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Details

Stereochemistry ACHIRAL
Molecular Formula C16H15Cl3O2
Molecular Weight 345.648
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHOXYCHLOR

SMILES

COC1=CC=C(C=C1)C(C2=CC=C(OC)C=C2)C(Cl)(Cl)Cl

InChI

InChIKey=IAKOZHOLGAGEJT-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C16H15Cl3O2
Molecular Weight 345.648
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Methoxychlor is a contact and stomach insecticide effective against a wide range of pests encountered in agriculture, households, and ornamental plantings. It was registered for use on fruits, vegetables, forage crops and on shade trees. Methoxychlor was also registered for veterinary use as a poison to kill parasites on dairy and beef cattle. Exposure to methoxychlor may occur during its manufacture or use as a pesticide. In an acute oral study in animals, changes in the liver were reported. Dermal contact with methoxychlor is slightly irritating to the skin. The use of methoxychlor as a pesticide was banned in the United States in 2003 and in the European Union in 2002.

CNS Activity

Curator's Comment: Known to be CNS penetrant in mouse. Human data not available.

Originator

Sources: DOI: 10.1002/prac.18930470103

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
15.47 µM [IC50]
22.45 µM [IC50]
14.84 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Marlate

Approved Use

Applied for the control of certain external parasites.
Curative
Marlate

Approved Use

Applied for the control of certain external parasites.
PubMed

PubMed

TitleDatePubMed
Identification of selected hormonally active agents and animal mammary carcinogens in commercial and residential air and dust samples.
2001 Apr
Metabolic activation of bisphenol A by rat liver S9 fraction.
2001 Aug
Effects of p-nonylphenol, methoxychlor, and endosulfan on vitellogenin induction and expression in sheepshead minnow (Cyprinodon variegatus).
2001 Feb
Optimization of a yeast estrogen screen and its applicability to study the release of estrogenic isoflavones from a soygerm powder.
2001 Jul
Effects of nutrient loading and planktivory on the accumulation of organochlorine pesticides in aquatic food chains.
2001 Jun
Mechanism of induction of cytochrome p450 enzymes by the proestrogenic endocrine disruptor pesticide-methoxychlor: interactions of methoxychlor metabolites with the constitutive androstane receptor system.
2001 Jun
Application of static liquid-phase microextraction to the analysis of organochlorine pesticides in water.
2001 Jun 15
Environmental toxicant effects on neuroendocrine function.
2001 Mar
Actions of the endocrine disruptor methoxychlor and its estrogenic metabolite on in vitro embryonic rat seminiferous cord formation and perinatal testis growth.
2001 May-Jun
Cell response endpoints enhance sensitivity of the immature mouse uterotropic assay.
2001 May-Jun
The diverse mechanism of action of dichlorodiphenyldichloroethylene (DDE) and methoxychlor in ovarian cells in vitro.
2001 Nov-Dec
Halogenated organic contaminants in sediments of the Havel and Spree rivers (Germany). Part 5 of organic compounds as contaminants of the Elbe river and its tributaries.
2001 Oct 15
Effects of prenatal exposure to low doses of diethylstilbestrol, o,p'DDT, and methoxychlor on postnatal growth and neurobehavioral development in male and female mice.
2001 Sep
Methoxychlor stimulates the mouse lactoferrin gene promoter through a GC-rich element.
2002
Modulation of mammary gland development in prepubertal male rats exposed to genistein and methoxychlor.
2002 Apr
Assessment of interactions of diverse ternary mixtures in an estrogen receptor-alpha reporter assay.
2002 Apr 1
The hidden effect of estrogenic/antiandrogenic methoxychlor on spermatogenesis.
2002 Apr 15
Genistein and methoxychlor modulate the activity of natural killer cells and the expression of phenotypic markers by thymocytes and splenocytes in F0 and F1 generations of Sprague-Dawley rats.
2002 Apr 2
