EA-2192

EA-2192

Names
Preferred IUPAC name S-{2-ethyl} methylphosphonothioate
Other names Diisopropylaminoethyl methyl thiolophosphonate
Identifiers
CAS Number	73207-98-4
3D model (JSmol)	Interactive image
ChemSpider	46845
PubChem CID	51760
UNII	5J7SBT85UY Y
CompTox Dashboard (EPA)	DTXSID00223454
SMILES CC(C)N(CCSP(=O)(C)O)C(C)C
Properties
Chemical formula	C9H22NO2PS
Molar mass	239.31 g·mol−1
Appearance	White solid
Solubility in water	Very soluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Extremely toxic
Lethal dose or concentration (LD, LC):
LD50 (median dose)	630 μg/kg (Rat, oral) 18 μg/kg (Rat, iv) 50 μg/kg (Mouse, iv)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

EA-2192 is an extremely toxic degradation product of the VX nerve agent. It is a white solid that is very soluble and stable in water.

EA-2192 is an extremely potent acetylcholinesterase inhibitor. It is almost as toxic as VX itself.

EA-2192 behaves similar to aged Soman as it is the dealkylated form of VX and cannot be reversed with common oxime reactivators.

EA-2192 from VX

See also

• Nerve agent
• VX (nerve agent)

References

1. ^ Ellison, D. Hank (2007). Handbook of chemical and biological warfare agents (2nd ed.). Boca Raton, Fla.: CRC. ISBN 9780849314346.
2. ^ Hoenig, Steven L. (2007), Compendium of Chemical Warfare Agents, Springer, ISBN 978-0-387-34626-7
3. ^ Munro, NB; Talmage, SS; Griffin, GD; Waters, LC; Watson, AP; King, JF; Hauschild, V (December 1999). "The sources, fate, and toxicity of chemical warfare agent degradation products". Environmental Health Perspectives. 107 (12): 933–74. doi:10.1289/ehp.99107933. PMC 1566810. PMID 10585900.

