Jump to content

Melamine: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous editNext edit →
Content deleted Content added
VisualWikitext
m Solid phase extraction
→‎Uses: + ref re: protein testing and spoofing
Line 89: Line 89:
Melamine use as [[Chinese protein export scandal#Non-protein nitrogen as legitimate and illegitimate feed additive|non-protein nitrogen]] (NPN) for cattle was described in a 1958 patent.<ref>"Ruminant feed compositions, Robert W. Colby and Robert J. Mesler Jr., U.S. Patent No. 2819968, 1958</ref> 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.<ref name="MelamineNPN1978">“Melamine as a dietary nitrogen source for ruminants", G.L.Newton and P.R.Utley, Journal of Animal Science, vol.47, p1338–44, 1978, [http://jas.fass.org/cgi/content/abstract/47/6/1338 Abstract] |accessdate=2008-09-17</ref>
Melamine use as [[Chinese protein export scandal#Non-protein nitrogen as legitimate and illegitimate feed additive|non-protein nitrogen]] (NPN) for cattle was described in a 1958 patent.<ref>"Ruminant feed compositions, Robert W. Colby and Robert J. Mesler Jr., U.S. Patent No. 2819968, 1958</ref> 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.<ref name="MelamineNPN1978">“Melamine as a dietary nitrogen source for ruminants", G.L.Newton and P.R.Utley, Journal of Animal Science, vol.47, p1338–44, 1978, [http://jas.fass.org/cgi/content/abstract/47/6/1338 Abstract] |accessdate=2008-09-17</ref>


Melamine is sometimes illegally added to food products in order to increase the apparent protein content. Standard tests such as the [[Kjeldahl method|Kjeldahl]] and [[Dumas method|Dumas]] tests estimate protein levels by measuring the nitrogen content, so they can be misled by adding nitrogen-rich compounds such as melamine.<ref name="Protein Pretense">"Protein Pretense", Alison Snyder, Scientific American Magazine, August 2008 [http://www.sciamdigital.com/index.cfm?fa=Products.ViewIssuePreview&ISSUEID_CHAR=9CF7413B-2B35-221B-666A12FA3B8AAF86&ARTICLEID_CHAR=9D1E5F83-2B35-221B-63B40A92E545BDD9] |accessdate=2008-09-19</ref>
Melamine is sometimes illegally added to food products in order to increase the apparent protein content. Standard tests such as the [[Kjeldahl method|Kjeldahl]] and [[Dumas method|Dumas]] tests estimate protein levels by measuring the nitrogen content, so they can be misled by adding nitrogen-rich compounds such as melamine.<ref name="Protein Pretense">"Protein Pretense", Alison Snyder, Scientific American Magazine, August 2008 [http://www.sciamdigital.com/index.cfm?fa=Products.ViewIssuePreview&ISSUEID_CHAR=9CF7413B-2B35-221B-666A12FA3B8AAF86&ARTICLEID_CHAR=9D1E5F83-2B35-221B-63B40A92E545BDD9] |accessdate=2008-09-19</ref><ref>{{cite journal |url=http://onlinelibrary.wiley.com/doi/10.1111/j.1541-4337.2010.00114.x/full |title=Total Protein Methods and Their Potential Utility to Reduce the Risk of Food Protein Adulteration | last =Moore | first =J.C. |authorlink= | journal =Comprehensive Reviews in Food Science and Food Safety | volume =9 | issue =4 | pages =330–357 |date = 2010-08-17 |doi =10.1111/j.1541-4337.2010.00114.x |accessdate=2010-09-01 |quote= |work= }}</ref>


==Toxicity==
==Toxicity==

Revision as of 23:39, 1 September 2010

This article is about the chemical compound. For the plastic also called "melamine", see melamine resin.
Melamine
File:Melamine.svg
Names
IUPAC name
1,3,5-Triazine-2,4,6-triamine
Other names
2,4,6-Triamino-s-triazine
Cyanurotriamide
Cyanurotriamine
Cyanuramide
Identifiers
3D model (JSmol)
ECHA InfoCard 100.003.288 Edit this at Wikidata
  • Nc1nc(N)nc(N)n1
Properties
C3H6N6
Molar mass 126.12 g/mol
Appearance White solid
Density 1574 kg/m3
Melting point 345 °C (653 °F; 618 K)
Boiling point Sublimes
3.240 g/l (20 °C)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Melamine (Template:Pron-en) is an organic base and a trimer of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 66% nitrogen by mass and, if mixed with resins, has fire retardant properties due to its release of nitrogen gas when burned or charred, and has several other industrial uses. Melamine is also a metabolite of cyromazine, a pesticide. It is formed in the body of mammals who have ingested cyromazine.[2] It has been reported that cyromazine can also be converted to melamine in plants.[3][4]

Melamine combines with cyanuric acid and related compounds to form melamine cyanurate and related crystal structures, which have been implicated as contaminants or biomarkers in Chinese protein adulterations.

