Trisamine is the organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with the formula

Chemical formula

A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 N(CH₂CH₂Cl)₃. Often abbreviated HN3, it is a powerful blister agent  and a nitrogen mustard gas (although it is not a gas) used for chemical warfare

Chemical warfare

Chemical warfare involves using the toxic properties of chemical substances as weapons. This type of warfare is distinct from Nuclear warfare and Biological warfare, which together make up NBC, the military acronym for Nuclear, Biological, and Chemical...

. 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

Sulfur mustard

The sulfur mustards, or sulphur mustards, commonly known as mustard gas, are a class of related cytotoxic, vesicant chemical warfare agents with the ability to form large blisters on exposed skin. Pure sulfur mustards are colorless, viscous liquids at room temperature...

 and thus the analogy between the two types of mustard is the strongest. As a vesicant the use and production is strongly restricted within the Chemical Weapons Convention

Chemical Weapons Convention

The Chemical Weapons Convention is an arms control agreement which outlaws the production, stockpiling and use of chemical weapons. Its full name is the Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on their Destruction...

 where it is classified as a Schedule 1 substance.

Mode of action

Nitrogen mustards react via an initial cyclization to the corresponding iminium 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 mustard

Sulfur mustard

The sulfur mustards, or sulphur mustards, commonly known as mustard gas, are a class of related cytotoxic, vesicant chemical warfare agents with the ability to form large blisters on exposed skin. Pure sulfur mustards are colorless, viscous liquids at room temperature...

s.

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
  Nitrogen mustard
  The nitrogen mustards are cytotoxic chemotherapy agents similar to mustard gas. Although their common use is medicinal, in principle these compounds can also be deployed as chemical warfare agents. Nitrogen mustards are nonspecific DNA alkylating agents. Nitrogen mustard gas was stockpiled by...
  
  
  • HN1
    Bis(2-chloroethyl)ethylamine
    Bisethylamine is the organic compound with the formula C2H5N2. Often abbreviated HN1, it is a powerful vesicant and a nitrogen mustard gas used for chemical warfare. HN1 was developed in the 1920s and 1930s to remove warts and later as a military agent...
    
    
  • HN2