Metaldehyde
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Basic Info
| Common Name | Metaldehyde(F04849) |
| 2D Structure | |
| Description | Metaldehyde is a cyclic tetramer of acetaldehyde commonly used as a pesticide against slugs, snails, and other gastropods. Metaldehyde intoxication leads to central nervous system depression, and liver and kidney injury. (L1782) |
| FRCD ID | F04849 |
| CAS Number | 108-62-3 |
| PubChem CID | 61021 |
| Formula | C8H16O4 |
| IUPAC Name | 2,4,6,8-tetramethyl-1,3,5,7-tetraoxocane |
| InChI Key | GKKDCARASOJPNG-UHFFFAOYSA-N |
| InChI | InChI=1S/C8H16O4/c1-5-9-6(2)11-8(4)12-7(3)10-5/h5-8H,1-4H3 |
| Canonical SMILES | CC1OC(OC(OC(O1)C)C)C |
| Isomeric SMILES | CC1OC(OC(OC(O1)C)C)C |
| Wikipedia | Metaldehyde |
| Synonyms |
Halizan
Corry's Slug Death
METALDEHYDE
Metacetaldehyde
108-62-3
Cekumeta
Ariotox
Metason
Acetaldehyde, tetramer
Slug-Tox
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Ethers |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Acetals |
| Alternative Parents | |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Substituents | Oxacycle - Organoheterocyclic compound - Acetal - Hydrocarbon derivative - Aliphatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as acetals. These are compounds having the structure R2C(OR')2 ( R' not Hydrogen) and thus diethers of geminal diols. Originally, the term was confined to derivatives of aldehydes (one R = H), but it now applies equally to derivatives of ketones (neither R = H ). Mixed acetals have different R' groups. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 176.212 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 0 |
| Complexity | 91 |
| Monoisotopic Mass | 176.105 |
| Exact Mass | 176.105 |
| XLogP | 1.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 12 |
| 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+ | 0.9711 |
| Human Intestinal Absorption | HIA+ | 0.9806 |
| Caco-2 Permeability | Caco2+ | 0.6242 |
| P-glycoprotein Substrate | Non-substrate | 0.7888 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9254 |
| Non-inhibitor | 0.9626 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9569 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5031 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8544 |
| CYP450 2D6 Substrate | Non-substrate | 0.8798 |
| CYP450 3A4 Substrate | Non-substrate | 0.7298 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8434 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9532 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9634 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9493 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9312 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9415 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9739 |
| Non-inhibitor | 0.9874 | |
| AMES Toxicity | Non AMES toxic | 0.7231 |
| Carcinogens | Non-carcinogens | 0.6612 |
| Fish Toxicity | Low FHMT | 0.7599 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.8381 |
| Honey Bee Toxicity | High HBT | 0.8345 |
| Biodegradation | Not ready biodegradable | 0.9007 |
| Acute Oral Toxicity | II | 0.7434 |
| Carcinogenicity (Three-class) | Non-required | 0.5705 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.8295 | LogS |
| Caco-2 Permeability | 1.0638 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.8586 | LD50, mol/kg |
| Fish Toxicity | 2.0680 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.8869 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Kidney Beans,Immature(With Pods) | Japan | 1ppm | |||
| Soybeans,Dry | Japan | 1ppm | |||
| Broad Beans | Japan | 1ppm | |||
| Peas | Japan | 1ppm | |||
| Corn(Maize) | Japan | 1ppm | |||
| Potato | Austria | 0. 2mg/kg | |||
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.05* | 20/10/2017 | |
| Citrus fruits | 0110000 | European Union | 0.05* | 20/10/2017 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.05* | 20/10/2017 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.05* | 20/10/2017 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.05* | 20/10/2017 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.05* | 20/10/2017 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.05* | 20/10/2017 | |
| Others (2) | 0110990 | European Union | 0.05* | 20/10/2017 | |
| Tree nuts | 0120000 | European Union | 0.05* | 20/10/2017 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.05* | 20/10/2017 | |
| Brazil nuts | 0120020 | European Union | 0.05* | 20/10/2017 | |
| Cashew nuts | 0120030 | European Union | 0.05* | 20/10/2017 | |
| Chestnuts | 0120040 | European Union | 0.05* | 20/10/2017 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.05* | 20/10/2017 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Metaldehyde Poisoning of Companion Animals: A Three-year Retrospective Study. | J Vet Res | 2017 Sep 19 | 29978088 |
| Toxicoses of the Ruminant Nervous System. | Vet Clin North Am Food Anim Pract | 2017 Mar | 28166935 |
| Pesticide incidence in poisoned baits: A 10-year report. | Sci Total Environ | 2017 Dec 1 | 28564626 |
| Dissipation, residues and risk assessment of metaldehyde and niclosamideethanolamine in pakchoi after field application. | Food Chem | 2017 Aug 15 | 28372221 |
| Evaluation of the in vitro efficacy of hemodialysis, hemoperfusion, and thecombined approach on the removal of metaldehyde from canine plasma. | J Vet Emerg Crit Care (San Antonio) | 2016 Jul | 27219514 |
| Suspected poisoning of domestic animals by pesticides. | Sci Total Environ | 2016 Jan 1 | 26367188 |
| Control measures for slug and snail hosts of Angiostrongylus cantonensis, withspecial reference to the semi-slug Parmarion martensi. | Hawaii J Med Public Health | 2013 Jun | 23901389 |
| Death by caffeine: presumptive malicious poisoning of a dog by incorporation inground meat. | J Med Toxicol | 2012 Dec | 23104127 |
| Analysis of molluscicide metaldehyde in vegetables by dispersive solid-phaseextraction and liquid chromatography-tandem mass spectrometry. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2011Aug | 21598139 |
| Backbone cyclised peptides from plants show molluscicidal activity against the rice pest Pomacea canaliculata (golden apple snail). | J Agric Food Chem | 2008 Jul 9 | 18557620 |
| Identification of environmental factors limiting plant uptake of metaldehyde seedtreatments under field conditions. | J Agric Food Chem | 2006 May 17 | 19127739 |
| A laboratory-based comparison of a molluscicide and an alternative food source(red clover) as means of reducing slug damage to winter wheat. | Pest Manag Sci | 2005 Jul | 15838932 |
| [Case report-fatal snail bait (metaldehyde) overdose presenting aspirationpneumonia]. | Chudoku Kenkyu | 2003 Oct | 14740568 |
| Seed dressings to control slug damage in oilseed rape. | Pest Manag Sci | 2002 Jul | 12146169 |
| Determination of metaldehyde in suspected cases of animal poisoning using gaschromatography-ion trap mass spectrometry. | J Agric Food Chem | 1999 Nov | 10552870 |
| 4-week oral toxicity study of a combination of eight chemicals in rats:comparison with the toxicity of the individual compounds. | Food Chem Toxicol | 1990 Sep | 2272560 |
| Practical toxicologic diagnosis. | Mod Vet Pract | 1984 Aug | 6493203 |
| Long-term toxicity and reproduction studies with metaldehyde in rats. | Toxicology | 1975 | 1129810 |
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 ]