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MEL

MELA

MELAM

Melamine

Melamine is an organic base and a trimer of cyanamide, with a 1,3,5triazine skeleton. Like cyanamide, it contains 67% 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 that have ingested cyromazine.[1] It has been reported that
cyromazine can also be converted to melamine in plants.[2] [3]
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.

The German word melamin was coined by combining the words: melam (a
derivative of ammonium thiocyanate) and amine.[4] [5] Melamine is,
therefore, unrelated etymologically to the root melas (, meaning black
in Greek), from which the words melanin, a pigment, and melatonin, a
hormone, are formed.

Melamine is combined with formaldehyde to produce melamine resin, a very

durable thermosetting plastic used in high pressure decorative laminates
such as Formica, melamine dinnerware, laminate flooring, and dry erase
boards.
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 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 lifetime.
The use of melamine as fertilizer for crops had been envisaged during the
1950s and 1960s because of its high nitrogen content (2/3). However,
melamine is much more expensive to produce than are 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 and its salts are used as fire-retardant additives in paints, plastics,
and paper.[6]

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Melamine derivatives of arsenical drugs are potentially important in the

treatment of African trypanosomiasis.[7]
Melamine use as non-protein nitrogen (NPN) for cattle was described in a
1958 patent.[8] 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.[9]
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.
An instrument (SPRINT) developed by the company CEM Corp allows the
determination of protein content directly in some applications; the
instrument cannot be fooled by adding melamine in the sample.[10] [11]
Melamine is also used as a nitrogen and carbon source for N-doped carbon
nanotube. N-CNTs can be prepared via Chemical Vapor Deposition (CVD)
method by pyrolysizing melamine under an Ar atmosphere in a horizontal
glass tube. A thin film of iron (5 nm) is first deposited on a Si/SiO2 wafer.
N-CNT synthesis occurs at a furnace temperatures between 800 and
980 C.[12]

Melamine is described as "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 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.[14]
The European Union set a standard for acceptable human consumption
(tolerable daily intake, TDI) of melamine at 0.2 mg per kg of body mass,[15]
(previously 0.5 milligrams), Canada declared a limit of 0.35 mg and the US
FDA's limit was put at 0.063 mg daily (previously 0.63 mg). 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 kg of body mass.[16]
Toxicity of melamine can be mediated by intestinal microbes. In culture,
Klebsiella terrigena, which rarely colonizes mammalian intestines,[17] was
shown to convert melamine to cyanuric acid directly. Rats colonized by K.
terrigena showed greater melamine-induced kidney damage compared to
those not colonized.[18]

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.A study by USSR

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researchers in the 1980s suggested that melamine cyanurate, commonly

used as a fire retardant,[19] could be more toxic than either melamine or
cyanuric acid alone.[20] 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.[21] A 2008 study produced similar
experimental results in rats and characterized the melamine and cyanuric
acid in contaminated pet food from the 2007 outbreak.[22] A 2010 study
from Lanzhou University attributed renal failure in humans to uric acid stone
accumulation after ingestion of melamine resulting in a rapid aggregation of
metabolites such as cyanuric acid diamide (ammeline) and cyanuric acid.

Ingestion of melamine may lead to reproductive damage, or bladder or

kidney stones, which can lead to bladder cancer.[23] [24] [25] [26] [27]
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.[28]
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."[29] [30]
[31]

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.

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.[32]

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:

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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 cyanuric acid which condenses with
the liberated ammonia forming melamine which releases water which then
reacts with cyanic acid present(which helps to drive the reaction) generating
carbon dioxide and ammonia.
6 HCNO + 3 NH3 C3H6N6 + 3 CO2 + 3NH3
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
Major
further concentrated and crystallized to yield melamine.[33]
manufacturers and licensors such as Orascom Construction Industries, 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 (1.55% 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).[34] 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.[35]

Between the late 1990s and early 2000s, both consumption and production
of melamine grew considerably in mainland China. By early 2006, melamine
production in mainland China is reported to be in "serious surplus".[36]
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

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nitrogen content detected by some simple protein tests. Actions taken in

2008 by the Government of China have 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.[37] [38]

Melamine has been involved in several food recalls after the discovery of
severe kidney damage to children and pets poisoned by melamineadulterated food.

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.[39] [40] [41] 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[42] as well as in crystalline form in the kidneys
and in urine of affected animals.[43] 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.[44] 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."[45] 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.[46]
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.[47]

In September 2008, several companies, including Nestl, 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.[48] [49]
[50] 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.[51] 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

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versus approx. 1012% for typical protein), it can cause the protein content
of food to appear higher than the true value.[52] [53] 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.[54]
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.[55]
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.[56] [57]
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.[58]
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.[59]
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 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.[60]
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."[61] Another 2010 follow-up 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.[62]

Until the 2007 pet food recalls, melamine had not routinely been monitored

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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 deaths of children in China from powdered milk in 2008, 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).
Ultrasound-assisted extractive electrospray ionization mass spectrometry
(EESI-MS) has been developed at ETH Zurich (Switzerland) by Zhu et al.,
(2008)[68] 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) 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.[69]
The Melaminometer[70] [71] 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.[72] Small
amounts of melamine have also been reported in foodstuff as a metabolite
product of cyromazine, an insecticide used on animals and crops.[73]
The Food Safety and Inspection Service (FSIS) of the United

States

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Department of Agriculture (USDA) provides a test method for analyzing

cyromazine and melamine in animal tissues.[74] [75] In 2007, the FDA began
using a high performance liquid chromatography test to determine the
melamine, ammeline, ammelide, and cyanuric acid contamination in food.[76]
another procedure is based on surface-enhanced Raman spectroscopy
(SERS).[77] [78]
Member States of the European Union are required under Commission
Decision 2008/757/EC[79] 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.

Melamine has been determined in urine specimens from children who

consumed adulterated milk products by liquid chromatography-mass
spectrometry.[80]

It is reported that melamine molecules adsorbed on Au(111)[81] or

Ag(111)[82] surface tend to arrange into honeycomb or closed-packed
structures. Such a self-assembly occurs due to the inter-molecular hydrogen
bond interaction. This ordering was further investigated using classical Monte
Carlo[83] and DFT[84] methods.

Zhao Lianhai

[https://fscimage.fishersci.com/msds/96668.htm Melamine Materials

Safety Data Sheet (MSDS)]
OECD Screening Information DataSet (SIDS): Melamine (High
Production Volume Chemicals Screening InformationPDF, 89 pages).
FDA Web Page with Information on Pet Food Recall (due to Melamine
contamination)
European Commission decision (2008/798/EC) imposing special
conditions governing the import of products containing milk or milk
products originating from China
Statement on melamine from the International Fertilizer Industry
Association
Toxicological and Health Aspects of Melamine and Cyanuric Acid:
Report of a WHO Expert Meeting In collaboration with FAO
Melmac Central's History on Melamine .

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Corporation. January 22, 2009. January 22, 2009.

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