melamine cyanurate
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 428736138
| Name = Melamine-cyanuric acid complex
| ImageFile = Melamine-cyanuric acid chemical structure color.png
| PIN = 1,3,5-Triazinane-2,4,6-trione—1,3,5-triazine-2,4,6-triamine (1/1)
| OtherNames = Melamine–cyanuric acid compound, melamine–cyanuric acid adduct, melamine cyanurate, melamine isocyanurate
|Section1={{Chembox Identifiers
| Abbreviations =
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 37640-57-6
| CASNo2_Ref = {{cascite|changed|??}}
| CASNo2 = 70371-20-9
| EINECS =
| PubChem = 93198
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 84141
| SMILES = c1(nc(nc(n1)N)N)N.c1(=O)[nH]c(=O)[nH]c(=O)[nH]1
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = ZQKXQUJXLSSJCH-UHFFFAOYSA-N
| RTECS =
| MeSHName = melamine+cyanurate
| ChEBI =
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG =
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|Section2={{Chembox Properties
| Formula = C6H9N9O3
(C3H6N6·C3H3N3O3)
| MolarMass = 255.19 g/mol
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| Solubility = none
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|Section7={{Chembox Hazards
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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.
{{cite journal
|vauthors=Perdigão LM, Champness NR, Beton PH | year = 2006
| title = Surface self-assembly of the cyanuric acid-melamine hydrogen bonded network
| journal = Chem. Commun.
| volume =
| issue = 5
| pages = 538–540
| pmid = 16432575
| doi = 10.1039/b514389f
| url =
}}
Melamine cyanurate forms spoke-like crystals from aqueous solutions {{cite journal
| author = Lili He
| author2 = Yang Liu
| author3 = Mengshi Lin
| author4 = Joseph Awika
| author5 = David R Ledoux
| author6 = Hao Li
| author7 = Azlin Mustapha
| year = 2008
| title = A new approach to measure melamine, cyanuric acid, and melamine cyanurate using surface enhanced Raman spectroscopy coupled with gold nanosubstrates
| journal = Sens. & Instrumen. Food Qual.
| volume = 2
| issue =
| pages = 66–71
| pmid =
| doi = 10.1007/s11694-008-9038-0
| s2cid = 93425738
| url =
}}
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.{{cite book |last=Lehn |first=J. M. |title=Supramolecular Chemistry: Concepts and Perspectives |publisher=VCH |location=Weinheim |year=1995 }}
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).{{cite journal |last1=Gijsman |first1=Pieter |last2=Steenbakkers |first2=Rieky |last3=Fürst |first3=Christian |last4=Kersjes |first4=Joyce |title=Differences in the flame retardant mechanism of melamine cyanurate in polyamide 6 and polyamide 66 |journal=Polymer Degradation and Stability |date=2002 |volume=78 |issue=2 |pages=219–224 |doi=10.1016/S0141-3910(02)00136-2}} 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.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.
{{LD50}} in rats and mice (ingested):
- 4.1 g/kg – Melamine cyanurate
- 6.0 g/kg – Melamine{{Clarify|date=February 2009}}
- 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.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.{{cite journal
| title=Identification and characterization of toxicity of contaminants in pet food leading to an outbreak of renal toxicity in cats and dogs.
| last=Dobson| journal=Toxicological Sciences
| date=August 2008 | volume=106| issue=1| pages=251–62| doi=10.1093/toxsci/kfn160| pmid=18689873|display-authors=etal| doi-access=free}}