Persistent chlorinated pesticides in fish and cattle fat and their implications for human serum concentrations from the Sene-Gambian region.
2002 Aug
Methoxychlor may cause ovarian follicular atresia and proliferation of the ovarian epithelium in the mouse.
2002 Aug
Analysis of pesticides and PCB congeners in serum by GC/MS with SPE sample cleanup.
2002 Aug 5
A binary screening assay for pro-oestrogens in food: metabolic activation using hepatic microsomes and detection with oestrogen sensitive recombinant yeast cells.
2002 Dec
Cognitive testing (delayed non-match to sample) during oral treatment of female adolescent monkeys with the estrogenic pesticide methoxychlor.
2002 Jan-Feb
Ethological methods to study the effects of maternal exposure to estrogenic endocrine disrupters: a study with methoxychlor.
2002 Jan-Feb
Altered behaviors in male mice, male quail, and salamander larvae following early exposures to the estrogenic pesticide methoxychlor.
2002 Jan-Feb
Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.
2002 Jul
Workshop report. Children as a special subpopulation: focus on immunotoxicity. Federal Institute for Health Protection of Consumers and Veterinary Medicine (BgVV), 15-16 November 2001, Berlin, Germany.
2002 Jul
Enhancing effects of beta-estradiol 3-benzoate but not methoxychlor on the promotion/progression stage of chemically-induced mammary carcinogenesis in ovariectomized rats.
2002 Jul
Is exposure to endocrine disrupting compounds during fetal/post-natal development affecting the reproductive potential of farm animals?
2002 Jul
Effect of methoxychlor on the antioxidant system in mitochondrial and microsome-rich fractions of rat testis.
2002 Jul 1
Detection of estrogenic activity in sediment-associated compounds using in vitro reporter gene assays.
2002 Jul 3
Organochlorine pesticides directly regulate gonadotropin-releasing hormone gene expression and biosynthesis in the GT1-7 hypothalamic cell line.
2002 Jun 28
Combined effects of dietary phytoestrogen and synthetic endocrine-active compound on reproductive development in Sprague-Dawley rats: genistein and methoxychlor.
2002 Mar
Oral estrogen masculinizes female zebra finch song system.
2002 Mar
The pesticide methoxychlor disrupts the fusion of myoblasts into myotubes in skeletal muscle cell culture.
2002 Mar 1
The effect of methoxychlor on the epididymal antioxidant system of adult rats.
2002 Mar-Apr
Comparative assessment of endocrine modulators with oestrogenic activity. II. Persistent organochlorine pollutants.
2002 May
Effects of subchronic exposure to a complex mixture of persistent contaminants in male rats: systemic, immune, and reproductive effects.
2002 May
Effects of primary exposure to environmental and natural estrogens on vitellogenin production in carp (Cyprinus carpio) hepatocytes.
2002 May
Effect of xenoestrogen exposure on the expression of cytochrome P450 isoforms in rainbow trout liver.
2002 Nov
The pesticide methoxychlor given orally during the perinatal/juvenile period, reduced the spermatogenic potential of males as adults by reducing their Sertoli cell number.
2002 Nov-Dec
A comparison of the estrogenic potencies of estradiol, ethynylestradiol, diethylstilbestrol, nonylphenol and methoxychlor in vivo and in vitro.
2002 Oct 2
Thymic atrophy induced by methoxychlor in rat pups.
2002 Oct 5
Metabolism of the endocrine disruptor pesticide-methoxychlor by human P450s: pathways involving a novel catechol metabolite.
2002 Sep
The rat as a model in developmental immunotoxicology.
2002 Sep-Oct
Environmental estrogens alter early development in Xenopus laevis.
2003 Apr
[Contents of organochlorine pesticides in water, pore water and sediment in Minjiang River Estuary of China].
2003 Jan
Resistance status of house flies (Diptera: Muscidae) from southeastern Nebraska beef cattle feedlots to selected insecticides.
2003 Jun
Effect of organochlorine pesticides on maturation of starfish and mouse oocytes.
2003 May
Isolation of four aquatic streptomycetes strains capable of growth on organochlorine pesticides.
2003 Sep
Patents

