HN1 (nitrogen mustard)
This article relies largely or entirely on a single source. (February 2023) |
Names | |
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IUPAC name
2-Chloro-N-(2-chloroethyl)-N-ethylethanamine
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Other names
Bis(2-chloroethyl)(ethyl)amine
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Identifiers | |
3D model (
JSmol ) |
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ChemSpider | |
MeSH | bis(2-chloroethyl)ethylamine |
PubChem CID
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RTECS number
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UNII | |
UN number | 2810 |
CompTox Dashboard (EPA)
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Properties | |
C6H13Cl2N | |
Molar mass | 170.08 g·mol−1 |
Appearance | Colourless to pale yellow oily liquid |
Odor | Fishy, musty |
Density | 1.0861 g mL−1 (at 20 °C) |
Melting point | −34 °C (−29 °F; 239 K) |
Boiling point | 85.5 °C (185.9 °F; 358.6 K) |
Related compounds | |
Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Bis(2-chloroethyl)ethylamine is the
It is an oily liquid with a colorless to pale yellow appearance and a faint fishy or musty odor. HN1 is also an alkylating agent.[1]
Reactions
Nitrogen mustards react via an initial cyclization to the corresponding aziridinium salt. The rate of this reaction is pH dependent because the protonated amine cannot cyclize. The aziridinium ion reacts with water in a slower reaction. At pH 8, the nitrogen mustards are essentially quantitatively converted to the aziridinium ion for subsequent slow reaction with water. In contrast, at pH 4 cyclization and hydrolysis show the classic form of reactions in series.[citation needed] Hydrolysis of HN1 produces toxic intermediates.[1]
HN1 reacts with
Toxicity
Because HN1 is an alkylating agent, it damages DNA, causes immunosuppression, and causes injury to areas that come into contact with it. Exposure to HN1 can be fatal, and its effects on skin and mucous membranes are worsened when they are moist. The alkylation effects cause damage to the spleen, bone marrow, and lymph nodes, which causes anemia, low white cell counts, and internal bleeding. The vesicant effects cause blistering and damage to the skin.[1]
The symptoms of exposure depend on the route of exposure. Eye exposure to vapor can cause
Inhaling the vapor causes symptoms that begin in the upper airway and expand to the lower airway. Increased concentrations cause worse symptoms. Mild inhalation exposure causes
Skin contact with nitrogen mustard in low concentrations causes symptoms beginning with redness, then moving to blistering, itching, and burning pain. More severe exposure can cause necrosis (cell death) in the blisters, and systemic toxicity, which causes malaise, vomiting, exhaustion, and fever. Skin exposure that causes symptoms over more than 25% of the body area is often fatal. Though ingestion is uncommon, nitrogen mustard can burn the GI tract and cause nausea, vomiting, hemorrhagic diarrhea, and abdominal pain.[1]
Nitrogen mustard exposure does not cause symptoms until several hours to several days afterwards, but more severe exposure causes symptoms sooner. With severe exposure, eye injury can manifest within 1-2 hours, airway damage within 2-6 hours, and skin damage within 6-12 hours (sooner in hot or humid weather). Mild exposure takes longer to manifest symptoms: eye injury within 3-12 hours, airway damage within 12-24 hours, and skin damage up to 48 hours post-exposure.[1]
Long-term sequelae
Effects of nitrogen mustard exposure can be long-term or permanent; it is also a known
Treatment
Treatment for HN1 exposure is primarily supportive, since there is no