Trientine

Triethylenetetramine

Names
Other names N,N'-Bis(2-aminoethyl)ethane-1,2-diamine; TETA; Trien; Trientine (INN); Syprine (brand name)
Identifiers
CAS Number	112-24-3 Y
3D model (Jmol)	Interactive image
Beilstein Reference	605448
ChEBI	CHEBI:39501 Y
ChemSpider	21106175 Y
ECHA InfoCard	100.003.591
EC Number	203-950-6
Gmelin Reference	27008
KEGG	C07166 Y
MeSH	Trientine
PubChem CID	5565
RTECS number	YE6650000
UNII	SJ76Y07H5F Y
UN number	2259
InChI InChI=1S/C6H18N4/c7-1-3-9-5-6-10-4-2-8/h9-10H,1-8H2 Y Key: VILCJCGEZXAXTO-UHFFFAOYSA-N Y
SMILES NCCNCCNCCN
Properties
Chemical formula	C6H18N4
Molar mass	146.24 g·mol−1
Appearance	Colorless liquid
Odor	Fishy, ammoniacal
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
Solubility in water	Miscible
log P	1.985
Vapor pressure	<1 Pa (at 20 °C)
Refractive index (nD)	1.496
Thermochemistry
Specific heat capacity (C)	376 J K−1 mol−1 (at 60 °C)
Pharmacology
ATC code	A16AX12 (WHO)
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H312, H314, H317, H412
GHS precautionary statements	P273, P280, P305+351+338, P310
EU classification (DSD)	C
R-phrases	R21, R34, R43, R52/53
S-phrases	(S1/2), S26, S36/37/39, S45
Flash point	129 °C (264 °F; 402 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	550 mg kg−1(dermal, rabbit) 2.5 g kg−1(oral, rat)
Related compounds
Related amines	Ethylenediamine Diethylenetriamine Cyclam
Related compounds	Ethylenediaminetetraacetic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Triethylenetetramine, abbreviated TETA and trien and 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.

TETA is prepared by heating ethylenediamine or ethanolamine/ammonia mixtures over an oxide catalyst. This process gives a variety of amines, which are separated by distillation and sublimation.

The reactivity and uses of TETA are similar to those for the related polyamines ethylenediamine and diethylenetriamine. It was primarily used as a crosslinker ("hardener") in epoxy curing.

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.

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.