847:(AChE) by forming an adduct with the enzyme via a serine residue on that enzyme. These adducts may be decomposed hydrolytically or, for example, by the action of some oximes and thereby regenerate the enzyme. A second reaction type, one in which the enzyme–organophosphate (OP) complex undergoes a subsequent reaction, is usually described as "aging". Once the enzyme–OP complex has aged it is no longer regenerated by the common, oxime reactivators. The rate of this process is dependent on the OP. Soman is an OP that stimulates the rate of aging most rapidly decreasing the half-life to just a few minutes.
777:
239:
45:
812:
36:
457:
508:
462:
461:
965:
caused alterations of the behavior. The active avoidance of the exposed rats was less than the avoidance of non-exposed rats (two-way shuttlebox experiment). Also the motor coordination (hurdle-stepping task), open field behavior and active as well as passive avoidance behavior were affected. One can
862:
Soman can be hydrolyzed by a so-called A-esterase, more specific a diisopropylfluorophosphatase. This esterase, also called somanase, reacts with the anhydride bond between phosphorus and fluorine and accounts for the hydrolysis of the fluoride. Somanase also hydrolyses the methyl group of soman
969:
The knowledge of the effects of low doses of soman and other choline esterase inhibitors on rats could possibly be used to explain the relatively high incidence of airplane accidents due to errors of agricultural pilots. If this knowledge could be applied to humans, one could explain this high
920:
In addition to the direct toxic effects on the nervous system, people exposed to soman may experience long-term effects, most of which are psychological. Subjects who were exposed to a small dose of soman suffered severe toxic effects; once treated, the subjects often developed depression, had
72:
GD; Phosphonofluoridic acid, methyl-, 1, 2, 2-trimethylpropyl ester; 2-(Fluoromethylphosphoryl)oxy-3,3-dimethylbutane; Pinacolyl methylphosphonofluoridate; 1,2,2-Trimethylpropyl methylphosphonofluoridate; Methylpinacolyloxyfluorophosphine oxide; Pinacolyloxymethylphosphonyl fluoride; Pinacolyl
717:
During World War II, research into nerve agents continued in the United States and
Germany. In summer 1944, soman, a colorless liquid with a camphor odor (designated GD by the United States), was developed by the Germans. Soman proved to be even more toxic than tabun and sarin. Nobel Laureate
791:
Soman has a phosphonyl group with a fluoride and a (large) hydrocarbon covalently bound to it. The structure is thus similar to that of sarin, which has only a smaller hydrocarbon group attached (isopropyl). Because of the similarity between the chemical structures, the reactivity of the two
460:
966:
conclude that rats that are exposed to soman performed with less success in tasks that require motor activity as well as the function of higher structures of the central nervous system (CNS) on the same time. In this, soman has a predominantly central effect.
858:
Once taken up in the human body, soman not only inhibits AChE, but it is also a substrate for other esterases. Reaction of soman with these esterases allows for the detoxication of the compound. No metabolic toxification reactions are known for soman.
1185:
Langenberg JP, Spruit HE, Van Der Wiel HJ, Trap HC, Helmich RB, Bergers WW, Van Helden HP, Benschop HP (1998-07-01). "Inhalation
Toxicokinetics of Soman Stereoisomers in the Atropinized Guinea Pig with Nose-Only Exposure to Soman Vapor".
3835:
960:
Experiments have been done in which rats were exposed to soman to test if behavioral effects could be seen at low doses without generating overt symptoms. Exposure of the rats to soman in a dose of less than 3 percent of the
73:
methanefluorophosphonate; Methylfluoropinacolylphosphonate; Fluoromethylpinacolyloxyphosphine oxide; Methylpinacolyloxyphosphonyl fluoride; Pinacolyl methylfluorophosphonate; 1,2,2-Trimethylpropoxyfluoromethylphosphine oxide
827:. The result of this reaction is the forming of soman which is described as “colorless liquid with a somewhat fruity odor.” The low vapor pressure of soman will also produce the volatile gas form of soman. Also, the acid
1476:
Bey TA, Sullivan JB, Walter FG (2001) Organophosphate and carbamate insecticides. In: Sullivan JB, Krieger GR (eds) Clinical environmental health and toxic exposures. Lippincott
Williams & Williams, Philadelphia, pp
3845:
917:. Some, but not all of the later indications are vomiting, extreme muscle pain and peripheral nervous system problems. Those symptoms show as soon as 10 minutes after exposure and may last for many days.
