Record Information
Version1.0
Creation Date2009-06-09 17:20:39 UTC
Update Date2026-08-17 20:56:54 UTC
Accession NumberCHEM000740
Identification
Common NameMirex
ClassSmall Molecule
Description
Mirex is a a chlorinated hydrocarbon , a manufactured insecticide. It was used to control fire ants, and as a flame retardant in plastics, rubber, paint, paper, and electrical goods. However, its used was banned in 1976 due to its toxicity and nature as a persistent organic pollutant. (4, 5). Mirex is only moderately toxic in single-dose animal studies (oral LD50 values range from 365Р3000 mg/kg body weight).[6] It can enter the body via inhalation, ingestion, and via the skin. The most sensitive effects of repeated exposure in animals are principally associated with the liver, and these effects have been observed with doses as low as 1.0 mg/kg diet (0.05 mg/kg body weight per day), the lowest dose tested. At higher dose levels, it is fetotoxic (25 mg/kg in diet) and teratogenic (6.0 mg/kg per day). Mirex was not generally active in short-term tests for genetic activity. There is sufficient evidence of its carcinogenicity in mice and rats. Delayed onset of toxic effects and mortality is typical of mirex poisoning. Mirex is toxic for a range of aquatic organisms, with crustacea being particularly sensitive.
Contaminant Sources
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • Pesticide
  • Pollutant
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
1,2,3,4,5,5,6,7,8,9,10,10-Dodecachloropentacyclo[5.3.0.0(2,6).0(3,9).0(4,8)]decaneChEBI
CG-1283ChEBI
DechloraneChEBI
Dodecachlorooctahydro-1,3,4-metheno-2H-cyclobuta[CD]pentaleneChEBI
PerchlorodihomocubaneChEBI
Perchloropentacyclo[5.2.1.0(2,6).0(3,9).0(5,8)]decaneChEBI
PerchloropentacyclodecaneChEBI
Chemical FormulaC10Cl12
Average Molecular Mass545.543 g/mol
Monoisotopic Mass539.626 g/mol
CAS Registry Number2385-85-5
IUPAC Namedodecachloropentacyclo[5.3.0.0²,⁶.0³,⁹.0⁴,⁸]decane
Traditional Namemirex
SMILESClC12C3(Cl)C4(Cl)C5(Cl)C(Cl)(C1(Cl)C4(Cl)Cl)C2(Cl)C(Cl)(Cl)C35Cl
InChI IdentifierInChI=1S/C10Cl12/c11-1-2(12)7(17)4(14)3(13,5(1,15)9(7,19)20)6(1,16)10(21,22)8(2,4)18
InChI KeyGVYLCNUFSHDAAW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMonoterpenoids
Alternative Parents
Substituents
  • Norbornane monoterpenoid
  • Monoterpenoid
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite crystals.
Experimental Properties
PropertyValue
Melting Point485°C
Boiling PointNot Available
Solubility8.5e-05 mg/mL at 25°C [YALKOWSKY,SH & HE,Y (2003)]
Predicted Properties
PropertyValueSource
Water Solubility0.00022 g/LALOGPS
logP6.61ALOGPS
logP7.63ChemAxon
logS-6.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity92.36 m³·mol⁻¹ChemAxon
Polarizability39.41 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4)
Mechanism of ToxicityMirex inhibits sodium/potassium-transporting ATPases, producing neurotoxic effects and impairing energy-dependent cellular processes. (1)
MetabolismMirex is mainly absorbed through the gastrointestional tract, but may also be absorbed through the lungs and skin. Once absorbed, mirex is widely distributed throughout the body but is sequestered in the adipose tissue. It has a long retention time in the body. Mirex is not metabolized by humans and is excreted unchanged in the feces. (4)
Toxicity ValuesLD50: 306 mg/kg (Oral, Rat) (6) LD50: 800 mg/kg (Subcutaneous, Rabbit) (6) LD50: 2000 mg/kg (Dermal, Rabbit) (7) LD50: 365 mg/kg (Intraperitoneal, Rat) (7)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (3)
Uses/SourcesMirex is an insecticide used to control fire ants. It was also used as a flame retardant in plastics, rubber, paint, paper, and electrical goods. (4)
Minimum Risk LevelChronic Oral: 0.0008 mg/kg/day (2)
Health EffectsAnimal studies have shown that ingesting high levels of mirex can harm the stomach, intestine, liver, kidneys, eyes, thyroid, and nervous and reproductive systems. (4)
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0059573
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMirex
Chemspider ID16054
ChEBI ID34852
PubChem Compound ID16945
Kegg Compound IDC14184
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. The lipid handbook with CD-ROM