Etymology

The German word melamin was coined by combining the names of 2 other chemical products: Melam (a distillation derivative of ammonium thiocyanate) and Amine.[5][6]

Melamine etymology is thus not derived from the root mela (μελα, meaning black in Greek), such as, e.g., the pigment melanin, the hormone melatonin, or the melanotan peptides.

Uses

Melamine is combined with formaldehyde to produce melamine resin, a very durable thermosetting plastic used in Formica, and melamine foam, a polymeric cleaning product. The end products include countertops, dry erase boards, fabrics, glues, housewares, guitar saddles, guitar nuts, and flame retardants. Melamine is one of the major components in Pigment Yellow 150, a colorant in inks and plastics.

Melamine also enters the fabrication of melamine poly-sulfonate used as superplasticizer for making high-resistance concrete. Sulfonated melamine formaldehyde (SMF) is a polymer used as cement admixture to reduce the water content in concrete while increasing the fluidity and the workability of the mix during its 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 life-time.

The use of melamine as fertilizer for crops had been envisaged during the '50s and '60s because of its high nitrogen content (2/3).[7] However melamine is much more expensive to produce than other common nitrogen fertilizers, such as urea. To be effective as a fertilizer, it is essential that the plant nutrients are released or made available in a manner that matches the needs of the growing crop. The nitrogen mineralization process for melamine is extremely slow, making this product both economically and scientifically impractical for use as a fertilizer.

Melamine derivatives of arsenical drugs are potentially important in the treatment of African trypanosomiasis.[8]

Melamine use as non-protein nitrogen (NPN) for cattle was described in a 1958 patent.[9] 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.[10]

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 adding nitrogen-rich compounds such as melamine.[11][12]

Toxicity

Melamine is described as being "Harmful if swallowed, inhaled or absorbed through the skin. Chronic exposure may cause cancer or reproductive damage. Eye, skin and respiratory irritant.” However, the short-term lethal dose is on a par with common table salt with an LD50 of more than 3 grams per kilogram of bodyweight.[13] 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 microtubules, 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.[14]

The European Union set a standard for acceptable human consumption (Tolerable Daily Intake) of melamine at 0.5 milligrams per kg of body mass (reduced to 0.2 mg per kg in April 2010),[15] Canada declared a limit of 0.35 mg and the US FDA’s limit was put at 0.63 mg, but was later reduced to 0.063 mg daily. 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 "tolerable daily intake" (TDI), was 0.2 mg per kg of body mass.[16]

Acute toxicity

Melamine is reported to have an oral LD50 of 3248 mg/kg based on rat data. It is also an irritant when inhaled or in contact with the skin or eyes. The reported dermal LD50 is >1000 mg/kg for rabbits.[17] A study by USSR researchers in the 1980s suggested that melamine cyanurate, commonly used as a fire retardant,[18] could be more toxic than either melamine or cyanuric acid alone.[19] For rats and mice, the reported LD50 for melamine cyanurate was 4.1 g/kg (given inside the stomach) and 3.5 g/kg (via inhalation), compared to 6.0 and 4.3 g/kg for melamine and 7.7 and 3.4 g/kg for cyanuric acid, respectively.

A toxicology study in animals conducted after recalls of contaminated pet food concluded that the combination of melamine and cyanuric acid in diet does lead to acute renal failure in cats.[20] A 2008 study produced similar experimental results in rats and characterized the melamine and cyanuric acid in contaminated pet food from the 2007 outbreak.[21] A 2010 study from Lanzhou University attributed renal failure in humans to uric acid stone accumulation after ingestion of melamine resulting in a rapid aggradation of metabolites such as cyanuric acid diamide (ammeline) and cyanuric acid.[22]

Chronic toxicity

Ingestion of melamine may lead to reproductive damage, or bladder or kidney stones, which can lead to bladder cancer.[17][23][24][25][26]

A study in 1953 reported that dogs fed 3% melamine for a year had the following changes in their urine: (1) reduced specific gravity, (2) increased output, (3) melamine crystalluria, and (4) protein and occult blood.[27]

A survey commissioned by the American Association of Veterinary Laboratory Diagnosticians suggested that crystals formed in the kidneys when melamine combined with cyanuric acid, "don't dissolve easily. They go away slowly, if at all, so there is the potential for chronic toxicity."[28][29][30]

Treatment of urolithiasis

Fast diagnosis and treatment of acute obstructive urolithiasis may prevent the development of acute renal failure. Urine alkalinization and stone liberalization have been reported to be the most effective treatments in humans.[22]

Regulation in food and feed

The United Nations' food standards body, 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.[31]

Synthesis

Melamine was first synthesized by the German chemist Justus von Liebig in 1834. In early production, first calcium cyanamide is converted into dicyandiamide, then heated above its melting temperature to produce melamine. However, today most industrial manufacturers use urea in the following reaction to produce melamine:

6 (NH2)2CO → C3H6N6 + 6 NH3 + 3 CO2

It can be understood as two steps.

