title: Direct reaction of oximes with crotylsarin, cyclosarin, or VX in vitro.
abstract: The direct reaction of seven pyridinium oximes with the organophosphorus compounds (OPCs) crotylsarin, cyclosarin, and VX was studied by spectrophotometry. This method allows to quantify different parameters: (a) the half-life times (t (1/2)) of the oxime-OPC reactions on the basis of the changes in the absorption at the zwitterion (betaine) peak maximum, (b) the first- and second-order rate constants (k (1), k (2)), and (c) the maximum reaction velocities (v (max)). The results of the study show that the reaction velocity of the nerve agents with any of the oximes investigated decreased in the order crotylsarin > cyclosarin > VX. The comparison of the reaction rates of the three therapeutically used oximes (2-PAM, obidoxime, HI 6) with the respective OPC gave the highest rate for crotylsarin and cyclosarin with obidoxime and to a similar degree with HI 6, while in the case of VX the most reactive oxime was HI 6. The reaction velocity of the nerve agents with the monopyridinium oxime 2-PAM was lower as compared to the bispyridinium oximes (obidoxime, HI 6). The results obtained with the two sarin analogues indicate that the direct reaction with 2-PAM, obidoxime, or HI 6 could be used for non-corrosive decontamination purposes, especially, if sensitive biological surfaces like skin, mucous membranes, or wounds are considered. However, in view of the concentrations of nerve agents and oximes, which could be expected during OPC poisoning in man, the maximum reaction velocities would not be high enough to contribute markedly to the detoxication of nerve agents in vivo.
authors.affiliation: Institut für Pharmakologie und Toxikologie der Bundeswehr, Neuherbergstrasse 11, 80937 München, Germany.
authors.forename: G
authors.initials: G
authors.lastname: Becker
authors.forename: A
authors.initials: A
authors.lastname: Kawan
authors.forename: D
authors.initials: D
authors.lastname: Gutzeit
authors.forename: F
authors.initials: F
authors.lastname: Worek
authors.forename: L
authors.initials: L
authors.lastname: Szinicz
mesh_terms: D002800:Cholinesterase Inhibitors / Q000737:chemistry* / Q000633:toxicity; D002801:Cholinesterase Reactivators / Q000737:chemistry* / Q000627:therapeutic use; D003666:Decontamination / Q000379:methods; D006207:Half-Life; D007700:Kinetics; D008956:Models, Chemical; D009768:Obidoxime Chloride / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry* / Q000633:toxicity; D009946:Organothiophosphorus Compounds / Q000737:chemistry* / Q000633:toxicity; D010091:Oximes / Q000737:chemistry* / Q000627:therapeutic use; D011041:Poisoning / Q000517:prevention & control; D011220:Pralidoxime Compounds / Q000737:chemistry; D011726:Pyridinium Compounds / Q000737:chemistry; D012524:Sarin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000633:toxicity; D013056:Spectrophotometry, Ultraviolet
chemical_list: D002800:Cholinesterase Inhibitors; D002801:Cholinesterase Reactivators; D009768:Obidoxime Chloride; D009943:Organophosphorus Compounds; D009946:Organothiophosphorus Compounds; D010091:Oximes; D011220:Pralidoxime Compounds; D011726:Pyridinium Compounds; D012524:Sarin; C071511:crotylsarin; C009680:VX-agent; C022870:asoxime chloride; C028797:pralidoxime; C053914:cyclohexyl methylphosphonofluoridate