N,N'-Bis(2-aminoethyl)ethane-1,2-diamine; TETA; Trien; Trientine (INN); Syprine (brand name)
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||146.238 g·mol−1|
|Density||982 mg mL−1|
|Melting point||−34.6 °C; −30.4 °F; 238.5 K|
|Boiling point||266.6 °C; 511.8 °F; 539.7 K|
|Vapor pressure||<1 Pa (at 20 °C)|
Refractive index (nD)
Heat capacity (C)
|376 J K−1 mol−1 (at 60 °C)|
|GHS signal word||DANGER|
|H312, H314, H317, H412|
|P273, P280, P305+351+338, P310|
|Flash point||129 °C (264 °F; 402 K)|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Triethylenetetramine (TETA and trien), also called trientine (INN), is an organic compound with the formula [CH2NHCH2CH2NH2]2. This oily liquid is colorless but, like many amines, assumes 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 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. Some recommend trientine as first-line treatment, but experience with penicillamine is more extensive.
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. The New York Times said that this "egregious" price increase caused public outrage. Teva Pharmaceuticals developed a generic, which patients and doctors expected to be cheaper, but when it was introduced in February, 2018, Teva's price was $18,375 for 100 pills. Aaron Kesselheim, who studies drug pricing at Harvard Medical School, said that drug companies price the product at what they think the market will bear.
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.
TETA is a tetradentate ligand in coordination chemistry, where it is referred to as trien. Octahedral complexes of the type M(trien)Cl3 can adopt several diastereomeric structures, most of which are chiral.
- "Ethyleneamines" (PDF). Huntsman. 2007.
- Eller, K.; Henkes, E.; Rossbacher, R.; Höke, H. (2005). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001.
- Roberts, E. A.; Schilsky, M. L. (2003). "A practice guideline on Wilson disease" (pdf). Hepatology. 37 (6): 1475–1492. doi:10.1053/jhep.2003.50252. PMID 12774027.[dead link]
- Patients Eagerly Awaited a Generic Drug. Then They Saw the Price. By KATIE THOMAS. New York Times. FEB. 23, 2018
- Brydson, J. A. (1999). "Epoxide Resins". In J. A. Brydson (ed.). Plastics Materials (Seventh Edition). Oxford: Butterworth-Heinemann. doi:10.1016/B978-075064132-6/50067-X.
- von Zelewsky, A. (1995). Stereochemistry of Coordination Compounds. Chichester: John Wiley. ISBN 047195599X.
- Utsuno, S.; Sakai, Y.; Yoshikawa, Y.; Yamatera, H. (1985). "Three Isomers of the Trans-Diammine-[N,N′-bis(2-Aminoethyl)-1,2-Ethanediamine]-Cobalt(III) Complex Cation". Inorganic Syntheses. 23: 79–82. doi:10.1002/9780470132548.ch16.