First, urea decomposes into cyanic acid and ammonia in an endothermic reaction:

(NH2)2CO → HCNO + NH3

Then, cyanic acid polymerizes to form melamine and carbon dioxide:

6 HCNO → C3H6N6 + 3 CO2

The second reaction is exothermic but the overall process is endothermic.

The above reaction can be carried out by either of two methods: catalyzed gas-phase production or high pressure liquid-phase production. In one method, molten urea is introduced onto a fluidized bed with catalyst for reaction. Hot ammonia gas is also present to fluidize the bed and inhibit deammonization. The effluent then is cooled. Ammonia and carbon dioxide in the off-gas are separated from the melamine-containing slurry. The slurry is further concentrated and crystallized to yield melamine.[32] Major manufacturers and licensors such as DSM, BASF, and Eurotecnica have developed some proprietary methods.

The off-gas contains large amounts of ammonia. Therefore melamine production is often integrated into urea production which uses ammonia as feedstock.

Crystallization and washing of melamine generates a considerable amount of waste water, which is a pollutant if discharged directly into the environment. The waste water may be concentrated into a solid (1.5–5% of the weight) for easier disposal. The solid may contain approximately 70% melamine, 23% oxytriazines (ammeline, ammelide, and cyanuric acid), 0.7% polycondensates (melem, melam, and melon).[33] In the Eurotecnica process, however, there is no solid waste and the contaminants are decomposed to ammonia and carbon dioxide and sent as off gas to the upstream urea plant; accordingly, the waste water can be recycled to the melamine plant itself or used as clean cooling water make-up.[34]

Production in mainland China

Between the late 1990s and early 2000s, both consumption and production of melamine grew considerably in mainland China. In the United States Geological Survey 2004 Minerals Survey Yearbook, in a report on worldwide nitrogen production, the author stated that "(mainland) China continued to plan and construct new ammonia and urea plants using coal gasification technology."[35]

By early 2006, melamine production in mainland China is reported to be in "serious surplus".[36] In April 2007, DSM's melamine industry update painted a grave global picture.[37] Between 2002 and 2007, while the global melamine price remained stable, a steep increase in the price of urea (feedstock for melamine) has reduced the profitability of melamine manufacturing. Currently, China is the world's largest exporter of melamine, while its domestic consumption still grows by 10% per year. However, reduced profit has already caused other joint melamine ventures to be postponed there.

Surplus melamine has been an adulterant for feedstock and milk in mainland China for several years now because it can make diluted or poor quality material appear to be higher in protein content by elevating the total nitrogen content detected by some simple protein tests. Actions taken in 2008 by the Government of China has reduced the practice of adulteration, with the goal of eliminating it. Court trials began in December 2008 for six people linked to the scandal and ended in January 2009 with two of the convicts being sentenced to death and executed.[38][39]

Melamine poisoning by tainted food

Melamine has been involved in several food recalls after the discovery of severe kidney damages of children and pets poisoned by melamine adulterated food.

2007 Animal feed recalls

Further information: 2007 pet food recalls and Chinese protein adulteration

In 2007 a pet food recall was initiated by Menu Foods and other pet food manufacturers who had found their products had been contaminated and caused serious illnesses or deaths in some of the animals that had eaten them.[40][41][42] In March 2007, the US Food and Drug Administration reported finding white granular melamine in the pet food, in samples of white granular wheat gluten imported from a single source in China, Xuzhou Anying Biologic Technology[43] as well as in crystalline form in the kidneys and in urine of affected animals.[44] Further vegetable protein imported from China was later implicated.

