Showing Compound Card for Melamine (CDB000497)

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Record Information
Version1.0
Created at2020-03-19 00:40:13 UTC
Updated at2020-12-07 19:07:28 UTC
CannabisDB IDCDB000497
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMelamine
DescriptionMelamine, also known as cyanurotriamide or pluragard, belongs to the class of organic compounds known as 1,3,5-triazines. Melamine is an organic compound with the formula C3H6N6. 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. Melamine is an extremely strong basic compound (based on its pKa). Melamine is a potentially toxic compound. This white solid is a trimer of cyanamide, with a 1,3,5-triazine skeleton. Like cyanamide, it contains 67 % nitrogen by mass and, if mixed with resins, has fire retardant properties due to its release of nitrogen gas when burned or charred. Additionally, it has several other industrial uses. Melamine is also a metabolite of the pesticide cyromazine, formed in the body of mammals after ingesting 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 wastewater, which is a pollutant if discharged directly into the environment. The wastewater 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 wastewater 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 lifetime. Melamine has been detected as a volatile component of cannabis (PMID: 26657499 ) and, as such, it can also be detected as constituent of marijuana smoke ( Ref:DOI ).
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 Weight126.12
Monoisotopic Molecular Weight126.0654
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
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
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
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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004i-9800000000-c6f386c1797fc99957342014-09-20View Spectrum
Predicted GC-MSMelamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-3900000000-71dbc7269c93dda90b2cSpectrum
Predicted GC-MSMelamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-a41f1e20c8ec4934d3602017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-ae6d1e3320b13071b8332017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-0900000000-206bb0a304c5a84400702017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-1900000000-7e8a77b9e84e57bd7cef2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-1900000000-8e0523cbbcafd9f9db922017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-4900000000-e45e493846516172500b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-002r-9600000000-a6d255dfed4fa6c2633f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-9200000000-d8433e44aa15ddcbc0862017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-1900000000-738eb18fe28cac9035092017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-9200000000-dae6ee5dfe2d8ac93f802017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014l-9000000000-fc1d6d3837aeaab952332017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-1900000000-91f26f642ce9612598a12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-000i-9200000000-d8433e44aa15ddcbc0862021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-002r-9600000000-a6d255dfed4fa6c2633f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-1900000000-838ef9febd7e2e0b2fea2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-004i-1900000000-736ea73ed36f89306de12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0900000000-2c40f1fca432608a00d32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0900000000-00f72d1e1bb88e391cb82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-ab81cf47f2116f7fa3242021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-3e8b6a1a6fdb2209d0ea2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-d113db88468963a77c182016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-e1ef56b1bf95f453711f2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-1bfb2f0efa2647a0552d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-9600000000-9cf3208803e0b283879f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9000000000-425ba1390c5b2c68ebe32016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0041922
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 IDNot Available
ChEBI ID27915
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]