Structure via PubChem · Public domain (PubChem)
triethylenetetramine
Sign in to saveAlso known as TETA, N'-[2-(2-azanylethylamino)ethyl]ethane-1,2-diamine, 2-aminoethyl-[2-(2-aminoethylamino)ethyl]amine, N'-[2-(2-aminoethylamino)ethyl]ethane-1,2-diamine, triethylene tetramine, trientine, trien
Triethylenetetramine (TETA and trien), also known as trientine (INN) when used medically, is an organic compound with the formula [CH2NHCH2CH2NH2]2. The pure free base 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 TETA. The hydrochloride salts are used medically as a treatment for copper toxicity.
Key facts
- Drug.drug_name
- Trientine
- Drug.tradename
- Syprine, Cuprior, Cufence, others
- Drug.DailyMedID
- Trientine
- Drug.ATC_prefix
- A16
- Drug.ATC_suffix
- AX12
- Drug.legal_AU
- S4
- Drug.legal_CA
- Rx-only
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
- Drug.legal_EU
- Rx-only
- Drug.pregnancy_AU
- D
- Drug.routes_of_administration
- By mouth
- Drug.DrugBank
- DB06824
- Drug.DrugBank2
- DBSALT001269
- Drug.PDB_ligand
- 104
- Drug.IUPAC_name
- (2-aminoethyl)({2-[(2-aminoethyl)amino]ethyl})amine
via Wikipedia infobox
Chemical data
- Formula
- C6H18N4
- Molecular weight
- 146.23 g/mol
- IUPAC name
- N'-[2-(2-aminoethylamino)ethyl]ethane-1,2-diamine
- SMILES
- C(CNCCNCCN)N
- InChIKey
- VILCJCGEZXAXTO-UHFFFAOYSA-N
- XLogP
- -2.5
- Polar surface area
- 76.1 Ų
- H-bond donors
- 4
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1985
- Admin. routes
- oral
- Indications
- melanoma, hypertrophic cardiomyopathy, Wilson disease, cancer
via ChEMBL · EBI
Research
1,060 papers- Triethylenetetramine (TETA).Toxicology and industrial health · 2023
- Triethylenetetramine pharmacology and its clinical applications.Molecular cancer therapeutics · 2010
- Wilson Disease: Diagnosis, Treatment, and Follow-up.Clinics in liver disease · 2017
- Trientine.2006
- Trientine.2012
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 146.153
- Has use
- medication
Show 5 more facts
- chemical formula
- C₆H₁₈N₄
- canonical SMILES
- C(CNCCNCCN)N
- medical condition treated
- Wilson disease
- melting point
- -35.0
- Commons category
- Triethylenetetramine
via Wikidata · CC0
~5 min read
Encyclopedic overview
8 sectionsContents
- Uses
- Epoxy uses
- Medical uses
- Society and culture
- Controversies
- Production
- Coordination chemistry
- References
Triethylenetetramine (TETA and trien), also known as trientine (INN) when used medically, is an organic compound with the formula [CH2NHCH2CH2NH2]2. The pure free base 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 TETA. The hydrochloride salts are used medically as a treatment for copper toxicity.
==Uses== ===Epoxy uses=== The reactivity and uses of TETA are similar to those for the related polyamines ethylenediamine and diethylenetriamine. It is primarily used as a crosslinker ("hardener") in epoxy curing. TETA, like other aliphatic amines, react quicker and at lower temperatures than aromatic amines due to less negative steric effects since the linear nature of the molecule provides it the ability to rotate and twist.
Excerpted from Wikipedia’s “triethylenetetramine” article, available under the CC BY-SA 4.0 licence.