In April 2007, The New York Times reported that the addition of "melamine scrap" into fish and livestock feed to give the false appearance of a higher level of protein was an "open secret" in many parts of mainland China, reporting that this melamine scrap was being produced by at least one plant processing coal into melamine.[45] Four days later, the New York Times reported that, despite the widely reported ban on melamine use in vegetable proteins in mainland China, at least some chemical manufacturers continued to report selling it for use in animal feed and in products for human consumption. Li Xiuping, a manager at Henan Xinxiang Huaxing Chemical in Henan Province, stated, "Our chemical products are mostly used for additives, not for animal feed. Melamine is mainly used in the chemical industry, but it can also be used in making cakes."[46] Shandong Mingshui Great Chemical Group, the company reported by the New York Times as producing melamine from coal, produces and sells both urea and melamine but does not list melamine resin as a product.[47]

Another recall incident in 2007 involved melamine which had been purposely added as a binder to fish and livestock feed manufactured in the United States. This was traced to suppliers in Ohio and Colorado.[48]

2008 Chinese outbreak

Further information: 2008 Chinese milk scandal

In September 2008, several companies were implicated in a scandal involving milk and infant formula which had been adulterated with melamine, leading to kidney stones and other renal failure, especially among young children. By December 2008, nearly 300,000 people had become ill, with more than 50,000 infant hospitalizations and six infant deaths.[49][50][51] In a study published in the New England Journal of Medicine, it was reported that melamine exposure increased the incidence of urinary tract stones by seven times in children.[52] Melamine may have been added to fool government protein content tests after water was added to fraudulently dilute the milk. Because of melamine's high nitrogen content (66% by mass versus approx. 10–12% for typical protein), it can cause the protein content of food to appear higher than the true value.[53][54] Officials estimate that about 20 percent of the dairy companies tested in China sell products tainted with melamine. On January 22, 2009, three of those involved in the scandal (including one conditional sentence) were sentenced to death in a Chinese court.[55]

In October 2008, "Select Fresh Brown Eggs" imported to Hong Kong from the Hanwei Group in Dalian in northeastern China, were found to be contaminated with nearly twice the legal limit of melamine. York Chow, the health secretary of Hong Kong, said he thought animal feeds might be the source of the contamination and announced that the Hong Kong Centre for Food Safety would henceforward be testing all mainland Chinese pork, farmed fish, animal feed, chicken meat, eggs, and offal products for melamine.[56]

As of July 2010, Chinese authorities were still reporting some seizures of melamine-contaminated dairy product in some provinces, though it was unclear whether these new contaminations constituted wholly new adulterations or were the result of illegal reuse of material from the 2008 adulterations.[57][58]

On characterization and treatment of urinary stones in affected infants, the New England Journal of Medicine printed an editorial in March 2009, along with reports on cases from Beijing, Hong Kong and Taipei.[59]

Urinary calculi specimens were collected from 15 cases treated in Beijing and were analyzed as unknown objects for their components at Beijing Institute of Microchemistry using infrared spectroscopy, nuclear magnetic resonance, and high performance liquid chromatography. The result of the analysis showed that the calculus was composed of melamine and uric acid, and the molecular ratio of uric acid to melamine was around 2:1.[60]

In a 2009 study of 683 children diagnosed in Beijing in 2008 with nephrolithiasis and 6,498 children without nephrolithiasis aged < 3 years, investigators found that in children exposed to melamine levels < 0.2 mg/kg per day, the risk for nephrolithiasis was still 1.7 times higher than in those without melamine exposure, suggesting that the risk of melamine-induced nephrolithiasis in young children starts at a lower intake level than the levels recommended by the World Health Organization.[61]

In a study published in 2010, researchers from Beijing University studying ultrasound images of infants who fell ill in the 2008 contamination found that while most children in a rural Chinese area recovered, 12 per cent still showed kidney abnormalities six months later. "The potential for long-term complications after exposure to melamine remains a serious concern," the report said. "Our results suggest a need for further follow-up of affected children to evaluate the possible long-term impact on health, including renal function."[62] Another 2010 followup study from Lanzhou University attributed the uric acid stone accumulation after ingestion of melamine to a rapid aggradation of metabolites such as cyanuric acid diamide (ammeline) and cyanuric acid and reported that urine alkalinization and stone liberalization were the most effective treatments.[22]

Testing in food

Until the 2007 pet food recalls, melamine had not routinely been monitored in food, except in the context of plastic safety or insecticide residue. This could be due to the previously assumed low toxicity of melamine, and the relatively expensive methods of detection.

