Chemistry of Mustard Compounds

  • Mahmood Sadeghi
  • Beeta Balali-MoodEmail author


The two main categories of mustard compounds are sulfur mustards and nitrogen mustards. Sulfur mustard was the first vesicant chemical weapon used. Its first widespread use was recorded in the World War One. After a number of sporadic military attacks, another widespread use of sulfur mustard occurred in the Iran-Iraq war. Nitrogen mustard derivatives are used in chemotherapy. HN-1, HN-2, HN-3 are the most important forms of nitrogen mustards. Nitrogen mustard HN-2 is chlormethine (Mechlorethamine) and has been used for treatment of multiple cancer diseases such as Hodgkin’s disease. Sulfur mustard has the chemical name bis(2-chloroethyl) sulfide and the IUPAC name 1-chloro-2-(2-chloroethylsulfanyl) ethane. It is also known as mustard, mustard gas, HD or Yperite. The compound is highly reactive and has carcinogenic, cytotoxic and powerful vesicant characteristics. Mustard gas was first synthesized from the reaction of ethylene and sulfur dichloride (Levinstein process) through an electrophilic addition mechanism. Later, it was prepared by the reaction of thiodiglycol with phosphorus trichloride (Meyer reaction) in a substitution reaction. Finally, reaction of concentrated hydrochloric acid (HCl) and thiodiglycol resulted in the production of sulfur mustard. Pure mustard is a viscous, colorless and odorless liquid which evaporates slowly in the atmosphere. Cytotoxicity of sulfur mustard stems from the formation of electrophilic species called sulfonium cation upon nucleophilic attack. This transient cation then readily reacts with macromolecules of DNA, RNA and proteins or with water to form the corresponding hydroxyl compounds. DNA Cross-linking of guanine by sulfur mustard and its interaction with imidazole are well studied. Nitrogen mustard (NM) and sulfur mustard (SM) slightly differ in properties. Like sulfur mustard, nitrogen mustard compounds are also alkylating agents and are reactive compounds that covalently bind to nucleophilic groups such as amine, carboxyl, sulfhydryl and imidazole moieties in DNA, RNA and proteins. Decontamination of SM can be achieved via hydrolysis in presence of aqueous solutions of sodium hypochlorite and or chloramine-T; in which HD decomposes into thiodiglycol non-poisonous product. No specific antidote for SM poisoning has been introduced. However, some formulations have been introduced as effective skin decontaminants.


Sulfur mustard Nitrogen mustards HN-1 HN-2 HN-3 Mechlorethamine Synthesis Reaction Physical characteristics Chemical properties Mechanism of cytotoxicity DNA-crosslinking Aziridinium ion 




Reaction involving a transfer of an alkyle group from one molecule to another for instance to a DNA molecule which can consequently result in cell death.


Medicines for counteracting/neutralizing the harmful effects of a poison


Genetic alterations such as DNA strand breaks and unscheduled DNA synthesis that may lead to cancer development

Chemical Properties

The ability to undergo changes that alter a material’s composition and are observed during a reaction

CWA: chemical warfare agents

Toxic chemical compounds in munitions/devices causing death or harm to human beings.


Being toxic to cells which may result in cell death


Ways of detoxifying hazardous chemicals using specific compounds


Being subjected to radiation or chemicals with potentially harmful effect.

Nitrogen Mustards

A family of mustard compounds with the central atom of nitrogen. Nitrogen mustards derivatives are used as chemotherapy drugs

Physical Properties

Properties that account for identifying substances. And are observed without changing the composition of matter

SM: Sulfur Mustard

A toxic and vesicant chemical warfare agent which is highly reactive and forms large blisters on the exposed skin


Study of the absorption and emission of light and matter. Spectral data shed light on the structure of compounds and can also be used in the analysis of a known analyte in a matrix


Production of chemical compounds


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Copyright information

© Springer International Publishing Switzerland 2015

Authors and Affiliations

  1. 1.Medical Toxicology Research Center, School of Medicine, Mashhad University of Medical SciencesMashhadIran
  2. 2.MoodBioPharmLondonUK

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