ContaminantDB: Endrin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (42)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:57:58 UTC

Update Date

2026-04-05 10:22:29 UTC

Accession Number

CHEM000037

Identification

Common Name

Endrin

Class

Small Molecule

Description

Endrin has been found as a contaminant throughout the environment, including foodstuffs, fish, human milk, etc. Endrin belongs to the family of Benzoxepines. These are organic compounds containing a benzene ring fused to an oxepine ring (unsaturated seven-member heterocycle with one oxygen atom replacing a carbon atom.).

Contaminant Sources

Clean Air Act Chemicals
FooDB Chemicals
HPV EPA Chemicals
IARC Carcinogens Group 3
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Ether
Food Toxin
Metabolite
Organic Compound
Organochloride
Pesticide
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-Dimethanonaph[2,3-b]oxirene, 9ci	HMDB
Compd. 269	HMDB
Compound 269	HMDB
EN 57	HMDB
Endrex	HMDB
Endricol	HMDB
Endrin 20 ec	HMDB
Endrin and metabolites	HMDB
Endrin isomer	HMDB
Endrin mixture	HMDB
Endrine	HMDB
ent 17251	HMDB
Experimental insecticide 269	HMDB
hexachloroepoxyoctahydro-endo, endo-Dimethanonaphthalene	HMDB
hexachloroepoxyoctahydro-endo,endo-Dimethanonaphthalene	HMDB
hexachloroepoxyoctahydro-endo,endo-Dimethanonapthalene	HMDB
Hexadrin	HMDB, MeSH
Latka 269	HMDB
Mendrin	HMDB
Nendrin	HMDB
Oktanex	HMDB
OMS 197	HMDB
SD 3419 Illoxol	HMDB
Stardrin	HMDB
Stardrin 20	HMDB
Endrin	MeSH, HMDB

Chemical Formula

C₁₂H₈Cl₆O

Average Molecular Mass

380.909 g/mol

Monoisotopic Mass

377.871 g/mol

CAS Registry Number

72-20-8

IUPAC Name

3,4,5,6,13,13-hexachloro-10-oxapentacyclo[6.3.1.1³,⁶.0²,⁷.0⁹,¹¹]tridec-4-ene

Traditional Name

endrin

SMILES

ClC1=C(Cl)C2(Cl)C3C4CC(C5OC45)C3C1(Cl)C2(Cl)Cl

InChI Identifier

InChI=1S/C12H8Cl6O/c13-8-9(14)11(16)5-3-1-2(6-7(3)19-6)4(5)10(8,15)12(11,17)18/h2-7H,1H2

InChI Key

DFBKLUNHFCTMDC-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Monoterpenoids

Alternative Parents

Substituents

Monoterpenoid
Norbornane monoterpenoid
Oxepane
Oxane
Dialkyl ether
Oxirane
Ether
Oxacycle
Vinyl chloride
Vinyl halide
Organoheterocyclic compound
Haloalkene
Chloroalkene
Organooxygen compound
Hydrocarbon derivative
Alkyl chloride
Alkyl halide
Organic oxygen compound
Organohalogen compound
Organochloride
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	226 - 230°C
Boiling Point	Not Available
Solubility	0.00025 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	0.0002 g/L	ALOGPS
logP	4.98	ALOGPS
logP	3.95	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	78.01 m³·mol⁻¹	ChemAxon
Polarizability	31.56 Å³	ChemAxon
Number of Rings	5	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	splash10-053r-9424000000-cb0fe872a410e47acde6	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 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 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	splash10-004i-0009000000-4e3ab80ba2cb5f78445d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01t9-0009000000-47b57ee68ea2b95cb4a8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-003r-9124000000-f5c8679adbd456c1b9e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-c15682ff19a328a64b01	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0009000000-41a18726a0ad03aeb1f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-2209000000-4c9e51dcaa850bbc46a8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-e47142fe4621b138f5c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0009000000-e47142fe4621b138f5c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-2009000000-263852a3083150cbd869	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0009000000-bbc098baf89f49ef5fc5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0009000000-bbc098baf89f49ef5fc5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0009000000-9a33d936efbb436cac20	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-9350000000-1c4e09990ac9de8ef901	Spectrum

Toxicity Profile

Route of Exposure

Oral (1)

Mechanism of Toxicity

Endrin 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. Endrin 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. Endrin also causes increased lipid peroxidation, decreased membrane fluidity, and DNA damage in hepatocytes, but the exact mechanism is unknown. (6, 2)

Metabolism

Endrin 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. Endrin 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)

3, not classifiable as to its carcinogenicity to humans. (4)

Uses/Sources

Endrin 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

Endrin poisoning affects primarily the nerve system. Exposure causes various harmful effects including hyperexcitability, severe central nervous system damage, and death. Endrin 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

HMDB0253129

FooDB ID

FDB003234

Phenol Explorer ID

Not Available

KNApSAcK ID

C00000723

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Endrin

Chemspider ID

2940

ChEBI ID

Not Available

PubChem Compound ID

Not Available

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

Endrin (CHEM000037)

Structure for CHEM000037: Endrin