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Record Information
Version2.0
Creation Date2009-07-30 17:59:01 UTC
Update Date2014-12-24 20:26:07 UTC
Accession NumberT3D3520
Identification
Common NameMelamine
ClassSmall Molecule
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 described as Harmful if swallowed, inhaled or absorbed through the skin. Chronic exposure may cause cancer or reproductive damage. Eye, skin and respiratory irritant. However, the short-term lethal dose is on a par with common table salt with an LD50 of more than 3 grams per kilogram of bodyweight.[15] U.S. Food and Drug Administration (FDA) scientists explained that when melamine and cyanuric acid are absorbed into the bloodstream, they concentrate and interact in the urine-filled renal tubules, then crystallize and form large numbers of round, yellow crystals, which in turn block and damage the renal cells that line the tubes, causing the kidneys to malfunction.
Compound Type
  • Amine
  • Aromatic Hydrocarbon
  • Food Toxin
  • Household Toxin
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Lachrymator
  • Metabolite
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
1,3, 5-Triazine-2,4,6-triamine
1,3,5-Triazine-2,4,6(1H,3H,5H)-triimine
1,3,5-Triazine-2,4,6-triamine
2,4, 6-Triamino-1,3,5-triazine
2,4,6-Triamino-1,3,5-triazine
2,4,6-Triamino-S-Triazine
2,4,6-Triaminotriazine
2,4,6-Tris(1-aziridinyl)-S-triazine
4,6-Diamino-1,2-dihydro-2-imino-S-Triazine
ADK Stab ZS 27
Aero
Cyanuramide
Cyanuric triamide
Cyanurotriamide
Cyanurotriamine
Cyanurtriamide
Cymel
DG 002 (amine)
Hicophor PR
Isomelamine
Mark ZS 27
Pluragard
Pluragard C 133
S-Triazinetriamine
Spinflam ML 94M
Sym-triaminotriazine
Teoharn
Theoharn
Triaminotriazine
Virset 656-4
Yukamelamine
Chemical FormulaC3H6N6
Average Molecular Mass126.120 g/mol
Monoisotopic Mass126.065 g/mol
CAS Registry Number108-78-1
IUPAC Name1,3,5-triazinane-2,4,6-triimine
Traditional Namemelamine
SMILESN=C1NC(=N)NC(=N)N1
InChI IdentifierInChI=1S/C3H6N6/c4-1-7-2(5)9-3(6)8-1/h(H6,4,5,6,7,8,9)
InChI KeyInChIKey=JDSHMPZPIAZGSV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,3,5-triazines. 1,3,5-triazines 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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder. (1)
Experimental Properties
PropertyValue
Melting Point345°C
Boiling Point> 280 °C
Solubility3.24 mg/mL at 20°C
LogP-1.37
Predicted Properties
PropertyValueSource
Water Solubility0.625 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity62.14 m3·mol-1ChemAxon
Polarizability11.24 Å3ChemAxon
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-MSsplash10-004i-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 Available
Toxicity Profile
Route of ExposureOral (1) ; inhalation (1) ; dermal (1)
Mechanism of ToxicityMelamine causes carcinomas of the urinary bladder at high doses (in male rats). Formation of bladder stones occurred and these calculi are necessary for the induction of tumours. Carcinomas are induced by continuous irritation of the bladder epithelium by the calculi, so that melamine acts only indirectly as a non-genotoxic carcinogen. (2)
MetabolismMelamine is not metabolized and is rapidly eliminated via urine in a study with oral application to rats. (2)
Toxicity ValuesLD50: 3161 mg/kg (Oral, Rat) (2) LD50: 3296 mg/kg (Oral, Mouse) (2) LD50: > 1000 mg/kg (Dermal, Rabbit) (2) LC50: 3248 mg/m3 (Inhalation, Rat) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (4)
Uses/SourcesMelamine has many industrial uses, including the production of laminates, glues, adhesives, moulding compounds, coatings and flame retardants. It is also used in some fertilizers and in the production of melamine resins, typically by reaction with formaldehyde. Melamine is a metabolite of the pesticide cyromazine in plants, goats, hens and rats. (1) (3)
Minimum Risk LevelNot Available
Health EffectsStudies ranging from skin irritation to carcinogenicity are available. Melamine is not genotoxic but it causes carcinomas of the urinary bladder at high doses. Melamine is not irritating to skin and eye, not sensitising and not teratogenic. (2)
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB41922
PubChem Compound ID7955
ChEMBL IDCHEMBL1231106
ChemSpider ID7667
KEGG IDC08737
UniProt IDNot Available
OMIM ID
ChEBI ID27915
BioCyc IDDIHYDRO-DIOH-BENZOATE
CTD IDNot Available
Stitch IDMelamine
PDB IDAX2
ACToR ID817
Wikipedia LinkMelamine
References
Synthesis ReferenceNot Available
MSDSLink
General References
  1. Wikipedia. Melamine. Last updated 10 August 2009. [Link]
  2. International Programme on Chemical Safety (IPCS) INCHEM (2002). OECD Screening Information DataSet (SIDS). High Production Volume Chemicals. Melamine. [Link]
  3. World Health Organization (2008). Melamine and Cyanuric acid: toxicity, preliminary risk assessment and guidance on levels in food. [Link]
  4. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available

Targets

General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]