Sarin
The organophosphate nerve agents tabun (GA), sarin (GB), soman (GD), and cyclosarin (GF) are among the most toxic chemical warfare agents known. The G-series nerve agents are named because German scientists led by Dr Gerhard Schraderfirst synthesized them during World War II, beginning with GA in 1936. GB was discovered next in 1938, followed by GD in 1944 and finally GF in 1949. The only other known nerve agent, O-ethyl S-(2-diisopropylaminoethyl) methylphosphonothioate (VX), V-series - VE, VG, VM, Russian VX). G-series nerve agents share a number of common physical and chemical properties. At room temperature, the G-series nerve agents are volatile liquids, making them a serious risk for 2 types of exposure: dermal contact with liquid nerve agent or inhalation of nerve agent vapor.Sarin is an acronym for the names of the members of the development team: Schrader. Ambrose. Rudriger. and van der Linde. The Germans deignated it T-I44 or Trilon-46. The United Slates eventually designated it GB
General
Type : Chemical Warfare Agent, Organophosphate, Nerve Agent G-series, Derivative of Sarin
Chemical_Nomenclature : 2-[fluoro(methyl)phosphoryl]oxypropane
Canonical SMILES : CC(C)OP(=O)(C)F
InChI : InChI=1S\/C4H10FO2P\/c1-4(2)7-8(3,5)6\/h4H,1-3H3
InChIKey : DYAHQFWOVKZOOW-UHFFFAOYSA-N
Other name(s) : Zarin, Sarin II, Trilone 46, IMPF, Methylphosphonofluoridic acid 1-methyl-ethyl esther, Isopropylmethylphosphonofluoridate, Isopropoxymethylphosphorylfluoride, GB, T144, T-144, Trilon-46
MW : 140.09
Formula : C4H10FO2P
CAS_number : 107-44-8
PubChem : 7871
UniChem : DYAHQFWOVKZOOW-UHFFFAOYSA-N
Wikipedia : Sarin
Target
Families : Sarin ligand of proteins in family
ACHE
BCHE
PAF-Acetylhydrolase
Carboxypeptidase_S10
Protein :
human-ACHE
human-BCHE
human-CTSA
References (48)
| 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 |
| PubMedID: 34360916 |
| 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 |
| PubMedID: 33513869 |
| Gene_locus related to this paper: 9bact-TtEst2 |
| 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 |
| PubMedID: 33538594 |
| Gene_locus related to this paper: human-ACHE |
| Title : Covalent inhibition of hAChE by organophosphates causes homodimer dissociation through long-range allosteric effects - Blumenthal_2021_J.Biol.Chem__ |
| Author(s) : Blumenthal DK , Cheng X , Fajer M , Ho KY , Rohrer J , Gerlits O , Taylor P , Juneja P , Kovalevsky A , Radic Z |
| Ref : Journal of Biological Chemistry , :101007 , 2021 |
| PubMedID: 34324828 |
| Gene_locus related to this paper: human-ACHE |
| Title : Structural and Kinetic Evidence of Aging after Organophosphate Inhibition of Human Cathepsin A - Bouknight_2020_Biochem.Pharmacol__113980 |
| Author(s) : Bouknight KD , Jurkouich KM , Compton JR , Khavrutskii IV , Guelta MA , Harvey SP , Legler PM |
| Ref : Biochemical Pharmacology , :113980 , 2020 |
| PubMedID: 32305437 |
| Gene_locus related to this paper: human-CTSA |
| Title : Fatal sarin poisoning in Syria 2013: forensic verification within an international laboratory network - John_2018_Forensic.Toxicol_36_61 |
| Author(s) : John H , van der Schans MJ , Koller M , Spruit HET , Worek F , Thiermann H , Noort D |
| Ref : Forensic Toxicol , 36 :61 , 2018 |
| PubMedID: 29367863 |
| Title : Sarin Exposures in A Cohort of British Military Participants in Human Experimental Research at Porton Down 1945-1987 - Keegan_2017_Ann.Work.Expo.Health_62_17 |
| Author(s) : Keegan TJ , Carpenter LM , Brooks C , Langdon T , Venables KM |
| Ref : Ann Work Expo Health , 62 :17 , 2017 |
| PubMedID: 29136135 |
| Title : Structure of a prereaction complex between the nerve agent sarin, its biological target acetylcholinesterase, and the antidote HI-6 - Allgardsson_2016_Proc.Natl.Acad.Sci.U.S.A_113_5514 |
| Author(s) : Allgardsson A , Berg L , Akfur C , Hornberg A , Worek F , Linusson A , Ekstrom F |
| Ref : Proc Natl Acad Sci U S A , 113 :5514 , 2016 |
| PubMedID: 27140636 |
| Gene_locus related to this paper: human-ACHE |
| Title : Crystal structures of human group-VIIA phospholipase A2 inhibited by organophosphorus nerve agents exhibit non-aged complexes - Samanta_2009_Biochem.Pharmacol_78_420 |
