). <ref>{{Cite book |last=Gates |first=Marshall |title=Chemical warfare agents, and related chemical problems |last2=Moore |first2=Stanford |publisher=Washington, D.C. : Office of Scientific Research and Development, National Defense Research Committee, Division 9 |year=1946 |language=en |chapter=Mustard Gas and Other Sulfur Mustards}}</ref>

* '''[[Yellow Cross (chemical warfare)|Yellow Cross]]'''&nbsp;– any of several blends containing sulfur mustard.<ref>{{Cite journal |last=Frescoln |first=Leonard D. |date=1918-12-07 |title=Mustard (Yellow Cross) Burns |url=http://jama.jamanetwork.com/article.aspx?doi=10.1001/jama.1918.26020490013010b |journal=JAMA: The Journal of the American Medical Association |language=en |volume=71 |issue=23 |pages=1911 |doi=10.1001/jama.1918.26020490013010b |issn=0098-7484|url-access=subscription }}</ref> Named for the yellow cross painted on artillery shells.<ref name=":0">{{Cite book |title=Veterans at Risk: the health effects of mustard gas and Lewisite |date=1993 |publisher=National Academy Press |isbn=978-0-309-04832-3 |editor-last=Institute of Medicine (U.S.) |___location=Washington, D.C |editor-last2=Pechura |editor-first2=Constance M. |editor-last3=Rall |editor-first3=David P.}}</ref>

==Commonly-stockpiled mustard agents (class)==

{| class="wikitable" style="text-align:center;"

|+

|- class="hintergrundfarbe5"

! Chemical

! Code

! Trivial name

! CAS number

! PubChem

! Structure

|-

| [[Bis(2-chloroethyl)sulfide]]

| H, HD

| Mustard

| 505-60-2

| {{PubChem|10461}}

| [[File:Sulfur mustard.svg|150px]]

|-

| 1,2-Bis(2-chloroethylsulfanyl) ethane

| Q

| [[Sesquimustard]]

| 3563-36-8

| {{PubChem|19092}}

| [[File:Sesquimustard.svg|200px]]

|-

| 2-Chloroethyl ethyl sulfide

|

| [[2-Chloroethyl ethyl sulfide|Half mustard]]

| 693-07-2

| {{PubChem|12733}}

| [[File:Chloroethyl ethyl sulfide.svg|175px]]

|-

| Bis(2-(2-chloroethylsulfanyl)ethyl) ether

| T

| [[O-mustard]]

| 63918-89-8

| {{PubChem|45452}}

| [[File:O-Mustard.svg|250px]]

|-

| 2-Chloroethyl chloromethyl sulfide

|

|

| 2625-76-5

|

| [[File:2-Chlorethylchlormethylsulfid.svg|125px]]

|-

| Bis(2-chloroethylsulfanyl) methane

| HK

|

| 63869-13-6

|

| [[File:Bis(2-chlorethylthio)methan.svg|195px]]

|-

| 1,3-Bis(2-chloroethylsulfanyl) propane

|

|

| 63905-10-2

|

| [[File:Bis-1,3-(2-chlorethylthio)-n-propan.svg|240px]]

|-

| 1,4-Bis(2-chloroethylsulfanyl) butane

|

|

| 142868-93-7

|

| [[File:Bis-1,4-(2-chlorethylthio)-n-butan.svg|245px]]

|-

| 1,5-Bis(2-chloroethylsulfanyl) pentane

|

|

| 142868-94-8

|

| [[File:Bis-1,5-(2-chlorethylthio)-n-pentan.svg|245px]]

|-

| Bis((2-chloroethylsulfanyl)methyl) ether

|

|

| 63918-90-1

|

| [[File:Bis(2-chlorethylthiomethyl)ether.svg|230px]]

|}

==History==

===Development===

It was first used by the German army against [[Canada|Canadian]] soldiers in 1917 and later also against the [[France|French]] &ndash; the name ''Yperite'' comes from its usage by the German army near the city of [[Ypres]]. It took the British over a year to develop their own mustard gas weapon, first using it in September [[1918]] during the breaking of the [[Hindenburg Line]].

Mustard gases were possibly developed as early as 1822 by [[César-Mansuète Despretz]] (1798–1863).<ref name="mustardgas">[http://itech.dickinson.edu/chemistry/?p=408 By Any Other Name: Origins of Mustard Gas] {{Webarchive|url=https://web.archive.org/web/20140201220058/http://itech.dickinson.edu/chemistry/?p=408 |date=2014-02-01 }}. Itech.dickinson.edu (2008-04-25). Retrieved on 2011-05-29.</ref> Despretz described the reaction of [[sulfur dichloride]] and [[ethylene]] but never made mention of any irritating properties of the reaction product. In 1854, another French chemist, Alfred Riche (1829–1908), repeated this procedure, also without describing any adverse physiological properties. In 1860, the British scientist [[Frederick Guthrie (scientist)|Frederick Guthrie]] synthesized and characterized the mustard agent compound and noted its irritating properties, especially in tasting.<ref name="Guthrie">{{cite journal |author=F. Guthrie |title=XIII.—On some derivatives from the olefines |journal=Q. J. Chem. Soc. |volume=12 |pages=109–126 |year=1860 |doi=10.1039/QJ8601200109 |issue=1 |url=https://zenodo.org/record/1885270 }}</ref> Also in 1860, chemist [[Albert Niemann (chemist)|Albert Niemann]], known as a pioneer in [[cocaine]] chemistry, repeated the reaction, and recorded blister-forming properties. In 1886, [[Viktor Meyer]] published a paper describing a synthesis that produced good yields. He combined [[2-Chloroethanol|2-chloroethanol]] with [[aqueous]] [[potassium sulfide]], and then treated the resulting [[thiodiglycol]] with [[phosphorus trichloride]]. The purity of this compound was much higher and consequently the adverse health effects upon exposure were much more severe. These symptoms presented themselves in his assistant, and in order to rule out the possibility that his assistant was suffering from a mental illness (psychosomatic symptoms), Meyer had this compound tested on laboratory [[rabbit]]s, most of which died. In 1913, the English chemist [[Hans Thacher Clarke]] (known for the [[Eschweiler-Clarke reaction]]) replaced the phosphorus trichloride with [[hydrochloric acid]] in Meyer's formulation while working with [[Hermann Emil Fischer|Emil Fischer]] in [[Berlin]]. Clarke was hospitalized for two months for burns after one of his flasks broke. According to Meyer, Fischer's report on this accident to the [[German Chemical Society]] sent the [[German Empire]] on the road to chemical weapons.<ref>{{Cite journal|author1=Duchovic, Ronald J. |author2=Vilensky, Joel A. |title=Mustard Gas: Its Pre-World War I History |journal=J. Chem. Educ. |volume=84 |page=944 |year=2007 |doi=10.1021/ed084p944|bibcode=2007JChEd..84..944D |issue=6}}</ref>

The [[German Empire]] during [[World War I]] relied on the Meyer-Clarke method because [[2-chloroethanol]] was readily available from the German dye industry of that time.<ref>{{Cite journal |last1=Duchovic |first1=Ronald J. |last2=Vilensky |first2=Joel A. |date=2007 |title=Mustard Gas: Its Pre-World War I History |url=https://pubs.acs.org/doi/abs/10.1021/ed084p944 |journal=Journal of Chemical Education |language=en |volume=84 |issue=6 |pages=944 |doi=10.1021/ed084p944 |issn=0021-9584|url-access=subscription }}</ref>

Mustard gas was dispersed as an [[aerosol]] in a mixture with other chemicals, giving it a yellow-brown colour and a distinctive odour. Mustard gas was lethal in only about 1% of cases. Its effectiveness was as an incapacitating agent: a wounded soldier slows an advancing army much more than a dead one. The countermeasures against the gas were quite ineffective, since a soldier wearing a [[gas mask]] was not protected against absorbing it through the skin.

