Tabun
nerve gas GA || On December 23. 1936 Dr. Gerhard Schrader of I.G. FarBen in Germany accidentally isollated ethyl N,N-dimelhylphosphoramidocyanidate) while engaged in his progrm to develop new insecticides since 1934. It was a colorless to brown liquid with a fainty fruity odor. Controlled animal laboratory studies revealed that death could occur within 20 min of exposure. In January 1937. Schrader and his assistant were the first to experierience the effects on humans. A smalldrop spilled on a laboratory bench caused both of them to experience miosis and difficulty in breathing. The chemical was quickly recognized as a new, more deadly. chemical warfare agent. It was inilially designated as Le-lOO, and later as Trilon-83, Tabun. The United States, designated it GA for German Agent A. The first Tabun production was at Elberfeld. Relocated inn 1940 Dyhemfurth. Tabun was apparenlly tested on German death camp inmates
General
Type : Cyanide, Chemical Warfare Agent, Organophosphate, Nerve Agent G-series
Chemical_Nomenclature : [dimethylamino(ethoxy)phosphoryl]formonitrile
Canonical SMILES : CCOP(=O)(C#N)N(C)C
InChI : InChI=1S\/C5H11N2O2P\/c1-4-9-10(8,5-6)7(2)3\/h4H2,1-3H3
InChIKey : PJVJTCIRVMBVIA-UHFFFAOYSA-N
Other name(s) : Ethyl-N-dimethylphosphoramidocyanidate || Dimethylamidoethoxyphosphoryl cyanide || d7 || Gelan || Trilon 83 || Trilon-83 || GA || Le-100
MW : 162.12
Formula : C5H11N2O2P
CAS_number : 77-81-6
PubChem : 6500
UniChem : PJVJTCIRVMBVIA-UHFFFAOYSA-N
Wikipedia : Tabun_(nerve_agent)
References (25)
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| Author(s) : Jacquet P , Remy B , Bross RPT , van Grol M , Gaucher F , Chabriere E , De Koning MC , Daude D |
| Ref : Int J Mol Sci , 22 : , 2021 |
| Abstract : |
| PubMedSearch : Jacquet_2021_Int.J.Mol.Sci_22_ |
| PubMedID: 34360916 |
| Title : Structural and Biochemical Insights into the Inhibition of Human Acetylcholinesterase by G-Series Nerve Agents and Subsequent Reactivation by HI-6 - McGuire_2021_Chem.Res.Toxicol_34_804 |
| Author(s) : McGuire JR , Bester SM , Guelta MA , Cheung J , Langley C , Winemiller MD , Bae SY , Funk V , Myslinski JM , Pegan SD , Height JJ |
| Ref : Chemical Research in Toxicology , 34 :804 , 2021 |
| Abstract : |
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| PubMedID: 33538594 |
| Gene_locus related to this paper: human-ACHE |
| Title : A Thermophilic Bacterial Esterase for Scavenging Nerve Agents: A Kinetic, Biophysical and Structural Study - Bzdrenga_2021_Molecules_26_657 |
| Author(s) : Bzdrenga J , Trenet E , Chantegreil F , Bernal K , Nachon F , Brazzolotto X |
| Ref : Molecules , 26 :657 , 2021 |
| Abstract : |
| PubMedSearch : Bzdrenga_2021_Molecules_26_657 |
| PubMedID: 33513869 |
| Gene_locus related to this paper: 9bact-TtEst2 |
| Title : Reversal of Tabun Toxicity Enabled by a Triazole-Annulated Oxime Library-Reactivators of Acetylcholinesterase - Kovarik_2019_Chemistry_25_4100 |
| Author(s) : Kovarik Z , Kalisiak J , Macek Hrvat N , Katalinic M , Zorbaz T , Zunec S , Green C , Radic Z , Fokin VV , Sharpless KB , Taylor P |
| Ref : Chemistry , 25 :4100 , 2019 |
| Abstract : |
| PubMedSearch : Kovarik_2019_Chemistry_25_4100 |
| PubMedID: 30458057 |