v t e Agents used in chemical warfare incapacitation riot control
Blood agents	Cyanogen Cyanogen bromide Cyanogen chloride (CK) Hydrogen cyanide (AC) Arsine Cacodyl cyanide Cacodyl oxide Hydrogen sulfide Phosphine Carbon monoxide Phosphorus trifluoride Methyl cyanoformate Iron pentacarbonyl Nickel tetracarbonyl 2,3,7,8-Tetrachlorodibenzodioxin Glycolonitrile Lactonitrile Acetone cyanohydrin Stibine Chloral cyanohydrin
Blister agents	Arsenicals Ethyldichloroarsine (ED) Methyldichloroarsine (MD) Phenyldichloroarsine (PD) Lewisite (L) Lewisite 2 (L2) Lewisite 3 (L3) Sulfur mustards Levinstein mustard (EA-229) T Q CEES Nitrogen mustards HN1 HN2 HN3 TL-301 Nettle agents Phosgene oxime (CX) Other KB-16 Dibutylchloromethyltin chloride Selenium oxychloride
Nerve agents	G-agents Tabun (GA) Sarin (GB) Chlorosarin (ClGB) Thiosarin (SGB) Soman (GD) Chlorosoman (ClGD) Ethylsarin (GE) GH Cyclosarin (GF) GP Fluorotabun EA-1356 EA-4352 Crotylsarin V-agents EA-2192 EA-3148 VE VG VM VP VR VS VX EA-1763 Chinese VX V-sub x (GD-7) GV agents GV (EA-5365) Novichok agents A-208 A-232 A-234 A-242 A-262 C01-A035 C01-A039 C01-A042 Carbamates Dimethylcarbamoyl fluoride EA-3887 EA-3887A EA-3966 EA-3990 EA-4056 T-1123 T-1152 T-1194 Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) TL-599 TL-1238 TL-1299 TL-1317 Miotine (AR-28/T-1843) 3152 CT 4-686-293-01 (Agent 1-10) Other Diisopropyl fluorophosphate Dicyclohexyl phosphorofluoridate EA-2012 EA-2054 EA-2098 EA-2613 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Neopentylene fluorophosphate Selenophos Phospholine R-16661 Ro 3-0422 Methanesulfonyl fluoride Dimefox (TL-792) MSPI Precursors Acetonitrile AT ATO AlP A.P.C. complex Chlorosarin Chlorosoman Cyclohexanol 1,8-Dibromooctane N,N-Diisopropylaminoethanol (KB) EA-1250 DIHP ZS DEHP EA-1224 Dimethylamidophosphoric dichloride Dimethylamidophosphoric dicyanide DMHP Ethylphosphonoselenoic dichloride Formaldoxime Nital 4-Hydroxycoumarin Isopropyl alcohol (TB) Methyldichlorophosphine (SW) Methylphosphonyl difluoride (difluoro) (DF) Methylphosphonyl dichloride (dichloro) Nitromethane OPA mixture Phosphoryl chloride Phosphorus pentachloride Phosphorus trichloride (TH) Pinacolone Pinacolyl alcohol Phenacyl chloride QL 2,4,5-Trichlorophenol 3,3,5-Trimethylcyclohexanol Triethyl phosphite Trimethyl phosphite TC TG
Neurotoxins	Anatoxin-a Saxitoxin (TZ) Bungarotoxin Botulinum toxin (BTX) Tetanospasmin (TeNT) Ryanodine Ciguatoxin (CTX) Guanitoxin (GTX) Chlorophenylsilatrane Palytoxin (PTX) Maitotoxin (MTX) Tetrodotoxin Aconitine Brevetoxin (PbTX) Strychnine Antillatoxin (ATX) Tetraethyllead Dimethylmercury HN1 hydrochloride HN2 hydrochloride HN3 hydrochloride A-8564 Picrotoxin Sulfuryl fluoride Tremorine Oxotremorine Batrachotoxin Tetramethylenedisulfotetramine (TETS) Bicyclic phosphates IPTBO TBPO TBPS Cloflubicyne Trimethylolpropane phosphite Domoic acid
Pulmonary/ choking agents	Chlorine Bromine Phosgene (CG) Fluorine Perfluoroisobutene Chloropicrin (PS) Dimethyl(trifluoromethylthio)arsine Diphosgene (DP) Disulfur decafluoride (Z) Acrolein Ethyl bromoacetate Perchloromethyl mercaptan Phenylcarbylamine chloride Tetranitromethane Tetrachlorodinitroethane Chlorine trifluoride Perchloryl fluoride Cadmium oxide Cadmium chloride Mercuric chloride Selenium dioxide Selenoyl fluoride Trifluoronitrosomethane Trichloronitrosomethane Nitric oxide Nitrogen dioxide Dinitrogen tetroxide Sulfur dioxide Phosphorus trichloride Methyl isocyanate Ethenone Methyl vinyl ketone Trifluoroacetyl chloride Salcomine Fluomine Uranium hexafluoride Diborane Green Cross
Vomiting agents	Adamsite (DM) Chloropicrin Litharge-glycerine Diphenylchlorarsine Diphenylcyanoarsine Cacodyl cyanide o-Dianisidine
Incapacitating agents	BZ (CS-4030) Apomorphine Butyrophenone EA-4941 (CS-4640) Etorphine EA-2092 CS-4297 Etoxadrol Dimethylheptylpyran (DMHP) EA-2148 EA-3167 EA-3443 Pethidine EA-3580 Ibogaine EA-3834 Kolokol-1 LSD-25 PAVA spray Psilocybin Sleeping gas Carfentanil JB-318 JB-336 CS-27349 CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,668 Benperidol Desflurane Enflurane Bufotenin Isoflurane Halothane Sevoflurane Pentazocine Procarbazine Fluphenazine Chlorpromazine
Lachrymatory agents	Xylyl bromide Pepper spray (OC) Mace (spray) CN CS CR CNS Benzyl chloride Benzyl bromide Benzyl iodide Bromobenzyl cyanide Thiophosgene Chloroacetone Bromoacetone Bromomethyl ethyl ketone Acrolein Phenacyl bromide Chloroacetophenone oxime Ethyl bromoacetate Ethyl iodoacetate Iodoacetone Allyl isothiocyanate Hexamethylene diisocyanate Crotonaldehyde
Malodorant agents	Thioacetone Allicin Skatole Cadaverine Putrescine
Cornea-clouding agents	Lewisite CX KB-16 Methyl cyanoacrylate N-Methylmorpholine Allyl alcohol Osmium tetroxide Acrolein
Biological toxins	Abrin Aconitine Cyclopiazonic acid Histrionicotoxins Aflatoxins Anatoxin-a Batrachotoxin Botulinum toxin Brevetoxin Ciguatoxin Domoic acid Enterotoxin type B Grayanotoxin Guanitoxin Maitotoxin Modeccin Palytoxin Ricin Saxitoxin Shiga toxin T-2 mycotoxin Tetanospasmin Tetrodotoxin Volkensin Veratridine
Other	Methyl fluoroacetate Napalm (variants and mixtures) Fluoroethyl fluoroacetate Depleted uranium post-combustion uranium oxides Plutonium and its compounds Polonium White phosphorus
List of chemical warfare agents CB military symbol