3740:
940:
value for a rat, the human lethal concentration is much lower (954.3 mg min/m versus 70 mg min/m). For compounds such as soman, which may also be used as a weapon, often a fraction of the LC
831:
will form due to the elimination of fluoride and a proton. This acid is indirectly dangerous to humans. Skin contact with hydrogen fluoride will cause an immediate reaction with water which produces
694:
was signed in an attempt to ban chemical warfare. Nevertheless, research into chemical warfare agents and the use of them continued. In 1936 a new, more dangerous chemical agent was discovered when
3805:
1229:
De Jong LP, Van Dijk C, Benschop HP (1988-08-01). "Hydrolysis of the four stereoisomers of soman catalyzed by liver homogenate and plasma from rat, guinea pig and marmoset, and by human plasma".
3855:
901:
3840:
1162:"Report of the OPCW on the Implementation of the Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on their Destruction in 2017"
638:, corrosive, and colorless liquid with a faint odor like that of mothballs or rotten fruit. More commonly, it is a yellow to brown color and has a strong odor described as similar to
3850:
1005:
Millard CB, Kryger G, Ordentlich A, et al. (June 1999). "Crystal structures of aged phosphonylated acetylcholinesterase: nerve agent reaction products at the atomic level".
3733:
921:
antisocial thoughts, were withdrawn and subdued, slept restlessly and had bad dreams. These symptoms lasted six months after exposure but disappeared without lasting damage.
3815:
3800:
913:
As soman is closely related to compounds such as sarin, indications for a soman poisoning are relatively similar. One of the first observable signs of a soman poisoning is
4174:
3820:
2238:
850:
AChE is an enzyme involved with neurotransmission. Because of the severe decrease of the half-life of this enzyme, neurotransmission is abolished in a matter of minutes.
4220:
2319:
886:(MPA). Binding to CarbE reduce the total concentration of soman in the blood, thus resulting in a lower toxicity. Furthermore, CarbE are involved in the detoxication by
995:
United States Senate, 103d
Congress, 2d Session. (May 25, 1994). Material Safety Data Sheet -- Lethal Nerve Agents Somain (GD and Thickened GD). Retrieved Nov. 6, 2004.
3726:
463:
3810:
897:
inhibited AChE in rats, resulting in acute toxic effects. This shows that metabolic reactions accounted for the detoxification of the remaining 95% of the dose.
5408:
2076:
970:
incidence with depressed choline esterase activity due to exposure to pesticides. It is not known whether the extrapolation from rats to humans can be made.
5413:
5313:
5309:
5305:
5301:
5278:
5274:
521:
3825:
893:
The importance of the detoxication of soman after exposure was illustrated in experiments of Fonnum and Sterri (1981). They reported that only 5% of
882:(CarbE). In this binding, soman loses its fluoride. After binding to AChE or ChE soman also loses its phosphoryl group, leading to the formation of
788:, each with a different toxicity, though largely similar. The stereoisomers are C(+)P(+)-soman, C(+)P(−)-soman C(−)P(−)-soman and C(−)P(+)-soman.
5125:
4080:
3938:
745:. When the convention entered force, the parties declared worldwide stockpiles of 9,057 tonnes of soman. The stockpiles were destroyed by 2018.
