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Details

Stereochemistry ACHIRAL
Molecular Formula C16H15Cl3O2
Molecular Weight 345.6485
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHOXYCHLOR

SMILES

COc1ccc(cc1)C(c2ccc(cc2)OC)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 345.6485
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
Differential estrogen receptor binding of estrogenic substances: a species comparison.
2000 Nov 15
Effect of methoxychlor on antioxidant system of goat epididymal sperm in vitro.
2001 Dec
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
Description and evaluation of a short-term reproduction test with the fathead minnow (Pimephales promelas).
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
Inhibition of basal and stimulated progesterone synthesis by dichlorodiphenyldichloroethylene and methoxychlor in a stable pig granulosa cell line.
2001 Mar
Cell response endpoints enhance sensitivity of the immature mouse uterotropic assay.
2001 May-Jun
Analysis of organochlorine pesticides in human milk: preliminary results.
2001 Nov
Response of MCF-7 human breast cancer cells to some binary mixtures of oestrogenic compounds in-vitro.
2001 Nov
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
Differential gene expression in response to methoxychlor and estradiol through ERalpha, ERbeta, and AR in reproductive tissues of female mice.
2001 Sep
Modulation of mammary gland development in prepubertal male rats exposed to genistein and methoxychlor.
2002 Apr
The hidden effect of estrogenic/antiandrogenic methoxychlor on spermatogenesis.
2002 Apr 15
Improvement of a two-stage carcinogenesis model to detect modifying effects of endocrine disrupting chemicals on thyroid carcinogenesis in rats.
2002 Apr 8
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
Determination of estrogenic activity in landfill leachate by simplified yeast two-hybrid assay.
2002 Dec
An avian bioassay for environmental estrogens: the growth response of zebra finch (Taeniopygia guttata) chick oviduct to oral estrogens.
2002 Dec
Increases in mouse uterine heat shock protein levels are a sensitive and specific response to uterotrophic agents.
2002 Dec
Ethological methods to study the effects of maternal exposure to estrogenic endocrine disrupters: a study with methoxychlor.
2002 Jan-Feb
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
The effect of methoxychlor on the epididymal antioxidant system of adult rats.
2002 Mar-Apr
PCDDs/PCDFs, PCBs, and organochlorine pesticides in eggs of Eurasian sparrowhawks (Accipiter nisus), hobbies (Falco subbuteo), and northern goshawks (Accipiter gentilis) collected in the area of Berlin-Brandenburg, Germany.
2002 May
Effects of primary exposure to environmental and natural estrogens on vitellogenin production in carp (Cyprinus carpio) hepatocytes.
2002 May
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
Environmental estrogens alter early development in Xenopus laevis.
2003 Apr
The multidrug resistance-associated protein 1 transports methoxychlor and protects the seminiferous epithelium from injury.
2003 Apr 30
Inhibition of gonadotropin-induced oviposition and ovarian steroidogenesis in the African clawed frog (Xenopus laevis) by the pesticide methoxychlor.
2003 Feb 12
Expression profiling of estrogenic compounds using a sheepshead minnow cDNA macroarray.
2003 Jan
[Contents of organochlorine pesticides in water, pore water and sediment in Minjiang River Estuary of China].
2003 Jan
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.
2003 Jan 1
Preimplantation mouse embryo development as a target of the pesticide methoxychlor.
2003 Jan-Feb
Effects of exogenous estrogenic agents on pubertal growth and reproductive system maturation in female rhesus monkeys.
2003 Jul
Resistance status of house flies (Diptera: Muscidae) from southeastern Nebraska beef cattle feedlots to selected insecticides.
2003 Jun
Evaluation of alternative tactics for management of insecticide-resistant horn flies (Diptera: Muscidae).
2003 Jun
Methoxychlor modifies the ultradian secretory pattern of prolactin and affects its TRH response.
2003 May
Analysis of pesticides in water and sediment under different storage conditions using gas chromatography.
2003 May
Effect of organochlorine pesticides on maturation of starfish and mouse oocytes.
2003 May
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 Sat Jun 26 11:24:06 UTC 2021
Edited
by admin
on Sat Jun 26 11:24:06 UTC 2021
Record UNII
RIA79UD69L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHOXYCHLOR
HSDB   ISO   MART.   MI   WHO-DD  
Systematic Name English
METHOXYCHLOR [WHO-DD]
Common Name English
METHOXYCHLOR [MI]
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 Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
Code System Code Type Description
MERCK INDEX
M7331
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
METHOXYCHLOR
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
PRIMARY
EPA CompTox
72-43-5
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-779-9
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
PRIMARY
PUBCHEM
4115
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
PRIMARY
FDA UNII
RIA79UD69L
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
PRIMARY
HSDB
1173
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
PRIMARY
CAS
72-43-5
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
PRIMARY
MESH
D008731
Created by admin on Sat Jun 26 11:24:07 UTC 2021 , Edited by admin on Sat Jun 26 11:24:07 UTC 2021
PRIMARY
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