ContaminantDB: Isodrin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (63)XML

Record Information

Version

1.0

Creation Date

2009-06-18 04:16:52 UTC

Update Date

2026-03-27 00:47:43 UTC

Accession Number

CHEM000881

Identification

Common Name

Isodrin

Class

Small Molecule

Description

Isodrin is an exogenous organic compound with the formula C12H8Cl6 and an average molecular weight of 364.91 g/mol. It exists as a solid at room temperature. Isodrin belongs to the vinyl chlorides, a subclass of vinyl halides within the organic compounds. It has been recorded as a source of contamination in drinking water and water supplies, with oral exposure as a recorded route. The compound interacts with 32 recorded protein targets. As an organochloride, it inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, including Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 (ATP2A1), Sarcoplasmic/endoplasmic reticulum calcium ATPase 2 (ATP2A2), Calcium-transporting ATPase type 2C member 1 (ATP2C1), and Sodium/potassium-transporting ATPase subunit gamma (FXYD2). These proteins are essential for transporting calcium across membranes; their inhibition leads to the accumulation of intracellular free calcium ions, which promotes the release of neurotransmitters from storage vesicles, the depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. Additionally, isodrin antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) at GABA-A receptors, involving Gamma-aminobutyric acid receptor subunits alpha-1 (GABRA1), alpha-2 (GABRA2), alpha-3 (GABRA3), and alpha-4 (GABRA4), as well as 15 other proteins. This action blocks the GABA-induced uptake of chloride ions, resulting in hyperexcitability of the central nervous system. Isodrin also causes endocrine disruption in humans by binding to and inhibiting the Estrogen receptor (ESR1) and Estrogen receptor beta (ESR2).

Contaminant Sources

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

Contaminant Type

Human Neurotoxin
Organic Compound
Organochloride
Pesticide
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Aldrin	MeSH, HMDB
Isodrin	MeSH

Chemical Formula

C₁₂H₈Cl₆

Average Molecular Mass

364.910 g/mol

Monoisotopic Mass

361.876 g/mol

CAS Registry Number

465-73-6

IUPAC Name

Not Available

Traditional Name

aldrin

SMILES

ClC1=C(Cl)C2(Cl)C3C4CC(C=C4)C3C1(Cl)C2(Cl)Cl

InChI Identifier

InChI=1S/C12H8Cl6/c13-8-9(14)11(16)7-5-2-1-4(3-5)6(7)10(8,15)12(11,17)18/h1-2,4-7H,3H2

InChI Key

QBYJBZPUGVGKQQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as vinyl chlorides. These are vinyl halides in which a chlorine atom is bonded to an sp2-hybridised carbon atom.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Vinyl halides

Sub Class

Vinyl chlorides

Direct Parent

Vinyl chlorides

Alternative Parents

Substituents

Chloroalkene
Haloalkene
Vinyl chloride
Hydrocarbon derivative
Organochloride
Alkyl halide
Alkyl chloride
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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

White powder.

Experimental Properties

Property	Value
Melting Point	240-242°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	8.1e-05 g/L	ALOGPS
logP	5.9	ALOGPS
logP	4.73	ChemAxon
logS	-6.6	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.76 m³·mol⁻¹	ChemAxon
Polarizability	30.85 Å³	ChemAxon
Number of Rings	4	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	splash10-0006-9052000000-7e5a2cf802522b0e5bf4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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	splash10-03di-0009000000-f59a33bac61e223629e8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1009000000-9f0f5ee8cc7ef936e439	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9011000000-f481be09ccdad3a9a74b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-ac5868ba988c7979afc7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0009000000-a617cd50d032984b3345	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dr-6039000000-90b52871fd508073880a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0009000000-4a489529f237f300bef4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0009000000-4a489529f237f300bef4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-2009000000-99a64c210e8ea8af7881	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-1bfe1c74ad297f9855ba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0009000000-1bfe1c74ad297f9855ba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-2009000000-72e1dbe72048ac74b27a	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-02tc-5391000000-fdb72f5621f8c21bf762	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

It antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. It also inhibits Na+ K+ ATPase and Ca2+ and Mg2+ ATPase which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. It also causes increased lipid peroxidation, decreased membrane fluidity, and DNA damage in hepatocytes, but the exact mechanism is unknown. (6, 2)

Metabolism

It is absorbed orally and distributed primarily to the fat and skin. The major biotransformation product is anti-l 2-hydroxyendrin and the corresponding sulfate, as well as glucuronide metabolites. Anti- and syn-12-hydroxyendrin and 12-ketoendrin are the main toxic metabolites of endrin. It and its metabolites are excreted in urine and feces. (2)

Toxicity Values

LD50: 3 mg/kg (Oral, Rat) (7) LD50: 12 mg/kg (Dermal, Rat) (7)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity (not listed by IARC). (4)

Uses/Sources

It is used as a pesticide. (1)

Minimum Risk Level

Intermediate Oral: 0.002 mg/kg/day (3) Chronic Oral: 0.0003 mg/kg/day (3)

Health Effects

Poisoning affects primarily the nerve system. Exposure causes various harmful effects including hyperexcitability, severe central nervous system damage, and death. It is also believed to cause birth defects. (6, 2)

Symptoms

Symptoms that may result from endrin poisoning are headaches, dizziness, nervousness, confusion, nausea, vomiting, and convulsions. (2)

Treatment

Treatment is symptomatic, aimed at controlling convulsions, coma, and respiratory depression. If ingested, gastric lavage may be performed, followed by administering activated charcoal powder. (5)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0248128

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

Isodrin

Chemspider ID

2003

ChEBI ID

Not Available

PubChem Compound ID

2087

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Isodrin (CHEM000881)

Structure for CHEM000881: Isodrin