トリエチレンテトラミン
Triethylenetetramine
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基本情報
- CAS
112-24-3- 標準SMILES
NCCNCCNCCN- InChIKey
VILCJCGEZXAXTO-UHFFFAOYSA-N- 分子式
- C6H18N4
- 平均分子量
- 146.23 g/mol
- 単同位体質量
- 146.15314659
概要
Triethylenetetramine appears as a yellowish liquid. Less dense than water. Combustible, though may be difficult to ignite. Corrosive to metals and tissue. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion. Used in detergents and in the synthesis of dyes, pharmaceuticals and other chemicals.
名称と識別子
- 優先名称
- Triethylenetetramine
- IUPAC
- N'-[2-(2-aminoethylamino)ethyl]ethane-1,2-diamine
- 現地名
- トリエチレンテトラミン
- 英語名
- Triethylenetetramine
- 分子式
- C6H18N4
- 分子量
- 146.23
名称と別名
TRIETHYLENETETRAMINEtrientine112-24-3TrienTeczaTriethylene tetramineTrientinaDEH 24Araldite hardener HY 9511,2-Ethanediamine, N,N'-bis(2-aminoethyl)-1,4,7,10-TetraazadecaneAraldite HY 951
名称をさらに表示
トリエチレンテトラミンN-[2-(2-アミノ-エチルアミノ)-エチル]-エタン-1,2-ジアミン2,2'-[エチレンビスイミノ]ビス(エタンアミン)1,4,7,10-テトラアザデカンN,N'-ビス(2-アミノエチル)-1,2-エタンジアミントリエチン2,2'-(エチレンビスイミノ)ジ(エタンアミン)トリエチレンテトラアミン3,6-ジアザオクタン-1,8-ジアミン2,2'-(エチレンビスイミノ)ビス(エタンアミン)N,N'-ジ(2-アミノエチル)エチレンジアミンアラルジット硬膜剤HY-9512,2'-エチレンビス(イミノ)ビス(エタンアミン)2,2'-(エチレンビスイミノ)ビス(エタン-1-アミン)2,2'-(エチレンビスイミノ)ビスエタンアミンN,N''-エチレンビス(エタン-1,2-ジアミン)N,N''-エチレンビス(エチレンジアミン)2,2'-[エチレンビス(イミノ)]ビス(エタンアミン)アラルジットHY-951N,N'-ビス(2-アミノエチル)エチレンジアミンTETAtriethylentetramineTRIETHYLENETETRAMINE (TETA)deh24N1,N1'-(ethane-1,2-diyl)bis(ethane-1,2-diaMine)TRIETHYLTETRAMINE3,6-Diazaoctanethylenediamin
1,8-Diamino-3,6-diazaoctane3,6-Diazaoctane-1,8-diamineTrientinumtriethylene tetraamineN,N'-Bis(2-aminoethyl)-1,2-ethanediamineTrethylenetetramineN,N'-Bis(2-aminoethyl)ethylenediamineHY 951
データベース識別子
- CAS
112-24-3- PubChem CID
- 5565
- DTXSID
DTXSID9023702- ChEMBL
CHEMBL609- ChEBI
CHEBI:39501- UNII
- SJ76Y07H5F
- EC Number
- 203-950-6
- Nikkaji
- J5.120I
物性
構造計算による物性補完中
- XLogP
- -2.5
- 極性表面積
- 76.1 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 4
- 回転可能結合数
- 7
- 重原子数
- 10
- 形式電荷
- 0
- 複雑度
- 49.7
実験および物理化学的性質
Chemical Classes
Nitrogen Compounds -> Amines, Aliphatic
Corrosives
DrugsPharmaceuticals -> Listed in ZINC15
pHSTRONGLY BASIC (PH 10 IN 1% AQ SOLN)
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP-1.4/-1.66
Density
0.982 at 68 °F (USCG, 1999) - Less dense than water; will float
0.9818 @ 20 °C/20 °C
0.98 g/cm³
Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.00
0.982
0.982 @25 °C
Viscosity27.24 mm²/s at 20 °C
Color/FormMODERATELY VISCOUS, YELLOWISH LIQUID
Solubility
greater than or equal to 100 mg/mL at 68.4 °F (NTP, 1992)
Soluble
SOL IN ALCOHOL, ACID
COMPLETE SOLUBILITY IN WATER
Solubility in water: miscible
Flash Point
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Danger
H312: Harmful in contact with skin [Warning Acute toxicity, dermal]
P260, P261, P264, P272, P273, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P333+P317, P362+P364, P363, P405, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for 0.4% (10 of 2507) of reports.