Following the 2008 health scare in China over powdered milk, the Joint Research Centre (JRC) of the European Commission in Belgium set-up a website about methods to detect melamine.[63] In May 2009, the JRC published the results of a study that benchmarked the ability of labs around the world to accurately measure melamine in food. The study concluded that the majority of labs can effectively detect melamine in food.[64]

In October 2008, the U.S. Food and Drug Administration (FDA) issued new methods for the analysis of melamine and cyanuric acid in infant formulations in the Laboratory Information Bulletin No 4421.[65] Similar recommendations have been issued by other authorities, like the Japanese Ministry of Health, Labor and Welfare,[66] both based on liquid chromatography – mass spectrometry (LC/MS) detection after hydrophilic interaction liquid chromatography (HILIC) separation.[67]

The existing methods for melamine determination using a triple quadrupole liquid chromatography – mass spectrometry (LC/MS) after solid phase extraction (SPE) are often complex and time consuming. However, electrospray ionization methods coupled with mass spectrometry allow a rapid and direct analysis of samples with complex matrices: the native liquid samples are directly ionized under ambient conditions in their original solution. In December 2008, two new fast and inexpensive methods for detecting melamine in liquids have been published on-line in the Chem. Comm. Journal of the Royal Society of Chemistry (UK).[68]

Ultrasound-assisted extractive electrospray ionization mass spectrometry (EESI-MS) has been developed at ETH Zurich (Switzerland) by Zhu et al., (2008)[69][70] for a rapid detection of melamine in untreated food samples. Ultrasounds are used to nebulize the melamine-containing liquids into a fine spray. The spray is then ionised by extractive electrospray ionisation (EESI) and analysed using tandem mass spectrometry (MS/MS). An analysis requires 30 seconds per sample. The limit of detection of melamine is a few nanograms of melamine per gram of milk.

Huang et al., (2008)[71][72] have also developed at Purdue University (US) a simpler instrumentation and a faster method by using a low-temperature plasma probe to ionize the samples. The major obstacles being solved, the ESI-MS technique allows now high-throughput analysis of melamine traces in complex mixtures.

The Melaminometer[73][74] was a hypothetical design for a synthetic biology circuit, to used for detecting melamine and related chemical analogues such as cyanuric acid. The conceptual project is hosted at OpenWetWare as open source biology in collaboration with DIYbio and has been discussed in various newspapers in the context of homebrew biotechnology. As of October 2009, the design has not been verified.

Because melamine resin is often used in food packaging and tableware, melamine at ppm level (1 part per million) in food and beverage has been reported due to migration from melamine-containing resins.[75] Small amounts of melamine have also been reported in foodstuff as a metabolite product of cyromazine, an insecticide used on animals and crops.[76]

The Food Safety and Inspection Service (FSIS) of the United States Department of Agriculture (USDA) provides a test method for analyzing cyromazine and melamine in animal tissues.[77][78] In 2007, the FDA began using a high performance liquid chromatography test to determine the melamine, ammeline, ammelide, and cyanuric acid contamination in food.[79] Another procedure is based on surface-enhanced Raman spectroscopy (SERS).[80][81]

Member States of the European Union are required under Commission Decision 2008/757/EC[82] to ensure that all composite products containing at least 15% of milk product, originating from China, are systematically tested before import into the Community and that all such products which are shown to contain melamine in excess of 2.5 mg/kg are immediately destroyed.

