Aldrin (CED0000015)

Record Information

Version

1.0

Creation Date

2009-03-06 18:57:56 UTC

Update Date

2026-04-06 04:05:18 UTC

Accession Number

CHEM000021

Identification

Common Name

Aldrin

Class

Small Molecule

Description

Aldrin 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 and is classified as a persistent organic pollutant. Aldrin belongs to the vinyl chlorides, a subclass of vinyl halides within the organic compounds. Recorded sources of the compound include antennas in electrical and electronic equipment, food contact materials in food processing and cookware, and drinking water and water supply. Exposure can occur via oral, inhalation, and touch routes. The compound interacts with 34 recorded protein targets. It antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) at GABA-A receptors, including Gamma-aminobutyric acid receptor subunits alpha-1, alpha-2, alpha-3, and alpha-4, as well as 15 other proteins; this blocks the GABA-induced uptake of chloride ions, causing hyperexcitability of the central nervous system. Aldrin also inhibits Na+/K+ ATPase and Ca2+ and Mg2+ ATPase, including Sodium/potassium-transporting ATPase subunits alpha-1, alpha-2, alpha-3, alpha-4, and 7 other proteins. This inhibition prevents the transport of calcium across membranes, leading 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, aldrin causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor (ESR1 and ESR2). Other recorded protein targets include the Progesterone receptor (PGR) and Nuclear receptor subfamily 1 group I member 2 (NR1I2).

Contaminant Type

Ether
Human Neurotoxin
Organic Compound
Organochloride
Pesticide
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₂H₈Cl₆

Average Molecular Mass

364.910 g/mol

Monoisotopic Mass

361.876 g/mol

CAS Registry Number

309-00-2

IUPAC Name

(1R,8S)-1,8,9,10,11,11-hexachlorotetracyclo[6.2.1.1³,⁶.0²,⁷]dodeca-4,9-diene

Traditional Name

(1R,8S)-1,8,9,10,11,11-hexachlorotetracyclo[6.2.1.1³,⁶.0²,⁷]dodeca-4,9-diene

SMILES

ClC1=C(Cl)[C@]2(Cl)C3C4CC(C=C4)C3[C@@]1(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/t4?,5?,6?,7?,10-,11+

InChI Key

QBYJBZPUGVGKQQ-LYSYVJQESA-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

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

persistent organic pollutant

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	104°C
Boiling Point	Not Available
Solubility	1.7e-05 mg/mL at 25 °C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

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	Yes	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	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0009000000-f59a33bac61e223629e8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-1009000000-9f0f5ee8cc7ef936e439	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9011000000-f481be09ccdad3a9a74b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0009000000-ac5868ba988c7979afc7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0009000000-a617cd50d032984b3345	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dr-6039000000-90b52871fd508073880a	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Aldrin 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. Aldrin 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 CNS. This results in hyperexcitation and generalized seizures. (6, 1)

Carcinogenicity (IARC Classification)

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

Minimum Risk Level

Acute Oral: 0.002 mg/kg/day (2) Chronic Oral: 0.00003 mg/kg/day (2)

Symptoms

Exposure to aldrin results in headaches, dizziness, irritability, nausea and vomiting, cardiac arrhythmias, muscular weakness, uncontrolled muscle movements, hyperexcitability, seizures and coma. (1)

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)

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
39.0	mg/kg	Not Available	Rat	LD50	Oral	experimental	T18
98.0	mg/kg	Not Available	Rat	LD50	Dermal	experimental	T18
150.0	mg/kg	Not Available	Rat	LD50	Intraperitoneal	experimental	T17
21.0	mg/kg	Not Available	Mouse	LD50	Intravenous	experimental	T17

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
115	Drinking water	Drinking water & water supply	Not Available
494	Food contact materials	Food, food processing & cookware	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	histidine kinase	O32393	Arthrospira platensis	Predicted (SEA)	0.0778492
Click to view 3D structure	GABA receptor subunit	Q75NA5	Musca domestica	Predicted (SEA)	0.0778492
Click to view 3D structure	Amine oxidase [flavin-containing] B	P27338	Humans	Predicted (SEA)	6335.14
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	7624.86
Click to view 3D structure	Amine oxidase [flavin-containing] A	P21397	Humans	Predicted (SEA)	6692.07
Click to view 3D structure	Poly [ADP-ribose] polymerase tankyrase-2	Q3UES3	Mus musculus	Predicted (SEA)	1043.65
Click to view 3D structure	Poly [ADP-ribose] polymerase tankyrase-1	Q6PFX9	Mus musculus	Predicted (SEA)	1043.65
Click to view 3D structure	Lysine-specific histone demethylase 1A	O60341	Humans	Predicted (SEA)	6213.22
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit beta-3	P28472	Humans	Predicted (SEA)	1.01204
Click to view 3D structure	Sodium-dependent dopamine transporter	P23977	Rattus norvegicus	Predicted (SEA)	6196.8
Click to view 3D structure	Sodium-dependent serotonin transporter	P31652	Rattus norvegicus	Predicted (SEA)	7063.49
Click to view 3D structure	Kynurenine 3-monooxygenase	P38169	Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast)	Predicted (SEA)	471.844
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q60492	Cavia porcellus	Predicted (SEA)	6854.55
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	7680.37
Click to view 3D structure	Cytochrome P450 2B6	P20813	Humans	Predicted (SEA)	7466.67
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	7752.85
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	7698.04
Click to view 3D structure	Transporter	Q63380	Rattus norvegicus	Predicted (SEA)	5065.65
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	7767.17
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	7757.29
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	7719.45
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	7733.62
Click to view 3D structure	Metabotropic glutamate receptor 4	P31423	Rattus norvegicus	Predicted (SEA)	4705.21
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Predicted (SEA)	7737.59
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	7712.68
Click to view 3D structure	Nuclear receptor subfamily 1 group I member 2	O75469	Humans	Known	Not Available
Click to view 3D structure	Estrogen receptor	P03372	Humans	Known	Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (A590)
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Known	Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (A590)
Click to view 3D structure	Calcium-transporting ATPase type 2C member 1	P98194	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit alpha-1	P14867	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit alpha-2	P47869	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit alpha-3	P34903	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit alpha-4	P48169	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit alpha-5	P31644	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit alpha-6	Q16445	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit beta-1	P18505	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit beta-2	P47870	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit beta-3	P28472	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit delta	O14764	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit epsilon	P78334	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit gamma-1	Q8N1C3	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit gamma-2	P18507	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit gamma-3	Q99928	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit pi	O00591	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit rho-1	P24046	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit rho-2	P28476	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit rho-3	A8MPY1	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Gamma-aminobutyric acid receptor subunit theta	Q9UN88	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Progesterone receptor	P06401	Humans	Known	Not Available
Click to view 3D structure	Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	O14983	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Sarcoplasmic/endoplasmic reticulum calcium ATPase 2	P16615	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Sodium/potassium-transporting ATPase subunit alpha-1	P05023	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Sodium/potassium-transporting ATPase subunit alpha-2	P50993	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Sodium/potassium-transporting ATPase subunit alpha-3	P13637	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Sodium/potassium-transporting ATPase subunit alpha-4	Q13733	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Sodium/potassium-transporting ATPase subunit beta-1	P05026	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Sodium/potassium-transporting ATPase subunit beta-2	P14415	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Sodium/potassium-transporting ATPase subunit beta-3	P54709	Humans	Known	This organochloride 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. (T10)
Click to view 3D structure	Sodium/potassium-transporting ATPase subunit gamma	P54710	Humans	Known	This organochloride 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. (T10)