2-Chloro-N,N-bis(2-chloroethyl)ethanamine, also known as trichlormethine, tris(2-chloroethyl)amine is the organic compound with the formula N(CH2CH2Cl)3. Often abbreviated HN3 or HN-3, it is a powerful blister agent and a nitrogen mustard used for chemical warfare. HN3 was the last of the nitrogen mustard agents developed. It was designed as a military agent and is the only one of the nitrogen mustards that is still used for military purposes. It is the principal representative of the nitrogen mustards because its vesicant properties are almost equal to those of HD and thus the analogy between the two types of mustard is the strongest.[1] As a vesicant the use and production is strongly restricted within the Chemical Weapons Convention where it is classified as a Schedule 1 substance.
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| Names | |
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| Preferred IUPAC name
2-Chloro-N,N-bis(2-chloroethyl)ethanamine | |
| Other names
Trichlormethine
Tris(2-chloroethyl)amine EA-1053 TL-145 | |
| Identifiers | |
3D model (JSmol)
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| MeSH | 2,2',2+-trichlorotriethylamine |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C6H12Cl3N | |
| Molar mass | 204.52 g·mol−1 |
| Appearance | Colourless liquid |
| Odor | Fishy, ammoniacal |
| Density | 1.24 g mL−1 |
| Melting point | −4 to −3.7 °C (24.8 to 25.3 °F; 269.1 to 269.4 K) |
| Boiling point | 143 °C (289 °F; 416 K) |
| log P | 1.306 |
| Related compounds | |
Related amines
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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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Mode of action
editNitrogen mustards react via an initial cyclization to the corresponding quaternary aziridine salt. The rate of this reaction is pH dependent because the protonated amine cannot cyclize.
Applications
editHN-3 has found some applications in chemotherapy, e.g., for Hodgkin's disease, and in some compound semiconductor research[2] but it is mainly of interest for its military uses and is the only one of these agents that remains anywhere as a military agent.[citation needed] These agents are more immediately toxic than the sulfur mustards.
Exposure
editHN-3 can be absorbed into the body by inhalation, ingestion, eye contact, and skin contact (though inhalation is the most common). The chemical is extremely toxic and may damage the eyes, skin, and respiratory tract and suppress the immune system. HN-3 penetrates and binds quickly to cells of the body, but its health effects develop slowly. The full extent of cellular injury may not be known for days.[1]
See also
editReferences
edit- ^ a b NITROGEN MUSTARD HN-3. Emergency Response Safety and Health Database. National Institute for Occupational Safety and Health. August 22, 2008. Accessed April 10, 2009.
- ^ Benard, C. (1997). Chemical Vapor Deposition. Pennington, NJ, USA: The Electrochemical Society, INC. p. 78. ISBN 1-56677-178-1.