Danger
H302+H312 (18.4%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]
危険有害性情報
Regulatory Information
Chemical: 1,2-Ethanediamine, N,N'-bis(2-aminoethyl)-
1,2-Ethanediamine, N1,N2-bis(2-aminoethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Ethanediamine, N1,N2-bis(2-aminoethyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
REACH registered substance: Trientine (EC: 203-950-6)
Triethylenetetramine: Does not have an individual approval but may be used under an appropriate group standard
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Other Safety InformationIMAP assessments - Selected linear polyethyleneamines: Human health tier II assessment
DOT LabelCorrosive
Fire Hazards
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
· Combustible material: may burn but does not ignite readily.
Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Risk of fire and explosion on contact with oxidants. See Chemical Dangers.
化学と産業
薬理情報
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Pharmacodynamics
Triethylenetetramine (TETA) is a selective copper(II) chelator that works to promote urinary copper excretion. It was shown to reduce excess body copper storage and ameliorate symptoms of Wilson’s disease. In rats with diabetes mellitus, intravenous administration of TETA led to a dose-dependent increase in urinary copper excretion. In preliminary studies, TETA was shown to ameliorate left ventricular hypertrophy in both human and animal subjects with diabetes. In animal models, TETA was also shown to reverse manifestations of diabetic nephropathy, including nephromegaly, renal fibrosis, glomerulosclerosis, and albuminuria, without lowering hyperglycemia. This finding may be explained by TETA chelating copper cations, which are pro-oxidant and activate pathways that produce excessive reactive oxygen species (ROS) that cause tissue injury. TETA was shown to possess anti-angiogenesis properties, as copper is an essential element for angiogenesis in cancer cells. TETA was shown to inhibit telomerase, suggesting that it may exhibit an inhibitory effect or cytotoxicity on tumor growth. Based on these early findings, TETA has been studied for its anticancer effects.
Mechanism of Action
Wilson's disease is an autosomal recessive genetic disorder that leads to copper accumulation in the tissues. It is characterized by an array of neurologic or psychiatric symptoms as well as liver disease. One of the treatments for Wilson's disease is the use of copper-chelating agents, such as triethylenetetramine (TETA). TETA forms a stable complex with copper(II), which is then is readily eliminated through urinary excretion. TETA also chelates copper in the intestinal tract, reducing intestinal copper absorption by 80%. TETA and its metabolite, N<sub>1</sub>-acetyltriethylenetetramine (MAT), are also capable of binding divalent iron, divalent zinc, magnesium, and manganese.
Biological Half-LifeThe mean terminal half-life (t1/2) ranged from 13.8 to 16.5 hours.
Metabolism/Metabolites
The majority of absorbed TETA is extensively metabolized into acetyl-metabolites. TETA undergoes acetylation mediated by diamine acetyltransferase, also known as spermidine/spermine N<sub>1</sub>-acetyltranferase, to form two major active metabolites, N<sub>1</sub>-acetyltriethylenetetramine (MAT) and N<sub>1</sub>,N<sub>10</sub>-diacetyltriethylenetetramine (DAT). The chelating activity of MAT is significantly lower than that of TETA.
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