VX
The V-series weapons, including VX, are the most highly toxic chemical warfare nerve agents. Nerve agents are compounds that have the capacity to inactivate the enzyme acetylcholinesterase (AChE). The first compounds to be synthesized were known as the G agents (G stands for German): tabun (GA), sarin (GB), and soman (GD). These compounds were discovered and synthesized by German scientists, led by Dr Gerhard Schrader, during World War II. The V agents are part of the group of persistent agents, which are nerve agents that can remain on skin, clothes, and other surfaces for long periods of time. The consistency of these agents is similar to oil; thus, the inhalation hazard is less than with the G agents. This consistency thus renders them toxic mainly by dermal exposures. The British first synthesized O-ethyl S-(2-diisopropylaminoethyl) methylphosphonothioate (VX) in 1954.
General
Type : Chemical Warfare Agent, Organophosphate, Nerve Agent V-series, Derivative of VX, Sulfur Compound
Chemical_Nomenclature : N-[2-[ethoxy(methyl)phosphoryl]sulfanylethyl]-N-propan-2-ylpropan-2-amine
Canonical SMILES : CCOP(=O)(C)SCCN(C(C)C)C(C)C
InChI : InChI=1S\/C11H26NO2PS\/c1-7-14-15(6,13)16-9-8-12(10(2)3)11(4)5\/h10-11H,7-9H2,1-6H3
InChIKey : JJIUCEJQJXNMHV-UHFFFAOYSA-N
Other name(s) : O-ethyle methylphosphonothiolate, S-2 diiso propylaminoethyl || O-ehtyl-S2-diisopropylaminoethyl methyl-phosphonothinate || methylthiophosphorous acid O-ethyl-S-2-diisopropyl-aminoethylester || EDIM || VX (van) || Tx 60 || CCRIS 3351 || HSDB 6459 || BRN 1949015 || NISTC50782699 || EA 1701 || Ethyl S-dimethylaminoethyl methylphosphonothiolate || Ethyl-S-diisopropylaminoethyl methylthiophosphonate || MPT || EA-1701 || methylphosphonothioic acid
MW : 267.37
Formula : C11H26NO2PS
CAS_number : 50782-69-9
PubChem : 39793
UniChem : JJIUCEJQJXNMHV-UHFFFAOYSA-N
Wikipedia : VX_(nerve_agent)
References (76)
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| Gene_locus related to this paper: 9bact-TtEst2 |
| Title : Rational design, synthesis and evaluation of uncharged, smart bis-oxime antidotes of organophosphate-inhibited human acetylcholinesterase - Gorecki_2020_J.Biol.Chem_295_4079 |
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| Gene_locus related to this paper: human-ACHE |
| Title : The use of VX as a terrorist agent: action by Aum Shinrikyo of Japan and the death of Kim Jong-Nam in Malaysia: four case studies - Tu_2020_Global.Security.Health.Science.Policy_5_45 |
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| Gene_locus related to this paper: human-ACHE |
| Title : Tracing and attribution of V-type nerve agents in human exposure by strategy of assessing the phosphonylated and disulfide adducts on ceruloplasmin - Fu_2019_Toxicology_430_152346 |
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| Gene_locus related to this paper: human-ACHE |
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| Gene_locus related to this paper: human-ACHE |
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| Gene_locus related to this paper: human-BCHE |
| Title : Simultaneous quantification of VX and its toxic metabolite in blood and plasma samples and its application for in vivo and in vitro toxicological studies - Reiter_2011_J.Chromatogr.B.Analyt.Technol.Biomed.Life.Sci_879_2704 |
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| Gene_locus related to this paper: torca-ACHE |
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| Gene_locus related to this paper: human-BCHE |
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| Title : Use of hemoperfusion in experimental intoxication with nerve agents - Monhart_1994_Artif.Organs_18_770 |
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| Title : Binding of 125I-fasciculin to rat brain acetylcholinesterase. The complex still binds diisopropyl fluorophosphate - Marchot_1993_J.Biol.Chem_268_12458 |