See also

References

  1. ^ a b Melamine on ChemIDplus
  2. ^ Report on cyromazine of the European Medicines Agency
  3. ^ Lori 0. Lim, Susan J. Scherer, Kenneth D. Shuler, and John P. Toth. Disposition of Cyromazine in Plants under Environmental Conditions J. Agric. Food Chem. 1990, 38, 860–864 [1]
  4. ^ FAO report on cyromazine
  5. ^ "Melamine. The American Heritage Dictionary of the English Language: Fourth Edition. 2000". Retrieved 2008-09-28.
  6. ^ Bann B. and Miller S.A. (1958) "Melamines and derivatives of melamine". Chemical Reviews, vol.58, 131–172.
  7. ^ Hauck, R.D. (1964). "Nitrification of triazine nitrogen". Fertilizer Nitrogen Sources. 12 (2): 147. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  8. ^ Barrett MP, Gilbert IH (2006). "Targeting of toxic compounds to the trypanosome's interior". Adv. Parasitol. 63: 125–83. doi:10.1016/S0065-308X(06)63002-9. PMID 17134653.
  9. ^ "Ruminant feed compositions, Robert W. Colby and Robert J. Mesler Jr., U.S. Patent No. 2819968, 1958
  10. ^ “Melamine as a dietary nitrogen source for ruminants", G.L.Newton and P.R.Utley, Journal of Animal Science, vol.47, p1338–44, 1978, Abstract |accessdate=2008-09-17
  11. ^ "Protein Pretense", Alison Snyder, Scientific American Magazine, August 2008 [2] |accessdate=2008-09-19
  12. ^ Moore, J.C. (2010-08-17). "Total Protein Methods and Their Potential Utility to Reduce the Risk of Food Protein Adulteration". Comprehensive Reviews in Food Science and Food Safety. 9 (4): 330–357. doi:10.1111/j.1541-4337.2010.00114.x. Retrieved 2010-09-01.
  13. ^ "Melamine in milk by David Bradley". Sciencebase. 17 September 2008. Retrieved 2008-09-27.
  14. ^ Weise, Elizabeth (5 August 2007). "Poison pet food woes seem to hit cats harder". USA Today. Retrieved 2008-10-01.
  15. ^ Rory Harrington (15 April 2010). "EFSA cuts melamine TDI by 60 per cent". FoodQualityNews.com. Retrieved 2010-04-16.
  16. ^ Lara Endreszl (10 December 2008). "Safe Melamine Levels Named by World Health Organization". Health News.
  17. ^ a b MSDS
  18. ^ Flame Retardants Center: Melamine Compounds
  19. ^ A.A. Babayan, A.V.Aleksandryan, "Toxicological characteristics of melamine cyanurate, melamine and cyanuric acid", Zhurnal Eksperimental'noi i Klinicheskoi Meditsiny, Vol.25, 345-9 (1985). Original article in Russian, English abstract retrieved from SciFinder on either 2007-07-05 or 2007-05-07.
  20. ^ Puschner; et al. (2007). "Assessment of melamine and cyanuric acid toxicity in cats". Journal of Veterinary Diagnostic Investigation. Retrieved 2007-11-16. {{cite web}}: Explicit use of et al. in: |last= (help); Unknown parameter |month= ignored (help)
  21. ^ Dobson; et al. (2008). "Identification and characterization of toxicity of contaminants in pet food leading to an outbreak of renal toxicity in cats and dogs". Toxicological Sciences. Retrieved 2009-08-13. {{cite web}}: Explicit use of et al. in: |last= (help); Unknown parameter |month= ignored (help)
  22. ^ a b c Zhang X.; et al. (2010). "Melamine-induced infant urinary calculi: a report on 24 cases and a 1-year follow-up". Urological Research. doi:10.1007/s00240-010-0279-0. PMID 20517603. Retrieved 2010-07-01. {{cite journal}}: Explicit use of et al. in: |author= (help)
  23. ^ International Chemical Safety Card
  24. ^ OSHA – Chemical sampling information
  25. ^ WHO – Some Chemicals that Cause Tumors of the Kidney or Urinary Bladder in Rodents and Some Other Substances
  26. ^ HD Heck and RW Tyl (1985). "The induction of bladder stones by terephthalic acid, dimethyl terephthalate, and melamine (2,4,6-triamino-s-triazine) and its relevance to risk assessment". Regul Toxicol Pharmacol. 5 (3): 294–313. doi:10.1016/0273-2300(85)90044-3. PMID 3903881. {{cite journal}}: Unknown parameter |month= ignored (help)
  27. ^ T.W. Tusing, "Chronic Feeding - Dogs", cited by "Summary of toxicity data - trichloromelamine" by California Environmental Protection Agency, last revised on 04-02-2002, URL accessed on 05-09-2007
  28. ^ "Culprit in pet food deaths may be combination of contaminants". Michigan State University. November 29, 2007. Retrieved 2007-12-07.
  29. ^ "Proceedings of the American Association of Veterinarian Laboratory Diagnosticians 50th Annual Conference" (PDF). AAVLD. 2007. Retrieved 2007-11-30. {{cite web}}: Unknown parameter |month= ignored (help)
  30. ^ "Researchers examine contaminants in food, deaths of pets". AVMA. 2007. Retrieved 2007-11-30. {{cite web}}: Unknown parameter |month= ignored (help)