===Use===

Furthermore, mustard gas was a persistent agent which would remain in the environment for days and continue to cause sickness. If mustard gas contaminated a soldier's clothing and equipment, then other soldiers he came into contact with would also be poisoned. Towards the end of the war it was even used in high concentrations as an area-denial weapon, which often forced soldiers to abandon heavily contaminated positions.

[[Image:155mmMustardGasShells.jpg|thumb|right|Pallets of 155 mm [[artillery shell]]s containing "HD" (distilled mustard gas agent) at the [[Pueblo Chemical Depot]]. The distinctive [[Bottled gas#Colour coding|color-coding]] scheme on each shell is visible.]]

Mustard gas was first [[Chemical weapons in World War I|used in World War I]] by the German army against British and Canadian soldiers near [[Ypres]], Belgium, on July 12, 1917,<ref>{{Cite book |last1=Fries |first1=Amos A. (Amos Alfred) |url=http://archive.org/details/chemicwar00frierich |title=Chemical warfare |last2=West |first2=Clarence J. (Clarence Jay) |date=1921 |publisher=New York [etc.] McGraw-Hill Book Company, inc. |others=University of California Libraries |pages=176 |quote=(...) on the night of July 12, 1917 (...)}}</ref> and later also against the [[French Second Army]]. '''''Yperite''''' is "a name used by the French, because the compound was first used at Ypres."<ref>{{Cite book |last1=Fries |first1=Amos A. (Amos Alfred) |url=http://archive.org/details/chemicwar00frierich |title=Chemical warfare |last2=West |first2=Clarence J. (Clarence Jay) |date=1921 |publisher=New York [etc.] McGraw-Hill Book Company, inc. |others=University of California Libraries |pages=150 |quote=(...) 'Ypres,' a name used by the French, because the compound was first used at Ypres (...)}}</ref> The Allies used mustard gas for the first time on November 1917 at [[Cambrai]], France, after the armies had captured a stockpile of German mustard shells. It took the British more than a year to develop their own mustard agent weapon, with production of the chemicals centred on [[Avonmouth Docks]] (the only option available to the British was the Despretz–Niemann–Guthrie process).<ref>{{cite book|title=The Port of Bristol, 1848-1884|editor=David Large}}</ref><ref>{{cite web|url=http://www.bristolpast.co.uk/#/avonmouth/4546933962|archive-url=https://web.archive.org/web/20110703094556/http://www.bristolpast.co.uk/#/avonmouth/4546933962|url-status=dead|archive-date=July 3, 2011|title=Photographic Archive of Avonmouth Bristol BS11|publisher=BristolPast.co.uk|access-date=12 May 2014}}</ref>

Mustard gas was originally assigned the name LOST, after the scientists Wilhelm Lommel and [[Wilhelm Steinkopf]], who developed a method of large-scale production for the [[German Army (German Empire)|Imperial German Army]] in 1916.<ref>{{cite book

Since then, mustard gas has also been reportedly used by:

| last = Fischer

* [[Spain]] against [[Morocco]] in [[1923]]-[[1926]];

| first = Karin

* [[Italy]] against [[Ethiopia]] in [[1935]]-[[1940]];

| editor = Schattkowsky, Martina

* [[Soviet Union]] in a province of [[China]] in [[1930]];

| date=June 2004

* [[Japan]] against [[China]] in [[1937]]-[[1945]];

| title = Steinkopf, Georg Wilhelm, in: Sächsische Biografie

* [[Egypt]] against [[North Yemen]] in [[1963]]-[[1967]];

| publisher = Institut für Sächsische Geschichte und Volkskunde

* [[Iraq]] against [[Iran]] in [[1983]]-[[1988]]; and

| edition = Online

* [[Iraq]] against [[Kurds]] in [[1988]].

| url = http://saebi.isgv.de/biografie/Wilhelm_Steinkopf_%281879-1949%29

| access-date = 2010-12-28

| language = de}}</ref>

Mustard gas was dispersed as an [[aerosol]] in a mixture with other chemicals, giving it a yellow-brown color. Mustard agent has also been dispersed in such munitions as [[aerial bomb]]s, [[land mine]]s, [[mortar (weapon)|mortar rounds]], [[artillery shell]]s, and [[rocket]]s.<ref name="FM 3-8"/> Exposure to mustard agent was lethal in about 1% of cases. Its effectiveness was as an [[incapacitating agent]]. The early countermeasures against mustard agent were relatively ineffective, since a soldier wearing a [[WWI gas mask|gas mask]] was not protected against absorbing it through his skin and being blistered. A common countermeasure was using a urine-soaked mask or facecloth to prevent or reduce injury, a readily available remedy attested by soldiers in documentaries (e.g., ''They Shall Not Grow Old'' in 2018) and others (such as forward aid nurses) interviewed between 1947 and 1981 by the British Broadcasting Corporation for various World War One history programs; however, the effectiveness of this measure is unclear.

Also, in [[1943]] a [[US]] stockpile held for retaliatory purposes, was bombed in [[Bari]], [[Italy]], accidentally exposing thousands of civilians and 628 friendly troops.

Mustard gas can remain in the ground for weeks, and it continues to cause ill effects. If mustard agent contaminates one's clothing and equipment while cold, then other people with whom they share an enclosed space could become poisoned as contaminated items warm up enough material to become an airborne toxic agent. An example of this was depicted in a British and Canadian documentary about life in the trenches, particularly once the "sousterrain" (subways and berthing areas underground) were completed in Belgium and France. Towards the end of World War I, mustard agent was used in high concentrations as an [[area denial weapons|area-denial weapon]] that forced troops to abandon heavily contaminated areas.

Most of the mustard gas found in [[Germany]] after [[World War II]] was dumped into the [[Baltic Sea]]. It is possible to mistake a piece of [[polymerization|polymerised]] mustard gas for [[amber]], which can lead to severe health problems. [[shell (projectile)|Shell]]s containing mustard gas and other toxic ammunition from [[World War I]] (as well as conventional explosives) can still occasionally be found in [[France]]; they used to be disposed of by explosion at sea, but current environmental regulations prohibit this; the French government is building an automated factory to dispose of the backlog of shells.