4865:
4861:
4857:
4853:
4090:
4047:
3998:
5454:
5439:
4475:
4052:
3918:
4033:
3933:
288:
5044:
4725:
4710:
4700:
4695:
4690:
4685:
4680:
4675:
4670:
4209:
4149:
4139:
4003:
3903:
792:
compounds is almost the same. Soman and sarin will both react using the phospho oxygen group, which can bind to amino acids like serine.
4790:
478:
4535:
4023:
1623:
1399:
Sidell FR (1974). "Soman and Sarin: Clinical
Manifestations and Treatment of Accident of Accidental Poisoning by Organophosphates".
1059:
485:
5469:
5449:
5434:
4730:
1321:
Jokanović M (2009-07-10). "Current understanding of the mechanisms involved in metabolic detoxification of warfare nerve agents".
726:
discovered soman during research into the pharmacology of tabun and sarin at the Kaiser
Wilhelm Institute for Medical Research at
4490:
4365:
361:
When pure, colorless liquid with odor resembling rotten fruit. With impurities, amber or dark brown, with odor of camphor oil.
120:
1538:
988:
1364:
Fonnum, F., Sterri, S.H. (1981). "Factors modifying the toxicity of organophosphorus compounds including soman and sarin".
5459:
5287:
5200:
2835:
612:
1434:
Sidell FR (1974). "Soman and sarin: clinical manifestations and treatment of accidental poisoning by organophosphates".
5256:
4060:
2451:
1487:
WOLTHUIS OL, VANWERSCH RA (1984-04-01). "Behavioral
Changes in the Rat after Low Doses of Cholinesterase Inhibitors".
2466:
2456:
1145:
253:
730:. This research was commissioned by the German Army. Soman was produced in small quantities at a pilot plant at the
4340:
2294:
1737:
1080:
Schmaltz F (September 2006). "Neurosciences and research on chemical weapons of mass destruction in Nazi
Germany".
528:
3702:
1925:
516:
5444:
3879:
3183:
2992:
2746:
424:
1161:
4555:
3178:
2426:
1616:
863:
resulting in the formation of pinacolyl methylphosphonic acid (PMPA), which is a less potent AChE inhibitor.
604:
471:
1601:
5403:
5142:
3756:
2778:
2324:
843:
Soman is an organophosphorus nerve agent with a mechanism of action similar to Tabun. Nerve agents inhibit
196:
4350:
2560:
2504:
2498:
2420:
2395:
2289:
1852:
824:
742:
663:
608:
217:
3168:
140:
5035:
5013:
3689:
3399:
2867:
2446:
2193:
592:
5464:
3784:
3657:
3065:
2862:
948:
is one of the first symptoms of soman intoxication and can be seen in doses of less than 1% of the LC
3718:
5230:
4883:
4780:
4505:
3374:
3359:
2967:
2877:
2711:
2524:
2349:
1609:
234:
1548:
2922:
2917:
2492:
800:
The manufacture of soman is very similar to the manufacture of sarin. The difference is that the
706:(named GA for German Agent A by the United States), the first nerve agent, while developing new
2947:
2701:
2529:
1880:
1870:
1717:
844:
659:
635:
22:
776:
5148:
5069:
3319:
2846:
2647:
2555:
883:
584:
4998:
4345:
3865:
3646:
3474:
3394:
3055:
2982:
2937:
2902:
2882:
2431:
1930:
1800:
1794:
1732:
1641:
871:
749:
580:
205:
57:
160:
8:
5159:
5059:
4988:
4805:
4755:
4280:
3679:
3339:
3107:
3035:
3030:
2962:
2887:
2570:
2519:
2390:
