Basic Info

Common NameMelamine(F04848)
2D Structure
Description

Melamine 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.

FRCD IDF04848
CAS Number108-78-1
PubChem CID7955
FormulaC3H6N6
IUPAC Name

1,3,5-triazine-2,4,6-triamine

InChI Key

JDSHMPZPIAZGSV-UHFFFAOYSA-N

InChI

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

Canonical SMILES

C1(=NC(=NC(=N1)N)N)N

Isomeric SMILES

C1(=NC(=NC(=N1)N)N)N

WikipediaMelamine
Synonyms
        
            MELAMINE
        
            1,3,5-Triazine-2,4,6-triamine
        
            108-78-1
        
            Cyanuramide
        
            Cyanurotriamide
        
            Cyanurotriamine
        
            Isomelamine
        
            Theoharn
        
            Teoharn
        
            Triaminotriazine
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassTriazines
Subclass1,3,5-triazines
Intermediate Tree NodesNot available
Direct Parent1,3,5-triazines
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
Substituents1,3,5-triazine - Heteroaromatic compound - Azacycle - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Aromatic heteromonocyclic compound
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.

Properties

Property NameProperty Value
Molecular Weight126.123
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count0
Complexity63.3
Monoisotopic Mass126.065
Exact Mass126.065
XLogP-1.4
Formal Charge0
Heavy Atom Count9
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.8805
Human Intestinal AbsorptionHIA+0.9592
Caco-2 PermeabilityCaco2+0.6815
P-glycoprotein SubstrateNon-substrate0.8019
P-glycoprotein InhibitorNon-inhibitor0.9809
Non-inhibitor0.9741
Renal Organic Cation TransporterNon-inhibitor0.8408
Distribution
Subcellular localizationLysosome0.5821
Metabolism
CYP450 2C9 SubstrateNon-substrate0.9000
CYP450 2D6 SubstrateNon-substrate0.8405
CYP450 3A4 SubstrateNon-substrate0.8372
CYP450 1A2 InhibitorNon-inhibitor0.7989
CYP450 2C9 InhibitorNon-inhibitor0.9769
CYP450 2D6 InhibitorNon-inhibitor0.9847
CYP450 2C19 InhibitorNon-inhibitor0.9654
CYP450 3A4 InhibitorNon-inhibitor0.9658
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9540
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9415
Non-inhibitor0.9336
AMES ToxicityNon AMES toxic0.9133
CarcinogensNon-carcinogens0.9202
Fish ToxicityLow FHMT0.9670
Tetrahymena Pyriformis ToxicityLow TPT0.7045
Honey Bee ToxicityLow HBT0.7980
BiodegradationNot ready biodegradable0.9289
Acute Oral ToxicityIII0.8086
Carcinogenicity (Three-class)Non-required0.5291

Model Value Unit
Absorption
Aqueous solubility-1.1392LogS
Caco-2 Permeability1.3097LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.6321LD50, mol/kg
Fish Toxicity2.9249pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.6563pIGC50, ug/L

References

TitleJournalDatePubmed ID
On-site detection of sub-mg/kg melamine mixed in powdered infant formula andchocolate using sharp-edged gold nanostar substrates.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2018Jun29727263
An Aptamer-Based Biosensor for Direct, Label-Free Detection of Melamine in Raw Milk.Sensors (Basel)2018 Sep 2530257498
Hits and misses in research trends to monitor contaminants in foods.Anal Bioanal Chem2018 Sep29951771
A Sensitive "Turn-On" Fluorescent Sensor for Melamine Based on FRET Effectbetween Polydopamine-Glutathione Nanoparticles and Ag Nanoparticles.J Agric Food Chem2018 Mar 729420884
Rapid, On-Site, Ultrasensitive Melamine Quantitation Method for Protein BeveragesUsing Time-Resolved Fluorescence Detection Paper.J Agric Food Chem2018 Jun 629719144
Melamine sponge decorated with copper sheets as a material with outstandingproperties for microextraction of sulfonamides prior to their determination byhigh-performance liquid chromatography.J Chromatogr A2018 Jun 1529653779
Liquid chromatography-mass spectrometry method for evaluating the dissipationdynamics of cyromazine and its metabolite in Agaricus bisporus and dietary riskassessment.Environ Sci Pollut Res Int2018 Jan29119493
Direct Detection of Toxic Contaminants in Minimally Processed Food Products Using Dendritic Surface-Enhanced Raman Scattering Substrates.Sensors (Basel)2018 Aug 1930126248
Cd-doped Sb<sub>2</sub>O<sub>4</sub> nanostructures modified glassy carbon electrode for efficient detection of melamine by electrochemical approach.Biosens Bioelectron2018 Apr 1529248717
Palliative effects of Moringa olifera ethanolic extract on hemato-immunologic impacts of melamine in rats.Food Chem Toxicol2018 Apr29438774
Non-targeted detection of milk powder adulteration using Raman spectroscopy andchemometrics: melamine case study.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2017Feb27841972
The effects of melamine with or without cyanuric acid on immune function in ovalbumin-sensitized mice.Res Vet Sci2017 Oct28527399
Colorimetric detection of melamine in milk by using gold nanoparticles-based LSPRvia optical fibers.PLoS One2017 May 528475597
Rapid sensing of melamine in milk by interference green synthesis of silvernanoparticles.Mater Sci Eng C Mater Biol Appl2017 May 128254292
Ultrafast self-assembly of silver nanostructures on carbon-coated copper gridsfor surface-enhanced Raman scattering detection of trace melamine.J Colloid Interface Sci2017 Mar 1527870955
One-step synthesis of graphitic carbon nitride nanosheets with the help ofmelamine and its application for fluorescence detection of mercuric ions.Talanta2017 Mar 128107958
Advantage of Eu3+ -Doped Polystyrene Microspheres Compared with Colloidal GoldUsed in Immunochromatographic Assays for the Detection of Melamine in Milk.J Food Sci2017 Mar28192612
Chromatographic separation and detection of contaminants from whole milk powderusing a chitosan-modified silver nanoparticles surface-enhanced Raman scattering device.Food Chem2017 Jun 128159284
A survey on trace organic chemicals in a German water protection area and theproposal of relevant indicators for anthropogenic influences.Environ Monit Assess2017 Jun28462476
Effects of the Adulteration Technique on the Near-Infrared Detection of Melamine in Milk Powder.J Agric Food Chem2017 Jul 1928617599

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 ]