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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:48:08 UTC
Update Date2017-12-07 04:29:30 UTC
HMDB IDHMDB0041922
Secondary Accession Numbers
  • HMDB41922
Metabolite Identification
Common NameMelamine
DescriptionMelamine is an organic base and a trimer of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 66% nitrogen by mass and, if mixed with resins, has fire retardant properties due to its release of nitrogen gas when burned or charred, and has several other industrial uses. Melamine is also a metabolite of cyromazine, a pesticide. It is formed in the body of mammals who have ingested cyromazine. It has been reported that cyromazine can also be converted to melamine in plants. Melamine is combined with formaldehyde to produce melamine resin, a very durable thermosetting plastic used in Formica, and melamine foam, a polymeric cleaning product. The end products include countertops, dry erase boards, fabrics, glues, housewares, dinnerware, cooking spoons, guitar saddles, guitar nuts, acoustic foam paneling, and flame retardants. Melamine is one of the major components in Pigment Yellow 150, a colorant in inks and plastics. Melamine is sometimes illegally added to food products in order to increase the apparent protein content. Standard tests, such as the Kjeldahl and Dumas tests, estimate protein levels by measuring the nitrogen content, so they can be misled by adding nitrogen-rich compounds such as melamine.There is an instrument (SPRINT) developed by the company CEM Corp that allows the determination of protein content directly in some applications; this cannot be fooled by adding melamine in the sample. Ultrasound-assisted extractive electrospray ionization mass spectrometry (EESI-MS) has been developed at ETH Zurich (Switzerland) by Zhu et al., (2008) for a rapid detection of melamine in untreated food samples. Ultrasounds are used to nebulize the melamine-containing liquids into a fine spray. The spray is then ionised by extractive electrospray ionisation (EESI) and analysed using tandem mass spectrometry (MS/MS). An analysis requires 30 seconds per sample. The limit of detection of melamine is a few nanograms of melamine per gram of milk. Crystallization and washing of melamine generates a considerable amount of waste water, which is a pollutant if discharged directly into the environment. The waste water may be concentrated into a solid (1.5-5% of the weight) for easier disposal. The solid may contain approximately 70% melamine, 23% oxytriazines (ammeline, ammelide, and cyanuric acid), 0.7% polycondensates (melem, melam, and melon). In the Eurotecnica process, however, there is no solid waste and the contaminants are decomposed to ammonia and carbon dioxide and sent as off gas to the upstream urea plant; accordingly, the waste water can be recycled to the melamine plant itself or used as clean cooling water make-up. Melamine also enters the fabrication of melamine poly-sulfonate used as superplasticizer for making high-resistance concrete. Sulfonated melamine formaldehyde (SMF) is a polymer used as cement admixture to reduce the water content in concrete while increasing the fluidity and the workability of the mix during its handling and pouring. It results in concrete with a lower porosity and a higher mechanical strength, exhibiting an improved resistance to aggressive environments and a longer life-time.
Structure
Thumb
Synonyms
ValueSource
1,3,5-Triazine-2,4,6-triamineChEBI
2,4,6-triamino-1,3,5-TriazineChEBI
2,4,6-triamino-S-TriazineChEBI
CyanuramideChEBI
Cyanuric triamideChEBI
CyanurotriamideChEBI
CyanurotriamineChEBI
S-TriazinetriamineChEBI
Sym-triaminotriazineChEBI
TriaminotriazineChEBI
1,3, 5-Triazine-2,4,6-triamineHMDB
1,3,5-Triazine-2,4,6(1H,3H,5H)-triimineHMDB
1,3,5-Triazine-2,4,6-triamine (acd/name 4.0)HMDB
2,4, 6-triamino-1,3,5-TriazineHMDB
2,4,6-TriaminotriazineHMDB
2,4,6-Tris(1-aziridinyl)-S-triazineHMDB
4,6-diamino-1,2-dihydro-2-imino-S-TriazineHMDB
ADK stab ZS 27HMDB
AeroHMDB
CyanurtriamideHMDB
CymelHMDB
DG 002 (Amine)HMDB
Hicophor PRHMDB
IsomelamineHMDB
Mark ZS 27HMDB
PluragardHMDB
Pluragard C 133HMDB
Spinflam ML 94mHMDB
TeoharnHMDB
TheoharnHMDB
TriethylenemelamineHMDB
TrisaziridinyltriazineHMDB
Virset 656-4HMDB
YukamelamineHMDB
Melamine sulfate (1:1)MeSH
Melamine sulfate (1:2)MeSH
Melamine sulfate (2:1), dihydrateMeSH
Melamine sulfate (4:1), tetrahydrateMeSH
Melamine oxalate (1:1)MeSH
Melamine phosphateMeSH
Melamine sulfite (1:1)MeSH
Melamine sulfite (2:1), tetrahydrateMeSH
Melaminium citrateMeSH
Melamine bis(oxymethyl)phosphonic acid saltMeSH
Melamine sulfite (2:1), dihydrateMeSH
Melaminium acetate acetic acid solvateMeSH
Chemical FormulaC3H6N6
Average Molecular Weight126.1199
Monoisotopic Molecular Weight126.065394222
IUPAC Name1,3,5-triazinane-2,4,6-triimine
Traditional Namemelamine
CAS Registry Number108-78-1
SMILES
N=C1NC(=N)NC(=N)N1
InChI Identifier
InChI=1S/C3H6N6/c4-1-7-2(5)9-3(6)8-1/h(H6,4,5,6,7,8,9)
InChI KeyJDSHMPZPIAZGSV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 1,3,5-triazines. These are compounds containing a triazine ring, which is a heterocyclic ring, similar to the six-member benzene ring but with three carbons replaced by nitrogen atoms, at ring positions 1, 3, and 5.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTriazines
Sub Class1,3,5-triazines
Direct Parent1,3,5-triazines
Alternative Parents
Substituents
  • 1,3,5-triazine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Role

Environmental role:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point345 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.24 mg/mL at 20 °CNot Available
LogP-1.37Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.62 g/LALOGPS
logP-1.9ALOGPS
logP-0.66ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)4.28ChemAxon
pKa (Strongest Basic)18.36ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area107.64 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity62.14 m³·mol⁻¹ChemAxon
Polarizability11.24 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-3900000000-71dbc7269c93dda90b2cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-a41f1e20c8ec4934d360View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-ae6d1e3320b13071b833View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-0900000000-206bb0a304c5a8440070View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-1900000000-7e8a77b9e84e57bd7cefView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-1900000000-8e0523cbbcafd9f9db92View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-4900000000-e45e493846516172500bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-002r-9600000000-a6d255dfed4fa6c2633fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-9200000000-d8433e44aa15ddcbc086View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-1900000000-738eb18fe28cac903509View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-9200000000-dae6ee5dfe2d8ac93f80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014l-9000000000-fc1d6d3837aeaab95233View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-1900000000-91f26f642ce9612598a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-3e8b6a1a6fdb2209d0eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-d113db88468963a77c18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-e1ef56b1bf95f453711fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-1bfb2f0efa2647a0552dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-9600000000-9cf3208803e0b283879fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9000000000-425ba1390c5b2c68ebe3View in MoNA
MSMass Spectrum (Electron Ionization)splash10-004i-9800000000-c6f386c1797fc9995734View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7667
KEGG Compound IDC08737
BioCyc IDCPD-7398
BiGG IDNot Available
Wikipedia LinkMelamine
METLIN IDNot Available
PubChem Compound7955
PDB IDAX2
ChEBI ID27915
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available