DFP

Inhibitor of cholinesterases and many serine hydrolases (not only alpha/beta hydrolases but also trypsin chymotrypsin etc.). DFP is a parasympathomimetic drug used in ophthalmology as a miotic agent in treatment of chronic glaucoma, as a miotic in veterinary medicine, and as an experimental agent in neuroscience because of its acetylcholinesterase inhibitory properties and ability to induce delayed peripheral neuropathy. DFP can phosphorylate other residues than active serine (tyrosine, lysine) see pdb 1TRN and Grigoryan et al. BChE appears to be about 100-200 times as sensitive as AChE to DFP and DFP was used to distinguish AChE and BChE before BW284C51 and Iso-OMPA were discovered. DFP is the oxygen analogue of Mipafox.(Structures of not alpha/beta hydrolases inhibited by DFP include: 4V08, 4H1D, 3VTA, 3TT7, 3TXT, 3MH5, 3MH6, 1RS0, 1CI9, 1DUI, 1AT3, 1SUE, 1DFP, 2TGD, 4PKA, 3LH3, 3GCN, 3GCO, 3GDS, 3GDU, 3GDV, 2RCE, 2Z2X, 1PPZ, 1GNV, 1A2Q, 5PTP)

General

Type : Organophosphate

Chemical_Nomenclature : Diisopropylphosphorofluoridate

Canonical SMILES : CC(C)OP(=O)(OC(C)C)F

InChI : InChI=1S\/C6H14FO3P\/c1-5(2)9-11(7,8)10-6(3)4\/h5-6H,1-4H3

InChIKey : MUCZHBLJLSDCSD-UHFFFAOYSA-N

Other name(s) : Diisopropylphosphorofluoridate,Dyflos,Diflupyl,Floropyl,isofluorophate,Fluostigmine,Isoflurophate,Difluorophate,Diflurphate,Dyphlos,isofluorphate,Neoglaucit,PF-3,PF3,T-1703,TL 466


MW : 184.1

Formula : C6H14FO3P

CAS_number : 55-91-4

PubChem : 5936

UniChem : MUCZHBLJLSDCSD-UHFFFAOYSA-N

IUPHAR :