v t e Neurotoxins
Animal toxins	Batrachotoxin Bestoxin Birtoxin Bungarotoxin Charybdotoxin Conotoxin Fasciculin Huwentoxin Poneratoxin Saxitoxin Tetrodotoxin Vanillotoxin Spooky toxin (SsTx) Epibatidine Zetekitoxin AB Dendrotoxin
Bacterial	Botulinum toxin Tetanospasmin
Cyanotoxins	Anatoxin-a Guanitoxin BMAA Saxitoxin
Plant toxins	Aconitine Bicuculline Penitrem A Picrotoxin Strychnine Tutin Rotenone Ginkgotoxin Cicutoxin Oenanthotoxin Thujone Volkensin Veratridine
Mycotoxins	Ibotenic acid Muscarine Muscimol
Pesticides	Fenpropathrin Tetramethylenedisulfotetramine Bromethalin Crimidine Methamidophos Endosulfan Fipronil Phenylsilatrane Chlorophenylsilatrane Sulfuryl fluoride Mipafox Schradan Dimefox
Nerve agents	Cyclosarin EA-3148 Novichok agent Sarin Soman Tabun VE VG VM VP VR VX GV EA-3990 EA-4056 T-1123 Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) Fluorotabun Chinese VX EA-2192
Bicyclic phosphates	TBPS TBPO IPTBO
Cholinergic neurotoxins	Acetylcholine mustard Catecholine Choline mustard Ethylcholine mustard Hemicholinium mustard
Other	Dimethylcadmium Dimethylmercury Toxopyrimidine IDPN Tetraethyllead