| Title : Counteracting tabun inhibition by reactivation by pyridinium aldoximes that interact with active center gorge mutants of acetylcholinesterase - Kovarik_2019_Toxicol.Appl.Pharmacol_372_40 |
| Author(s) : Kovarik Z , Macek Hrvat N , Kalisiak J , Katalinic M , Sit RK , Zorbaz T , Radic Z , Fokin VV , Sharpless KB , Taylor P |
| Ref : Toxicol Appl Pharmacol , 372 :40 , 2019 |
| Abstract : |
| PubMedSearch : Kovarik_2019_Toxicol.Appl.Pharmacol_372_40 |
| PubMedID: 30978400 |
| Gene_locus related to this paper: human-ACHE |
| Title : Structural evidence that human acetylcholinesterase inhibited by tabun ages through O-dealkylation - Carletti_2010_J.Med.Chem_53_4002 |
| Author(s) : Carletti E , Colletier JP , Dupeux F , Trovaslet M , Masson P , Nachon F |
| Ref : Journal of Medicinal Chemistry , 53 :4002 , 2010 |
| Abstract : |
| PubMedSearch : Carletti_2010_J.Med.Chem_53_4002 |
| PubMedID: 20408548 |
| Gene_locus related to this paper: human-ACHE |
| Title : Novel nerve-agent antidote design based on crystallographic and mass spectrometric analyses of tabun-conjugated acetylcholinesterase in complex with antidotes - Ekstrom_2007_Clin.Pharmacol.Ther_82_282 |
| Author(s) : Ekstrom F , Astot C , Pang YP |
| Ref : Clinical Pharmacology & Therapeutics , 82 :282 , 2007 |
| Abstract : |
| PubMedSearch : Ekstrom_2007_Clin.Pharmacol.Ther_82_282 |
| PubMedID: 17443135 |
| Gene_locus related to this paper: mouse-ACHE |
| Title : Crystal structures of human carboxylesterase 1 in covalent complexes with the chemical warfare agents soman and tabun - Fleming_2007_Biochemistry_46_5063 |
| Author(s) : Fleming CD , Edwards CC , Kirby SD , Maxwell DM , Potter PM , Cerasoli DM , Redinbo MR |
| Ref : Biochemistry , 46 :5063 , 2007 |
| Abstract : |
| PubMedSearch : Fleming_2007_Biochemistry_46_5063 |
| PubMedID: 17407327 |
| Gene_locus related to this paper: human-CES1 |
| Title : Structural changes of phenylalanine 338 and histidine 447 revealed by the crystal structures of tabun-inhibited murine acetylcholinesterase - Ekstrom_2006_Biochemistry_45_74 |
| Author(s) : Ekstrom F , Akfur C , Tunemalm AK , Lundberg S |
| Ref : Biochemistry , 45 :74 , 2006 |
| Abstract : |
| PubMedSearch : Ekstrom_2006_Biochemistry_45_74 |
| PubMedID: 16388582 |
| Gene_locus related to this paper: mouse-ACHE |
| Title : Pharmacological Prophylaxis and Antidotal Treatment of Acute Tabun Poisoning - Kassa_2004_Mil.Med.Sci.Lett_73_107 |
| Author(s) : Kassa J , Kunesova G , Vachek J , Kuca K , Cabal J |
| Ref : Military Medical Science Letters , 73 :107 , 2004 |
| Abstract : |
| PubMedSearch : Kassa_2004_Mil.Med.Sci.Lett_73_107 |
| PubMedID: |
| Title : The Effect of Repeated Antidotal Treatment on Tabun-Induced Toxicity in Mice - Kassa_2004_Mil.Med.Sci.Lett_73_142 |
| Author(s) : Kassa J |
| Ref : Military Medical Science Letters , 73 :142 , 2004 |
| Abstract : |
| PubMedSearch : Kassa_2004_Mil.Med.Sci.Lett_73_142 |
| PubMedID: |
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| Ref : Archives of Toxicology , 72 :237 , 1998 |
| Abstract : |
| PubMedSearch : Worek_1998_Arch.Toxicol_72_237 |
| PubMedID: 9587020 |
| Title : Oxime-induced reactivation of acetylcholinesterase inhibited by phosphoramidates - Jokanovic_1996_Toxicol.Lett_85_35 |
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| Ref : Toxicology Letters , 85 :35 , 1996 |
