HN3 (nitrogen mustard)

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.

HN3 (nitrogen mustard)
Skeletal formula of tris(2-chloroethyl)amine
Spacefill model of tris(2-chloroethyl)amine
Names
Preferred IUPAC name
2-Chloro-N,N-bis(2-chloroethyl)ethan-1-amine
Other names
Tris(2-chloroethyl)amine
EA-1053
TL-145
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
MeSH 2,2',2+-trichlorotriethylamine
UNII
  • InChI=1S/C6H12Cl3N/c7-1-4-10(5-2-8)6-3-9/h1-6H2 ☒N
    Key: FDAYLTPAFBGXAB-UHFFFAOYSA-N ☒N
  • ClCCN(CCCl)CCCl
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
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Mode of action

Nitrogen 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

HN-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. These agents are more immediately toxic than the sulfur mustards.

Exposure

HN-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

References
  1. NITROGEN MUSTARD HN-3. Emergency Response Safety and Health Database. National Institute for Occupational Safety and Health. August 22, 2008. Accessed April 10, 2009.
  2. Benard, C. (1997). Chemical Vapor Deposition. Pennington, NJ, USA: The Electrochemical Society, INC. p. 78. ISBN 1-56677-178-1.
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