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a complex consisting of an organic base in association with hydrogen chloride

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/09/08 01:12:49」(JST)

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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 N(CH₂CH₂NH₂)₃ and piperazine derivatives may also be present in commercial samples of TETA.^[1]

Production

Triethylenetetramine 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.^[2]

Uses

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.^[2]

The hydrochloride salt of triethylenetetramine, referred to as trientine hydrochloride, is a chelating agent, and is used to bind up 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.^[3]

Coordination chemistry

Triethylenetetramine is a tetradentate ligand in coordination chemistry, where it is referred to as trien.^[4] Octahedral complexes of the type M(trien)Cl₃ can adopt several diastereomeric structures, most of which are chiral.^[5]

References

^ "Ethyleneamines" (PDF). Huntsman. 2007.
^ ^a ^b 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.
^ 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.

UpToDate Contents

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1. ウィルソン病：治療および予後 wilson disease treatment and prognosis
2. 遺伝性運動失調の概要 overview of the hereditary ataxias

English Journal

Wilson's Disease Should Be Treated with Zinc rather than Trientine or Penicillamine.

Avan A1,2, de Bie RMA2, Hoogenraad TU3.
Neuropediatrics.Neuropediatrics.2017 Oct;48(5):394-395. doi: 10.1055/s-0037-1603975. Epub 2017 Jun 30.
PMID 28666288

Characteristics and prevalence of Wilson's disease: A 2013 observational population-based study in France.

Poujois A1, Woimant F1, Samson S2, Chaine P1, Girardot-Tinant N1, Tuppin P3.
Clinics and research in hepatology and gastroenterology.Clin Res Hepatol Gastroenterol.2017 Jun 22. pii: S2210-7401(17)30142-0. doi: 10.1016/j.clinre.2017.05.011. [Epub ahead of print]
PMID 28648494

Structure-activity relationship studies of 1,7-diheteroarylhepta-1,4,6-trien-3-ones with two different terminal rings in prostate epithelial cell models.

Wang R1, Zhang X1, Chen C1, Chen G1, Sarabia C1, Zhang Q2, Zheng S2, Wang G2, Chen QH3.
European journal of medicinal chemistry.Eur J Med Chem.2017 Jun 16;133:208-226. doi: 10.1016/j.ejmech.2017.03.067. Epub 2017 Mar 29.
PMID 28388523

Japanese Journal

塩酸トリエンチンを使用し2度の妊娠,出産を行い得たD-ペニシラミン不耐性Wilson病の1例

佐々木泰,高木紀美代,酒井正利,齋藤滋
日本新生児学会雑誌 36(3), 495-499, 2000-08-01
NAID 10005001219

SUBACUTE AND CHRONIC TOXICITY STUDIES OF TRIETHYLENETETRAMINE DIHYDROCHLORIDE (TJA-250) BY ORAL ADMINISTRATION TO F-344 RATS

YANAGISAWA Toshihiko,MAEMURA Shunichi,SASAKI Hiromi,ENDO Toru,OKADA Minoru,EAST Philip W.,VIRGO David M.,CREASY Dianne M.
Journal of toxicological sciences 23(Supplement IV), 619-642, 1998-10-28
… Triethylenetetramine dihydrochloride (trientine-2HCl, TJA-250), a copper chelating agent used to treat Wilson's disease, was administered orally to male and female F-344 rats for 4 or 8 weeks at dosages of 0, 100, 350 or 1200 mg/kg/day or for 26 weeks at dosages of 50, 175 or 600 mg/kg/day. …
NAID 110001815142

「トリエンチン」

Triethylenetetramine
Names
	Other names N,N'-Bis(2-aminoethyl)ethane-1,2-diamine
Identifiers
CAS Number	112-24-3
Beilstein Reference	605448
ChEBI	CHEBI:39501
ChEMBL	ChEMBL609
ChemSpider	21106175
EC Number	203-950-6
Gmelin Reference	27008
Jmol 3D model	Interactive image
KEGG	C07166
MeSH	Trientine
PubChem	5565
RTECS number	YE6650000
UNII	SJ76Y07H5F
UN number	2259
	InChI InChI=1S/C6H18N4/c7-1-3-9-5-6-10-4-2-8/h9-10H,1-8H2 Key: VILCJCGEZXAXTO-UHFFFAOYSA-N ;
	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)
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).
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	Infobox references