- 関
- trientine
WordNet
- a complex consisting of an organic base in association with hydrogen chloride
Wikipedia preview
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
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Names |
Other names
N,N'-Bis(2-aminoethyl)ethane-1,2-diamine
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Identifiers |
CAS Number
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112-24-3 Y |
Beilstein Reference
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605448 |
ChEBI |
CHEBI:39501 Y |
ChEMBL |
ChEMBL609 Y |
ChemSpider |
21106175 Y |
EC Number |
203-950-6 |
Gmelin Reference
|
27008 |
Jmol 3D model |
Interactive image |
KEGG |
C07166 Y |
MeSH |
Trientine |
PubChem |
5565 |
RTECS number |
YE6650000 |
UNII |
SJ76Y07H5F Y |
UN number |
2259 |
InChI
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InChI=1S/C6H18N4/c7-1-3-9-5-6-10-4-2-8/h9-10H,1-8H2 Y
Key: VILCJCGEZXAXTO-UHFFFAOYSA-N Y
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Properties |
Chemical formula
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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
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Miscible |
log P |
1.985 |
Vapor pressure |
<1 Pa (at 20 °C) |
Refractive index (nD)
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1.496 |
Thermochemistry |
Specific
heat capacity (C)
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376 J K−1 mol−1 (at 60 °C) |
Hazards |
GHS pictograms |
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GHS signal word |
DANGER |
GHS hazard statements
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H312, H314, H317, H412 |
GHS precautionary statements
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P273, P280, P305+351+338, P310 |
EU classification (DSD)
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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)
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- 550 mg kg−1 (dermal, rabbit)
- 2.5 g kg−1 (oral, rat)
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Related compounds |
Related amines
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- Ethylenediamine
- Diethylenetriamine
- Cyclam
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Related compounds
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- Ethylenediaminetetraacetic acid
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Y verify (what is YN ?) |
Infobox references |
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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]
Contents
- 1 Production
- 2 Uses
- 3 Coordination chemistry
- 4 References
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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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
- 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
Related Links
- SYPRINE - trientine hydrochloride capsule Aton Pharma, Inc.Capsules SYPRINE ® (TRIENTINE HYDROCHLORIDE) DESCRIPTION Trientine hydrochloride is N,N'-bis (2-aminoethyl)-1,2-ethanediamine dihydrochloride. It ...
- For medical information enquiries about Trientine, please complete the form below. Your Name Your Address Your Country Your Email Your Phone Are you: Patient Patient’s carer Medical professional Other (Specify) Nature of ...
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[★]
- 英
- trientine
- 商
- メタライト
- 化
- 塩酸トリエンチン trientine hydrochloride、トリエチレンテトラミン
- 関
- ウィルソン病
[★]
トリエンチン
- 関
- trientine hydrochloride、triethylenetetramine
[★]
塩酸塩、ハイドロクロライド