[[File:Mustard gas ww2 poster.jpg|thumb|upright|US Army World War II gas identification poster, {{Circa|1941}}–1945]]

The largest stockpile of mustard gas in the United States was stored at the Edgewood Arsenal, Aberdeen Proving Ground in Maryland. Mustard gas was stored in several one-ton (900 kg) containers on the base under heavy guard. A disposal plant built on site neutralized the last of this stockpile in February, 2005. This stockpile had priority due to its proximity to several populated areas and schools in the area. The closest schools were fitted with overpressurization units to protect the students and staff in the event of a catastrophic explosion and fire at the site. Unexploded shells containing mustard gas and other chemical agents are still present in several test ranges in proximity to Edgewood area schools, but the smaller amounts (4&ndash;14 pounds; 2&ndash;6 kg) present considerably less risk. They are being systematically detected and excavated for disposal. There are several other sites in the United States where smaller stockpiles are awaiting neutralization in compliance with international chemical weapons treaties.

Since World War I, mustard gas has been used in several wars and other conflicts, usually against people who cannot retaliate in kind:<ref name="CBWInfo">[http://www.cbwinfo.com/Chemical/Blister/HD.shtml Blister Agent: Mustard gas (H, HD, HS)] {{webarchive |url=https://web.archive.org/web/20070724063602/http://www.cbwinfo.com/Chemical/Blister/HD.shtml |date=July 24, 2007}}, CBWinfo.com</ref>

* United Kingdom against the [[Red Army]] in 1919<ref name="fas">{{cite web|url=https://fas.org/bwc/papers/review/cwtable.htm |title=Uses of CW since the First World War |last=Pearson |first=Graham S. |publisher=Federation of American Scientist |access-date=2010-06-28 | archive-url=https://web.archive.org/web/20100822165939/http://www.fas.org/bwc/papers/review/cwtable.htm |archive-date=August 22, 2010}}</ref>

* [[Alleged British use of chemical weapons in Mesopotamia in 1920|Alleged British use in Mesopotamia in 1920]]<ref>{{cite book|last=Townshend|first=Charles|authorlink=Charles Townshend (historian)|year=1986|chapter=Civilisation and "Frightfulness": Air Control in the Middle East Between the Wars|editor=Chris Wrigley|title=Warfare, diplomacy and politics: essays in honour of A.J.P. Taylor|url=https://books.google.com/books?id=rkhnAAAAMAAJ|publisher=Hamilton|isbn=978-0-241-11789-7|page=148}}</ref>

* [[Spain under the Restoration|Spain]] against the [[Riffian people|Rifian]] resistance in [[French protectorate of Morocco|Morocco]] during the [[Rif War]] of 1921–27 (see also: ''[[Spanish use of chemical weapons in the Rif War]]'')<ref name="CBWInfo" /><ref name="GCSY">{{Cite book|chapter=Global society and biological and chemical weapons |first=Daniel | last = Feakes |editor-first1=Mary | editor-last1 = Kaldor |editor-first2=Helmut | editor-last2 = Anheier |editor-first3=Marlies | editor-last3 = Glasius |title=Global Civil Society Yearbook 2003 |publisher=Oxford University Press |year=2003 |pages=87–117 |chapter-url=http://www.sussex.ac.uk/Units/spru/hsp/documents/Feakes%20chapter.pdf |archive-url=https://web.archive.org/web/20070711035041/http://www.sussex.ac.uk/Units/spru/hsp/Feakes%20chapter.pdf |url-status=dead|archive-date=2007-07-11 |isbn=0-19-926655-7}}</ref>

* [[Kingdom of Italy|Italy]] in [[Italian Libya|Libya]] in 1930<ref name="CBWInfo"/>

* The [[Soviet Union]] in [[Xinjiang]], [[Republic of China (1912–1949)|Republic of China]], during the [[Soviet Invasion of Xinjiang]] against the [[36th Division (National Revolutionary Army)]] in 1934, and also in the [[Xinjiang War (1937)]] in 1936–37<ref name="fas"/><ref name="GCSY"/>

* Italy against [[Ethiopian Empire|Abyssinia]] (now [[Ethiopia]]) in the [[Second Italo-Abyssinian War|1935–1936]]<ref name="CBWInfo"/>

* The [[Empire of Japan]] against [[Republic of China (1912–1949)|China]] in the [[Second Sino-Japanese War|1937–1945]]<ref name="fas"/>

* The US military conducted experiments with chemical weapons like lewisite and mustard gas on Japanese American, Puerto Rican and African Americans in the US military in World War II to see how non-white races would react to being mustard gassed, with Rollin Edwards describing it as "It felt like you were on fire, guys started screaming and hollering and trying to break out. And then some of the guys fainted. And finally they opened the door and let us out, and the guys were just, they were in bad shape." and "It took all the skin off your hands. Your hands just rotted".<ref>{{cite news |last=Dickerson |first=Caitlin |date=22 June 2015 |title=Secret World War II Chemical Experiments Tested Troops By Race |work=NPR |url=http://www.npr.org/2015/06/22/415194765/u-s-troops-tested-by-race-in-secret-world-war-ii-chemical-experiments}}</ref>

* After World War II, stockpiled mustard gas was dumped by South African military personnel under the command of [[William Bleloch]] off [[Port Elizabeth]], resulting in several cases of burns among local trawler crews.<ref>{{cite web |url=http://samilitaryhistory.org/92/92junnew.html |title=NEWSLETTER - JUNE 1992 NEWSLETTER - Johannesburg - South African Military History Society - Title page |publisher=Samilitaryhistory.org |access-date=2013-08-23}}</ref>

* The United States Government tested effectiveness on US Naval recruits in a laboratory setting at The Great Lakes Naval Base, June 3, 1945<ref>{{Cite web|date=2013-09-23|title=The Tox Lab: When U Chicago Was in the Chemical Weapons "Business" {{!}} Newcity|url=https://www.newcity.com/2013/09/23/the-tox-lab-when-u-chicago-was-in-the-chemical-weapons-business/|access-date=2021-07-02|language=en-US}}</ref>

* The 2 December 1943 [[air raid on Bari]] destroyed an Allied stockpile of mustard gas on the [[SS John Harvey|SS ''John Harvey'']],<ref name="Coleman2005">{{cite book |author=K. Coleman |title=A History of Chemical Warfare|url=https://books.google.com/books?id=RZp9DAAAQBAJ&pg=PA74|date=23 May 2005|publisher=Palgrave Macmillan UK |isbn=978-0-230-50183-6 |pages=74–}}</ref> killing 83 and hospitalizing 628.<ref name="faguet">{{cite book|last=Faguet|first=Guy B.|title=The War on Cancer|publisher=Springer|year=2005|page=71|isbn=1-4020-3618-3}}</ref>

* Egypt against [[Yemen Arab Republic|North Yemen]] in 1963–1967<ref name="CBWInfo" />

* Iraq against [[Kurds]] in the town of [[Halabja]] during the [[Halabja chemical attack]] in 1988<ref name="fas" /><ref name="Reuters">{{cite news |url=https://www.reuters.com/article/topNews/idUSBLA84491620080709 |title=Iran's Chemical Ali survivors still bear scars |last=Lyon |first=Alistair |date=2008-07-09 |work=Reuters |access-date=2008-11-17}}</ref>