Wikipedia : Diisopropyl_fluorophosphate

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Title : Role of water in aging of human butyrylcholinesterase inhibited by echothiophate: the crystal structure suggests two alternative mechanisms of aging - Nachon_2005_Biochemistry_44_1154
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Title : Effects of mutations of active site residues and amino acids interacting with the Omega loop on substrate activation of butyrylcholinesterase - Masson_2001_Biochim.Biophys.Acta_1544_166
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PubMedSearch : Keshavarz-Shokri_1999_Anal.Biochem_267_406
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Title : Modification of the rate of aging of diisopropylfluorophosphate- inhibited neuropathy target esterase of hen brain - Jokanovic_1998_Toxicol.Lett_95_93
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PubMedSearch : Jokanovic_1998_Toxicol.Lett_95_93
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Title : Inhibition of carboxylesterases in SH-SY5Y human and NB41A3 mouse neuroblastoma cells by organophosphorus esters - Ehrich_1998_J.Toxicol.Environ.Health_53_385
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Title : Augmented hydrolysis of diisopropyl fluorophosphate in engineered mutants of phosphotriesterase - Watkins_1997_J.Biol.Chem_272_25596
Author(s) : Watkins LM , Mahoney HJ , McCulloch JK , Raushel FM
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PubMedSearch : Watkins_1997_J.Biol.Chem_272_25596
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Title : Importance of aspartate-70 in organophosphate inhibition, oxime re-activation and aging of human butyrylcholinesterase - Masson_1997_Biochem.J_325_53
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Title : Down-regulation of cardiac muscarinic receptors induced by di- isopropylfluorophosphate - Valette_1997_J.Nucl.Med_38_1430
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Title : Characterization of monoclonal antibodies that inhibit the catalytic activity of acetylcholinesterases - Gentry_1995_J.Neurochem_64_842
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PubMedSearch : Gentry_1995_J.Neurochem_64_842
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Title : Comparison of the relative inhibition of acetylcholinesterase and neuropathy target esterase in rats and hens given cholinesterase inhibitors - Ehrich_1995_Fundam.Appl.Toxicol_24_94
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Ref : Fundamental & Applied Toxicology , 24 :94 , 1995
Abstract : Ehrich_1995_Fundam.Appl.Toxicol_24_94
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PubMedSearch : Ehrich_1995_Fundam.Appl.Toxicol_24_94
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Title : Strain differences in the laboratory rat: impact on the autonomic, behavioral, and biochemical response to cholinesterase inhibition - Gordon_1995_J.Toxicol.Env.Health_45_59
Author(s) : Gordon CJ , Watkinson WP
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Abstract : Gordon_1995_J.Toxicol.Env.Health_45_59
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PubMedSearch : Gordon_1995_J.Toxicol.Env.Health_45_59
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Ref : Biochimica & Biophysica Acta , 1249 :37 , 1995
Abstract : Aslanian_1995_Biochim.Biophys.Acta_1249_37
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PubMedSearch : Aslanian_1995_Biochim.Biophys.Acta_1249_37
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Author(s) : Barak D , Ordentlich A , Bromberg A , Kronman C , Marcus D , Lazar A , Ariel N , Velan B , Shafferman A
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Title : Site-directed mutagenesis of active site residues reveals plasticity of human butyrylcholinesterase in substrate and inhibitor interactions - Gnatt_1994_J.Neurochem_62_749
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PubMedSearch : Gnatt_1994_J.Neurochem_62_749
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Title : The timing of channel opening during miniature endplate currents at the frog and mouse neuromuscular junctions: effects of fasciculin-2, other anti-cholinesterases and vesamicol - Van der Kloot_1994_Pflugers.Arch_428_114
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PubMedSearch : Van der Kloot_1994_Pflugers.Arch_428_114
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Title : [A kinetic study of the blood serum cholinesterase activity in the freshwater fish Abramis ballerus] - Zhukovskii_1994_Zh.Evol.Biokhim.Fiziol_30_177
Author(s) : Zhukovskii Iu G , Kutsenko SA , Kuznetsova LP , Sochilina EE , Dmitrieva EN , Fartseiger NL , Tonkopii VD , Korkishko NN , Kozlovskaia VI , Fel'd VE
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ESTHER : Zhukovskii_1994_Zh.Evol.Biokhim.Fiziol_30_177
PubMedSearch : Zhukovskii_1994_Zh.Evol.Biokhim.Fiziol_30_177
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Title : Choline derivatives and sodium fluoride protect acetylcholinesterase against irreversible inhibition and aging by DFP and paraoxon - Dehlawi_1994_J.Biochem.Toxicol_9_261
Author(s) : Dehlawi MS , Eldefrawi AT , Eldefrawi ME , Anis NA , Valdes JJ
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PubMedSearch : Dehlawi_1994_J.Biochem.Toxicol_9_261
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Title : Phosphotriesterase--a promising candidate for use in detoxification of organophosphates - Tuovinen_1994_Fundam.Appl.Toxicol_23_578
Author(s) : Tuovinen K , Kaliste-Korhonen E , Raushel FM , Hanninen O
Ref : Fundamental & Applied Toxicology , 23 :578 , 1994
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Title : Physiologically based pharmacokinetic model for the inhibition of acetylcholinesterase by organophosphate esters - Gearhart_1994_Environ.Health.Perspect_11_51
Author(s) : Gearhart JM , Jepson GW , Clewell HJ , Andersen ME , Conolly RB
Ref : Environmental Health Perspectives , 11 :51 , 1994
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ESTHER : Gearhart_1994_Environ.Health.Perspect_11_51
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Title : The molecular forms of acetylcholinesterase from Necator americanus (Nematoda), a hookworm parasite of the human intestine - Pritchard_1994_Eur.J.Biochem_219_317
Author(s) : Pritchard DI , Brown A , Toutant JP
Ref : European Journal of Biochemistry , 219 :317 , 1994
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PubMedSearch : Pritchard_1994_Eur.J.Biochem_219_317
PubMedID: 8306998

Title : Immunochemical characterization of anti-acetylcholinesterase inhibitory monoclonal antibodies - Gentry_1993_Chem.Biol.Interact_87_227
Author(s) : Gentry MK , Saxena A , Ashani Y , Doctor BP
Ref : Chemico-Biological Interactions , 87 :227 , 1993
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PubMedSearch : Gentry_1993_Chem.Biol.Interact_87_227
PubMedID: 7688272

Title : Correlation of the anticholinesterase activity of a series of organophosphates with their ability to compete with agonist binding to muscarinic receptors - Ward_1993_Toxicol.Appl.Pharmacol_122_300
Author(s) : Ward TR , Ferris DJ , Tilson HA , Mundy WR
Ref : Toxicology & Applied Pharmacology , 122 :300 , 1993
Abstract : Ward_1993_Toxicol.Appl.Pharmacol_122_300
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PubMedSearch : Ward_1993_Toxicol.Appl.Pharmacol_122_300
PubMedID: 8212012

