Tri-o-cresylphosphate
metabolic precursor to a neuropathy target esterase (NTE, PNPLA6) inhibitor. TRI-O-CBESYL PHOSPHATE (TOCP) is metabolized in vitro and in vivo to form potent esterase inhibitors. CBDP and Phenyl-BDPO are potent NTE inhibitors
General
Type : Organophosphate,Organophosphorus flame retardant plasticizer,OPIDN-OP
Chemical_Nomenclature : tris(2-methylphenyl) phosphate
Canonical SMILES : CC1=CC=CC=C1OP(=O)(OC2=CC=CC=C2C)OC3=CC=CC=C3C
InChI : InChI=1S\/C21H21O4P\/c1-16-10-4-7-13-19(16)23-26(22,24-20-14-8-5-11-17(20)2)25-21-15-9-6-12-18(21)3\/h4-15H,1-3H3
InChIKey : YSMRWXYRXBRSND-UHFFFAOYSA-N
Other name(s) : Tri-o-cresyl phosphate,Triorthocresyl phosphate,Phosphoric acid tris(2-methylphenyl) ester,Tri-o-tolyl phosphate,tri-o-tolylphosphate,o-Tolyl phosphate,TOCP,TOTP,tri-cresyl phosphate,o-Cresyl phosphate,Phosflex 179C,Phosphoric acid, tri-o-tolyl ester,Phosphoric acid, tris(2-methylphenyl) ester,TCP,TOFK,tri-ortho-cresyl phosphate
MW : 368.37
Formula : C21H21O4P
CAS_number : 78-30-8
PubChem : 6527
UniChem : YSMRWXYRXBRSND-UHFFFAOYSA-N
IUPHAR :
Wikipedia :
Target
References (47)
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| Author(s) : Ji X , Li N , Ma M , Rao K , Yang R , Wang Z |
| Ref : Environ Pollut , 264 :114747 , 2020 |
| Abstract : Ji_2020_Environ.Pollut_264_114747 |
| ESTHER : Ji_2020_Environ.Pollut_264_114747 |
| PubMedSearch : Ji_2020_Environ.Pollut_264_114747 |
| PubMedID: 32559878 |
| Title : Assessment of neurotoxic effects of tri-cresyl phosphates (TCPs) and cresyl saligenin phosphate (CBDP) using a combination of in vitro techniques - Hausherr_2017_Neurotoxicol_59_210 |
| Author(s) : Hausherr V , Schobel N , Liebing J , van Thriel C |
| Ref : Neurotoxicology , 59 :210 , 2017 |
| Abstract : Hausherr_2017_Neurotoxicol_59_210 |
| ESTHER : Hausherr_2017_Neurotoxicol_59_210 |
| PubMedSearch : Hausherr_2017_Neurotoxicol_59_210 |
| PubMedID: 27288108 |
| Title : Cresyl saligenin phosphate makes multiple adducts on free histidine, but does not form an adduct on histidine 438 of human butyrylcholinesterase - Liyasova_2013_Chem.Biol.Interact_203_103 |
| Author(s) : Liyasova MS , Schopfer LM , Lockridge O |
| Ref : Chemico-Biological Interactions , 203 :103 , 2013 |
| Abstract : Liyasova_2013_Chem.Biol.Interact_203_103 |
| ESTHER : Liyasova_2013_Chem.Biol.Interact_203_103 |
| PubMedSearch : Liyasova_2013_Chem.Biol.Interact_203_103 |
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| Title : Effects of viscosity and osmotic stress on the reaction of human butyrylcholinesterase with cresyl saligenin phosphate, a toxicant related to aerotoxic syndrome: kinetic and molecular dynamics studies - Masson_2013_Biochem.J_454_387 |
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| Abstract : Masson_2013_Biochem.J_454_387 |
| ESTHER : Masson_2013_Biochem.J_454_387 |
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| Title : Differential sensitivity of plasma carboxylesterase-null mice to parathion, chlorpyrifos and chlorpyrifos oxon, but not to diazinon, dichlorvos, diisopropylfluorophosphate, cresyl saligenin phosphate, cyclosarin thiocholine, tabun thiocholine, and carbofuran - Duysen_2012_Chem.Biol.Interact_195_189 |
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| Ref : Chemico-Biological Interactions , 195 :189 , 2012 |
| Abstract : Duysen_2012_Chem.Biol.Interact_195_189 |
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| Title : Cresyl saligenin phosphate, an organophosphorus toxicant, makes covalent adducts with histidine, lysine, and tyrosine residues of human serum albumin - Liyasova_2012_Chem.Res.Toxicol_25_1752 |
| Author(s) : Liyasova MS , Schopfer LM , Lockridge O |
| Ref : Chemical Research in Toxicology , 25 :1752 , 2012 |
| Abstract : Liyasova_2012_Chem.Res.Toxicol_25_1752 |
| ESTHER : Liyasova_2012_Chem.Res.Toxicol_25_1752 |
| PubMedSearch : Liyasova_2012_Chem.Res.Toxicol_25_1752 |
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| Title : Exposure to tri-o-cresyl phosphate detected in jet airplane passengers - Liyasova_2011_Toxicol.Appl.Pharmacol_256_337 |
| Author(s) : Liyasova M , Li B , Schopfer LM , Nachon F , Masson P , Furlong CE , Lockridge O |
| Ref : Toxicol Appl Pharmacol , 256 :337 , 2011 |
| Abstract : Liyasova_2011_Toxicol.Appl.Pharmacol_256_337 |
| ESTHER : Liyasova_2011_Toxicol.Appl.Pharmacol_256_337 |
| PubMedSearch : Liyasova_2011_Toxicol.Appl.Pharmacol_256_337 |