* Iraq against Iranians in [[Iran–Iraq War|1983–1988]]<ref name="Benschopvan der Schans1997">{{cite journal |last1=Benschop |first1=Hendrik P. |last2=van der Schans |first2=Govert P. |last3=Noort |first3=Daan |last4=Fidder |first4=Alex |last5=Mars-Groenendijk |first5=Roos H. |last6=de Jong |first6=Leo P.A. |title=Verification of Exposure to Sulfur Mustard in Two Casualties of the Iran-Iraq Conflict |journal=Journal of Analytical Toxicology |date=1 July 1997 |volume=21 |issue=4 |pages=249–251 |doi=10.1093/jat/21.4.249 |pmid=9248939 |doi-access=free }}</ref>

* Possibly in Sudan against insurgents in the [[Second Sudanese Civil War|civil war]], in 1995 and 1997.<ref name="CBWInfo" />

* In the [[Iraq War]], abandoned stockpiles of mustard gas shells were destroyed in the open air,<ref>{{cite news|title=More Than 600 Reported Chemical Exposure in Iraq, Pentagon Acknowledges|work=The New York Times|date=6 Nov 2014|url=https://www.nytimes.com/2014/11/07/world/middleeast/-more-than-600-reported-chemical-weapons-exposure-in-iraq-pentagon-acknowledges.html}}</ref> and were used against Coalition forces in [[roadside bomb]]s.<ref>{{cite news|url=https://www.nytimes.com/2015/03/26/world/middleeast/army-apologizes-for-handling-of-chemical-weapon-exposure-cases.html?_r=0|title=Veterans Hurt by Chemical Weapons in Iraq Get Apology|work=The New York Times|date=25 Mar 2015}}</ref>

* By [[Islamic State of Iraq and the Levant|ISIS]] forces against [[Peshmerga|Kurdish]] forces in Iraq in August 2015.<ref>{{cite news |last=Deutsch |first=Anthony |title=Samples confirm Islamic State used mustard gas in Iraq - diplomat |work=[[Reuters]] |date=15 February 2016 |url=http://ca.reuters.com/article/topNews/idCAKCN0VO1IC |archive-url=https://web.archive.org/web/20160222110031/http://ca.reuters.com/article/topNews/idCAKCN0VO1IC |url-status=dead |archive-date=February 22, 2016 |access-date=15 February 2016}}</ref>

* By ISIS against another rebel group in the town of [[Mare']] in 2015.<ref>{{cite news|url=https://www.reuters.com/article/us-mideast-crisis-syria-chemicalweapons-idUSKCN0SU2PZ20151106|title=Chemical weapons used by fighters in Syria—sources|first=Anthony|last=Deutsch|work=Reuters|date=2015-11-06|access-date=2017-06-30}}</ref>

* According to Syrian state media, by ISIS against the [[Syrian Army]] during the battle in [[Deir ez-Zor]] in 2016.<ref>{{cite news|url=https://www.bbc.com/news/world-middle-east-35968604|title=Syria war: IS 'used mustard gas' on Assad troops |work=[[BBC News]]|date=2016-04-05|access-date=2017-06-30}}</ref>

The use of toxic gases or other chemicals, including mustard gas, during warfare is known as [[chemical warfare]], and this kind of warfare was prohibited by the [[Geneva Protocol|Geneva Protocol of 1925]], and also by the later [[Chemical Weapons Convention|Chemical Weapons Convention of 1993]]. The latter agreement also prohibits the development, production, stockpiling, and sale of such weapons.

In September 2012, a US official stated that the rebel militant group [[Islamic State of Iraq and the Levant|ISIS]] was manufacturing and using mustard gas in Syria and Iraq, which was allegedly confirmed by the group's head of chemical weapons development, Sleiman Daoud al-Afari, who has since been captured.<ref name=bbc-20150911>{{cite news |url=https://www.bbc.co.uk/news/world-us-canada-34211838 |title=US official: 'IS making and using chemical weapons in Iraq and Syria' |author=Paul Blake |publisher=BBC |date=11 September 2015 |access-date=16 September 2015}}</ref><ref name=independent-20150911>{{cite news |url=https://www.independent.co.uk/news/world/middle-east/isis-manufacturing-and-using-chemical-weapons-in-iraq-and-syria-us-official-claims-10496094.html |archive-url=https://ghostarchive.org/archive/20220618/https://www.independent.co.uk/news/world/middle-east/isis-manufacturing-and-using-chemical-weapons-in-iraq-and-syria-us-official-claims-10496094.html |archive-date=2022-06-18 |url-access=subscription |url-status=live |title=Isis 'manufacturing and using chemical weapons' in Iraq and Syria, US official claims |author=Lizzie Dearden |newspaper=The Independent |date=11 September 2015 |access-date=16 September 2015}}</ref>

====Development of the first chemotherapy drug====

As early as 1919 it was known that mustard agent was a suppressor of [[hematopoiesis]].<ref>{{cite journal |author=Krumbhaar EB |title=Rôle of the blood and the bone marrow in certain forms of gas poisoning: I. peripheral blood changes and their significance |journal=JAMA |doi=10.1001/jama.1919.26110010018009f|volume=72 |pages=39–41 |year=1919 |url=https://zenodo.org/record/1423423 }}</ref> In addition, autopsies performed on 75 soldiers who had died of mustard agent during [[World War I]] were done by researchers from the [[University of Pennsylvania]] who reported decreased counts of [[white blood cell]]s.<ref name="faguet" /> This led the American Office of Scientific Research and Development (OSRD) to finance the biology and chemistry departments at [[Yale University]] to conduct research on the use of chemical warfare during World War II.<ref name="faguet" /><ref name="gilman">{{cite journal |author=Gilman A |title=The initial clinical trial of nitrogen mustard |journal=Am. J. Surg. |volume=105 |pages=574–8 |date=May 1963 |pmid=13947966 |doi=10.1016/0002-9610(63)90232-0 |issue=5}}</ref>

As a part of this effort, the group investigated [[nitrogen mustard]] as a therapy for [[Hodgkin's lymphoma]] and other types of [[lymphoma]] and [[leukemia]], and this compound was tried out on its first human patient in December 1942. The results of this study were not published until 1946, when they were declassified.<ref name="gilman" /> In a parallel track, after the [[air raid on Bari]] in December 1943, the doctors of the U.S. Army noted that white blood cell counts were reduced in their patients. Some years after World War II was over, the incident in Bari and the work of the Yale University group with nitrogen mustard converged, and this prompted a search for other similar [[chemical compound]]s. Due to its use in previous studies, the nitrogen mustard called "HN2" became the first cancer [[chemotherapy]] drug, [[chlormethine]] (also known as mechlorethamine, mustine) to be used. Chlormethine and other mustard gas molecules are still used to this day as an chemotherapy agent albeit they have largely been replaced with more safe chemotherapy drugs like [[cisplatin]] and [[carboplatin]].<ref>{{Cite journal |last=Scott |first=Lesley J. |date=2017-06-01 |title=Chlormethine 160 mcg/g gel in mycosis fungoides-type cutaneous T-cell lymphoma: a profile of its use in the EU |url=https://doi.org/10.1007/s40267-017-0409-7 |journal=Drugs & Therapy Perspectives |language=en |volume=33 |issue=6 |pages=249–253 |doi=10.1007/s40267-017-0409-7 |s2cid=256367068 |issn=1179-1977|url-access=subscription }}</ref>