Sample Use Guides

Use 2 Ibs. of Marlate 50 (50% methoxychlor) in 25 gals. of water. As a spray, wet animals to the skin. Repeat treatment every 3 weeks as needed.
Route of Administration: Topical
Rat primary cortical neurons were exposed to 1 or 10 uM methoxychlor for 9 days. GluR2 expression in cultures treated with methoxychlor was decreased significantly to approximately 61% and 56% of that observed in untreated cultures.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:02:19 UTC 2023
Edited
by admin
on Fri Dec 15 15:02:19 UTC 2023
Record UNII
RIA79UD69L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHOXYCHLOR
HSDB   ISO   MART.   MI   WHO-DD  
Systematic Name English
METHOXYCHLOR [MI]
Common Name English
Methoxychlor [WHO-DD]
Common Name English
DIMETHOXY-DDT
Common Name English
1,1,1-TRICHLORO-2,2-BIS(4-METHOXYPHENYL)ETHANE
Systematic Name English
DIANISYLTRICHLORETHANE
Common Name English
DMDT
Common Name English
2,2-BIS(P-METHOXYPHENYL)-1,1,1-TRICHLOROETHANE
Common Name English
METHOXYCHLOR [MART.]
Common Name English
NSC-8945
Code English
1,1'-(2,2,2-TRICHLOROETHYLIDENE)BIS(4-METHOXYBENZENE)
Systematic Name English
2,2-BIS(P-ANISYL)-1,1,1-TRICHLOROETHANE
Common Name English
METHOXYCHLOR [ISO]
Common Name English
METHOXYCHLOR [IARC]
Common Name English
METHOXYCHLOR [HSDB]
Common Name English
Classification Tree Code System Code
IARC Methoxychlor
EPA PESTICIDE CODE 34001
Created by admin on Fri Dec 15 15:02:19 UTC 2023 , Edited by admin on Fri Dec 15 15:02:19 UTC 2023
Code System Code Type Description
MERCK INDEX
m7331
Created by admin on Fri Dec 15 15:02:19 UTC 2023 , Edited by admin on Fri Dec 15 15:02:19 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
METHOXYCHLOR
Created by admin on Fri Dec 15 15:02:19 UTC 2023 , Edited by admin on Fri Dec 15 15:02:19 UTC 2023
PRIMARY
EPA CompTox
DTXSID9020827
Created by admin on Fri Dec 15 15:02:19 UTC 2023 , Edited by admin on Fri Dec 15 15:02:19 UTC 2023
PRIMARY
CHEBI
6842
Created by admin on Fri Dec 15 15:02:19 UTC 2023 , Edited by admin on Fri Dec 15 15:02:19 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-779-9
Created by admin on Fri Dec 15 15:02:19 UTC 2023 , Edited by admin on Fri Dec 15 15:02:19 UTC 2023
PRIMARY
DAILYMED
RIA79UD69L
Created by admin on Fri Dec 15 15:02:19 UTC 2023 , Edited by admin on Fri Dec 15 15:02:19 UTC 2023
PRIMARY
ALANWOOD
methoxychlor
Created by admin on Fri Dec 15 15:02:19 UTC 2023 , Edited by admin on Fri Dec 15 15:02:19 UTC 2023
PRIMARY
NSC
8945
Created by admin on Fri Dec 15 15:02:19 UTC 2023 , Edited by admin on Fri Dec 15 15:02:19 UTC 2023
PRIMARY
PUBCHEM
4115
Created by admin on Fri Dec 15 15:02:19 UTC 2023 , Edited by admin on Fri Dec 15 15:02:19 UTC 2023
PRIMARY
FDA UNII
RIA79UD69L
Created by admin on Fri Dec 15 15:02:19 UTC 2023 , Edited by admin on Fri Dec 15 15:02:19 UTC 2023
PRIMARY
HSDB
1173
Created by admin on Fri Dec 15 15:02:19 UTC 2023 , Edited by admin on Fri Dec 15 15:02:19 UTC 2023
PRIMARY
CAS
72-43-5
Created by admin on Fri Dec 15 15:02:19 UTC 2023 , Edited by admin on Fri Dec 15 15:02:19 UTC 2023
PRIMARY
RXCUI
2598123
Created by admin on Fri Dec 15 15:02:19 UTC 2023 , Edited by admin on Fri Dec 15 15:02:19 UTC 2023
PRIMARY
SMS_ID
100000184171
Created by admin on Fri Dec 15 15:02:19 UTC 2023 , Edited by admin on Fri Dec 15 15:02:19 UTC 2023
PRIMARY
MESH
D008731
Created by admin on Fri Dec 15 15:02:19 UTC 2023 , Edited by admin on Fri Dec 15 15:02:19 UTC 2023
PRIMARY
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