  31. ^ "International experts limit melamine levels in food". World Health Organization. 2010-07-06. Retrieved 2010-07-07. Establishment of maximum levels will help governments differentiate between low levels of unavoidable melamine occurrence that do not cause health problems, and deliberate adulteration - thereby protecting public health without unnecessary impediments to international trade.
  32. ^ Kirk-Othmer encyclopedia of chemical technology, 3rd edition, Vol.7, p303–304, 1978.
  33. ^ SM Lahalih, M Absi-Halabi, "Recovery of solids from melamine waste effluents and their conversion to useful products", Industrial & Engineering Chemistry Research, vol.28, 500–504 (1989).
  34. ^ "How a golden chemical became greeneer", Nitrogen+Syngas, Issue 293, May-June 2008.
  35. ^ Kramer, Deborah (2005). "Nitrogen" (PDF). United States Geological Survey. Retrieved 2007-04-30.
  36. ^ Ruilin, Wang (6 January 2006). "Melamine capacity is serious surplus". China Chemical Reporter. Retrieved 2007-04-21.
  37. ^ Melamine industry update, by Royal DSM N.V., accessed on 2007-05-04
  38. ^ "Tainted milk trial opens in China". British Broadcasting Corporation. December 26, 2008. Retrieved January 7, 2009.
  39. ^ "Chinese Milk Scam Duo Face Death". British Broadcasting Corporation. January 22, 2009. Retrieved January 22, 2009.
  40. ^ CNN: Dry food added to pet food recall list[dead link]
  41. ^ AVMA: Pet food recall
  42. ^ Press release by Natural Balance Pet Foods[dead link]
  43. ^ FDA FAQ: Where did the contaminated wheat gluten come from?
  44. ^ FDA: Pet food recall
  45. ^ David Barboza and Alexei Barrionuevo (30 April 2007). "Filler in Animal Feed Is Open Secret in China". The New York Times. Retrieved 2007-04-30.
  46. ^ David Barboza and Alexei Barrionuevo (3 May 2007). "China Makes Arrest in Pet Food Case". The New York Times. Retrieved 2007-05-03.
  47. ^ "Products". Shandong Mingshui Great Chemical Group. Retrieved 2007-04-30.
  48. ^ Andrew Martin (31 May 2007). "Poison used in China is found in U.S.-made animal feed". The New York Times. Retrieved 2007-06-01.
  49. ^ Scott McDonald, "Nearly 53,000 Chinese children sick from milk", Associated Press (22 September 2008)
  50. ^ Jane Macartney, China baby milk scandal spreads as sick toll rises to 13,000, The Times (September 22, 2008)
  51. ^ "Toxicological and Health Aspects of Melamine and Cyanuric Acid" (PDF). WHO. 2009. Retrieved 2009-08-13.
  52. ^ Guan, N; Fan, Q; Ding, J; Zhao, Y; Lu, J; Ai, Y; Xu, G; Zhu, S; Yao, C; Jiang, L; Miao, J; Zhang, H; Zhao, D; Liu, X; Yao, Y (2009). "Melamine-contaminated powdered formula and urolithiasis in young children". The New England journal of medicine. 360 (11): 1067–74. doi:10.1056/NEJMoa0809550. PMID 19196669. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  53. ^ "Fonterra says somebody sabotaged milk". NZ Herald. September 15, 2008. Retrieved 2008-09-22.
  54. ^ "Toxic milk toll rockets in China". BBC NEWS. September 15, 2008. Retrieved 2008-09-22.
  55. ^ Tran, Tini (September 17, 2008). "6,200 Chinese babies ill, 3 die from tainted milk". Yahoo! News. Retrieved 2008-09-22.
  56. ^ "Hong Kong widens China food tests". BBC News. 27 October 2008. Retrieved 2008-10-27.
  57. ^ Pliny (2010-07-09). "Melamine tainted milk re-emerges in northwest China plant". Xinhua. Retrieved 2010-07-09. {{cite news}}: Cite has empty unknown parameter: |coauthors= (help)
  58. ^ Michael Wines (July 9, 2010). "Tainted Dairy Products Seized in Western China". New York Times. Retrieved 2010-07-09. {{cite news}}: Cite has empty unknown parameter: |coauthors= (help)
  59. ^ Langman, Craig (12 March 2009). "Melamine, Powdered Milk, and Nephrolithiasis in Chinese Infants". New England Journal of Medicine. Retrieved 2009-08-13.
  60. ^ Sun; et al. (2009). "Diagnosis and treatment of melamine-associated urinary calculus complicated with acute renal failure in infants and young children". Chinese Medical Journal. Retrieved 2009-08-17. {{cite web}}: Explicit use of et al. in: |author= (help)
  61. ^ Gang; et al. (1 September 2009). "The risk of melamine-induced nephrolithiasis in young children starts at a lower intake level than recommended by the WHO". Pediatric Nephrology. Retrieved 2009-10-08. {{cite web}}: Explicit use of et al. in: |author= (help)