====Disposal====

In the United States, storage and incineration of mustard gas and other chemical weapons were carried out by the U.S. Army Chemical Materials Agency.<ref>[http://www.cma.army.mil/home.aspx The U.S. Army's Chemical Materials Agency (CMA)] {{Webarchive|url=https://web.archive.org/web/20041015020742/http://www.cma.army.mil/home.aspx |date=October 15, 2004}}. cma.army.mil. Retrieved on November 11, 2011.</ref> Disposal projects at the two remaining American chemical weapons sites were carried out near [[Richmond, Kentucky]], and [[Pueblo, Colorado]]. The last of the declared mustard weapons stockpile of the United States was destroyed on June 22, 2023 in Pueblo with other remaining chemical weapons being destroyed later in 2023.<ref>{{Cite web |date=2023-07-07 |title=U.S. destroys last of its declared chemical weapons, closing a deadly chapter dating to World War I |url=https://apnews.com/article/chemical-weapons-war-kentucky-colorado-sarin-0737441e73aeb62f6a105c30ab067393 |access-date=2025-04-11 |website=AP News |language=en}}</ref>

New detection techniques are being developed in order to detect the presence of mustard gas and its metabolites. The technology is portable and detects small quantities of the hazardous waste and its oxidized products, which are notorious for harming unsuspecting civilians. The [[immunochromatographic]] assay would eliminate the need for expensive, time-consuming lab tests and enable easy-to-read tests to protect civilians from sulfur-mustard dumping sites.<ref>{{cite journal |url=https://docksci.com/competitive-immunochromatographic-assay-for-the-detection-of-thiodiglycol-sulfox_5a9bdc6fd64ab2d6e91e8ff2.html |title=Competitive immunochromatographic assay for the detection of thiodiglycol sulfoxide, a degradation product of sulfur mustard |journal=The Analyst|volume=139|issue=20|pages=5118–26|date=24 July 2014|doi=10.1039/C4AN00720D |pmid=25121638|last1=Sathe|first1=Manisha|last2=Srivastava|first2=Shruti|last3=Merwyn|first3=S.|last4=Agarwal|first4=G. S.|last5=Kaushik|first5=M. P.|bibcode=2014Ana...139.5118S |url-access=subscription}}</ref>

In 1946, 10,000 drums of mustard gas (2,800 tonnes) stored at the production facility of Stormont Chemicals in [[Cornwall, Ontario]], Canada, were loaded onto 187 boxcars for the {{convert|900|mi|km|}} journey to be buried at sea on board a {{Convert|400|foot|m|abbr=|adj=}} long barge {{Convert|40|mi|km|abbr=}} south of [[Sable Island]], southeast of [[Halifax, Nova Scotia|Halifax]], at a depth of {{convert|600|fathom|m|}}. The dump ___location is 42 degrees, 50 minutes north by 60 degrees, 12 minutes west.<ref>{{cite web|title=Hill 70 & Cornwall's Deadly Mustard Gas Plant|url=https://cornwallcommunitymuseum.wordpress.com/2016/09/18/hill-70-cornwalls-deadly-mustard-gas-plant/|website=Cornwall Community Museum|date=18 September 2016|publisher=Stormont, Dundas and Glengarry Historical Society|access-date=23 December 2016}}</ref>

A large British stockpile of old mustard agent that had been made and stored since World War I at [[M. S. Factory, Valley]] near [[Rhydymwyn]] in [[Flintshire]], Wales, was destroyed in 1958.<ref>{{cite web|title=Valley Factory, Rhydymwyn|date=24 July 2010|url=http://www.subbrit.org.uk/rsg/sites/r/rhydymwyn/defra_1.html}}</ref>

Most of the mustard gas found in Germany after [[World War II]] was dumped into the [[Baltic Sea]]. Between 1966 and 2002, fishermen have found about 700 chemical weapons in the region of [[Bornholm]], most of which contain mustard gas. One of the more frequently dumped weapons was "Sprühbüchse 37" (SprüBü37, Spray Can 37, 1937 being the year of its fielding with the German Army). These weapons contain mustard gas mixed with a [[thickener]], which gives it a tar-like viscosity. When the content of the SprüBü37 comes in contact with water, only the mustard gas in the outer layers of the lumps of viscous mustard [[hydrolysis|hydrolyzes]], leaving behind amber-colored residues that still contain most of the active mustard gas. On mechanically breaking these lumps (e.g., with the drag board of a fishing net or by the human hand) the enclosed mustard gas is still as active as it had been at the time the weapon was dumped. These lumps, when washed ashore, can be mistaken for amber, which can lead to severe health problems. [[shell (projectile)|Artillery shells]] containing mustard gas and other toxic ammunition from World War I (as well as conventional explosives) can still be found in France and Belgium. These were formerly disposed of by explosion undersea, but since the current environmental regulations prohibit this, the [[French government]] is building an automated factory to dispose of the accumulation of chemical shells.

In 1972, the [[United States Congress|U.S. Congress]] banned the practice of disposing of chemical weapons into the ocean by the United States. 29,000 tons of nerve and mustard agents had already been dumped into the ocean off the United States by the [[United States Army|U.S. Army]]. According to a report created in 1998 by William Brankowitz, a deputy project manager in the [[U.S. Army Chemical Materials Agency]], the army created at least 26 chemical weapons dumping sites in the ocean offshore from at least 11 states on both the [[East Coast of the United States|East Coast]] and the [[West Coast of the United States|West Coast]] (in [[Operation CHASE]], [[Operation Geranium]], etc.). In addition, due to poor recordkeeping, about one-half of the sites have only their rough locations known.<ref>{{cite web|last=Bull|first=John|title=The Deadliness Below|url=http://articles.dailypress.com/2005-10-30/news/0510300001_1_chemical-weapons-army-chemical-materials-agency-mustard-gas|publisher=Daily Press Virginia|date=30 October 2005|access-date=2013-01-28|archive-date=2012-07-23|archive-url=https://web.archive.org/web/20120723021132/http://articles.dailypress.com/2005-10-30/news/0510300001_1_chemical-weapons-army-chemical-materials-agency-mustard-gas|url-status=dead}}</ref>

In June 1997, India declared its stock of chemical weapons of {{convert|1044|tonne|ST}} of mustard gas.<ref name="dominicantoday.com">{{cite web|url=http://www.dominicantoday.com/dr/world/2007/12/30/26543/India-to-destroy-chemical-weapons-stockpile-by-2009 |title=India to destroy chemical weapons stockpile by 2009 |publisher=Dominican Today |access-date=30 April 2013 |url-status=dead|archive-url=https://web.archive.org/web/20130907155755/http://www.dominicantoday.com/dr/world/2007/12/30/26543/India-to-destroy-chemical-weapons-stockpile-by-2009 |archive-date=7 September 2013}}</ref><ref>{{cite web|author1=Amy Smithson |author2=Frank Gaffney Jr. |url=http://www.highbeam.com/doc/1P1-3987660.html |archive-url=https://web.archive.org/web/20121106050759/http://www.highbeam.com/doc/1P1-3987660.html |url-status=dead|archive-date=6 November 2012 |title=India declares its stock of chemical weapons |access-date=30 April 2013}}</ref> By the end of 2006, India had destroyed more than 75 percent of its chemical weapons/material stockpile and was granted extension for destroying the remaining stocks by April 2009 and was expected to achieve 100 percent destruction within that time frame.<ref name="dominicantoday.com"/> India informed the United Nations in May 2009 that it had destroyed its stockpile of chemical weapons in compliance with the international Chemical Weapons Convention. With this India has become the third country after South Korea and Albania to do so.<ref>{{cite web|url=http://zeenews.india.com/news531700.html |title=Zee News – India destroys its chemical weapons stockpile |publisher=Zeenews.india.com |date=14 May 2009 |access-date=30 April 2013}}</ref><ref name="in.news.yahoo.com">{{cite web|url=http://in.news.yahoo.com/43/20090514/812/tnl-india-destroys-its-chemical-weapons.html |title=India destroys its chemical weapons stockpile - Yahoo! India News |access-date=20 May 2009 |url-status=dead|archive-url=https://web.archive.org/web/20090521195550/http://in.news.yahoo.com/43/20090514/812/tnl-india-destroys-its-chemical-weapons.html |archive-date=21 May 2009}}</ref> This was cross-checked by inspectors of the United Nations.

