트라이에틸렌테트라민

Triethylenetetramine

HCID 5565CAS 112-24-3

기본 정보

표준 SMILES
NCCNCCNCCN
InChIKey
VILCJCGEZXAXTO-UHFFFAOYSA-N
분자식
C6H18N4
평균 분자량
146.23 g/mol
단동위원소 질량
146.15314658

개요

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.

이름 및 식별자

우선 이름
Triethylenetetramine
IUPAC
N'-[2-(2-aminoethylamino)ethyl]ethane-1,2-diamine
현지명
트라이에틸렌테트라민
영어명
Triethylenetetramine
분자식
C6H18N4
분자량
146.23

이름 및 동의어

TRIETHYLENETETRAMINEtrientine112-24-3TrienTriethylene tetramineTecza1,2-Ethanediamine, N,N'-bis(2-aminoethyl)-DEH 24Araldite hardener HY 9511,4,7,10-TetraazadecaneTrientinaAraldite HY 951
이름 더 보기
트라이에틸렌테트라민트리에틸렌테트라민트리에틸렌테트라아민N,N'-비스(2-아미노에틸)-에틸렌디아민N,N'-비스(2-아미노트리에틸렌테트라아민(TETA)트라이에틸렌테트라민1,2-다이-(아미노에틸아민)-에탄1,2-비스-(2-아미노에틸아미노)-에탄1,8-다이아미노-3,6 아이자-옥탄1.4.7.10-테트라아자데칸2,2'-(1,2 에틸렌비스-아미노-)비스-에탄아민3,6-다이아자옥탄-1,8-다이아민N,N'-다이-(2-아미노에틸)-1,2-에탄다이아민N,N'-다이-(2-아미노에틸)-1,2-에틸렌다이아민N,N'-비스-(2-아미노에틸)-1,2-에탄다이아민N,N'-비스-(2-아미노에틸)-에틸렌다이아민트라이에틸렌 테트라민TETAtriethylentetramineTRIETHYLENETETRAMINE (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

데이터베이스 식별자

CAS
112-24-3
PubChem CID
5565
DTXSID
DTXSID9023702
ChEMBL
CHEMBL609
ChEBI
CHEBI:39501
UNII
SJ76Y07H5F
EC Number
203-950-6
Nikkaji
J5.120I

물성

구조 계산 물성

XLogP
-2.5
극성 표면적
76.1 Ų
수소 결합 공여자 수
4
수소 결합 수용자 수
4
회전 가능 결합 수
7
무거운 원자 수
10

실험 및 물리화학적 성질

Chemical Classes · 2건

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 · 6건

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

물리화학적 성질

녹는점
12 °C · 12 °C(lit.)
끓는 점
266 · 266-267 °C(lit.)
밀도
0.982 g/mL · 0.982 g/mL at 25 °C(lit.)
증기 밀도
5 · ~5 (vs air)
증기압
0.01 mm · <0.01 mm Hg ( 20 °C)
굴절률
20 · n20/D 1.496(lit.)
화학적 성질 · 2건

Triethylenetetramine is a corrosive liquid.

Triethylenetetramine (TETA) is hygroscopic, corrosive, and has a strong ammoniacal odor. With water a crystalline hydrate is formed. Like DETA, it is completely miscible with water and many polar organic solvents, but less so with lipids; with CCl4 a violent reaction occurs. Its four pKa values are 3.32, 6.67, 9.20, and 9.92. Technical-grade TETA is sometimes available as a distillation cut that also contains branched isomers and cyclic compounds.

안전 및 규제

GHS 분류

GHS Classification · 6건

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]

유해성 정보

Regulatory Information · 5건

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)

Status: Active Update: 14-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33983

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 · 3건

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.

Fire PotentialSLIGHT, WHEN EXPOSED TO HEAT OR FLAME.
Health Hazards · 2건

Vapors from hot liquid can irritate eyes and upper respiratory system. Liquid burns eyes and skin. May cause sensitization of skin. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

안전 및 보호

Fire Fighting · 2건

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use powder, alcohol-resistant foam, water spray, carbon dioxide. In case of fire: keep cylinder cool by spraying with water.

First Aid Measures · 4건

Fresh air, rest. Half-upright position. Refer immediately for medical attention.

First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Refer immediately for medical attention.

Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention.

Accidental Release Measures · 2건

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2건

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

Safe StorageSeparated from food and feedstuffs. See Chemical Dangers. Cool. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

독성 정보

Hepatotoxicity · 1건

In clinical trials conducted in children with Wilson disease, serum aminotransferase levels generally improved or were stable during treatment with trientine. There have been no clinical reports of acute liver injury with jaundice attributed to trientine, even with overdoses. Patients with Wilson disease typically have mild-to-moderate serum aminotransferase elevations and may have signs and symptoms of cirrhosis. Improvement in liver injury in Wilson disease typically requires months to years of treatment.