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| Title : Successful pretreatment\/therapy of soman, sarin and VX intoxication - Lennox_1992_Drug.Chem.Toxicol_15_271 |
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| Title : VX enhances neuronal excitability and alters membrane properties of Rana catesbeiana sympathetic ganglion neurons - Heppner_1992_Comp.Biochem.Physiol.C_102_335 |
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| Title : An organophosphorus compound, Vx, selectively inhibits the rat cardiac Na+,K(+)-ATPase alpha 1 isoform. Biochemical basis of the cardiotoxicity of Vx - Robineau_1991_FEBS.Lett_281_145 |
| Author(s) : Robineau P , Leclercq Y , Gerbi A , Berrebi-Bertrand I , Lelievre LG |
| Ref : FEBS Letters , 281 :145 , 1991 |
| Abstract : |
| PubMedSearch : Robineau_1991_FEBS.Lett_281_145 |
| PubMedID: 1849836 |
| Title : Mechanisms of pulmonary edema induced by an organophosphorus compound in anesthetized dogs - Lainee_1991_Fundam.Appl.Toxicol_17_177 |
| Author(s) : Lainee P , Robineau P , Guittin P , Coq H , Benchetrit G |
| Ref : Fundamental & Applied Toxicology , 17 :177 , 1991 |
| Abstract : |
| PubMedSearch : Lainee_1991_Fundam.Appl.Toxicol_17_177 |
| PubMedID: 1916075 |
| Title : Enzymes as pretreatment drugs for organophosphate toxicity - Doctor_1991_Neurosci.Biobehav.Rev_15_123 |
| Author(s) : Doctor BP , Raveh L , Wolfe AD , Maxwell DM , Ashani Y |
| Ref : Neurosci Biobehav Rev , 15 :123 , 1991 |
| Abstract : |
| PubMedSearch : Doctor_1991_Neurosci.Biobehav.Rev_15_123 |
| PubMedID: 2052184 |
| Title : The influence of inhibitors and other factors on cholinesterases - Bajgar_1991_Sb.Ved.Pr.Lek.Fak.Karlovy.Univerzity.Hradci.Kralove_34_5 |
| Author(s) : Bajgar J |
| Ref : Sb Ved Pr Lek Fak Karlovy Univerzity Hradci Kralove , 34 :5 , 1991 |
| Abstract : |
| PubMedSearch : Bajgar_1991_Sb.Ved.Pr.Lek.Fak.Karlovy.Univerzity.Hradci.Kralove_34_5 |
| PubMedID: 1759111 |
| Title : Comparison of cholinergic and neuromuscular toxicity following acute exposure to sarin and VX in rat - Gupta_1991_Fundam.Appl.Toxicol_16_449 |
| Author(s) : Gupta RC , Patterson GT , Dettbarn WD |
| Ref : Fundamental & Applied Toxicology , 16 :449 , 1991 |
| Abstract : |
| PubMedSearch : Gupta_1991_Fundam.Appl.Toxicol_16_449 |
| PubMedID: 1855618 |
| Title : The effects of irreversible acetylcholinesterase inhibitors on transmission through sympathetic ganglia of the bullfrog - Heppner_1991_Neuropharmacol_30_843 |
| Author(s) : Heppner TJ , Fiekers JF |
| Ref : Neuropharmacology , 30 :843 , 1991 |
| Abstract : |
| PubMedSearch : Heppner_1991_Neuropharmacol_30_843 |
| PubMedID: 1664071 |
| Title : Anticonvulsive and protective effects of diazepam and midazolam in rats poisoned by highly toxic organophosphorus compounds - Bokonjic_1991_Arh.Hig.Rada.Toksikol_42_359 |
| Author(s) : Bokonjic D , Rosic N |
| Ref : Arh Hig Rada Toksikol , 42 :359 , 1991 |
| Abstract : |
| PubMedSearch : Bokonjic_1991_Arh.Hig.Rada.Toksikol_42_359 |
| PubMedID: 1815490 |
| Title : Effects of subacute pretreatment with carbamate together with acute adjunct pretreatment against nerve agent exposure - Anderson_1991_Drug.Chem.Toxicol_14_1 |
| Author(s) : Anderson DR , Harris LW , Lennox WJ , Solana RP |
| Ref : Drug & Chemical Toxicology , 14 :1 , 1991 |
| Abstract : |
| PubMedSearch : Anderson_1991_Drug.Chem.Toxicol_14_1 |
| PubMedID: 1889370 |
| Title : Putative M2 muscarinic receptors of rat heart have high affinity for organophosphorus anticholinesterases - Silveira_1990_Toxicol.Appl.Pharmacol_103_474 |
| Author(s) : Silveira CL , Eldefrawi AT , Eldefrawi ME |
| Ref : Toxicol Appl Pharmacol , 103 :474 , 1990 |
| Abstract : |
| PubMedSearch : Silveira_1990_Toxicol.Appl.Pharmacol_103_474 |
| PubMedID: 2339420 |