Producing or stockpiling mustard gas is prohibited by the [[Chemical Weapons Convention]]. When the convention entered force in 1997, the parties declared worldwide stockpiles of 17,440 tonnes of mustard gas. As of December 2015, 86% of these stockpiles had been destroyed.<ref>{{cite report |author=Organisation for the Prohibition of Chemical Weapons |date=30 November 2016 |title=Report of the OPCW on the Implementation of the Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on Their Destruction in 2015 |chapter-url=https://www.opcw.org/documents-reports/annual-reports/ |chapter=Annex 3 |page=42 |access-date=8 March 2017}}</ref>

A significant portion of the United States' mustard agent [[stockpile (military)|stockpile]] was stored at the Edgewood Area of [[Aberdeen Proving Ground]] in [[Maryland]]. Approximately 1,621 tons of mustard agents were stored in one-ton containers on the base under heavy guard. A chemical neutralization plant was built on the proving ground and neutralized the last of this stockpile in February 2005. This stockpile had priority because of the potential for quick reduction of risk to the community. The nearest schools were fitted with overpressurization machinery to protect the students and faculty in the event of a catastrophic explosion and fire at the site. These projects, as well as planning, equipment, and training assistance, were provided to the surrounding community as a part of the Chemical Stockpile Emergency Preparedness Program (CSEPP), a joint program of the Army and the [[Federal Emergency Management Agency]] (FEMA).<ref>{{cite web|url=http://www.fema.gov/government/grant/csepp1.shtm |title=CSEPP Background Information |publisher=US Federal Emergency Management Agency (FEMA) |date=2 May 2006 |url-status=dead|archive-url=https://web.archive.org/web/20060527013022/http://www.fema.gov/government/grant/csepp1.shtm |archive-date=27 May 2006}}</ref> Unexploded shells containing mustard gases and other chemical agents are still present in several test ranges in proximity to schools in the Edgewood area, but the smaller amounts of poison gas ({{convert|4|to|14|lb|kg|}}) present considerably lower risks. These remnants are being detected and excavated systematically for disposal. The U.S. Army Chemical Materials Agency oversaw disposal of several other chemical weapons stockpiles located across the United States in compliance with international chemical weapons treaties. These include the complete incineration of the chemical weapons stockpiled in [[Alabama]], [[Arkansas]], [[Indiana]], and [[Oregon]]. Earlier, this agency had also completed destruction of the chemical weapons stockpile located on [[Johnston Atoll]] located south of [[Hawaii]] in the [[Pacific Ocean]].<ref>{{Cite web |url=http://www.cma.army.mil/fndocumentviewer.aspx?docid=003676918 |title=Milestones in U.S. Chemical Weapons Storage and Destruction, fact sheet, US Chemical Materials Agency |access-date=15 January 2012 |archive-url=https://web.archive.org/web/20120915081558/http://www.cma.army.mil/fndocumentviewer.aspx?docid=003676918 |archive-date=15 September 2012 |url-status=dead}}</ref> The largest mustard agent stockpile, at approximately 6,200 [[short ton]]s, was stored at the [[Deseret Chemical Depot]] in northern [[Utah]]. The incineration of this stockpile began in 2006. In May 2011, the last of the mustard agents in the stockpile were incinerated at the Deseret Chemical Depot, and the last artillery shells containing mustard gas were incinerated in January 2012.

In 2008, many empty [[aerial bomb]]s that contained mustard gas were found in an excavation at the [[Marrangaroo Army Base]] just west of Sydney, Australia.<ref>{{Cite news|author=Ashworth L |title=Base's phantom war reveals its secrets |publisher=Fairfax Digital |date=7 August 2008 |url=http://lithgow.yourguide.com.au/news/local/news/general/bases-phantom-war-reveals-its-secrets/1237570.aspx |url-status=dead|archive-url=https://web.archive.org/web/20081205033022/http://lithgow.yourguide.com.au/news/local/news/general/bases-phantom-war-reveals-its-secrets/1237570.aspx |archive-date=5 December 2008}}</ref><ref name="MGOrg">[http://www.mustardgas.org/ Chemical Warfare in Australia]. Mustardgas.org. Retrieved on 29 May 2011.</ref> In 2009, a mining survey near [[Chinchilla, Queensland]], uncovered 144 105-millimeter [[howitzer]] shells, some containing "Mustard H", that had been buried by the U.S. Army during World War II.<ref name="MGOrg" /><ref>{{Cite news|author=Cumming, Stuart|title=Weapons await UN inspection|publisher=Toowoomba Chronicle|date=11 November 2009 |url=http://www.thechronicle.com.au/story/2009/11/11/weapons-await-un-inspection/}}</ref>

In 2014, a collection of 200 bombs was found near the [[Flanders|Flemish]] villages of [[Passendale]] and [[Moorslede]]. The majority of the bombs were filled with mustard agents. The bombs were left over from the German army and were meant to be used in the [[Battle of Passchendaele]] in World War I. It was the largest collection of chemical weapons ever found in Belgium.<ref>{{cite web|title=Farmer discovers 200 bombs (Dutch)|date=5 March 2014 |url=http://www.nieuwsblad.be/article/detail.aspx?articleid=DMF20140304_01009955}}</ref>

A large amount of chemical weapons, including mustard gas, was found in a neighborhood of [[Washington, D.C.]] The cleanup was completed in 2021.<ref>{{Cite web|title=Cleanup Complete At WWI Chemical Weapons Dump In D.C.'s Spring Valley|url=https://dcist.com/story/21/11/26/cleanup-complete-chemical-weapons-dump-dc-spring-valley/|access-date=2022-02-07|website=DCist|language=en|archive-date=2022-02-07|archive-url=https://web.archive.org/web/20220207135510/https://dcist.com/story/21/11/26/cleanup-complete-chemical-weapons-dump-dc-spring-valley/|url-status=live}}</ref>

