Nitrogen mustard
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The nitrogen mustards are cytotoxic chemotherapy agents similar to mustard gas. Although their common use is medicinal, in principle these compounds may also be used for chemical warfare purposes.
The prototype nitrogen mustard drug is mustine which is no longer commonly in use but was the first drug to be used as an anticancer chemotherapeutic. It is a schedule 1 substance in the Chemical Weapons Convention. Other nitrogen mustards include cyclophosphamide, chlorambucil, uramustine and melphalan.
Nitrogen mustards are nonspecific DNA alkylating agents, because they form cyclic aminium ions (aziridiniums) by attack of nitrogen on the organochloride center (see Sulfur mustard#Chemistry). All the therapeutically used alkylating agents have more than one alkylating group per molecule. Thus they are termed as di or polyalkylating. The effects are radiomimetic, i.e. the DNA damage is similar to that which is seen when genetic material is exposed to radiation.
Examples of nitrogen mustards that can be used for chemical warfare purposes and their military weapon designations include:
- HN1: Bis(2-chloroethyl) ethylamine
- HN2: Bis(2-chloroethyl) methylamine
- HN3: Tris(2-chloroethyl) amine
Several nations stock-piled large amounts of munitions containing nitrogen mustard gas during the Second World War, but none were used in combat. As with all types of mustard gas, nitrogen mustard is a powerful and persistent blister agent.
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