ContaminantDB: Metaldehyde

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2009-07-30 17:59:01 UTC

Update Date

2016-11-09 01:08:53 UTC

Accession Number

CHEM002524

Identification

Common Name

Metaldehyde

Class

Small Molecule

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. (1)

Contaminant Sources

STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Household Toxin
Lachrymator
Organic Compound
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Metacetaldehyde	MeSH

Chemical Formula

C₈H₁₆O₄

Average Molecular Mass

176.210 g/mol

Monoisotopic Mass

176.105 g/mol

CAS Registry Number

108-62-3

IUPAC Name

2,4,6,8-tetramethyl-1,3,5,7-tetraoxocane

Traditional Name

metaldehyde

SMILES

CC1OC(C)OC(C)OC(C)O1

InChI Identifier

InChI=1S/C8H16O4/c1-5-9-6(2)11-8(4)12-7(3)10-5/h5-8H,1-4H3

InChI Key

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Acetals

Alternative Parents

Substituents

Oxacycle
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

acetal (CHEBI:81931 )
Molluscacide (C18744 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Colourless or white powder crystals with a mild characteristic odour. (2)

Experimental Properties

Property	Value
Melting Point	246°C
Boiling Point	110-120 °C
Solubility	200 mg/L (at 17 °C)

Predicted Properties

Property	Value	Source
Water Solubility	87.8 g/L	ALOGPS
logP	0.96	ALOGPS
logP	1.17	ChemAxon
logS	-0.3	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	36.92 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	42.78 m³·mol⁻¹	ChemAxon
Polarizability	18.76 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0043-9600000000-aff896a31bab36179c25	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-1900000000-3a0583ef3e71ce6c831d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000j-9200000000-bc04a03537d8c1fc6e1b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-fb4cb731680420af219e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-1fbd74de738f9bd884cc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-2900000000-1526b460542bcfef4922	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9100000000-9c9a1554992bbbe5388a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-ca808b2786d3287a7be2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-2900000000-5a5f4674bce9964d8be1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006t-9100000000-c5f5078331472e7678c9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05i9-9500000000-7198ed360e8398923d71	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052f-9000000000-e7d24bbcda04dd8a7b2f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-7de1757678e99237833f	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-addd53e7c97dd0a41373	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (1) ; inhalation (1) ; dermal (1)

Mechanism of Toxicity

The 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)

Metabolism

Metaldehyde 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 Values

LD50: 630 mg/kg (Oral, Rat) (1) LD50: 600 mg/kg (Oral, Dog) (1)

Lethal Dose

50 to 500 mg/kg orally for an adult human. (1)

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Metaldehyde 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 Level

Not Available

Health Effects

Metaldehyde 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)

Symptoms

Ingestion 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)

Treatment

Measures 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)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Metaldehyde

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

61021

Kegg Compound ID

C18744

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Metaldehyde (CHEM002524)

Structure for CHEM002524: Metaldehyde