What Is Cadaverine?
Cadaverine is a diamine and a component of the toxic substance ptomaine, produced by the putrefaction of proteins. Its IUPAC name is pentane-1,5-diamine, and it is also known as 1,5-diaminopentane, 1,5-pentadiamine, or pentamethylenediamine. The name cadaverine is derived from the English word “cadaverous,” reflecting its association with the odor of decomposition. While cadaverine contributes to the characteristic smell of decaying matter and semen, and is known as a causative agent of bad breath, it does not participate in the decomposition process itself.
Uses of Cadaverine
1. In Vivo Substance
Cadaverine serves various functions in the body, similar to other polyamines. It acts as a growth factor essential for cell division and is thought to promote the synthesis of nucleic acids and proteins, including RNA. This can stimulate metabolism, help prevent aging, and guard against arteriosclerosis. Additionally, cadaverine, along with histamine and other non-volatile amines produced by decomposition, is implicated in histamine food poisoning. It can enhance the effects of histamine by inhibiting detoxification enzymes and promoting histamine absorption in the intestine. High levels of cadaverine have also been detected in the urine of patients with abnormal lysine metabolism, and it is associated with malodor in conditions such as bacterial vaginosis.
2. Raw Material for High Polymer Materials
Industrially, cadaverine is utilized as a monomer in the synthesis of polyamides, including nylon, highlighting its significance beyond biological contexts.
Properties of Cadaverine
With the chemical formula C5H14N2 and a molecular weight of 102.18, cadaverine is identified by the CAS number 462-94-2. It is a clear, colorless liquid at room temperature, with a melting point of 9°C (48.2°F), a boiling point of 179°C (354.2°F), and a specific, pungent odor. Cadaverine is soluble in water and ethanol, and slightly soluble in diethyl ether. It exhibits strong basicity, demonstrated by its acid dissociation constants, indicating its chemical reactivity.
Other Information on Cadaverine
1. How Cadaverine Is Produced
Cadaverine can be produced through the decarboxylation of lysine, using various methods including the use of 1,5-dichloropentane, glutardinitrile, or glutaraldehyde as starting materials. This process can occur naturally or synthetically, emphasizing the versatility of cadaverine’s production methods.
2. Legal Information
Due to its properties, cadaverine is subject to regulation under various national laws and regulations, reflecting the need for careful handling and storage to mitigate its potential hazards.
Precautions for Handling and Storage
Appropriate safety measures, including the use of personal protective equipment and adherence to storage recommendations, are crucial when dealing with cadaverine, to prevent accidents and health risks.