Melamine cyanurate
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| 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
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
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| MeSH | melamine+cyanurate |
PubChem CID
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CompTox Dashboard (EPA)
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| 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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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.[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]
Uses
[edit | edit source]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
[edit | edit source]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]
See also
[edit | edit source]References
[edit | edit source]- ^ EPA: Substance : Archived 2008-09-22 at the Wayback Machine
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- ^ 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.
- ^ Puschner et al. (November 2007). Assessment of melamine and cyanuric acid toxicity in cats. Journal of Veterinary Diagnostic Investigation. Retrieved on 2007-11-16.
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