Triethylenetetramine: Functions, Safety & Suppliers
Introduction
Triethylenetetramine (TETA), also known by the drug name trientine, is an organic compound with the molecular formula C 6H 18N 4. This colorless to light-yellow oily liquid is a selective copper(II) chelator used in the treatment of Wilson’s disease to promote urinary copper excretion and reduce excess copper storage in the body. Triethylenetetramine has a wide range of industrial and pharmaceutical applications due to its unique chemical properties and chelation abilities.
Chemical Properties
Triethylenetetramine has a molecular weight of 146.23 g/mol and a density of 0.982 g/mL at 20°C. Its CAS number is 112-24-3, and the compound exists as linear, branched, or cyclic molecules. TETA has a high boiling point and is soluble in water and various organic solvents. The presence of four nitrogen atoms in its structure allows triethylenetetramine to form stable complexes with metal ions, particularly copper(II) [1].
Synthesis and Production
Triethylenetetramine was first prepared by A. W. von Hoffmann in 1890. Modern synthesis methods involve the reaction of ethylene dichloride with ammonia or the ammonolysis of 1,2-dichloroethane. Industrial production of TETA yields a technical grade product with a purity of around 60%, which can be further purified to obtain pharmaceutical-grade material. The purity and isomer composition of triethylenetetramine can be analyzed using gas chromatography (GC) and spectroscopic techniques [2].
Uses and Applications
Triethylenetetramine finds extensive use in the manufacturing of polymers, epoxy curing agents, and other industrial products. In medicine, trientine hydrochloride, a salt of TETA, is used as a chelation therapy for treating Wilson’s disease, a genetic disorder characterized by excess copper accumulation in the body. TETA binds to copper(II) ions and promotes their excretion through urine, thereby reducing toxic copper levels in the liver and other organs [3].
Safety and Handling
Triethylenetetramine is a corrosive substance that can cause skin irritation and serious eye damage upon contact. Inhalation of TETA vapors may lead to respiratory tract irritation. Appropriate protective equipment, including gloves, eye protection, and adequate ventilation, should be used when handling triethylenetetramine. In case of accidental exposure, rinse the affected area with plenty of water and seek medical attention if necessary. Refer to the Material Safety Data Sheet ( MSDS) for detailed safety information.
Storage and Stability
Triethylenetetramine should be stored in a cool, dry, and well-ventilated area, away from incompatible substances and sources of heat or ignition. The recommended storage temperature is below 30°C. TETA is hygroscopic and tends to absorb moisture from the air, which can lead to degradation over time. Therefore, it is essential to store triethylenetetramine in tightly sealed containers and protect it from humidity. When stored under proper conditions, the shelf life of TETA is typically around 2 years.
Suppliers and Availability
Triethylenetetramine is available from various chemical suppliers worldwide, including Sigma-Aldrich, TCI Chemicals, and Alfa Aesar. It is supplied in different grades, such as technical grade (60% purity) and pharmaceutical grade (>95% purity), depending on the intended application. Some common trade names for triethylenetetramine include DEH 24 and EPH 925. When purchasing TETA, it is crucial to consider the required purity, quantity, and intended use to ensure the product meets the necessary specifications.
Conclusion
Triethylenetetramine is a versatile organic compound with significant applications in both industry and medicine. Its unique chemical properties, particularly its ability to chelate copper(II) ions, make it an essential tool in the treatment of Wilson’s disease and other disorders involving metal ion imbalances. As research continues to uncover new potential uses for TETA, it is crucial to understand its chemical properties, safety profile, and proper handling procedures to ensure its safe and effective use.
References
- Wichmann, K.A., Boyd, P.D.W., Söhnel, T., Allen, G.R., Phillips, A.R.J., & Cooper, G.J.S. (2007). Characterization of dicarboxylic salts of protonated triethylenetetramine useful for the treatment of copper-related pathologies. Crystal Growth & Design, 7(9), 1844-1850. https://pubs.acs.org/doi/10.1021/cg070176
- Miki, T., Nishimura, S., & Koyama, Y. (1997). Analysis of triethylenetetramine by gas chromatography/mass spectrometry as a pre-column derivatized carbamate. Journal of Mass Spectrometry, 32(10), 1088-1090. https://doi.org/10.1016/S1044-0305(97)00168-8
- Lu, J., Zheng, Y.L., & Wu, D.M. (2002). Advances in the study of triethylenetetramine, a selective copper(II) chelator in the treatment of Wilson’s disease. Toxicology Letters, 132(1), 1-7. https://doi.org/10.1016/S0009-2797(02)00109-9