| Author(s) : Samanta U , Kirby SD , Srinivasan P , Cerasoli DM , Bahnson BJ |
| Ref : Biochemical Pharmacology , 78 :420 , 2009 |
| PubMedID: 19394314 |
| Gene_locus related to this paper: human-PLA2G7 |
| Title : Structure of HI-6*sarin-acetylcholinesterase determined by X-ray crystallography and molecular dynamics simulation: reactivator mechanism and design - Ekstrom_2009_PLoS.One_4_e5957 |
| Author(s) : Ekstrom F , Hornberg A , Artursson E , Hammarstrom LG , Schneider G , Pang YP |
| Ref : PLoS ONE , 4 :e5957 , 2009 |
| PubMedID: 19536291 |
| Gene_locus related to this paper: mouse-ACHE |
| Title : Enzyme-kinetic investigation of different sarin analogues reacting with human acetylcholinesterase and butyrylcholinesterase - Bartling_2007_Toxicology_233_166 |
| Author(s) : Bartling A , Worek F , Szinicz L , Thiermann H |
| Ref : Toxicology , 233 :166 , 2007 |
| PubMedID: 16904809 |
| Title : Kinetic analysis of interactions between human acetylcholinesterase, structurally different organophosphorus compounds and oximes - Worek_2004_Biochem.Pharmacol_68_2237 |
| Author(s) : Worek F , Thiermann H , Szinicz L , Eyer P |
| Ref : Biochemical Pharmacology , 68 :2237 , 2004 |
| PubMedID: 15498514 |
| Title : Crystal structures of aged phosphonylated acetylcholinesterase: nerve agent reaction products at the atomic level - Millard_1999_Biochemistry_38_7032 |
| Author(s) : Millard CB , Kryger G , Ordentlich A , Greenblatt HM , Harel M , Raves ML , Segall Y , Barak D , Shafferman A , Silman I , Sussman JL |
| Ref : Biochemistry , 38 :7032 , 1999 |
| PubMedID: 10353814 |
| Gene_locus related to this paper: torca-ACHE |
| Title : Crystal structure of Aged phosphorylated and phosphonylated Torpedo Californica Acetylcholinesterase - |
| Author(s) : Millard CB , Kryger G , Ordentlich A , Harel M , Raves ML , Greenblatt HM , Segall Y , Barak D , Shafferman A , Silman I , Sussman JL |
| Ref : In Structure and Function of Cholinesterases and Related Proteins - Proceedings of Sixth International Meeting on Cholinesterases , (Doctor, B.P., Taylor, P., Quinn, D.M., Rotundo, R.L., Gentry, M.K. Eds) Plenum Publishing Corp. :425 , 1998 |
| PubMedID: |
| Gene_locus related to this paper: torca-ACHE |
| 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 |
| PubMedID: 9587020 |
| Title : A preliminary study on delayed vestibulo-cerebellar effects of Tokyo Subway Sarin Poisoning in relation to gender difference: frequency analysis of postural sway - Yokoyama_1998_J.Occup.Environ.Med_40_17 |
| Author(s) : Yokoyama K , Araki S , Murata K , Nishikitani M , Okumura T , Ishimatsu S , Takasu N |
| Ref : J Occup Environ Med , 40 :17 , 1998 |
| PubMedID: 9467116 |
| Title : [Legionella pneumonia caused by aspiration of hot spring water after sarin exposure] - Kamimura_1998_Nihon.Kokyuki.Gakkai.Zasshi_36_278 |
| Author(s) : Kamimura M , Katoh O , Kawata H , Kudo K , Yagishita Y , Niino H , Saitoh K , Saitoh A |
| Ref : Nihon Kokyuki Gakkai Zasshi , 36 :278 , 1998 |
| PubMedID: 9656677 |
| Title : Detection of the sarin hydrolysis product in formalin-fixed brain tissues of victims of the Tokyo subway terrorist attack - Matsuda_1998_Toxicol.Appl.Pharmacol_150_310 |
| Author(s) : Matsuda Y , Nagao M , Takatori T , Niijima H , Nakajima M , Iwase H , Kobayashi M , Iwadate K |
| Ref : Toxicol Appl Pharmacol , 150 :310 , 1998 |
| PubMedID: 9653062 |
| Title : Chronic neurobehavioral effects of Tokyo subway sarin poisoning in relation to posttraumatic stress disorder - Yokoyama_1998_Arch.Environ.Health_53_249 |
| Author(s) : Yokoyama K , Araki S , Murata K , Nishikitani M , Okumura T , Ishimatsu S , Takasu N , White RF |
| Ref : Archives of Environmental Health , 53 :249 , 1998 |
| PubMedID: 9709988 |
| Title : Organophosphorus acid anhydride hydrolase activity in human butyrylcholinesterase: synergy results in a somanase - Millard_1998_Biochemistry_37_237 |
| Author(s) : Millard CB , Lockridge O , Broomfield CA |
| Ref : Biochemistry , 37 :237 , 1998 |
| PubMedID: 9425044 |
| Gene_locus related to this paper: human-BCHE |
| Title : Effects of various drugs including organophosphorus compounds (OPC) and therapeutic compounds against OPC on DRL responding - Bizot_1998_Pharmacol.Biochem.Behav_59_1069 |
