Melamine is an organic compound with the formula C3H6N6. This white solid is a trimer of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 66% nitrogen by mass, and its derivatives have fire-retardant properties due to its release of nitrogen gas when burned or charred. Melamine can be combined with formaldehyde and other agents to produce melamine resins. Such resins are characteristically durable thermosetting plastic used in high-pressure decorative laminates such as Formica, melamine dinnerware including cooking utensils, plates, and plastic products, laminate flooring, and dry erase boards. Melamine foam is used as insulation and soundproofing material, and in polymeric cleaning products such as Magic Eraser. Melamine gained infamy when Chinese food producers Sanlu Group added it to baby formula in order to increase the apparent protein content, causing the 2008 Chinese milk scandal. Ingestion of melamine may lead to reproductive damage, or bladder or kidney stones, and bladder cancer. It is also an irritant when inhaled or in contact with the skin or eyes. The United Nations' food standards body, the Codex Alimentarius Commission, has set the maximum amount of melamine allowed in powdered infant formula to 1 mg/kg and the amount of the chemical allowed in other foods and animal feed to 2.5 mg/kg. While not legally binding, the levels allow countries to ban importation of products with excessive levels of melamine.
Etymology The German word Melamin was coined by combining the words melam (a derivative of ammonium thiocyanate) and amine. Melamine is, therefore, unrelated etymologically to the root melas (μέλας, meaning 'black' in Greek), from which the words melanin, a pigment, and melatonin, a hormone, are formed.
Uses
Plastics and building materials In one large-scale application, melamine is combined with formaldehyde and other agents to produce melamine resins. Such resins are characteristically durable thermosetting plastic used in high-pressure decorative laminates such as Wilsonart, melamine dinnerware, laminate flooring, and dry erase boards. Melamine cookware is not microwave-safe, and can be identified from the fact it is "slightly heavier and noticeably thicker than its plastic counterparts." Melamine foam is used as insulation, soundproofing material and in polymeric cleaning products, such as Magic Eraser. Melamine is one of the major components in Pigment Yellow 150, a colorant in inks and plastics. Melamine also is used in the fabrication of melamine polysulfonate, used as a superplasticizer for making high-resistance concrete. Sulfonated melamine formaldehyde (SMF) is a polymer used as a cement admixture to reduce the water content in concrete while increasing the fluidity and the workability of the mix during handling and pouring. It results in concrete with a lower porosity and a higher mechanical strength, exhibiting an improved resistance to aggressive environments and a longer lifetime.
Fertilizers Melamine was once envisioned as fertilizer for crops during the 1950s and 1960s because of its high (66% by mass) nitrogen content. However, melamine is much more expensive to produce than other common nitrogen fertilizers, such as urea. The mineralization (degradation to ammonia) for melamine is slow, making this product both economically and scientifically impractical for use as a fertilizer.
Fire-retardant additives Melamine and its salts are used as fire-retardant additives in paints, plastics, and paper. A melamine fiber, Basofil, has low thermal conductivity, excellent flame resistance and is self-extinguishing; this makes it useful for flame-resistant protective clothing, either alone or as a blend with other fibres.
Food adulterant Melamine is sometimes illegally added to food products in order to increase the apparent protein content. Standard tests, such as the Kjeldahl and Dumas tests, estimate protein levels by measuring the nitrogen content, so they can be misled by the addition of nitrogen-rich, but non-proteinaceous compounds such as melamine. There are instruments available today that can differentiate melamine nitrogen from protein nitrogen.
Medicine Melamine derivatives of arsenical drugs are potentially important in the treatment of African trypanosomiasis. Melamine use as non-protein nitrogen (NPN) for cattle was described in a 1958 patent. In 1978, however, a study concluded that melamine "may not be an acceptable non-protein N source for ruminants" because its hydrolysis in cattle is slower and less complete than other nitrogen sources such as cottonseed meal and urea.
Toxicity The short-term lethal dose of melamine is on a par with common table salt, with an LD50 of more than 3 grams per kilogram of bodyweight. U.S. Food and Drug Administration (FDA) scientists explained that when melamine and cyanuric acid are absorbed into the bloodstream, they concentrate and interact in the urine-filled renal tubules, then crystallize and form large numbers of round, yellow crystals, which in turn block and damage the renal cells that line the tubes, causing the kidneys to malfunction and lead to kidney stones, kidney failure, and death. Signs of melamine toxicity can include irritability, blood in the urine, little to no urine, symptoms of kidney infection, or high blood pressure. The European Union set a standard for acceptable human consumption (tolerable daily intake or TDI) of melamine at 0.2 mg per kilogram of body mass (previously 0.5 mg/kg), Canada declared a limit of 0.35 mg/kg, and the US FDA's limit was put at 0.063 mg/kg (previously 0.63 mg/kg). The World Health Organization's food safety director estimated that the amount of melamine a person could stand per day without incurring a bigger health risk, the TDI, was 0.2 mg per kilogram of body mass. Toxicity of melamine can be mediated by intestinal microbiota. In culture, Raoultella terrigena, which rarely colonizes mammalian intestines, was shown to convert melamine to cyanuric acid directly. Rats colonized by R. terrigena showed greater melamine-induced kidney damage compared to those not colonized.
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