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)

Target

Families : Tabun ligand of proteins in family
ACHE BCHE

Structure :
7BFT 7BFN 6WUV 6WUY 3ZLV 7R2F 6G17 2X8B 2WID 2WIF 2WIG 2WIJ 2WIK 2WIL 2WSL 3F98 3DJY 3DKK 3DL4 3DL7 2JF0 2JEZ 2HRR 2C0P 2C0Q

Protein :
mouse-ACHE

References (25)

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 :
PubMedSearch : McGuire_2021_Chem.Res.Toxicol_34_804
PubMedID: 33538594
Gene_locus related to this paper: human-ACHE

Title : Enzymatic Decontamination of G-Type, V-Type and Novichok Nerve Agents - Jacquet_2021_Int.J.Mol.Sci_22_
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 : A Thermophilic Bacterial Esterase for Scavenging Nerve Agents: A Kinetic, Biophysical and Structural Study - Bzdrenga_2021_Molecules_26_657
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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 , Hrvat NM , 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 : 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 : 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 : 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:

Title : Reactivating potency of obidoxime, pralidoxime, HI 6 and HLo 7 in human erythrocyte acetylcholinesterase inhibited by highly toxic organophosphorus compounds - Worek_1998_Arch.Toxicol_72_237
Author(s) : Worek F , Widmann R , Knopff O , Szinicz L
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
Author(s) : Jokanovic M , Maksimovic M , Kilibarda V , Jovanovic D , Savic D
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 : 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 : 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 : 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