Tris(2-chloroethyl)amine is the
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
with the
formula N(CH
2CH
2Cl)
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.
[NITROGEN MUSTARD HN-3]
Emergency Response Safety and Health Database. National Institute for Occupational Safety and Health
The National Institute for Occupational Safety and Health (NIOSH, ) is the United States federal agency responsible for conducting research and making recommendations for the prevention of work-related injury and illness. NIOSH is part of the C ...
. August 22, 2008. Accessed April 10, 2009. As a
vesicant
A blister agent (or vesicant), is a chemical compound that causes severe skin, eye and mucosal pain and irritation. They are named for their ability to cause severe chemical burns, resulting in painful water blisters on the bodies of those affe ...
the use and production is strongly restricted within the
Chemical Weapons Convention where it is classified as a
Schedule 1 substance.
Mode of action
Nitrogen mustards react via an initial cyclization to the corresponding quaternary
aziridine
Aziridine is an organic compound consisting of the three-membered heterocycle . It is a colorless, toxic, volatile liquid that is of significant practical interest. Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. Its derivati ...
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
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.
See also
*
Nitrogen mustard
References
{{Nitrogen mustards
Antineoplastic drugs
Amines
Organochlorides
IARC Group 2B carcinogens
Nitrogen mustard vesicants
Chloroethyl compounds