| Author(s) : Bizot JC |
| Ref : Pharmacol Biochem Behav , 59 :1069 , 1998 |
| PubMedID: 9586869 |
| Title : Definitive evidence for the acute sarin poisoning diagnosis in the Tokyo subway - Nagao_1997_Toxicol.Appl.Pharmacol_144_198 |
| Author(s) : Nagao M , Takatori T , Matsuda Y , Nakajima M , Iwase H , Iwadate K |
| Ref : Toxicol Appl Pharmacol , 144 :198 , 1997 |
| PubMedID: 9169085 |
| Title : Eighteen cases exposed to sarin in Matsumoto, Japan - Suzuki_1997_Intern.Med_36_466 |
| Author(s) : Suzuki J , Kohno T , Tsukagosi M , Furuhata T , Yamazaki K |
| Ref : Intern Med , 36 :466 , 1997 |
| PubMedID: 9240494 |
| Title : Sarin poisoning on Tokyo subway - Ohbu_1997_South.Med.J_90_587 |
| Author(s) : Ohbu S , Yamashina A , Takasu N , Yamaguchi T , Murai T , Nakano K , Matsui Y , Mikami R , Sakurai K , Hinohara S |
| Ref : South Med J , 90 :587 , 1997 |
| PubMedID: 9191733 |
| Title : [Acute poisoning by neuroparalytic agents and its long-term effects] - Ianno_1997_Med.Tr.Prom.Ekol_6_5 |
| Author(s) : Ianno LV , Musiichuk Iu I |
| Ref : Med Tr Prom Ekol , 6 :5 , 1997 |
| PubMedID: 9273141 |
| Title : Differential inhibition of the brain acetylcholinesterase molecular forms following sarin, soman and VX intoxication in laboratory rats - Bajgar_1997_Acta.Medica_40_89 |
| Author(s) : Bajgar J |
| Ref : Acta Medica , 40 :89 , 1997 |
| PubMedID: 9481881 |
| Title : Effect of atropine and bispyridinium oximes on respiratory and circulatory function in guinea-pigs poisoned by sarin - Worek_1995_Toxicology_95_123 |
| Author(s) : Worek F , Kirchner T , Szinicz L |
| Ref : Toxicology , 95 :123 , 1995 |
| PubMedID: 7825179 |
| Title : Use of hemoperfusion in experimental intoxication with nerve agents - Monhart_1994_Artif.Organs_18_770 |
| Author(s) : Monhart V , Fusek J , Brndiar M , Tlustakova M |
| Ref : Artif Organs , 18 :770 , 1994 |
| PubMedID: 7832660 |
| Title : Erythrocyte and plasma cholinesterase activity in male and female rhesus monkeys before and after exposure to sarin - Woodard_1994_Fundam.Appl.Toxicol_23_342 |
| Author(s) : Woodard CL , Calamaio CA , Kaminskis A , Anderson DR , Harris LW , Martin DG |
| Ref : Fundamental & Applied Toxicology , 23 :342 , 1994 |
| PubMedID: 7835534 |
| 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 |
| PubMedID: 7867909 |
| Title : Action of nerve agents to cholinesterases - Bajgar_1993_Sb.Ved.Pr.Lek.Fak.Karlovy.Univerzity.Hradci.Kralove_36_63 |
| Author(s) : Bajgar J |
| Ref : Sbornik Vedeckych Praci Lekarske Fakulty Karlovy Univerzity , 36 :63 , 1993 |
| PubMedID: 8165432 |
| Title : Long-term effects of the anticholinesterases sarin and soman on latencies of muscle action potentials in mouse diaphragm muscle - Smith_1993_J.Pharm.Pharmacol_45_176 |
| Author(s) : Smith AP |
| Ref : J Pharm Pharmacol , 45 :176 , 1993 |
| PubMedID: 8097774 |
| Title : Successful pretreatment\/therapy of soman, sarin and VX intoxication - Lennox_1992_Drug.Chem.Toxicol_15_271 |
| Author(s) : Lennox WJ , Harris LW , Anderson DR , Solana RP , Murrow ML , Wade JV |
| Ref : Drug & Chemical Toxicology , 15 :271 , 1992 |
| PubMedID: 1459040 |
| 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 |
| 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 |
| PubMedID: 1935706 |
| 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 |
| 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 |
| 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 |
| PubMedID: 1815490 |
| 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 |
| PubMedID: 1759111 |
| 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 |
| PubMedID: 2339420 |
| 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 |
| PubMedID: 2075700 |
| Title : Histochemical demonstration of calcium accumulation in muscle fibres after experimental organophosphate poisoning - Inns_1990_Hum.Exp.Toxicol_9_245 |
| Author(s) : Inns RH , Tuckwell NJ , Bright JE , Marrs TC |
| Ref : Hum Exp Toxicol , 9 :245 , 1990 |
| PubMedID: 2390321 |
| 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 |
| 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 |
| PubMedID: 2709438 |
| 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 |
| PubMedID: 4083033 |