Melamine cyanurate, also known as melamine–cyanuric acid adduct or melamine–cyanuric acid complex, is a
crystal
A crystal or crystalline solid is a solid material whose constituents (such as atoms, molecules, or ions) are arranged in a highly ordered microscopic structure, forming a crystal lattice that extends in all directions. In addition, macros ...
line
complex
Complex commonly refers to:
* Complexity, the behaviour of a system whose components interact in multiple ways so possible interactions are difficult to describe
** Complex system, a system composed of many components which may interact with each ...
formed from a 1:1 mixture of
melamine
Melamine is an organic compound with the formula C3H6N6. This white solid is a trimer (chemistry), trimer of cyanamide, with a 1,3,5-Triazine, 1,3,5-triazine skeleton. Like cyanamide, it contains 66% nitrogen by mass, and its derivatives ha ...
and
cyanuric acid
Cyanuric acid or 1,3,5-triazine-2,4,6-triol is a chemical compound with the chemical formula, formula (CNOH)3. Like many industrially useful chemicals, this triazine has many synonyms. This white, odorless solid finds use as a precursor or a com ...
. The substance is not a
salt
In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...
despite its non-systematic name ''melamine cyanurate''. The complex is held together by an extensive two-dimensional network of
hydrogen bond
In chemistry, a hydrogen bond (H-bond) is a specific type of molecular interaction that exhibits partial covalent character and cannot be described as a purely electrostatic force. It occurs when a hydrogen (H) atom, Covalent bond, covalently b ...
s between the two compounds, reminiscent of the
guanine
Guanine () (symbol G or Gua) is one of the four main nucleotide bases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, and thymine ( uracil in RNA). In DNA, guanine is paired with cytosine. The guanine nucleoside ...
–
cytosine
Cytosine () (symbol C or Cyt) is one of the four nucleotide bases found in DNA and RNA, along with adenine, guanine, and thymine ( uracil in RNA). It is a pyrimidine derivative, with a heterocyclic aromatic ring and two substituents attac ...
base pair
A base pair (bp) is a fundamental unit of double-stranded nucleic acids consisting of two nucleobases bound to each other by hydrogen bonds. They form the building blocks of the DNA double helix and contribute to the folded structure of both DNA ...
s found in
DNA
Deoxyribonucleic acid (; DNA) is a polymer composed of two polynucleotide chains that coil around each other to form a double helix. The polymer carries genetic instructions for the development, functioning, growth and reproduction of al ...
.
[
] Melamine cyanurate forms spoke-like
crystal
A crystal or crystalline solid is a solid material whose constituents (such as atoms, molecules, or ions) are arranged in a highly ordered microscopic structure, forming a crystal lattice that extends in all directions. In addition, macros ...
s from aqueous solutions
[
] and has been implicated as a causative agent for toxicity seen in the
Chinese protein export contamination
In China the adulteration and contamination of food and feed ingredients with inexpensive melamine and other compounds, such as cyanuric acid, ammeline and ammelide, are common practice. These adulterants can be used to inflate the apparent protei ...
and the
2007 pet food recall.
This complex is cited as an example of
supramolecular chemistry
Supramolecular chemistry refers to the branch of chemistry concerning Chemical species, chemical systems composed of a integer, discrete number of molecules. The strength of the forces responsible for spatial organization of the system range from w ...
.
Uses
Melamine cyanurate is used as a
flame retardant
Flame retardants are a diverse group of chemicals that are added to manufactured materials, such as plastics and textiles, and surface finishes and coatings. Flame retardants are activated by the presence of an combustion, ignition source and pr ...
, most commonly in
polybutylene terephthalate
Polybutylene terephthalate (PBT) is a thermoplastic engineering polymer that is used as an insulator in the electrical and electronics industries. It is a thermoplastic (semi-)crystalline polymer, and a type of polyester. PBT resists solvents, s ...
(PBT),
polyamide 6 (nylon 6) and
polyamide 6,6 (nylon 6:6). It is also used to fireproof in polyester fabrics.
Toxicity
It has been considered to be more toxic than either melamine or cyanuric acid alone.
in rats and mice (ingested):
* 4.1 g/kg – Melamine cyanurate
* 6.0 g/kg – Melamine
* 7.7 g/kg – Cyanuric acid
A toxicology study conducted after recent pet food recalls concluded that the combination of melamine and cyanuric acid in diet does lead to
acute kidney injury
Acute kidney injury (AKI), previously called acute renal failure (ARF), is a sudden decrease in renal function, kidney function that develops within seven days, as shown by an increase in serum creatinine or a decrease in urine output, or both.
...
in cats.
[Puschner et al. (November 2007). Assessment of melamine and cyanuric acid toxicity in cats. Journal of Veterinary Diagnostic Investigation. Retrieved on 2007-11-16.] A 2008 study produced similar experimental results in rats and characterized the melamine and cyanuric acid in contaminated pet food from the 2007 outbreak.
See also
*
1,3,5-Triazine
*
Hydrogen bonding
In chemistry, a hydrogen bond (H-bond) is a specific type of molecular interaction that exhibits partial covalent character and cannot be described as a purely electrostatic force. It occurs when a hydrogen (H) atom, Covalent bond, covalently b ...
References
{{Reflist
Amines
Triazines
Nephrotoxins
Flame retardants