Metaldehyde (T3D3521)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-07-30 17:59:01 UTC
Update Date2014-12-24 20:26:07 UTC
Accession NumberT3D3521
Identification
Common NameMetaldehyde
ClassSmall Molecule
DescriptionMetaldehyde 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. (1)
Compound Type
  • Household Toxin
  • Lachrymator
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
2,4,6,8-Tetramethyl-1,3,5,7-tetraoxacyclooctane
2,4,6,8-Tetramethyl-1,3,5,7-tetroxocane
Acetaldehyde tetramer
Agrimort
Ariotox
Cekumeta
Corry's slug death
Halizan
Helarion
Lumacrusk5
Metacetaldehyde
Metaldehyd
Metaldeide
Puzomor
r-2,c-4,c-6,c-8-Tetramethyl-1,3,5,7-tetroxocane
Slug-tox
Snail-kil
Suprasnail
Chemical FormulaC8H16O4
Average Molecular Mass176.210 g/mol
Monoisotopic Mass176.105 g/mol
CAS Registry Number108-62-3
IUPAC Name2,4,6,8-tetramethyl-1,3,5,7-tetraoxocane
Traditional Namemetaldehyde
SMILESCC1OC(C)OC(C)OC(C)O1
InChI IdentifierInChI=1S/C8H16O4/c1-5-9-6(2)11-8(4)12-7(3)10-5/h5-8H,1-4H3
InChI KeyInChIKey=GKKDCARASOJPNG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acetals. Acetals 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentAcetals
Alternative Parents
Substituents
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic 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 RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceColourless or white powder crystals with a mild characteristic odour. (2)
Experimental Properties
PropertyValue
Melting Point246°C
Boiling Point110-120 °C
Solubility200 mg/L (at 17 °C)
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility87.8 g/LALOGPS
logP0.96ALOGPS
logP1.17ChemAxon
logS-0.3ALOGPS
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area36.92 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.78 m³·mol⁻¹ChemAxon
Polarizability18.76 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0043-9600000000-aff896a31bab36179c252021-09-24View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-3a0583ef3e71ce6c831d2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-9200000000-bc04a03537d8c1fc6e1b2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-fb4cb731680420af219e2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-1fbd74de738f9bd884cc2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2900000000-1526b460542bcfef49222016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9100000000-9c9a1554992bbbe5388a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-ca808b2786d3287a7be22021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-5a5f4674bce9964d8be12021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-9100000000-c5f5078331472e7678c92021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05i9-9500000000-7198ed360e8398923d712021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-9000000000-e7d24bbcda04dd8a7b2f2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-7de1757678e99237833f2021-10-12View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-addd53e7c97dd0a413732014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-10-25View Spectrum
Toxicity Profile
Route of ExposureOral (1) ; inhalation (1) ; dermal (1)
Mechanism of ToxicityThe toxicologically active substance in metaldehyde intoxication is mainly the degradation product acetaldehyde; other toxic products are probably also formed. Acetaldehyde acts as a releasing factor for 5-hydroxytryptamine (5-HT) and noradrenaline (NA). It also competitively inhibits biogenic amine oxidation which, in turn, decreases 5-hydroxyindoleacetic acid (5-HIAA), a metabolite of 5-HT by competitively inhibiting 5-HT-oxidation. Acetaldehyde also increases monoamine oxidase activity and decreases central serotonin levels. (1)
MetabolismMetaldehyde is absorbed from the gastrointestinal tract and may be absorbed from the skin or lungs. Metaldehyde slowly hydrolyses to acetaldehyde in acid solutions (i.e., in the stomach). Acetaldehyde is then oxidized to acetic acid. (2)
Toxicity ValuesLD50: 630 mg/kg (Oral, Rat) (1) LD50: 600 mg/kg (Oral, Dog) (1)
Lethal Dose50 to 500 mg/kg orally for an adult human. (1)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesMetaldehyde is used as a pesticide against slugs, snails, and other gastropods, it is also used in tablets as a solid fuel for small heaters, and as fire-starter. (1)
Minimum Risk LevelNot Available
Health EffectsMetaldehyde intoxicatin leads to central nervous system depression, and liver and kidney injury. Death from respiratory failure can occur within a few hours of exposure. (2)
SymptomsIngestion is the most common route of metaldehyde poisoning. One to three hours after ingestion the following can occur: severe abdominal pain, nausea, salivation, vomiting, facial flushing, gastroenteritis, diarrhoea, metabolic acidosis, a marked rise in body temperature, drowsiness, convulsions, muscular rigidity, spasms, rhabdomyolysis and coma. Pulse and respiratory rate become progressively slower. Liver and kidney injury occurs at a later stage. Metaldehyde fumes may cause somnolence, uncoordinated movements, nausea, dizziness, CNS-depression, convulsions, and coma. Metaldehyde is also irritant to eyes and skin. (2)
TreatmentMeasures to eliminate the substance from the gastrointestinal tract should be especially emphasized because metaldehyde is slowly absorbed and eliminated in the gastrointestinal tract. There is no specific antidote. (2)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID61021
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDC00084
UniProt IDNot Available
OMIM ID100650
ChEBI ID15343
BioCyc IDACETALD
CTD IDNot Available
Stitch IDMetaldehyde
PDB IDNot Available
ACToR ID7888
Wikipedia LinkMetaldehyde
References
Synthesis ReferenceNot Available
MSDST3D3521.pdf
General References
  1. Wikipedia. Metaldehyde. Last updated 22 July 2009. [Link]
  2. International Programme on Chemical Safety (IPCS) INCHEM (1995). Poison Information Monograph for Metaldehyde. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Transient receptor potential cation channel subfamily A member 1
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 ]