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Triethylenetetramine

Triethylenetetramine (TETA and trien), also known as trientine (INN) when used medically, is an organic compound with the formula [CH2NHCH2CH2NH2]2. The pure free base is a colorless oily liquid, but, like many amines, older samples assume a yellowish color due to impurities resulting from air oxidation. It is soluble in polar solvents. The branched isomer tris(2-aminoethyl)amine and piperazine derivatives may also be present in commercial samples of TETA. The hydrochloride salts are used medically as a treatment for copper toxicity.

Uses
Epoxy uses The reactivity and uses of TETA are similar to those for the related polyamines ethylenediamine and diethylenetriamine. It is primarily used as a crosslinker ("hardener") in epoxy curing. TETA, like other aliphatic amines, react quicker and at lower temperatures than aromatic amines due to less negative steric effects since the linear nature of the molecule provides it the ability to rotate and twist. Medical uses The hydrochloride salt of TETA, referred to as trientine hydrochloride, is a chelating agent that is used to bind and remove copper in the body to treat Wilson's disease, particularly in those who are intolerant to penicillamine. Trientine hydrochloride (brand name Syprine) was approved for medical use in the United States in November 1985. It is indicated for the treatment of Wilson's disease in adults, adolescents and children five years of age or older who are intolerant to D-penicillamine therapy. It is indicated for the treatment of Wilson's disease in adults, adolescents and children five years of age or older who are intolerant to D-penicillamine therapy. The most common side effects include nausea, especially when starting treatment, skin rash, duodenitis (inflammation of the duodenum, the part of the gut leading out of the stomach), and severe colitis (inflammation in the large bowel causing pain and diarrhea). == Society and culture ==
Society and culture
Controversies In the United States, Valeant Pharmaceuticals International raised the price of its Syprine brand of TETA from $625 to $21,267 for 100 pills over five years. ==Production==
Production
TETA is prepared by heating ethylenediamine or ethanolamine/ammonia mixtures over an oxide catalyst. This process gives a variety of amines, especially ethylene amines which are separated by distillation and sublimation. An idealized equation follows: : ==Coordination chemistry==
Coordination chemistry
TETA is a tetradentate ligand in coordination chemistry, where it is referred to as trien. Octahedral complexes of the type M(trien)L2 can adopt several diastereomeric structures. 1,4,8,11-Tetraazaundecane is a closely related tetraamine ligand. == References ==
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