| Abstract : |
| PubMedSearch : Jokanovic_1996_Toxicol.Lett_85_35 |
| PubMedID: 8619258 |
| Title : [Anticholinesterase activity and delayed neurotoxic effects of tabun in hens] - Jokanovic_1993_Vojnosanit.Pregl_50_451 |
| Author(s) : Jokanovic M |
| Ref : Vojnosanit Pregl , 50 :451 , 1993 |
| Abstract : |
| PubMedSearch : Jokanovic_1993_Vojnosanit.Pregl_50_451 |
| PubMedID: 8128641 |
| Title : Neurotoxicity of acute and repeated treatments of tabun, paraoxon, diisopropyl fluorophosphate and isofenphos to the hen - Henderson_1992_Toxicology_72_117 |
| Author(s) : Henderson JD , Higgins RJ , Dacre JC , Wilson BW |
| Ref : Toxicology , 72 :117 , 1992 |
| Abstract : |
| PubMedSearch : Henderson_1992_Toxicology_72_117 |
| PubMedID: 1566275 |
| Title : Potential of memantine, D-tubocurarine, and atropine in preventing acute toxic myopathy induced by organophosphate nerve agents: soman, sarin, tabun and VX - Gupta_1992_Neurotoxicol_13_649 |
| Author(s) : Gupta RC , Dettbarn WD |
| Ref : Neurotoxicology , 13 :649 , 1992 |
| Abstract : |
| PubMedSearch : Gupta_1992_Neurotoxicol_13_649 |
| PubMedID: 1475066 |
| Title : Physostigmine (alone and together with adjunct) pretreatment against soman, sarin, tabun and VX intoxication - Harris_1991_Drug.Chem.Toxicol_14_265 |
| Author(s) : Harris LW , Talbot BG , Lennox WJ , Anderson DR , Solana RP |
| Ref : Drug & Chemical Toxicology , 14 :265 , 1991 |
| Abstract : |
| PubMedSearch : Harris_1991_Drug.Chem.Toxicol_14_265 |
| PubMedID: 1935706 |
| 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 : 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 : |
| PubMedSearch : Alberts_1990_Eur.J.Pharmacol_184_191 |
| PubMedID: 2209712 |
| 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 : 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 : |
| PubMedSearch : Tripathi_1989_J.Toxicol.Environ.Health_26_437 |
| PubMedID: 2709438 |
| Title : Acute tabun toxicity\; biochemical and histochemical consequences in brain and skeletal muscles of rat - Gupta_1987_Toxicology_46_329 |
| Author(s) : Gupta RC , Patterson GT , Dettbarn WD |
| Ref : Toxicology , 46 :329 , 1987 |
| Abstract : |
| PubMedSearch : Gupta_1987_Toxicology_46_329 |
| PubMedID: 3672538 |
| Title : Studies on low dose sub-acute administration of soman, sarin and tabun in the rat - Dulaney_1985_Acta.Pharmacol.Toxicol.(Copenh)_57_234 |
| Author(s) : Dulaney MD, Jr. , Hoskins B , Ho IK |
| Ref : Acta Pharmacologica et Toxicologica (Copenh) , 57 :234 , 1985 |
| Abstract : |
| PubMedSearch : Dulaney_1985_Acta.Pharmacol.Toxicol.(Copenh)_57_234 |
| PubMedID: 4083033 |
| Title : PAM-2 Cl, HI-6, and HGG-12 in soman and tabun poisoning - Boskovic_1984_Fundam.Appl.Toxicol_4_S106 |
| Author(s) : Boskovic B , Kovacevic V , Jovanovic D |
| Ref : Fundamental & Applied Toxicology , 4 :S106 , 1984 |
| Abstract : |
| PubMedSearch : Boskovic_1984_Fundam.Appl.Toxicol_4_S106 |
| PubMedID: 6724203 |
| Title : Delayed neuropathy by the organophosphorus nerve agents soman and tabun - Willems_1984_Arch.Toxicol_55_76 |
| Author(s) : Willems JL , Nicaise M , De Bisschop HC |
| Ref : Archives of Toxicology , 55 :76 , 1984 |
| Abstract : |
| PubMedSearch : Willems_1984_Arch.Toxicol_55_76 |
| PubMedID: 6329137 |