MetaCyc Compound: melamine

Synonyms: cyanurotriamide, cyanurotriamine, cyanuramide, isomelamine, theoharn, 2,4,6-triamino-1,3,5-triazine

Superclasses: an aromatic compounds-triazine

The s-triazine compounds have numerous applications throughout industry and agriculture. Those containing N-alkyl substituents have been applied successfully as herbicides. The worldwide production of melamine, an s-triazine compound, in 1994 was estimated to be 900 million lb. Melamine is most commonly used in the production of melamine-formaldehyde resins, which are used in laminates, adhesives, fire retardants, molding compounds, coatings, and concrete plasticizers.

Melamine has become internationally recognized as a chemical contaminant of pet foods and infant formula that caused mortality in pets and children [Ingelfinger08, Gossner09].

Melamine is metabolized by soil bacteria producing the intermediates ammeline, ammelide, and cyanurate, which is then metabolized to completion, producing CO2 amd ammonia [Jutzi82].

Chemical Formula: C3H6N6

Molecular Weight: 126.12 Daltons

Monoisotopic Molecular Weight: 126.06539422380001 Daltons

melamine compound structure

SMILES: C1(=NC(N)=NC(N)=N1)(N)

InChI: InChI=1S/C3H6N6/c4-1-7-2(5)9-3(6)8-1/h(H6,4,5,6,7,8,9)


Unification Links: ChEBI:27915, ChemSpider:7667, HMDB:HMDB41922, KEGG:C08737, PubChem:7955

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 99.15673Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

melamine degradation :
melamine + H+ + H2O → ammeline + ammonium


Gossner09: Gossner CM, Schlundt J, Ben Embarek P, Hird S, Lo-Fo-Wong D, Beltran JJ, Teoh KN, Tritscher A (2009). "The melamine incident: implications for international food and feed safety." Environ Health Perspect 117(12);1803-8. PMID: 20049196

Ingelfinger08: Ingelfinger JR (2008). "Melamine and the global implications of food contamination." N Engl J Med 359(26);2745-8. PMID: 19109571

Jutzi82: Jutzi K, Cook AM, Hutter R (1982). "The degradative pathway of the s-triazine melamine. The steps to ring cleavage." Biochem J 208(3);679-84. PMID: 6762212

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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