====Post-war accidental exposure====

In 2002, an archaeologist at the Presidio Trust archaeology lab in San Francisco was exposed to mustard gas, which had been dug up at the [[Presidio of San Francisco]], a former military base.<ref>{{cite news|author=Sullivan, Kathleen|title=Vial found in Presidio may be mustard gas / Army experts expected to identify substance|publisher=sfgate.com|date=2002-10-22|url=http://www.sfgate.com/green/article/Vial-found-in-Presidio-may-be-mustard-gas-Army-2760483.php}}</ref>

In 2010, a clamming boat pulled up some old [[artillery]] shells of World War I from the [[Atlantic Ocean]] south of [[Long Island, New York]]. Multiple fishermen suffered from blistering and respiratory irritation severe enough to require hospitalization.<ref>{{Cite news|author1=Wickett, Shana |author2=Beth Daley |title=Fishing crewman exposed to mustard gas from shell |work=The Boston Globe |date=2010-06-08 |url=http://www.boston.com/news/local/breaking_news/2010/06/signs_of_bliste.html |url-status=dead|archive-url=https://web.archive.org/web/20100609132933/http://www.boston.com/news/local/breaking_news/2010/06/signs_of_bliste.html |archive-date=June 9, 2010}}</ref>

===WWII-era tests on men===

[[File:Edgewood Arsenal - Mustard Gas Test Subjects March 1945.jpg|thumb|Mustard gas test subjects enter gas chamber in Edgewood Arsenal, March 1945.]]

From 1943 to 1944, mustard agent experiments were performed on Australian service volunteers in tropical [[Queensland, Australia]], by [[Royal Australian Engineers]], [[British Army]] and American experimenters, resulting in some severe injuries. One test site, the [[Brook Islands National Park]], was chosen to simulate Pacific islands held by the [[Imperial Japanese Army]].<ref>{{Cite book

|first=Bridget|last=Goodwin|year=1998|title=Keen as mustard: Britain's horrific chemical warfare experiments in Australia|___location=St. Lucia|publisher=University of Queensland Press |isbn=978-0-7022-2941-1}}</ref><ref>[http://home.st.net.au/~dunn/brook%20island%20trial.htm Brook Island Trials of Mustard Gas during WW2]. Home.st.net.au. Retrieved on 2011-05-29.</ref> These experiments were the subject of the documentary film ''[[Keen as Mustard (film)|Keen as Mustard]]''.<ref>{{Cite web |title=Keen as mustard {{!}} Bridget Goodwin {{!}} 1989 {{!}} ACMI collection |url=https://www.acmi.net.au/works/80685--keen-as-mustard/ |access-date=2024-07-23 |website=www.acmi.net.au |language=en}}</ref>

The United States tested sulfur mustards and other chemical agents including [[nitrogen mustard]]s and [[lewisite]] on up to 60,000 servicemen during and after WWII. The experiments were classified secret and as with [[Agent Orange#US Public Health Service, CDC and VA|Agent Orange]]{{Broken anchor|date=2024-12-20|bot=User:Cewbot/log/20201008/configuration|target_link=Agent Orange#US Public Health Service, CDC and VA|reason= The anchor (US Public Health Service, CDC and VA) [[Special:Diff/942788652|has been deleted]].}}, claims for medical care and compensation were routinely denied, even after the WWII-era tests were declassified in 1993. The [[Department of Veterans Affairs]] stated that it would contact 4,000 surviving test subjects but failed to do so, eventually only contacting 600. Skin cancer, severe eczema, leukemia, and chronic breathing problems plagued the test subjects, some of whom were as young as 19 at the time of the tests, until their deaths, but even those who had previously filed claims with the VA went without compensation.<ref name="NPR-1">{{cite web |url=https://www.npr.org/2015/06/23/416408655/the-vas-broken-promise-to-thousands-of-vets-exposed-to-mustard-gas |title=The VA's Broken Promise To Thousands Of Vets Exposed To Mustard Gas |last=Dickerson |first=Caitlin |date=2015-06-23 |website=[[National Public Radio|NPR]] |access-date=2019-05-03 |quote=... the Department of Veterans Affairs made two promises: to locate about 4,000 men who were used in the most extreme tests, and to compensate those who had permanent injuries.}}</ref>

[[File:Mustard gas four test subjects NRL.jpg|thumb| Arms of four test subjects after exposure to [[nitrogen mustard]] and [[lewisite]] agents]]

[[Military history of African Americans#World War II|African American servicemen]] were tested alongside white men in separate trials to determine whether their skin color would afford them a degree of immunity to the agents, and [[Nisei]] servicemen, some of whom had joined after their release from [[Internment of Japanese Americans|Japanese American Internment Camps]] were tested to determine susceptibility of [[Imperial Japanese Army|Japanese military personnel]] to these agents. These tests also included [[Puerto Ricans|Puerto Rican]] subjects.<ref name="NPR-2">{{cite web |url=https://www.npr.org/2015/06/22/415194765/u-s-troops-tested-by-race-in-secret-world-war-ii-chemical-experiments |title=Secret World War II Chemical Experiments Tested Troops By Race |last=Dickerson |first=Caitlin |date=2015-06-22 |website=[[National Public Radio|NPR]]|access-date=2019-05-03 |quote="And it wasn't just African-Americans. Japanese-Americans were used [...] so scientists could explore how mustard gas and other chemicals might affect Japanese troops. Puerto Rican soldiers were also singled out."}}</ref>

===Detection in biological fluids===

Concentrations of thiodiglycol in urine have been used to confirm a diagnosis of chemical poisoning in hospitalized victims. The presence in urine of 1,1'-sulfonylbismethylthioethane (SBMTE), a conjugation product with glutathione, is considered a more specific marker, since this metabolite is not found in specimens from unexposed persons. In one case, intact mustard gas was detected in postmortem fluids and tissues of a man who died one week post-exposure.<ref>R. Baselt, ''Disposition of Toxic Drugs and Chemicals in Man'', 10th edition, Biomedical Publications, Seal Beach, CA, 2014, pp. 1892–1894.</ref>

==See also==

* [[Bis(chloromethyl) ether]]

* [[Chlorine gas]]

* ''[[Keen as Mustard (film)|Keen as Mustard]]''

* [[Phosgene oxime]]

* [[Poison gas in World War I]]

* [[Rawalpindi experiments]]

* [[Selenium mustard]]

==References==

'''Notes'''

{{Reflist}}

{{commons category}}

==Further reading==

* Cook, Tim. "'Against God-Inspired Conscience': The Perception of Gas Warfare as a Weapon of Mass Destruction, 1915–1939." ''War & Society'' 18.1 (2000): 47-69.

* Dorsey, M. Girard. ''Holding Their Breath: How the Allies Confronted the Threat of Chemical Warfare in World War II'' (Cornell UP, 2023) [https://books.google.com/books?id=W4KiEAAAQBAJ&dq=mustard+gas+&pg=PR7 online].

