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Melamine cyanurate

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(Redirected from Melamine-cyanuric acid complex)
Melamine-cyanuric acid complex
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
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.048.687 Edit this at Wikidata
MeSH melamine+cyanurate
PubChem CID
CompTox Dashboard (EPA)
InChI
  • 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)Key: ZQKXQUJXLSSJCH-UHFFFAOYSA-N
SMILES
  • c1(nc(nc(n1)N)N)N.c1(=O)c(=O)c(=O)1
Properties
Chemical formula C6H9N9O3

(C3H6N6·C3H3N3O3)

Molar mass 255.19 g/mol
Solubility in water none
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 guanine–cytosine base pairs found in DNA. Melamine cyanurate forms spoke-like crystals from aqueous solutions and has been implicated as a causative agent for toxicity seen in the Chinese protein export contamination and the 2007 pet food recall. This complex is cited as an example of supramolecular chemistry.

Uses

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). 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.

LD50 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 in cats. A 2008 study produced similar experimental results in rats and characterized the melamine and cyanuric acid in contaminated pet food from the 2007 outbreak.

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

See also

References

  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. ^ 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.
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