| PubMedID: 21723309 |
| Title : Reaction of cresyl saligenin phosphate, the organophosphorus agent implicated in aerotoxic syndrome, with human cholinesterases: mechanistic studies employing kinetics, mass spectrometry, and X-ray structure analysis - Carletti_2011_Chem.Res.Toxicol_24_797 |
| Author(s) : Carletti E , Schopfer LM , Colletier JP , Froment MT , Nachon F , Weik M , Lockridge O , Masson P |
| Ref : Chemical Research in Toxicology , 24 :797 , 2011 |
| Abstract : Carletti_2011_Chem.Res.Toxicol_24_797 |
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| PubMedSearch : Carletti_2011_Chem.Res.Toxicol_24_797 |
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| Gene_locus related to this paper: human-BCHE |
| Title : Induction of plasma acetylcholinesterase activity in mice challenged with organophosphorus poisons - Duysen_2011_Toxicol.Appl.Pharmacol_255_214 |
| Author(s) : Duysen EG , Lockridge O |
| Ref : Toxicol Appl Pharmacol , 255 :214 , 2011 |
| Abstract : Duysen_2011_Toxicol.Appl.Pharmacol_255_214 |
| ESTHER : Duysen_2011_Toxicol.Appl.Pharmacol_255_214 |
| PubMedSearch : Duysen_2011_Toxicol.Appl.Pharmacol_255_214 |
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| Title : Effect of tri-o-cresyl phosphate on cytoskeleton in human neuroblastoma SK-N-SH cell - Chang_2006_Mol.Cell.Biochem_290_145 |
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| Abstract : Chang_2006_Mol.Cell.Biochem_290_145 |
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| Title : Organophosphate induced delayed neuropathy in genetically dissimilar chickens: studies with tri-ortho-cresyl phosphate (TOCP) and trichlorfon - Honorato_2002_Toxicol.Lett_136_143 |
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| ESTHER : Honorato_2002_Toxicol.Lett_136_143 |
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| Title : Comparison of neurotoxic effects and potential risks from oral administration or ingestion of tricresyl phosphate and jet engine oil containing tricresyl phosphate - Mackerer_1999_J.Toxicol.Environ.Health_57_293 |
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| Ref : J Toxicol Environ Health , 57 :293 , 1999 |
| Abstract : Mackerer_1999_J.Toxicol.Environ.Health_57_293 |
| ESTHER : Mackerer_1999_J.Toxicol.Environ.Health_57_293 |
| PubMedSearch : Mackerer_1999_J.Toxicol.Environ.Health_57_293 |
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| Author(s) : Ehrich M , Correll L |
| Ref : J Toxicol Environ Health , 53 :385 , 1998 |
| Abstract : Ehrich_1998_J.Toxicol.Environ.Health_53_385 |
| ESTHER : Ehrich_1998_J.Toxicol.Environ.Health_53_385 |
| PubMedSearch : Ehrich_1998_J.Toxicol.Environ.Health_53_385 |
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| Title : The effect of a single oral dose of tri-o-cresyl phosphate on neurotoxic esterase and acetylcholinesterase activities in the central nervous system, erythrocytes and plasma - Barrett_1994_Vet.Hum.Toxicol_36_1 |
| Author(s) : Barrett DS , Oehme FW |
| Ref : Vet Hum Toxicol , 36 :1 , 1994 |
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| Ref : Vet Hum Toxicol , 36 :103 , 1994 |
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| Title : Change in hen sciatic nerve calcium after a single oral dose of tri-o-tolyl phosphate - Luttrell_1993_Environ.Res_60_290 |
| Author(s) : Luttrell WE , Olajos EJ , Pleban PA |
| Ref : Environ Research , 60 :290 , 1993 |
| Abstract : Luttrell_1993_Environ.Res_60_290 |
| ESTHER : Luttrell_1993_Environ.Res_60_290 |
| PubMedSearch : Luttrell_1993_Environ.Res_60_290 |
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| Title : Decrease of phosphofructokinase activity in relation to the pathogenesis of triorthocresyl-phosphate-induced delayed neuropathy - Hernandez_1992_Rev.Esp.Fisiol_48_139 |
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| Abstract : Hernandez_1992_Rev.Esp.Fisiol_48_139 |
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| PubMedSearch : Hernandez_1992_Rev.Esp.Fisiol_48_139 |
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| Title : The interaction of Sertoli and Leydig cells in the testicular toxicity of tri-o-cresyl phosphate - Chapin_1990_Toxicol.Appl.Pharmacol_104_483 |
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| Ref : Toxicol Appl Pharmacol , 104 :483 , 1990 |
| Abstract : Chapin_1990_Toxicol.Appl.Pharmacol_104_483 |
