N-Nitrosomorpholine

N-Nitrosomorpholine is a nitrosamine that is classified as a potent carcinogen. It is a yellow, oily liquid at room temperature and is known for its high stability. N-Nitrosomorpholine is used primarily in laboratory research to induce tumors in experimental animals.

Chemical Structure

N-Nitrosomorpholine is a member of the class of compounds known as morpholines. It has a molecular formula of C4H8N2O2 and a molecular weight of 116.12 g/mol. The chemical structure consists of a six-membered ring containing four carbon atoms, one nitrogen atom, and one oxygen atom. The nitrogen atom is bonded to a nitroso group (-NO), which is responsible for the compound's carcinogenic properties.

Synthesis

N-Nitrosomorpholine can be synthesized by the nitrosation of morpholine in the presence of a nitrosating agent such as nitrite. The reaction is typically carried out in an acidic medium to promote the formation of the nitrosamine.

Carcinogenicity

N-Nitrosomorpholine is a potent carcinogen and has been shown to induce tumors in a variety of experimental animals, including rats, mice, and hamsters. The compound is thought to exert its carcinogenic effects by forming DNA adducts, which can lead to mutations and ultimately to the development of cancer.

Exposure and Risk

Exposure to N-Nitrosomorpholine can occur through a variety of routes, including inhalation, ingestion, and skin contact. The compound has been detected in certain types of foods, particularly those that have been cured or smoked. It can also be formed in the stomach from dietary nitrate and secondary amines.

Regulation

Due to its carcinogenic properties, N-Nitrosomorpholine is regulated in many countries. In the United States, for example, the Environmental Protection Agency (EPA) has set a maximum contaminant level for N-Nitrosomorpholine in drinking water.

See Also

• Nitrosamines
• Carcinogens
• Morpholines
• Environmental Protection Agency