Melamine
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Basic Info
Common Name | Melamine(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 ID | F04848 |
CAS Number | 108-78-1 |
PubChem CID | 7955 |
Formula | C3H6N6 |
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 |
Wikipedia | Melamine |
Synonyms | MELAMINE 1,3,5-Triazine-2,4,6-triamine 108-78-1 Cyanuramide Cyanurotriamide Cyanurotriamine Isomelamine Theoharn Teoharn Triaminotriazine |
Classifies | Pesticide |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Organoheterocyclic compounds |
Class | Triazines |
Subclass | 1,3,5-triazines |
Intermediate Tree Nodes | Not available |
Direct Parent | 1,3,5-triazines |
Alternative Parents | |
Molecular Framework | Aromatic heteromonocyclic compounds |
Substituents | 1,3,5-triazine - Heteroaromatic compound - Azacycle - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Aromatic heteromonocyclic compound |
Description | This 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 Name | Property Value |
---|---|
Molecular Weight | 126.123 |
Hydrogen Bond Donor Count | 3 |
Hydrogen Bond Acceptor Count | 6 |
Rotatable Bond Count | 0 |
Complexity | 63.3 |
Monoisotopic Mass | 126.065 |
Exact Mass | 126.065 |
XLogP | -1.4 |
Formal Charge | 0 |
Heavy Atom Count | 9 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.8805 |
Human Intestinal Absorption | HIA+ | 0.9592 |
Caco-2 Permeability | Caco2+ | 0.6815 |
P-glycoprotein Substrate | Non-substrate | 0.8019 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9809 |
Non-inhibitor | 0.9741 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.8408 |
Distribution | ||
Subcellular localization | Lysosome | 0.5821 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.9000 |
CYP450 2D6 Substrate | Non-substrate | 0.8405 |
CYP450 3A4 Substrate | Non-substrate | 0.8372 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.7989 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9769 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9847 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9654 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9658 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9540 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9415 |
Non-inhibitor | 0.9336 | |
AMES Toxicity | Non AMES toxic | 0.9133 |
Carcinogens | Non-carcinogens | 0.9202 |
Fish Toxicity | Low FHMT | 0.9670 |
Tetrahymena Pyriformis Toxicity | Low TPT | 0.7045 |
Honey Bee Toxicity | Low HBT | 0.7980 |
Biodegradation | Not ready biodegradable | 0.9289 |
Acute Oral Toxicity | III | 0.8086 |
Carcinogenicity (Three-class) | Non-required | 0.5291 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -1.1392 | LogS |
Caco-2 Permeability | 1.3097 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 1.6321 | LD50, mol/kg |
Fish Toxicity | 2.9249 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -0.6563 | pIGC50, ug/L |
References
Title | Journal | Date | Pubmed 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 Assess | 2018Jun | 29727263 |
An Aptamer-Based Biosensor for Direct, Label-Free Detection of Melamine in Raw Milk. | Sensors (Basel) | 2018 Sep 25 | 30257498 |
Hits and misses in research trends to monitor contaminants in foods. | Anal Bioanal Chem | 2018 Sep | 29951771 |
A Sensitive "Turn-On" Fluorescent Sensor for Melamine Based on FRET Effectbetween Polydopamine-Glutathione Nanoparticles and Ag Nanoparticles. | J Agric Food Chem | 2018 Mar 7 | 29420884 |
Rapid, On-Site, Ultrasensitive Melamine Quantitation Method for Protein BeveragesUsing Time-Resolved Fluorescence Detection Paper. | J Agric Food Chem | 2018 Jun 6 | 29719144 |
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 A | 2018 Jun 15 | 29653779 |
Liquid chromatography-mass spectrometry method for evaluating the dissipationdynamics of cyromazine and its metabolite in Agaricus bisporus and dietary riskassessment. | Environ Sci Pollut Res Int | 2018 Jan | 29119493 |
Direct Detection of Toxic Contaminants in Minimally Processed Food Products Using Dendritic Surface-Enhanced Raman Scattering Substrates. | Sensors (Basel) | 2018 Aug 19 | 30126248 |
Cd-doped Sb<sub>2</sub>O<sub>4</sub> nanostructures modified glassy carbon electrode for efficient detection of melamine by electrochemical approach. | Biosens Bioelectron | 2018 Apr 15 | 29248717 |
Palliative effects of Moringa olifera ethanolic extract on hemato-immunologic impacts of melamine in rats. | Food Chem Toxicol | 2018 Apr | 29438774 |
Non-targeted detection of milk powder adulteration using Raman spectroscopy andchemometrics: melamine case study. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2017Feb | 27841972 |
The effects of melamine with or without cyanuric acid on immune function in ovalbumin-sensitized mice. | Res Vet Sci | 2017 Oct | 28527399 |
Colorimetric detection of melamine in milk by using gold nanoparticles-based LSPRvia optical fibers. | PLoS One | 2017 May 5 | 28475597 |
Rapid sensing of melamine in milk by interference green synthesis of silvernanoparticles. | Mater Sci Eng C Mater Biol Appl | 2017 May 1 | 28254292 |
Ultrafast self-assembly of silver nanostructures on carbon-coated copper gridsfor surface-enhanced Raman scattering detection of trace melamine. | J Colloid Interface Sci | 2017 Mar 15 | 27870955 |
One-step synthesis of graphitic carbon nitride nanosheets with the help ofmelamine and its application for fluorescence detection of mercuric ions. | Talanta | 2017 Mar 1 | 28107958 |
Advantage of Eu3+ -Doped Polystyrene Microspheres Compared with Colloidal GoldUsed in Immunochromatographic Assays for the Detection of Melamine in Milk. | J Food Sci | 2017 Mar | 28192612 |
Chromatographic separation and detection of contaminants from whole milk powderusing a chitosan-modified silver nanoparticles surface-enhanced Raman scattering device. | Food Chem | 2017 Jun 1 | 28159284 |
A survey on trace organic chemicals in a German water protection area and theproposal of relevant indicators for anthropogenic influences. | Environ Monit Assess | 2017 Jun | 28462476 |
Effects of the Adulteration Technique on the Near-Infrared Detection of Melamine in Milk Powder. | J Agric Food Chem | 2017 Jul 19 | 28617599 |
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
- 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 ]