* Duchovic, Ronald J., and Joel A. Vilensky. "Mustard gas: its pre-World War I history." ''Journal of chemical education'' 84.6 (2007): 944. [https://www.academia.edu/download/88516562/ed084p94420220712-1-7in76q.pdf online]

* Feister, Alan J. ''Medical defense against mustard gas: toxic mechanisms and pharmacological implications'' (1991). [https://books.google.com/books?id=BkBfb8vC_LgC&dq=%22Mustard+Gas%22&pg=PA1 online]

* Fitzgerald, Gerard J. "Chemical warfare and medical response during World War I." ''American journal of public health'' 98.4 (2008): 611-625. [https://scholar.google.com/scholar?output=instlink&q=info:6O5L0KIoCV4J:scholar.google.com/&hl=en&as_sdt=0,27&scillfp=17145573770559279105&oi=lle online]

** {{Cite book |last=Freemantle |first=M. |title = Gas! GAS! Quick, boys! How Chemistry Changed the First World War |publisher=The History Press |year=2012 |isbn = 978-0-7524-6601-9}}

* Geraci, Matthew J. "Mustard gas: imminent danger or eminent threat?." ''Annals of Pharmacotherapy'' 42.2 (2008): 237-246. [https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=acb8be33b15f5b2fffa24c7629b0413c6adf9ded online]

* Ghabili, Kamyar, et al. "Mustard gas toxicity: the acute and chronic pathological effects." ''Journal of applied toxicology'' 30.7 (2010): 627-643. [https://www.researchgate.net/profile/Mostafa-Ghanei/publication/281109293_Mustard_gas_toxicity_The_acute_and_chronic_pathological_effects/links/5a0bd113aca2721a23fa1564/Mustard-gas-toxicity-The-acute-and-chronic-pathological-effects.pdf online]

* Jones, Edgar. "Terror weapons: The British experience of gas and its treatment in the First World War." ''War in History'' 21.3 (2014): 355-375. [https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5131841/ online]

* {{cite book |series=History of the Great War Based on Official Documents by Direction of the Historical Section of the Committee of Imperial Defence |title=Medical Services: Diseases of the War: Including the Medical Aspects of Aviation and Gas Warfare and Gas Poisoning in Tanks and Mines |volume=II |last1=MacPherson |first1=W. G. |last2=Herringham |first2=W. P. |last3=Elliott |first3=T. R. |last4=Balfour |first4=A. |year=1923 |publisher=HMSO |___location=London |url=https://archive.org/details/medicalservicesd02macp |access-date=19 October 2014 |oclc=769752656}}

* Padley, Anthony Paul. "Gas: the greatest terror of the Great War." ''Anaesthesia and intensive care'' 44.1_suppl (2016): 24-30. [https://journals.sagepub.com/doi/pdf/10.1177/0310057X1604401S05 online]

* Rall, David P., and Constance M. Pechura, eds. ''Veterans at risk: The health effects of mustard gas and lewisite'' (1993). [https://apps.dtic.mil/sti/pdfs/ADA263272.pdf online]

* {{Cite book

|title=Chemical Soldiers

|first=Donald |last=Richter

|year=1994

|publisher=Leo Cooper

|isbn=0850523885

}}

* Schummer, Joachim. "Ethics of chemical weapons research: Poison gas in World War One." ''Ethics of Chemistry: From Poison Gas to Climate Engineering'' (2021) pp. 55-83. [https://hyle.org/journal/issues/24-1/schummer.pdf online]

* Smith, Susan I. ''Toxic Exposures: Mustard Gas and the Health Consequences of World War II in the United States'' (Rutgers University Press, 2017) [https://www.h-net.org/reviews/showpdf.php?id=58530 online book review]

* Wattana, Monica, and Tareg Bey. "Mustard gas or sulfur mustard: an old chemical agent as a new terrorist threat." ''Prehospital and disaster medicine'' 24.1 (2009): 19-29. [https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=9adad7a31848ea5fa59f65c8414cc8e65e9bfc07 online]

*{{Cite journal |last=Jackson |first=Kirby E. |date=December 1934 |title=β,β' Dichloroethyl Sulfide (Mustard Gas). |journal=Chemical Reviews |language=en |volume=15 |issue=3 |pages=425–462 |doi=10.1021/cr60052a004 |issn=0009-2665}}

==External links==

* [http://www.inchem.org/documents/iarc/suppl7/mustardgas.html Mustard gas (Sulphur Mustard) (IARC Summary & Evaluation, Supplement7, 1987)]. Inchem.org (1998-02-09). Retrieved on 2011-05-29.

*[http://www.bris.ac.uk/Depts/Chemistry/MOTM/mustard/mustard.htm In-depth chemical information on Mustard Gas]

* {{cite book|author1=Institute of Medicine|title=Veterans at Risk: The Health Effects of Mustard Gas and Lewisite|year=1993|isbn=978-0-309-04832-3|chapter=History and Analysis of Mustard Agent and Lewisite Research Programs in the United States|publisher=National Academies Press |chapter-url=https://www.ncbi.nlm.nih.gov/books/NBK236059/}}

:This reference has several errors in it:

* [https://web.archive.org/web/20171011201218/https://ke.army.mil/bordeninstitute/published_volumes/chemBio/Ch7.pdf Textbook of Military Medicine – Intensive overview of mustard gas] Includes many references to scientific literature

:# The Fredrick Guthrie synthesis should be from ethylene and SCl₂, not ethylene and Cl₂ as stated.

* [http://www.inchem.org/documents/pims/chemical/mustardg.htm Detailed information on physical effects and suggested treatments]

:# The hydrolysis reaction pathway produces two molecules of HCl and the last one produced is H₂O, not three molecules of HCl as shown in the reference.

* {{Cite journal|author=Iyriboz Y |title=A Recent Exposure to Mustard Gas in the United States: Clinical Findings of a Cohort (n = 247) 6 Years After Exposure |journal=MedGenMed |volume=6 |issue=4 |page=4 |year=2004 |pmid=15775831 |pmc=1480580 }} Shows photographs taken in 1996 showing people with mustard gas burns.

:# The molecular structure given for nitrogen mustard (N-mustard) is not correct. The nitrogen atom should have a hydrogen bonded to it.

* [https://web.archive.org/web/20181012233739/http://www.counteract.rutgers.edu/ UMDNJ-Rutgers University CounterACT Research Center of Excellence] A research center studying mustard gas, includes [https://web.archive.org/web/20110430224324/http://www.ucdper.com/counteract/biblio searchable reference library] with many early references on mustard gas.

*[http://reference.allrefer.com/encyclopedia/M/mustardg.html mustard gas, Organic Chemistry]

* {{cite journal |last1=Clayton |first1=William |last2=Howard |first2=Alfred John |last3=Thomson |first3=David |title=Treatment of Mustard Gas Burns |journal=British Medical Journal |date=25 May 1946 |volume=1 |issue=4455 |pages=797–799 |doi=10.1136/bmj.1.4455.797 |pmid=20786722 |pmc=2058956 }}

:This reference also has an error in it.

* [http://www.burnsjournal.com/article/S0305-4179%2809%2900125-9/abstract surgical treatment of mustard gas burns]

:In the sentence on synthesis of mustard gas, the phrase "sulfur monochloride, S₂Cl₂" should be "sulfur dichloride, SCl₂"

* [https://web.archive.org/web/20120105155850/http://www.mod.uk/NR/rdonlyres/77CEDBCA-813A-4A6C-8E59-16B9E260E27A/0/ic_munitions_seabed_rep.pdf UK Ministry of Defence Report on disposal of weapons at sea and incidents arising]

*[http://cfrterrorism.org/weapons/mustard.html Questions and Answers for Mustard Gas]

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