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Bis(2-chloroethyl)ethylamine is the organic compound with the formula C2H5N(CH2CH2Cl)2. Often abbreviated HN1, it is a powerful vesicant and a so-called nitrogen mustard gas (it is not a gas) used for chemical warfare. HN-1 was developed in the 1920s and 1930s to remove warts and later as a military agent.
Additional recommended knowledge
Mode of action
Nitrogen mustards react via an initial cyclization to the corresponding iminium salt. The rate of this reaction is pH dependent because the protonated amine cannot cyclize. The iminium ion reacts with water in a slower reaction. At pH 8, the nitrogen mustards are essentially quantitatively converted to the iminium ion for subsequent slow reaction with water. In contrast, at pH 4 cyclization and hydrolysis show the classic form of reactions in series.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Bis(2-chloroethyl)ethylamine". A list of authors is available in Wikipedia.|