| Title : Immunologic protection against VX intoxication in experimental animals - Rong_1990_Pharmacol.Toxicol_67_255 |
| Author(s) : Rong KT , Zhang LJ |
| Ref : Pharmacol Toxicol , 67 :255 , 1990 |
| Abstract : |
| PubMedSearch : Rong_1990_Pharmacol.Toxicol_67_255 |
| PubMedID: 2255683 |
| Title : [Aerobic metabolism of VX and mixed function oxidases] - Fu_1990_Zhongguo.Yao.Li.Xue.Bao_11_123 |
| Author(s) : Fu FH , Sun MJ |
| Ref : Acta Pharmacol Sin , 11 :123 , 1990 |
| Abstract : |
| PubMedSearch : Fu_1990_Zhongguo.Yao.Li.Xue.Bao_11_123 |
| PubMedID: 2275385 |
| Title : Determination of O-ethyl S-2-diisopropylaminoethyl methylphosphonothioate (VX) by thermospray liquid chromatography-mass spectrometry - Wils_1990_J.Chromatogr_523_151 |
| Author(s) : Wils ER , Hulst AG |
| Ref : Journal of Chromatography , 523 :151 , 1990 |
| Abstract : |
| PubMedSearch : Wils_1990_J.Chromatogr_523_151 |
| PubMedID: 2090658 |
| Title : [The effect of the oxime HI-6 on miosis induced by topical administration of sarin and VX in the rabbit eye] - Macic_1990_Vojnosanit.Pregl_47_399 |
| Author(s) : Macic I , Vojvodic V , Knezevic D , Maksimovic M |
| Ref : Vojnosanit Pregl , 47 :399 , 1990 |
| Abstract : |
| PubMedSearch : Macic_1990_Vojnosanit.Pregl_47_399 |
| PubMedID: 2075700 |
| Title : Indirect determination of O-ethyl S-(2-diisopropylaminoethyl) methylphosphonothioate in air at low concentrations - Fowler_1989_J.Chromatogr_478_51 |
| Author(s) : Fowler WK , Smith JE, Jr. |
| Ref : Journal of Chromatography , 478 :51 , 1989 |
| Abstract : |
| PubMedSearch : Fowler_1989_J.Chromatogr_478_51 |
| PubMedID: 2600144 |
| 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 : |
| PubMedSearch : Hammond_1989_Anal.Biochem_180_380 |
| PubMedID: 2817369 |
| Title : Direct actions of organophosphate anticholinesterases on nicotinic and muscarinic acetylcholine receptors - Bakry_1988_J.Biochem.Toxicol_3_235 |
| Author(s) : Bakry NM , el-Rashidy AH , Eldefrawi AT , Eldefrawi ME |
| Ref : Journal of Biochemical Toxicology , 3 :235 , 1988 |
| Abstract : |
| PubMedSearch : Bakry_1988_J.Biochem.Toxicol_3_235 |
| PubMedID: 3236334 |
| 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 : |
| PubMedSearch : Wilson_1988_J.Toxicol.Environ.Health_23_103 |
| PubMedID: 3336055 |
| Title : The effect of spontaneous electromechanical activity on the metabolism of acetylcholinesterase in cultured embryonic rat myotubes - Brockman_1984_J.Neurosci_4_131 |
| Author(s) : Brockman SK , Younkin LH , Younkin SG |
| Ref : Journal of Neuroscience , 4 :131 , 1984 |
| Abstract : |
| PubMedSearch : Brockman_1984_J.Neurosci_4_131 |
| PubMedID: 6693937 |
| Title : Reactivation of VX-inhibited cholinesterase by 2-PAM and HS-6 in rats - Harris_1983_Drug.Chem.Toxicol_6_235 |
| Author(s) : Harris LW , Stitcher DL |
| Ref : Drug & Chemical Toxicology , 6 :235 , 1983 |
| Abstract : |
| PubMedSearch : Harris_1983_Drug.Chem.Toxicol_6_235 |
| PubMedID: 6628257 |
| Title : Penetration of VX into nerve cells, and effects on electrical function - |
| Author(s) : Farquharson DA , Hoskin FC , Hubbard K , Prusch RD |
| Ref : Bulletin of Environmental Contamination & Toxicology , 24 :719 , 1980 |
| PubMedID: 7459460 |
| Title : [Therapy of domestic animals affected by alkylphosphates] - Benes_1979_Vet.Med_24_623 |
| Author(s) : Benes J , Hrusovsky J , Proksova M |
| Ref : Vet Med , 24 :623 , 1979 |
| Abstract : |
| PubMedSearch : Benes_1979_Vet.Med_24_623 |
| PubMedID: 117593 |
| Title : Active-site catalytic efficiency of acetylcholinesterase molecular forms in Electrophorus, torpedo, rat and chicken - Vigny_1978_Eur.J.Biochem_85_317 |
| Author(s) : Vigny M , Bon S , Massoulie J , Leterrier F |
| Ref : European Journal of Biochemistry , 85 :317 , 1978 |
| Abstract : |
| PubMedSearch : Vigny_1978_Eur.J.Biochem_85_317 |
| PubMedID: 648523 |