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesThe substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion. Serious local effects by all routes of exposure.
Toxicity Summary · 1건

While TETA is severely irritating to the skin and eyes and produces skin sensitization, it is of low to moderate acute toxicity orally and dermally. Effects on lungs, liver, and spleen were found in mice in subchronic studies but were not found in rats. While TETA was genotoxic/mutagenic in short-term in vitro assays, it was not genotoxic/mutagenic in in vivo assays. No data on reproductive toxicity were available, and embryo/fetal toxicity was associated with copper deficiency and occurred at maternally toxic doses. The use of TETA·2HCl for treatment of Wilson’s disease during pregnancy in humans resulted in no miscarriages or fetal abnormalities. There was no evidence of carcinogenicity in a lifetime dermal mouse study.

Signs and Symptoms · 4건

Sore throat. Cough. Burning sensation. Laboured breathing. Shortness of breath.

Redness. Pain. Skin burns. Blisters.

Redness. Pain. Loss of vision. Severe deep burns.

Burns in mouth and throat. Burning sensation in the throat and chest. Abdominal pain. Shock or collapse.

ICSC Environmental DataThe substance is toxic to aquatic organisms. The substance may cause long-term effects in the aquatic environment. It is strongly advised not to let the chemical enter into the environment.

안전 데이터

wgk
2
tsca
TSCA listed
rtecs
YE6650000
ridadr
UN 2259
독성
LD50 orally in rats: 2.5 g/kg (Spitz)
HS 번호
29212900

화학 및 산업

약리 정보

ATC Code · 2건

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Pharmacodynamics · 1건

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 · 1건

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 · 1건

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.

FDA Pharmacological Classification · 6건

SJ76Y07H5F

TRIENTINE

Mechanisms of Action [MoA] - Metal Chelating Activity

Established Pharmacologic Class [EPC] - Copper Chelator

Mechanisms of Action [MoA] - Copper Chelating Activity

Trientine is a Copper Chelator. The mechanism of action of trientine is as a Metal Chelating Activity and Copper Chelating Activity.

용도 및 제조

Uses · 6건

Used as a chemical intermediate for polyamide resins, imidazoline, and aminoamide surfactants; as a curing agent for alkyl acrylate and methacrylonitrile polymers; and as a hardener for epoxy resins; [HSDB] The hydrochloride salt is used as a chelating agent in the treatment of Wilson's disease; [AIHA]

Plastic Composites Manufacturing [Category: Industry]

IN DETERGENTS; SYNTHESIS OF DYESTUFFS, PHARMACEUTICALS

MEDICATION (VET)

MEDICATION

CHEM INT FOR IMIDAZOLINE & AMINOAMIDE SURFACTANTS, WATER SOL PLASTIC FILMS & POLYAMIDE RESINS; CURING AGENT IN VULCANIZATION OF ALKYL ACRYLATE POLYMERS, METHACRYLONITRILE POLYMERS & COPOLYMERS; HARDENER FOR LIQUID EPOXY RESINS

U.S. Exports · 2건

(1972) No Data

(1975) No Data

U.S. Imports · 2건

(1972) No Data

(1975) No Data

U.S. Production · 3건

2023: 10,000,000 - <25,000,000 lb

(1972) 8.2X10+9 GRAMS

(1975) 1.36X10+6 GRAMS

Consumer UsesViscosity modifiers
Industry UsesViscosity modifiers
응용 분야 · 3건

개요Triethylenetetramine (TETA and trien) also known as trientine (INN) when used medically, is an organic compound with the formula [CH2NHCH2CH2NH2]2. The pure freebase is a colorless oily liquid, but, like many amines, older samples assume 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 Triethylenetetramine. The hydrochloride salts are used medically as a treatment for copper toxicity.

용도Triethylenetetramine is used as an amine hardener in epoxy resin of the bisphenol A type.It is used in synthesis of detergents, softeners, and dyestuffs; manufacture of pharmaceuticals; vulcanization accelerator of rubber; thermo setting resin; epoxy curing agent; lubricating-oil additive; analytical reagent for Cu, Ni; chelating agent; treatment of Wilson's disease.

일반 설명A 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.

제조 방법

생산 방법Triethylenetetramine(TETA) is manufactured by reacting ethylene dichloride and ammonia under controlled conditions.

공급사50 곳

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南通润丰石油化工有限公司66017690 19952660367 · [email protected]
上海毕合生物化学技术有限公司13816464724 · [email protected]

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