145 Dicofol Dicofol is an organochlorine pesticide that is chemically related to DDT. Specifically, it is used as a miticide against the red spider mite. Though difocol is not extremely toxic, its use is controverial because one of the intermediates used in its production is DDT. It also may accumulate in the environment and its use is restricted in many areas. (L631) 115-32-2 8268 C14H9Cl5O 367.909600 White powder. 77.5°C 0.0008 mg/mL at 25 °C [TOMLIN,C (1997)] Oral(L631) ; inhalation (L631) ; dermal (L631). Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 (Q9UL51) Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 (Q9Y3Q4) Sodium/potassium-transporting ATPase subunit alpha-1 (P05023) Sodium/potassium-transporting ATPase subunit alpha-2 (P50993) Sodium/potassium-transporting ATPase subunit alpha-3 (P13637) Sodium/potassium-transporting ATPase subunit alpha-4 (Q13733) Sodium/potassium-transporting ATPase subunit beta-1 (P05026) Sodium/potassium-transporting ATPase subunit beta-2 (P14415) Sodium/potassium-transporting ATPase subunit beta-3 (P54709) Sodium/potassium-transporting ATPase gamma chain (P54710) Calcium-transporting ATPase type 2C member 1 (P98194) Calcium-transporting ATPase type 2C member 2 (O75185) Plasma membrane calcium-transporting ATPase 1 (P20020) Plasma membrane calcium-transporting ATPase 2 (Q01814) Plasma membrane calcium-transporting ATPase 3 (Q16720) Plasma membrane calcium-transporting ATPase 4 (P23634) Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 (O14983) Sarcoplasmic/endoplasmic reticulum calcium ATPase 2 (P16615) Sarcoplasmic/endoplasmic reticulum calcium ATPase 3 (Q93084) Calmodulin (P62158) Estrogen receptor (P03372) Estrogen receptor beta (Q92731) Androgen receptor (P10275) (T10) Like other organochloride pesticides, dicofol is believed to act by at least four mechanisms, possibly all functioning simultaneously. It may reduce potassium transport across the membrane. Dicofol also alters the porous channels through which sodium ions pass. These channels activate (open) normally but are inactivated (closed) slowly, thus interfering with the active transport of sodium out of the nerve axon during repolarization. Dicofol inhibits neuronal adenosine triphosphatases (ATPases), particularly Na+K+-ATPase, and Ca2+-ATPase which play vital roles in neuronal repolarization. Dicofol also inhibits the ability of calmodulin, a calcium mediator in nerves, to transport calcium ions that are essential for the release of neurotransmitters. All these inhibited functions reduce the rate of depolarization and increase the sensitivity of neurons to small stimuli that would not elicit a response in a fully depolarized neuron. Difocol is also an endocrine disruptor and binds both the androgen and estrogen receptor. In addition, it may alter sex hormone metabolism by directly inhibiting cytochrome P-450 19A1. Difocol is able to competitively bind transthyretin, which lowers plasma thyroid hormone levels. (T10, A214, A228, A229) Dicofol can be absorbed via oral, inhahation, and dermal routes. It is distributed primarily to the adipose tissue, as well as the adrenal glands, thyroid, and liver. Metabolism of dicofol produces the metabolites 4,4'-dichloro-benzophenone and 4,4'-dichlorodicofol. Dicofol and its metabolites are excreted mainly in the faeces. (L631, L632) LD50: 595 mg/kg (Oral, Rat) (T90) LD50: 2100 mg/kg (Percutaneous, Rabbit) (T71) 3, not classifiable as to its carcinogenicity to humans. (L135) Dicofol is used as a pesticide on agricultural crops and ornamental plants, as well as for agricultural and domestic buildings for mite control. (L631) Dicofol poisoning affects the liver, kidneys and the central nervous system. Very severe cases may result in convulsions, coma, or death from respiratory failure. High doses may also cause reproductive damage. (L631) Symptoms exposure include nausea, dizziness, weakness and vomiting. Dermal exposure may cause skin irritation or a rash, and eye contact may cause conjunctivitis. (T10, L631) Treatment of dicofol poisoning is mainly symptomatic. Areas of contact should be washed with soap and water, and gastric lavage may be performed if ingested. (L632) 2009-03-06T18:58:09Z 2026-03-26T22:50:18Z C14301 34692 CPD-121 D004010 Dicofol 456 true OC(C1=CC=C(Cl)C=C1)(C1=CC=C(Cl)C=C1)C(Cl)(Cl)Cl C14H9Cl5O InChI=1S/C14H9Cl5O/c15-11-5-1-9(2-6-11)13(20,14(17,18)19)10-3-7-12(16)8-4-10/h1-8,20H UOAMTSKGCBMZTC-UHFFFAOYSA-N 370.486 367.909603445 Exogenous Solid CHEMBL228511 7970 CHEM000134 DTXSID4020450 NS00004774 2,2,2-trichloro-1,1-bis(4-chlorophenyl)ethan-1-ol