ContaminantDB: Telodrin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (38)XML

Record Information

Version

1.0

Creation Date

2009-06-18 04:01:16 UTC

Update Date

2026-04-03 10:05:02 UTC

Accession Number

CHEM000880

Identification

Common Name

Telodrin

Class

Small Molecule

Description

A chlorinated hydrocarbon used as an insecticide on cotton, maize, and rice. It also acts as an avicide and rodenticide. Due it its toxicity and tendency to bioaccumulate, its use is now banned in most parts of the world. (1)

Contaminant Sources

Clean Air Act Chemicals
My Exposome Chemicals
T3DB toxins

Contaminant Type

Ether
Organic Compound
Organochloride
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₉H₄Cl₈O

Average Molecular Mass

411.751 g/mol

Monoisotopic Mass

407.777 g/mol

CAS Registry Number

297-78-9

IUPAC Name

1,3,5,7,8,9,10,10-octachloro-4-oxatricyclo[5.2.1.0²,⁶]dec-8-ene

Traditional Name

isobenzan

SMILES

ClC1OC(Cl)C2C1C1(Cl)C(Cl)=C(Cl)C2(Cl)C1(Cl)Cl

InChI Identifier

InChI=1S/C9H4Cl8O/c10-3-4(11)8(15)2-1(5(12)18-6(2)13)7(3,14)9(8,16)17/h1-2,5-6H

InChI Key

LRWHHSXTGZSMSN-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydrofurans

Sub Class

Not Available

Direct Parent

Tetrahydrofurans

Alternative Parents

Substituents

Tetrahydrofuran
Oxacycle
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

oxolanes (CHEBI:82099 )
Organochlorine insecticides (C18960 )

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	121°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0004 g/L	ALOGPS
logP	5.59	ALOGPS
logP	5.24	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	77.42 m³·mol⁻¹	ChemAxon
Polarizability	31.56 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000900000-60a6931ba39e0c19ff34	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0020900000-f30ea11e5ff45fc99630	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dr-0119000000-3dc1fea21a54cfabcb93	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000900000-f5f26fddde9a0689b987	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0004900000-f552965cd5c18f34cc8a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00e9-0009000000-4788a3c05c2ae63d1e66	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-116r-6975000000-a877c30bac55ea290f67	Spectrum

Toxicity Profile

Route of Exposure

Oral (1)

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

Not Available

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

Isobenzan

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

9271

Kegg Compound ID

C18960

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Telodrin (CHEM000880)

Structure for CHEM000880: Telodrin