ContaminantDB: Methoxychlor

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (51)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:00 UTC

Update Date

2026-03-26 21:38:44 UTC

Accession Number

CHEM000057

Identification

Common Name

Methoxychlor

Class

Small Molecule

Description

Methoxychlor is a manufactured organochlorine used as an insecticide against flies, mosquitoes, cockroaches, chiggers, and a wide variety of other insects. It is used on agricultural crops and livestock, and in animal feed, barns, grain storage bins, home garden, and on pets. (4)

Contaminant Sources

Clean Air Act Chemicals
HPV EPA Chemicals
IARC Carcinogens Group 3
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Ether
Household Toxin
Organic Compound
Organochloride
Pesticide
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,1,1-Trichloro-2,2-bis(p-anisyl)ethane	ChEBI
1,1,1-Trichloro-2,2-bis(p-methoxyphenyl)ethane	ChEBI
1,1,1-Trichloro-2,2-di(4-methoxyphenyl)ethane	ChEBI
2,2-Bis(p-anisyl)-1,1,1-trichloroethane	ChEBI
2,2-Bis(p-methoxyphenyl)-1,1,1-trichloroethane	ChEBI
2,2-Di(p-methoxyphenyl)-1,1,1-trichloroethane	ChEBI
Dimethoxy-DDT	ChEBI
Methoxy-DDT	ChEBI
p,P'-methoxychlor	ChEBI
DMDT	MeSH
Dianisyl trichloroethane	MeSH
Metox	MeSH
Trichloroethane, dianisyl	MeSH

Chemical Formula

C₁₆H₁₅Cl₃O₂

Average Molecular Mass

345.648 g/mol

Monoisotopic Mass

344.014 g/mol

CAS Registry Number

72-43-5

IUPAC Name

1-methoxy-4-[2,2,2-trichloro-1-(4-methoxyphenyl)ethyl]benzene

Traditional Name

methoxychlor

SMILES

COC1=CC=C(C=C1)C(C1=CC=C(OC)C=C1)C(Cl)(Cl)Cl

InChI Identifier

InChI=1S/C16H15Cl3O2/c1-20-13-7-3-11(4-8-13)15(16(17,18)19)12-5-9-14(21-2)10-6-12/h3-10,15H,1-2H3

InChI Key

IAKOZHOLGAGEJT-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
Alkyl aryl ether
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organochlorine insecticide (CHEBI:6842 )
Organochlorine pesticides (C11043 )
Organochlorine insecticides (C11043 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

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

Pale-yellow powder.

Experimental Properties

Property	Value
Melting Point	87°C
Boiling Point	decomposes
Solubility	0.0001 mg/mL at 25 °C [RICHARDSON,LT & MILLER,DM (1960)]

Predicted Properties

Property	Value	Source
Water Solubility	5.0e-05 g/L	ALOGPS
logP	5.12	ALOGPS
logP	4.93	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	88.63 m³·mol⁻¹	ChemAxon
Polarizability	33.73 Å³	ChemAxon
Number of Rings	2	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	splash10-004i-1971000000-4fbe894594f70340930a	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	splash10-0002-0009000000-2e804c4f3f24a4e46581	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0009000000-516eca78c6054fdac1c9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056s-0094000000-0899ba6b67a346aceb9a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-18acae4dc611644d1dbc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0009000000-0329df7d38acce6cb9e0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-0096000000-8cdb61fec75829abaaff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0009000000-dce8fb33a0c965cbe9f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0009000000-dce8fb33a0c965cbe9f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0abc-0936000000-264ea7b60a4327600cb8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-759859808f25135a319c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0119000000-a719a8b43c24aa70e92b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-022a-1190000000-34b6b5934b45b81b92ff	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-0290000000-06ed9842894de6c2fed3	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (4) ; dermal (4)

Mechanism of Toxicity

Certain mono- and bis-hydroxy metabolites of methoxychlor, especially 2,2-bis(p-hydroxyphenyl)-1,1, 1-trichloroethane (HPTE), act as estrogen analogues. HPTE is an estrogen receptor alpha agonist, and also acts as an antagonist at the estrogen receptor beta and androgen receptor. This affects protein synthesis, which is believed to cause many of methoxychlor's estrogenic effects, such as decreased fertility. As methoxychlor is also a structural analogue of DDT, it is believed to have the same neurotoxic effects. This includes preventing the deactivation of the sodium gate after neuron activation and membrane depolarization, resulting in hyperexcitability of the nerve. Like DDT, methoxychlor may also inhibit neuronal adenosine triphosphatases (ATPases), particularly Na+K+-ATPase and Ca2+-ATPase, which play vital roles in neuronal repolarization. This contributes to the reduced rate of depolarization and increases the sensitivity of neurons to small stimuli that would not elicit a response in a fully depolarized neuron. (5, 1)

Metabolism

Methoxychlor is well absorbed by the gastrointestinal tract and to a lesser extent by the skin. Once in the bloodstream, methoxychlor appears to distribute to most tissues of the body, with highest levels usually found in fat. Methoxychlor is metabolized rapidly by cytochrome P450 enzymes in the liver, undergoing demethylation to form phenolic derivatives, with dechlorination and dehydrochlorination reactions occurring to a lesser extent. The metabolites of methoxychlor are excreted mainly in the faeces. (4)

Toxicity Values

LD50: 3460 mg/kg (Oral, Rat) (4)

Lethal Dose

6400 mg/kg for an adult human. (6)

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (3)

Uses/Sources

Methoxychlor is used as an insecticide against flies, mosquitoes, cockroaches, chiggers, and a wide variety of other insects. It is used on agricultural crops and livestock, and in animal feed, barns, grain storage bins, home garden, and on pets. (4)

Minimum Risk Level

Intermediate Oral: 0.005 mg/kg/day (2)

Health Effects

Animal studies show that methoxychlor may affect the reproductive system, causing harm to the ovaries, uterus, and mating cycle in females, and the testes and prostate in males, as well as decreased fertility in both sexes. Methoxychlor exposure may also cause EEG pattern changes. (5, 4)

Symptoms

High levels of methoxychlor may cause fatigue, lethargy, tremors, convulsions and seizures. (5, 4)

Treatment

Not Available

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

Methoxychlor

Chemspider ID

Not Available

ChEBI ID

6842

PubChem Compound ID

4115

Kegg Compound ID

C11043

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Methoxychlor (CHEM000057)

Structure for CHEM000057: Methoxychlor