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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
Effect of methoxychlor on antioxidant system of goat epididymal sperm in vitro.
2001 Dec
A repeated 28-day oral dose toxicity study of methoxychlor in rats, based on the 'enhanced OECD test guideline 407' for screening endocrine-disrupting chemicals.
2001 Nov
Analysis of organochlorine pesticides in human milk: preliminary results.
2001 Nov
Diet and organochlorine contaminants in women of reproductive age under 40 years old.
2001 Nov
Response of MCF-7 human breast cancer cells to some binary mixtures of oestrogenic compounds in-vitro.
2001 Nov
The diverse mechanism of action of dichlorodiphenyldichloroethylene (DDE) and methoxychlor in ovarian cells in vitro.
2001 Nov-Dec
Insecticide susceptibility in Coptotermes formosanus and Reticulitermes virginicus (Isoptera: Rhinotermitidae).
2001 Oct
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
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
Uterine responsiveness to estradiol and DNA methylation are altered by fetal exposure to diethylstilbestrol and methoxychlor in CD-1 mice: effects of low versus high doses.
2002 Aug 15
Determination of organochlorine pesticides in seawater using liquid-phase hollow fibre membrane microextraction and gas chromatography-mass spectrometry.
2002 Aug 30
Analysis of pesticides and PCB congeners in serum by GC/MS with SPE sample cleanup.
2002 Aug 5
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
Induction of oxidative stress in the rat testis after short-term exposure to the organochlorine pesticide methoxychlor.
2002 Dec
Enantioselective metabolism of the endocrine disruptor pesticide methoxychlor by human cytochromes P450 (P450s): major differences in selective enantiomer formation by various P450 isoforms.
2002 Dec
Utility of a juvenile fathead minnow screening assay for detecting (anti-)estrogenic substances.
2002 Feb
Cognitive testing (delayed non-match to sample) during oral treatment of female adolescent monkeys with the estrogenic pesticide methoxychlor.
2002 Jan-Feb
Endocrine disruption caused by two common pollutants at "acceptable" concentrations.
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
Effect of methoxychlor on the antioxidant system in mitochondrial and microsome-rich fractions of rat testis.
2002 Jul 1
Methoxychlor alters the predator-prey relationship between dragonfly naiads and salamander larvae.
2002 Jun
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
Development of two androgen receptor assays using adenoviral transduction of MMTV-luc reporter and/or hAR for endocrine screening.
2002 Mar
Oral estrogen masculinizes female zebra finch song system.
2002 Mar
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 subchronic exposure to a complex mixture of persistent contaminants in male rats: systemic, immune, and reproductive effects.
2002 May
Effect of xenoestrogen exposure on the expression of cytochrome P450 isoforms in rainbow trout liver.
2002 Nov
Effect of tolerance to insecticides on substrate penetration by Formosan subterranean termites (Isoptera: Rhinotermitidae).
2002 Oct
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
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes.
2003 Jan 1
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
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 GMT 2023
Edited
by admin
on Fri Dec 15 15:02:19 GMT 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 GMT 2023 , Edited by admin on Fri Dec 15 15:02:19 GMT 2023
Code System Code Type Description
MERCK INDEX
m7331
Created by admin on Fri Dec 15 15:02:19 GMT 2023 , Edited by admin on Fri Dec 15 15:02:19 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
METHOXYCHLOR
Created by admin on Fri Dec 15 15:02:19 GMT 2023 , Edited by admin on Fri Dec 15 15:02:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID9020827
Created by admin on Fri Dec 15 15:02:19 GMT 2023 , Edited by admin on Fri Dec 15 15:02:19 GMT 2023
PRIMARY
CHEBI
6842
Created by admin on Fri Dec 15 15:02:19 GMT 2023 , Edited by admin on Fri Dec 15 15:02:19 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-779-9
Created by admin on Fri Dec 15 15:02:19 GMT 2023 , Edited by admin on Fri Dec 15 15:02:19 GMT 2023
PRIMARY
DAILYMED
RIA79UD69L
Created by admin on Fri Dec 15 15:02:19 GMT 2023 , Edited by admin on Fri Dec 15 15:02:19 GMT 2023
PRIMARY
ALANWOOD
methoxychlor
Created by admin on Fri Dec 15 15:02:19 GMT 2023 , Edited by admin on Fri Dec 15 15:02:19 GMT 2023
PRIMARY
NSC
8945
Created by admin on Fri Dec 15 15:02:19 GMT 2023 , Edited by admin on Fri Dec 15 15:02:19 GMT 2023
PRIMARY
PUBCHEM
4115
Created by admin on Fri Dec 15 15:02:19 GMT 2023 , Edited by admin on Fri Dec 15 15:02:19 GMT 2023
PRIMARY
FDA UNII
RIA79UD69L
Created by admin on Fri Dec 15 15:02:19 GMT 2023 , Edited by admin on Fri Dec 15 15:02:19 GMT 2023
PRIMARY
HSDB
1173
Created by admin on Fri Dec 15 15:02:19 GMT 2023 , Edited by admin on Fri Dec 15 15:02:19 GMT 2023
PRIMARY
CAS
72-43-5
Created by admin on Fri Dec 15 15:02:19 GMT 2023 , Edited by admin on Fri Dec 15 15:02:19 GMT 2023
PRIMARY
RXCUI
2598123
Created by admin on Fri Dec 15 15:02:19 GMT 2023 , Edited by admin on Fri Dec 15 15:02:19 GMT 2023
PRIMARY
SMS_ID
100000184171
Created by admin on Fri Dec 15 15:02:19 GMT 2023 , Edited by admin on Fri Dec 15 15:02:19 GMT 2023
PRIMARY
MESH
D008731
Created by admin on Fri Dec 15 15:02:19 GMT 2023 , Edited by admin on Fri Dec 15 15:02:19 GMT 2023
PRIMARY
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