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Name Description
id 54
T3DB ID T3D0061
Name Methoxychlor
Class SmallMolecule
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. (L167)
Categories "Pesticide", "Household Toxin", "Pollutant", "Airborne Pollutant", "Synthetic Toxin"
Types "Organic Compound", "Organochloride", "Aromatic Hydrocarbon", "Pesticide", "Ether", "Pollutant", "Household Toxin", "Synthetic Compound"
Synonyms "1, 1-Bis(p-methoxyphenyl)-2,2,2-trichloroethane", "1,1'-(2,2, 2-Trichloroethylidene)bis(4-methoxybenzene)", "1,1'-(2,2,2-trichloroethane-1,1-diyl)bis(4-methoxybenzene)", "1,1'-(2,2,2-Trichloroethylidene)bis(4-methoxybenzene)", "1,1,1-Trichloro-2, 2-bis(p-anisyl)ethane", "1,1,1-Trichloro-2, 2-bis(p-methoxyphenyl)ethane", "1,1,1-Trichloro-2, 2-di(4-methoxyphenyl)ethane", "1,1,1-Trichloro-2,2-bis(4-methoxyphenyl)ethane", "1,1,1-Trichloro-2,2-bis(p-anisyl)ethane", "1,1,1-Trichloro-2,2-bis(p-methoxyphenyl)ethane", "1,1,1-Trichloro-2,2-bis-(p-methoxyphenyl)ethane", "1,1,1-Trichloro-2,2-di(4-methoxyphenyl)ethane", "1,1-Bis(p-methoxyphenyl)-2,2,2-trichloroethane", "2, 2-Di(p-methoxyphenyl)-1,1,1-trichloroethane", "2,2,2-t richloro-1,1-bis(4-methoxyphenyl)ethane", "2,2,2-Trichloro-1,1-bis(4-methoxyphenyl)ethane", "2,2-Bis (p-methoxyphenol)-1,1,1-trichloroethane", "2,2-Bis(4-methoxyphenyl)-1,1,1-trichloroethane", "2,2-Bis(p-anisyl)-1, 1,1-trichloroethane", "2,2-Bis(p-anisyl)-1,1,1-trichloroethane", "2,2-Bis(p-methoxyphenyl)-1,1, 1-trichloroethane", "2,2-Bis(p-methoxyphenyl)-1,1,1-trichloroethane", "2,2-Di(p-anisyl)-1,1,1-trichloroethane", "2,2-Di(p-methoxyphenyl)-1,1,1-trichloroethane", "2,2-Di-(p-methoxyphenyl)-1,1,1-trichloroethane", "2,2-Di-p-anisyl-1,1,1-trichloroethane", "4,4-(2,2,2-Trichloroethylidene)dianisole", "Bis(p-anisyl)-1,1,1-trichloroethane", "Bis(p-methoxyphenyl)-1,1,1-trichloroethane", "Di(p-methoxyphenyl) trichloromethyl methane", "Di(p-methoxyphenyl)trichloromethyl methane", "Dianisyl trichloroethane", "Dianisyltrichlorethane", "Dianisyltrichloroethane", "Dimethox ydiphenyltrichloroethane", "Dimethoxy-DDT", "Dimethoxy-DT", "Dimethoxydiphenyltrichloroethane", "Maralate", "Marlate", "Maxie", "Meocl", "Methoxcide", "Methoxo", "Methoxy DDT", "Methoxy-DDT", "Metoksychlor", "p, p'-methoxychlor", "p,p'-(dimethoxydiphenyl)trichloroethane", "p,p'-dimethoxydiphenyltrichl oroethane", "p,p'-dimethoxydiphenyltrichloroethane", "p,p'-DMDT", "p,p'-methoxychlor", "Pmethoxychlor", "Prentox", "Trichloroethane dianisyl"
CAS Number 72-43-5
Chemical Formula C16H15Cl3O2
Average Molecular Mass 345.65
Monoisotopic Mass 344.01
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 InChIKey=IAKOZHOLGAGEJT-UHFFFAOYSA-N
Kingdom Organic Compounds
Super Class Benzenoids
Class Benzene and Substituted Derivatives
Sub Class Diphenylmethanes
Direct Parent Diphenylmethanes
Alternate Parents "Anisoles", "Alkyl Aryl Ethers", "Alkyl Chlorides", "Organochlorides"
Geometric Description Aromatic Homomonocyclic Compounds
Substituents "organochloride", "alkyl chloride", "phenol ether", "anisole", "alkyl aryl ether", "Ether", "Organooxygen Compound", "Aromatic Homomonocyclic Compound", "Organohalogen Compound", "Alkyl Halide", "Diphenylmethane"
Descriptors "organochlorine insecticide (ChEBI)", "Organochlorine pesticides (KEGG)", "Organochlorine insecticides (KEGG)"
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Membrane"
Biofluids
Tissues
Pathways
State Solid
Appearance Pale-yellow powder.
Melting Point 87°C
Boiling Point decomposes
Solubility 0.0001 mg/mL at 25 °C [RICHARDSON,LT & MILLER,DM (1960)]
LogP
Route of Exposure Oral (L167) ; dermal (L167)
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. (T10, A118)
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. (L167)
Toxicity LD50: 3460 mg/kg (Oral, Rat) (L167)
Lethal Dose 6400 mg/kg for an adult human. (T28)
Carcinogenicity 3, not classifiable as to its carcinogenicity to humans. (L135)
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. (L167)
Minimum Risk Level Intermediate Oral: 0.005 mg/kg/day (L134)
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. (T10. L167)
Symptoms High levels of methoxychlor may cause fatigue, lethargy, tremors, convulsions and seizures. (T10, L167)
Treatment
DrugBank ID
HMDB ID
PubChem Compound ID 4115
ChEMBL ID CHEMBL362919
ChemSpider ID 3972
KEGG Compound ID C11043
UniProt ID 0
OMIM ID 0
ChEBI ID 6842
BioCyc ID
CTD ID D008731
Stitch ID Methoxychlor
PDB ID
ACToR ID 843
Wikipedia Link http://en.wikipedia.org/wiki/Methoxychlor
Creation Date 2009-03-06 18:58:00
Update Date 2014-12-24 20:21:00