Melamine (CHEM002523)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2009-07-30 17:59:01 UTC
Update Date2016-11-09 01:08:53 UTC
Accession NumberCHEM002523
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.
Contaminant Sources
  • HPV EPA Chemicals
  • IARC Carcinogens Group 3
  • OECD HPV Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Aromatic Hydrocarbon
  • Food Toxin
  • Household Toxin
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Lachrymator
  • Metabolite
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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)HMDB
Melamine sulfate (1:2)HMDB
Melamine sulfate (2:1), dihydrateHMDB
Melamine sulfate (4:1), tetrahydrateHMDB
Melamine oxalate (1:1)HMDB
Melamine phosphateHMDB
Melamine sulfite (1:1)HMDB
Melamine sulfite (2:1), tetrahydrateHMDB
Melaminium citrateHMDB
Melamine bis(oxymethyl)phosphonic acid saltHMDB
Melamine sulfite (2:1), dihydrateHMDB
Melaminium acetate acetic acid solvateHMDB
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 KeyJDSHMPZPIAZGSV-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
Predicted Properties
PropertyValueSource
Water Solubility0.62 g/LALOGPS
logP-1.9ALOGPS
logP-0.66ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)4.11ChemAxon
pKa (Strongest Basic)23.07ChemAxon
Physiological Charge1ChemAxon
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-3900000000-71dbc7269c93dda90b2cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-a41f1e20c8ec4934d360Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-ae6d1e3320b13071b833Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-0900000000-206bb0a304c5a8440070Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-1900000000-7e8a77b9e84e57bd7cefSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-1900000000-8e0523cbbcafd9f9db92Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-4900000000-e45e493846516172500bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-002r-9600000000-a6d255dfed4fa6c2633fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-9200000000-d8433e44aa15ddcbc086Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-1900000000-738eb18fe28cac903509Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-9200000000-dae6ee5dfe2d8ac93f80Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014l-9000000000-fc1d6d3837aeaab95233Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-1900000000-91f26f642ce9612598a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-000i-9200000000-d8433e44aa15ddcbc086Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-002r-9600000000-a6d255dfed4fa6c2633fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-1900000000-838ef9febd7e2e0b2feaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-004i-1900000000-736ea73ed36f89306de1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0900000000-2c40f1fca432608a00d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0900000000-00f72d1e1bb88e391cb8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-ab81cf47f2116f7fa324Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-3e8b6a1a6fdb2209d0eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-d113db88468963a77c18Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-e1ef56b1bf95f453711fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-1bfb2f0efa2647a0552dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-9600000000-9cf3208803e0b283879fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9000000000-425ba1390c5b2c68ebe3Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-9800000000-c6f386c1797fc9995734Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0041922
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-7398
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMelamine
Chemspider ID7667
ChEBI ID27915
PubChem Compound ID7955
Kegg Compound IDC08737
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19193777
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19899757
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23752785
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24121226
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24182201
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24206822
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24297478
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24327168
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24339199
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24355167
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24397789
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24460139
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=24507656
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=24530299
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24533440
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=24582682
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=24607582
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=24720965
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=24725874
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=24727351
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=24730385
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=24734554
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=24742261
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=24759748
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=24767052
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=24785124