v t e Acetylcholine metabolism and transport modulators
Enzyme (modulators)	ChATTooltip Choline acetyltransferase Inhibitors: 1-(-Benzoylethyl)pyridinium 2-(α-Naphthoyl)ethyltrimethylammonium 3-Chloro-4-stillbazole 4-(1-Naphthylvinyl)pyridine Acetylseco hemicholinium-3 Acryloylcholine AF64A B115 BETA CM-54,903 N,N-Dimethylaminoethylacrylate N,N-Dimethylaminoethylchloroacetate AChETooltip Acetylcholinesterase Inhibitors: Reversible: Carbamates: Aldicarb Aminocarb Bendiocarb Bufencarb Carbaryl Carbendazim Carbetamide Carbofuran Carbosulfan Chlorbufam Chloropropham Dimetilan Ethienocarb Ethiofencarb Fenobucarb Formetanate Formparanate Methiocarb Methomyl Metolcarb Miotine Oxamyl Phenmedipham Pinmicarb Pirimicarb Promecarb Propamocarb Propham Propoxur Thiodicarb Thiofanox; Stigmines: Distigmine Eptastigmine Ganstigmine Neostigmine +glycopyrronium bromide Phenserine Physostigmine Pyridostigmine Quilostigmine Rivastigmine Terestigmine; Others: Acotiamide Ambenonium Caffeine Donepezil EA-3990 EA-4056 Edrophonium Galantamine Huperzine A Huprine W Huprine X Huprine Y Ipidacrine Itopride Ladostigil Minaprine Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) T-1123 T-1152 T-1194 TL-599 TL-1238 Tacrine Zanapezil Irreversible: Organophosphates: 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Acephate Armine Azinphos-ethyl Azinphos-methyl BAY-29952 Bensulide Cadusafos Carbophenothion Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Crotylsarin Cyanophos Cyclosarin (GF) Demephion Demeton Demeton-S-methyl Dialifor Diazinon Dichlorvos Dicrotophos Dicyclohexyl phosphorofluoridate Diisopropylphosphate Diisopropyl fluorophosphate Dimefox Dimethoate Dimethyl 4-(methylthio)phenyl phosphate Dioxathion Disulfoton EA-2012 EA-2054 EA-2098 EA-2192 EA-2613 EA-3148 EA-4352 Echothiophate Ethylsarin (GE) Endothion EPN Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fluorotabun Fonofos Formothion Fosthiazate GD-42 GH GT-45 GV Guanitoxin Hexaethyl tetraphosphate (HETP) Isofluorophate Isoxathion Leptophos Malaoxon Malathion Mazidox Methamidophos Methidathion Methyl phenkapton Methylfluorophosphonylcholine (MFPCh) Metrifonate Mevinphos Mipafox Monocrotophos MSPI Naled Novichok agent Omethoate Oxydemeton-methyl Paraoxon Parathion Parathion-methyl Phorate Phosalone Phosfolan Phosmet Phosphamidon Phoxim Pirimiphos-methyl Profenofos Prothoate R-16661 Ro 3-0340 Ro 3-0346 Ro 3-0347 Ro 3-0351 Ro 3-0352 Ro 3-0397 Ro 3-0411 Ro 3-0412 Ro 3-0417 Ro 3-0419 Ro 3-0422 Ro 3-0433 Ronnel Sarin (GB) Schradan Soman (GD) Sulfotep (TEDP) Tabun (GA) Tebupirimfos Temefos Terbufos Tetrachlorvinphos Tetraethyl pyrophosphate (TEPP) Triazofos Tribufos Trichlorfon Trichloronate Tricresyl phosphate VE VG VM VP VS VR VX; Others: Demecarium Fasciculins (green mamba toxins) (1, 2, 3, 4) Onchidal (Onchidella binneyi) Methanesulfonyl fluoride Unsorted: α-Pinene α-Viniferin Affinine Affinisine Arisugacin A Bulbocapnine Conodurine Coronaridine Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol Ungeremine Ungiminorine Dimethylcarbamoyl fluoride BW284C51 TMTFA 3152 CT Reactivators: Asoxime chloride Methoxime Obidoxime Pralidoxime Trimedoxime bromide BChETooltip Butyrylcholinesterase Inhibitors: Affinine Affinisine Conodurine Cymserine Ladostigil Profenamine (ethopropazine) Rivastigmine Tacrine ZINC-12613047 Many of the other AChE inhibitors listed above
Transporter (modulators)	CHTTooltip Choline transporter Inhibitors: Hemicholinium-3 (hemicholine) Triethylcholine Enhancers: Coluracetam VAChTTooltip Vesicular acetylcholine transporter Inhibitors: Vesamicol
Release (modulators)	Inhibitors SNAP-25Tooltip Synaptosomal-associated protein 25 inactivators: Botulinum toxin (A, C, E) VAMPTooltip Vesicle-associated membrane protein inactivators: Botulinum toxin (B, D, F, G) Others: Bungarotoxins (β-bungarotoxin, γ-bungarotoxin) Enhancers LPHNTooltip Latrophilin agonists: α-Latrotoxin Others: Atracotoxins (e.g., robustoxin, versutoxin) Crotoxin
See also Receptor/signaling modulators Muscarinic acetylcholine receptor modulators Nicotinic acetylcholine receptor modulators

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