2-Naphthylamine and cancer
2-Naphthylamine, also known as 2-Aminonaphthalene or beta-naphthylamine, is an aromatic amine recognized as a known human carcinogen since 1980. It is a yellowish crystalline solid that can turn purplish-red when exposed to air and has a distinct ammoniacal odor. The primary routes of exposure for the general public include inhalation of emissions from burning organic matter containing nitrogen, particularly from coal furnaces and tobacco smoke. Occupational exposure is mainly a concern for laboratory personnel who work directly with this chemical in research contexts.
The substance has been linked to an increased risk of bladder cancer, as its metabolites can form DNA adducts that may lead to genetic damage. Laboratory studies have shown that 2-naphthylamine can cause serious alterations in DNA structure, including strand breaks and chromosome changes, which may trigger cancerous transformations. Historically, 2-naphthylamine was commercially produced in the U.S. from the 1920s until the early 1970s, primarily for use in dyes, rubber production, and agrochemicals. Due to its carcinogenic properties, its production was banned after the International Agency for Research on Cancer (IARC) established its link to bladder cancer. Today, it is primarily found in laboratory settings, with limited commercial manufacturing largely restricted to research purposes.
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2-Naphthylamine and cancer
ROC STATUS: Known human carcinogen since 1980
ALSO KNOWN AS: 2-Aminonaphthalene, beta-naphthylamine
RELATED CANCERS: Bladder cancer
DEFINITION: 2-Naphthylamine, an aromatic amine, is a yellowish crystalline solid that turns purplish-red in air and has an ammoniacal odor.
Exposure routes: For the general public, exposure to 2-naphthylamine comes from inhalation of emissions from burning organic matter that contains nitrogen. Two primary sources are coal furnaces and tobacco smoke. Occupational exposure occurs through inhalation by laboratory personnel doing research with 2-naphthylamine.
Where found: 2-Naphthylamine is used only in laboratory research. It is still found in some dyes and rubber compounds that were manufactured before 1974. It is a by-product of tobacco smoke and coal burning and is an impurity found in commercially produced 1-naphthylamine.
At risk: Scientists and laboratory technicians who work where 2-naphthylamine is used in research as a catalyst or an antioxidant have a high risk for 2-naphthylamine contamination. Because 2-naphthylamine is generated in tobacco smoke, people who smoke are at high risk for contamination. The general public is at risk for contamination from secondhand tobacco smoke and burning organic matter containing nitrogen, such as coal.
Etiology and symptoms of associated cancers: When 2-naphthylamine is metabolized, it can be activated by liver enzymes to form adducts (addition reaction intermediaries) with blood-serum proteins, such as hemoglobin. In some cases, 2-naphthylamine can undergo additional metabolism to form reactive compounds that are transported to the bladder, where they bind to deoxyribonucleic acid (DNA) molecules. In experimental laboratory animals, 2-naphthylamine DNA adducts have been found in the bladder and liver. In laboratory tests on cultured human cells, 2-naphthylamine caused genetic damage that involved DNA strand breaks, changes in chromosome structure or number, addition or deletion of chromosomes, and cell transformation.
History: 2-Naphthylamine was commercially produced in the United States from the early 1920s until the early 1970s. It was used to produce 2-chloronaphthalene, sulfonic acids, red dye, and agrochemicals and as a catalyst and antioxidant in the vulcanization of rubber. After the International Agency for Research on Cancer (IARC) showed its link to the increased risk of bladder cancer, its commercial production was banned in the late 1960s and early 1970s. The last time it was imported into the United States in a significant amount was in 1967. In 2009, only ten companies in the United States manufactured 2-naphthylamine for use in laboratory research.
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