| ESTHER : Chapin_1990_Toxicol.Appl.Pharmacol_104_483 |
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| Title : Low non-neuropathic tri-o-cresyl phosphate (TOCP) doses inhibit neuropathy target esterase near the neuropathic threshold in n-hexane pretreated hens - Pellin_1988_Toxicology_49_99 |
| Author(s) : Pellin MC , Vilanova E , Barril J |
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| Abstract : Pellin_1988_Toxicology_49_99 |
| ESTHER : Pellin_1988_Toxicology_49_99 |
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| Abstract : Wilson_1988_J.Toxicol.Environ.Health_23_103 |
| ESTHER : Wilson_1988_J.Toxicol.Environ.Health_23_103 |
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| Abstract : Luttrell_1988_Neurotoxicol_9_539 |
| ESTHER : Luttrell_1988_Neurotoxicol_9_539 |
| PubMedSearch : Luttrell_1988_Neurotoxicol_9_539 |
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| Abstract : Olson_1988_J.Toxicol.Environ.Health_23_499 |
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| Title : Sensitivity to tri-o-cresylphosphate neurotoxicity on n-hexane exposed hens as a model of simultaneous hexacarbon solvent and organophosphorus occupational intoxication - Pellin_1987_Arch.Toxicol_59_311 |
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| Ref : Toxicol Appl Pharmacol , 78 :78 , 1985 |
| Abstract : Padilla_1985_Toxicol.Appl.Pharmacol_78_78 |
| ESTHER : Padilla_1985_Toxicol.Appl.Pharmacol_78_78 |
| PubMedSearch : Padilla_1985_Toxicol.Appl.Pharmacol_78_78 |
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| Title : Characterization of delayed neurotoxicity in the mouse following chronic oral administration of tri-o-cresyl phosphate - Lapadula_1985_Toxicol.Appl.Pharmacol_79_83 |
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| Abstract : Lapadula_1985_Toxicol.Appl.Pharmacol_79_83 |
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| PubMedSearch : Lapadula_1985_Toxicol.Appl.Pharmacol_79_83 |
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| Ref : Biokhimiia , 48 :1634 , 1983 |
| Abstract : Volkova_1983_Biokhimiia_48_1634 |
| ESTHER : Volkova_1983_Biokhimiia_48_1634 |
| PubMedSearch : Volkova_1983_Biokhimiia_48_1634 |
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| Title : Degenerative changes in skeletal muscle of hens with tri-ortho-cresyl phosphate-induced delayed neurotoxicity: altered acetylcholinesterase molecular forms and increased plasma creatine phosphokinase activity - Cisson_1982_Toxicol.Appl.Pharmacol_64_289 |
| Author(s) : Cisson CM , Wilson BW |
| Ref : Toxicol Appl Pharmacol , 64 :289 , 1982 |
| Abstract : Cisson_1982_Toxicol.Appl.Pharmacol_64_289 |
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| PubMedSearch : Cisson_1982_Toxicol.Appl.Pharmacol_64_289 |
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| ESTHER : Wilson_1982_Am.J.Vet.Res_43_1954 |
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| Author(s) : Boskovic B |
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| Abstract : Boskovic_1979_Arch.Toxicol_42_207 |
| ESTHER : Boskovic_1979_Arch.Toxicol_42_207 |
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| Abstract : Brown_1976_Experientia_32_1540 |
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| Title : Changes in the central nervous system in the cat as the result of tri-o-cresylphosphate poisoning - |
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| Title : Comparison of the functional effects of dyflos, tri-o-cresyl phosphate and tri-p-ethylphenyl phosphate in chickens - Cavanagh_1961_Br.J.Pharmacol.Chemother_17_21 |
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| PubMedSearch : Cavanagh_1961_Br.J.Pharmacol.Chemother_17_21 |
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| Title : Biological activity of a tri-o-cresyl phosphate metabolite - Casida_1961_Nature_191_1396 |
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| Abstract : Casida_1961_Nature_191_1396 |
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| Title : Tricresyl phosphates and cholinesterase - |
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| Title : Observations on the specificity of the inhibition of cholinesterases by tri-orthocresyl phosphate - |
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| Title : Specificity of cholinesterase inhibition by tri-o-cresyl phosphate - |
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