Melamine cyanurate, also known as melamine–cyanuric acid adduct or melamine–cyanuric acid complex, is a crystalline complex formed from a 1:1 mixture of melamine and cyanuric acid. The substance is not a salt despite its non-systematic name melamine cyanurate. The complex is held together by an extensive two-dimensional network of hydrogen bonds between the two compounds, reminiscent of the guaninecytosine base pairs found in DNA.[2] Melamine cyanurate forms spoke-like crystals from aqueous solutions [3] and has been implicated as a causative agent for toxicity seen in the Chinese protein export contamination and the 2007 pet food recall.[3] This complex is cited as an example of supramolecular chemistry.[4]

Melamine-cyanuric acid complex[1]
Names
Preferred IUPAC name
1,3,5-Triazinane-2,4,6-trione—1,3,5-triazine-2,4,6-triamine (1/1)
Other names
Melamine–cyanuric acid compound, melamine–cyanuric acid adduct, melamine cyanurate, melamine isocyanurate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.048.687 Edit this at Wikidata
MeSH melamine+cyanurate
  • InChI=1S/C3H6N6.C3H3N3O3/c4-1-7-2(5)9-3(6)8-1;7-1-4-2(8)6-3(9)5-1/h(H6,4,5,6,7,8,9);(H3,4,5,6,7,8,9) ☒N
    Key: ZQKXQUJXLSSJCH-UHFFFAOYSA-N ☒N
  • c1(nc(nc(n1)N)N)N.c1(=O)[nH]c(=O)[nH]c(=O)[nH]1
Properties
C6H9N9O3

(C3H6N6·C3H3N3O3)

Molar mass 255.19 g/mol
none
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Uses

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Melamine cyanurate is used as a flame retardant, most commonly in polybutylene terephthalate (PBT), polyamide 6 (nylon 6) and polyamide 6,6 (nylon 6:6).[5] It is also used to fireproof in polyester fabrics.

Toxicity

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It has been considered to be more toxic than either melamine or cyanuric acid alone.[6]

LD50 in rats and mice (ingested):

  • 4.1 g/kg – Melamine cyanurate
  • 6.0 g/kg – Melamine[clarification needed]
  • 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 in cats.[7] A 2008 study produced similar experimental results in rats and characterized the melamine and cyanuric acid in contaminated pet food from the 2007 outbreak.[8]

 
Section of the extensive two-dimensional hydrogen bond network (dashed) between melamine (blue) and cyanuric acid (red)

See also

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References

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  1. ^ EPA: Substance : Archived 2008-09-22 at the Wayback Machine
  2. ^ Perdigão LM, Champness NR, Beton PH (2006). "Surface self-assembly of the cyanuric acid-melamine hydrogen bonded network". Chem. Commun. (5): 538–540. doi:10.1039/b514389f. PMID 16432575.
  3. ^ a b 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. S2CID 93425738.
  4. ^ Lehn, J. M. (1995). Supramolecular Chemistry: Concepts and Perspectives. Weinheim: VCH.
  5. ^ Gijsman, Pieter; Steenbakkers, Rieky; Fürst, Christian; Kersjes, Joyce (2002). "Differences in the flame retardant mechanism of melamine cyanurate in polyamide 6 and polyamide 66". Polymer Degradation and Stability. 78 (2): 219–224. doi:10.1016/S0141-3910(02)00136-2.
  6. ^ 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.
  7. ^ Puschner et al. (November 2007). Assessment of melamine and cyanuric acid toxicity in cats. Journal of Veterinary Diagnostic Investigation. Retrieved on 2007-11-16.
  8. ^ Dobson; et al. (August 2008). "Identification and characterization of toxicity of contaminants in pet food leading to an outbreak of renal toxicity in cats and dogs". Toxicological Sciences. 106 (1): 251–62. doi:10.1093/toxsci/kfn160. PMID 18689873.