  62. ^ Liu; Ren, A; Yang, L; Gao, J; Pei, L; Ye, R; Qu, Q; Zheng, X; et al. (22 February 2010). "Urinary tract abnormalities in Chinese rural children who consumed melamine-contaminated dairy products: a population-based screening and follow-up study". CMAJ : Canadian Medical Association journal = journal de l'Association medicale canadienne. 182 (5). Canadian Medical Association Journal: 439–43. doi:10.1503/cmaj.091063. PMC 2842835. PMID 20176755. Retrieved 23 February 2010. {{cite journal}}: Explicit use of et al. in: |author= (help); Missing pipe in: |journal= (help)
  63. ^ http://irmm.jrc.ec.europa.eu/melamine
  64. ^ Breidbach, A., Bouten, K., Kroger, K., Ulberth, F. "Melamine Proficiency Test 2009"
  65. ^ U.S. FDA Laboratory Information Bulletin No 4421 - http://www.cfsan.fda.gov/~frf/lib4421.html
  66. ^ Japanese Ministry of Health, Labor and Welfare - http://www.forth.go.jp/keneki/kanku/syokuhin/tsuuchi/2008/10/3_1.pdf
  67. ^ Zwitterionic HILIC separation of melamine and cyanuric acid - http://www.sequant.com/melamine
  68. ^ Hodge, James (2008-12-12). "Dairy detection: monitoring melamine in milk". Chemical Science (Royal Chemical Society, RCS Publishing). No. 02. Retrieved 2009-01-04.
  69. ^ Zhu, Liang (2008). "Rapid detection of melamine in untreated milk and wheat gluten by ultrasound-assisted extractive electrospray ionization mass spectrometry (EESI-MS)". Chemical Communications (5): 559. doi:10.1039/b818541g. PMID 19283290. {{cite journal}}: |access-date= requires |url= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)
  70. ^ Zhu, Liang (2008-01-12). "Rapid detection of melamine in untreated milk and wheat gluten by ultrasound-assisted extractive electrospray ionization mass spectrometry (EESI-MS)". Royal Chemical Society, RCS Publishing. Retrieved 2009-01-05. {{cite web}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  71. ^ Huang, Guangming (2008). "High-throughput trace melamine analysis in complex mixtures". Chemical Communications (5): 556. doi:10.1039/b818059h. PMID 19283289. {{cite journal}}: |access-date= requires |url= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)
  72. ^ Huang, Guangming (2008-01-12). "High-throughput trace melamine analysis in complex mixtures". Royal Chemical Society, RCS Publishing. Retrieved 2009-01-05. {{cite web}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  73. ^ McKenna, Phil (2009-01-07). "Rise of the garage genome hackers". New Scientist. Retrieved 2009-02-17.
  74. ^ Marcus, Wohlsen (2008-12-26). "Amateurs are trying genetic engineering at home". Copyright 2008 The Associated Press. Retrieved 2009-02-17.
  75. ^ Ishiwata H, Inoue T, Yamazaki T, Yoshihira K (1987). "Liquid chromatographic determination of melamine in beverages". J Assoc off Anal Chem. 70 (3): 457–60. PMID 3610957.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  76. ^ J.V. Sancho, M. Ibanez, S. Grimalt, O.J. Pozo, F. Hernandez, "Residue determination of cyromazine and its metabolite melamine in chard samples by ion-pair liquid chromatography coupled to electrospray tandem mass spectrometry", Analytica Chimica Acta Vol.530, p237–243 (2005) Abstract accessed 05-06-2007.
  77. ^ "Cyromazine and Melamine" (PDF). USDA FSIS. 1991. Retrieved 2007-04-27. {{cite web}}: Unknown parameter |month= ignored (help)
  78. ^ "Chemistry Laboratory Guidebook". USDA FSIS. Retrieved 2007-04-27.
  79. ^ "HPLC Determination of Melamine, Ammeline, Ammelide, and Cyanuric Acid Contamination in Wheat Gluten and Rice Protein Concentrate". U.S. Food and Drug Administration. 25 April 2007. Retrieved 2007-05-09.
  80. ^ Lili He, Yang Liu, Mengshi Lin, Joseph Awika, David R. Ledoux, Hao Li, Azlin Mustapha, (2008). "A new approach to measure melamine, cyanuric acid, and melamine cyanurate using surface enhanced Raman spectroscopy coupled with gold nanosubstrates". Sens. & Instrumen. Food Qual. 2: 66–71. doi:10.1007/s11694-008-9038-0.{{cite journal}}: CS1 maint: extra punctuation (link) CS1 maint: multiple names: authors list (link)
  81. ^ Mengshi Lin, Lili He, Joseph Awika, Liyi Yang, David R. Ledoux, Hao Li, Azlin Mustapha, (2008). "Detection of melamine in gluten, chicken feed and processed foods using surface-enhanced Raman spectroscopy and HPLC". Journal of Food Science. 73 (8): T129–T134. doi:10.1111/j.1750-3841.2008.00901.x. PMID 19019134.{{cite journal}}: CS1 maint: extra punctuation (link) CS1 maint: multiple names: authors list (link)
  82. ^ European Commission decision (2008/798/EC) imposing special conditions governing the import of products containing milk or milk products originating from China
Look up melamine in Wiktionary, the free dictionary.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Melamine&oldid=382370692"