Title : Therapeutic efficacy of bis-pyridinium oximes against diisopropyl fluorophosphate (DFP) and soman intoxication in rodents -
Author(s) : Dube SN , Kumar D , Sikder AK , Sikder N , Jaiswal DK , Das Gupta S
Ref : Pharmazie , 47 :68 , 1992
PubMedID: 1608992

Title : In vitro protection of acetylcholinesterase and butyrylcholinesterase by tetrahydroaminoacridine. Comparison with physostigmine - Galli_1992_Biochem.Pharmacol_43_2427
Author(s) : Galli A , Mori F , Gori I , Lucherini M
Ref : Biochemical Pharmacology , 43 :2427 , 1992
Abstract : Galli_1992_Biochem.Pharmacol_43_2427
ESTHER : Galli_1992_Biochem.Pharmacol_43_2427
PubMedSearch : Galli_1992_Biochem.Pharmacol_43_2427
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Title : Cholinesterases of heart muscle. Characterization of multiple enzymes using kinetics of irreversible organophosphorus inhibition - Chemnitius_1992_Biochem.Pharmacol_43_823
Author(s) : Chemnitius JM , Chemnitius GC , Haselmeyer KH , Kreuzer H , Zech R
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Abstract : Chemnitius_1992_Biochem.Pharmacol_43_823
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PubMedSearch : Chemnitius_1992_Biochem.Pharmacol_43_823
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Title : Acylpeptide hydrolase: inhibitors and some active site residues of the human enzyme - Scaloni_1992_J.Biol.Chem_267_3811
Author(s) : Scaloni A , Jones WM , Barra D , Pospischil M , Sassa S , Popowicz AM , Manning LR , Schneewind O , Manning JM
Ref : Journal of Biological Chemistry , 267 :3811 , 1992
Abstract : Scaloni_1992_J.Biol.Chem_267_3811
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Title : Isolation of a tripeptide (Ala-Gly-Ser) exhibiting weak acetylthiocholine hydrolyzing activity from a high-salt soluble form of monkey diaphragm acetylcholinesterase - Jayanthi_1992_Neurochem.Res_17_351
Author(s) : Jayanthi LD , Balasubramanian AS
Ref : Neurochemical Research , 17 :351 , 1992
Abstract : Jayanthi_1992_Neurochem.Res_17_351
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PubMedSearch : Jayanthi_1992_Neurochem.Res_17_351
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Title : Hypothermia: limited tolerance to repeated soman administration and cross-tolerance to oxotremorine - Clement_1991_Pharmacol.Biochem.Behav_39_305
Author(s) : Clement JG
Ref : Pharmacol Biochem Behav , 39 :305 , 1991
Abstract : Clement_1991_Pharmacol.Biochem.Behav_39_305
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Title : A new H-oxime restores rat diaphragm contractility after esterase inhibition in vitro - Alberts_1990_Eur.J.Pharmacol_184_191
Author(s) : Alberts P
Ref : European Journal of Pharmacology , 184 :191 , 1990
Abstract : Alberts_1990_Eur.J.Pharmacol_184_191
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PubMedSearch : Alberts_1990_Eur.J.Pharmacol_184_191
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Title : Inhibition of cholinesterases by DFP and induction of organophosphate-detoxicating enzymes in rats - Kaliste-Korhonen_1990_Gen.Pharmacol_21_527
Author(s) : Kaliste-Korhonen E , Torronen R , Ylitalo P , Hanninen O
Ref : General Pharmacology , 21 :527 , 1990
Abstract : Kaliste-Korhonen_1990_Gen.Pharmacol_21_527
ESTHER : Kaliste-Korhonen_1990_Gen.Pharmacol_21_527
PubMedSearch : Kaliste-Korhonen_1990_Gen.Pharmacol_21_527
PubMedID: 2165959

Title : Repeated exposure to diisopropylfluorophosphate (DFP) produces increased sensitivity to cholinergic antagonists in discrimination retention and reversal - Raffaele_1990_Psychopharmacology_100_267
Author(s) : Raffaele K , Olton D , Annau Z
Ref : Psychopharmacology , 100 :267 , 1990
Abstract : Raffaele_1990_Psychopharmacology_100_267
ESTHER : Raffaele_1990_Psychopharmacology_100_267
PubMedSearch : Raffaele_1990_Psychopharmacology_100_267
PubMedID: 2305015

