Triethylenetetramine

A chelating agent used in the treatment of Wilson's disease

Triethylenetetramine, also known as TETA, is a chelating agent primarily used in the treatment of Wilson's disease, a genetic disorder that leads to excessive accumulation of copper in the body. TETA works by binding to copper, facilitating its excretion from the body, and thereby reducing copper toxicity.

Chemical Properties

Triethylenetetramine is an organic compound with the formula C₆H₁₈N₄. It is a colorless to pale yellow liquid with a fishy odor, characteristic of amines. TETA is a polyamine, containing four amine groups, which contribute to its ability to chelate metal ions.

Mechanism of Action

TETA acts as a chelating agent by binding to copper ions in the bloodstream. The complex formed between TETA and copper is more water-soluble than free copper ions, allowing it to be excreted through the urinary system. This process helps to lower copper levels in patients with Wilson's disease, preventing damage to organs such as the liver and brain.

Medical Uses

Wilson's Disease

Wilson's disease is an autosomal recessive disorder characterized by the accumulation of copper in tissues, leading to hepatic and neurological symptoms. TETA is used as a second-line treatment for patients who cannot tolerate penicillamine, the first-line therapy. It is particularly useful in patients with neurological symptoms, as it is less likely to exacerbate these symptoms compared to penicillamine.

Other Potential Uses

Research is ongoing into the use of TETA for other conditions involving metal ion dysregulation, such as certain types of cancer and cardiovascular disease. However, these uses are not yet established in clinical practice.

Side Effects

Common side effects of TETA include gastrointestinal disturbances such as nausea and diarrhea. Some patients may experience allergic reactions, including skin rashes. Long-term use requires monitoring of blood counts and liver function tests to detect potential toxicity.

Pharmacokinetics

TETA is administered orally and is absorbed through the gastrointestinal tract. It is metabolized in the liver and excreted primarily in the urine. The half-life of TETA allows for dosing typically twice daily, although this may vary based on individual patient needs and response.

Synthesis

The synthesis of triethylenetetramine involves the reaction of ethylene dichloride with ammonia, followed by further reaction with ethyleneimine. This process yields a mixture of polyamines, from which TETA can be isolated and purified.

Safety and Handling

TETA should be handled with care, as it can cause skin and eye irritation. Appropriate personal protective equipment, such as gloves and goggles, should be used when handling the compound. In case of contact with skin or eyes, the affected area should be rinsed thoroughly with water.

Related Pages

• Wilson's disease
• Chelation therapy
• Copper metabolism
• Penicillamine

Triethylenetetramine

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  Triethylenetetramine chemical structure

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  Triethylenetetramine 3D ball model

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  Triethylenetetramine 3D space-filling model