Title : Down-regulation of muscarinic receptors in the striatum of organophosphate-treated swine - Yang_1990_Toxicol.Appl.Pharmacol_104_375
Author(s) : Yang CM , Dwyer TM , Mohan PM , Ho IK , Farley JM
Ref : Toxicol Appl Pharmacol , 104 :375 , 1990
Abstract : Yang_1990_Toxicol.Appl.Pharmacol_104_375
ESTHER : Yang_1990_Toxicol.Appl.Pharmacol_104_375
PubMedSearch : Yang_1990_Toxicol.Appl.Pharmacol_104_375
PubMedID: 2385834

Title : [Catalytic properties of cholinesterases immobilized in a gelatin membrane] - Kuznetsova_1990_Ukr.Biokhim.Zh_62_42
Author(s) : Kuznetsova LP , Kugusheva LI , Nikol'skaia EB
Ref : Ukr Biokhim Zh , 62 :42 , 1990
Abstract : Kuznetsova_1990_Ukr.Biokhim.Zh_62_42
ESTHER : Kuznetsova_1990_Ukr.Biokhim.Zh_62_42
PubMedSearch : Kuznetsova_1990_Ukr.Biokhim.Zh_62_42
PubMedID: 2087792

Title : Cold exposure decreases the effectiveness of atropine-oxime treatment in organophosphate intoxication in rats and mice - Kaliste-Korhonen_1989_Gen.Pharmacol_20_805
Author(s) : Kaliste-Korhonen E , Ryhanen R , Ylitalo P , Hanninen O
Ref : General Pharmacology , 20 :805 , 1989
Abstract : Kaliste-Korhonen_1989_Gen.Pharmacol_20_805
ESTHER : Kaliste-Korhonen_1989_Gen.Pharmacol_20_805
PubMedSearch : Kaliste-Korhonen_1989_Gen.Pharmacol_20_805
PubMedID: 2687080

Title : Comparison of the effects of diisopropylfluorophosphate, sarin, soman, and tabun on toxicity and brain acetylcholinesterase activity in mice - Tripathi_1989_J.Toxicol.Environ.Health_26_437
Author(s) : Tripathi HL , Dewey WL
Ref : J Toxicol Environ Health , 26 :437 , 1989
Abstract : Tripathi_1989_J.Toxicol.Environ.Health_26_437
ESTHER : Tripathi_1989_J.Toxicol.Environ.Health_26_437
PubMedSearch : Tripathi_1989_J.Toxicol.Environ.Health_26_437
PubMedID: 2709438

Title : A microassay-based procedure for measuring low levels of toxic organophosphorus compounds through acetylcholinesterase inhibition - Hammond_1989_Anal.Biochem_180_380
Author(s) : Hammond PS , Forster JS
Ref : Analytical Biochemistry , 180 :380 , 1989
Abstract : Hammond_1989_Anal.Biochem_180_380
ESTHER : Hammond_1989_Anal.Biochem_180_380
PubMedSearch : Hammond_1989_Anal.Biochem_180_380
PubMedID: 2817369

Title : Toxicity of an acute dose of agent VX and other organophosphorus esters in the chicken - Wilson_1988_J.Toxicol.Environ.Health_23_103
Author(s) : Wilson BW , Henderson JD , Chow E , Schreider J , Goldman M , Culbertson R , Dacre JC
Ref : J Toxicol Environ Health , 23 :103 , 1988
Abstract : Wilson_1988_J.Toxicol.Environ.Health_23_103
ESTHER : Wilson_1988_J.Toxicol.Environ.Health_23_103
PubMedSearch : Wilson_1988_J.Toxicol.Environ.Health_23_103
PubMedID: 3336055

Title : Effect of the cold environment on organophosphate toxicity and inhibition of cholinesterase activity - Ryhanen_1988_Gen.Pharmacol_19_741
Author(s) : Ryhanen R , Honkakoski P , Harri M , Ylitalo P , Hanninen O
Ref : General Pharmacology , 19 :741 , 1988
Abstract : Ryhanen_1988_Gen.Pharmacol_19_741
ESTHER : Ryhanen_1988_Gen.Pharmacol_19_741
PubMedSearch : Ryhanen_1988_Gen.Pharmacol_19_741
PubMedID: 3215484

Title : Effects of the organophosphate cholinesterase inhibitor (DFP) on hypothalamic acetylcholinesterase and pituitary-adrenal activity -
Author(s) : Kokka N , Clemons GK , Lomax P
Ref : Proc West Pharmacol Soc , 30 :219 , 1987
PubMedID: 3628281

Title : A peptidase activity exhibited by human serum pseudocholinesterase - Boopathy_1987_Eur.J.Biochem_162_191
Author(s) : Boopathy R , Balasubramanian AS
Ref : European Journal of Biochemistry , 162 :191 , 1987
Abstract : Boopathy_1987_Eur.J.Biochem_162_191
ESTHER : Boopathy_1987_Eur.J.Biochem_162_191
PubMedSearch : Boopathy_1987_Eur.J.Biochem_162_191
PubMedID: 3545820

Title : Kinetic investigations into the interactions of aprophen with cholinesterases and a carboxylesterase - Rush_1986_Biochem.Pharmacol_35_4167
Author(s) : Rush RS , Doctor BP , Wolfe AD
Ref : Biochemical Pharmacology , 35 :4167 , 1986
Abstract : Rush_1986_Biochem.Pharmacol_35_4167
ESTHER : Rush_1986_Biochem.Pharmacol_35_4167
PubMedSearch : Rush_1986_Biochem.Pharmacol_35_4167
PubMedID: 3098245

Title : In-vitro and in-vivo protection of acetylcholinesterase by eseroline against inactivation by diisopropyl fluorophosphate and carbamates - Galli_1985_J.Pharm.Pharmacol_37_42
Author(s) : Galli A , Malmberg-Aiello P , Renzi G , Bartolini A
Ref : J Pharm Pharmacol , 37 :42 , 1985
Abstract : Galli_1985_J.Pharm.Pharmacol_37_42
ESTHER : Galli_1985_J.Pharm.Pharmacol_37_42
PubMedSearch : Galli_1985_J.Pharm.Pharmacol_37_42
PubMedID: 2858526

Title : Polymorphism of pseudocholinesterase in Torpedo marmorata tissues: comparative study of the catalytic and molecular properties of this enzyme with acetylcholinesterase - Toutant_1985_J.Neurochem_44_580
Author(s) : Toutant JP , Massoulie J , Bon S
Ref : Journal of Neurochemistry , 44 :580 , 1985
Abstract : Toutant_1985_J.Neurochem_44_580
ESTHER : Toutant_1985_J.Neurochem_44_580
PubMedSearch : Toutant_1985_J.Neurochem_44_580
PubMedID: 2578181

Title : Mechanisms involved in the development of tolerance to DFP toxicity - Gupta_1985_Fundam.Appl.Toxicol_5_S17
Author(s) : Gupta RC , Patterson GT , Dettbarn WD
Ref : Fundamental & Applied Toxicology , 5 :S17 , 1985
Abstract : Gupta_1985_Fundam.Appl.Toxicol_5_S17
ESTHER : Gupta_1985_Fundam.Appl.Toxicol_5_S17
PubMedSearch : Gupta_1985_Fundam.Appl.Toxicol_5_S17
PubMedID: 4092885

Title : Brain cholinesterases. Differentiation of target enzymes for toxic organophosphorus compounds - Chemnitius_1983_Biochem.Pharmacol_32_1693
Author(s) : Chemnitius JM , Haselmeyer KH , Zech R
Ref : Biochemical Pharmacology , 32 :1693 , 1983
Abstract : Chemnitius_1983_Biochem.Pharmacol_32_1693
ESTHER : Chemnitius_1983_Biochem.Pharmacol_32_1693
PubMedSearch : Chemnitius_1983_Biochem.Pharmacol_32_1693
PubMedID: 6870909

Title : Differential effects of di-isopropylfluorophosphate poisoning and its treatment on opioid antinociception in the mouse - Kitchen_1983_Life.Sci_1_669
Author(s) : Kitchen I , Green PG
Ref : Life Sciences , 1 :669 , 1983
Abstract : Kitchen_1983_Life.Sci_1_669
ESTHER : Kitchen_1983_Life.Sci_1_669
PubMedSearch : Kitchen_1983_Life.Sci_1_669
PubMedID: 6664242

Title : Evaluation of cytotoxic responses caused by selected organophosphorus esters in chick sympathetic ganglia cultures - Obersteiner_1978_Can.J.Comp.Med_42_80
Author(s) : Obersteiner EJ , Sharma RP
Ref : Can J Comp Med , 42 :80 , 1978
Abstract : Obersteiner_1978_Can.J.Comp.Med_42_80
ESTHER : Obersteiner_1978_Can.J.Comp.Med_42_80
PubMedSearch : Obersteiner_1978_Can.J.Comp.Med_42_80
PubMedID: 565668

Title : A radiometric study of cholinesterase and its inhibition -
Author(s) : Winteringham FP , Disney RW
Ref : Biochemical Journal , 91 :506 , 1964
PubMedID: 5840710