2380:
2150:
1961:
1788:
1762:
1752:
1722:
1051:
703:
620:
86:
567:-pinacolyl methylphosphonofluoridate) is an extremely toxic chemical substance. It is a
238:
96:
4876:
4580:
3759:
3707:
3565:
3520:
3479:
3379:
2857:
2824:
2751:
2565:
2359:
1727:
1113:
1030:
930:
894:
1377:
1288:
658:
for use as a chemical spray using an acryloid copolymer. It can also be deployed as a
5328:
5270:
5247:
5236:
4775:
4650:
4600:
4550:
4430:
4230:
3525:
3384:
3304:
2952:
2912:
2872:
2726:
2545:
2540:
2486:
2481:
2461:
2415:
1675:
1512:
1504:
1459:
1451:
1416:
1381:
1346:
1338:
1300:
1292:
1254:
1246:
1242:
1211:
1203:
1141:
1105:
1097:
1022:
832:
828:
820:
805:
667:
600:
5332:
1117:
1034:
5362:
5343:
5039:
4840:
4835:
4830:
4825:
4820:
4815:
4810:
4615:
4495:
4485:
4315:
3773:
3662:
3489:
3369:
2932:
2907:
2897:
2575:
2441:
2385:
2140:
2122:
2091:
2086:
2081:
2071:
2066:
2061:
2013:
2002:
1862:
1702:
1681:
1670:
1636:
1496:
1443:
1408:
1373:
1330:
1284:
1238:
1195:
1089:
1014:
879:
695:
397:
311:
2043:
1953:
1534:
1500:
986:
5297:
5266:
5180:
5175:
4983:
4270:
4260:
4240:
3545:
3324:
3040:
2793:
2716:
2696:
2618:
1712:
1692:
1542:
1334:
992:
785:
691:
588:
185:
756:. Other solved acetylcholinesterase structures with soman bound to them include
4590:
4510:
4265:
4235:
4075:
3464:
3404:
3329:
3268:
3002:
2942:
2691:
2132:
1903:
1828:
1742:
1593:
875:
596:
576:
572:
499:
408:
44:
4898:
1535:
Material Safety Data Sheet -- Lethal Nerve Agents Somain (GD and
Thickened GD)
1447:
1412:
1167:. Organisation for the Prohibition of Chemical Weapons. 2018-11-19. p. 45
1138:
Chemical
Warfare Agents: Chemistry, Pharmacology, Toxicology, and Therapeutics
1093:
5428:
4968:
4800:
4575:
4540:
4415:
4070:
3749:
3668:
3615:
3610:
3540:
3484:
3349:
3334:
3288:
3113:
3076:
3045:
2892:
2741:
2624:
2550:
2476:
1847:
1772:
1697:
1631:
1508:
1455:
1342:
1296:
1275:
Jokanović M (2001-09-25). "Biotransformation of organophosphorus compounds".
1250:
1207:
1101:
936:
of soman in air is estimated to be 70 mg min per m. Compared with the LC
811:
723:
386:
376:
5324:
5115:
5008:
4963:
4928:
4918:
4913:
4760:
4640:
4545:
4450:
4275:
4085:
3968:
3953:
3620:
3570:
3354:
3344:
3299:
3293:
3263:
3258:
3016:
2927:
2829:
2773:
2736:
2685:
2664:
2613:
2580:
2509:
2471:
2410:
2375:
2273:
1895:
1875:
1747:
1646:
1350:
1304:
1199:
1109:
1026:
890:
soman to PMPA. So CarbE account for the detoxication of soman in two ways.
735:
719:
714:(designated GB by the United States) in 1938, also discovered by Schrader.
1516:
1463:
1420:
1385:
1258:
1215:
484:
5352:
5190:
5110:
5054:
4948:
4795:
4560:
4460:
4335:
4290:
4134:
4129:
4124:
4057:
4018:
3963:
3948:
3928:
3913:
3630:
3605:
3560:
3423:
3389:
3253:
3248:
3213:
3208:
3203:
3198:
3193:
3173:
3092:
3081:
3071:
2783:
2514:
2405:
2400:
2334:
2033:
2018:
1990:
1972:
1944:
1836:
1657:
1588:
1579:
1570:
1561:
1552:
801:
707:
683:
568:
35:
4893:
1584:
1575:
1566:
1557:
470:
5377:
5373:
5105:
5095:
5090:
5003:
4978:
4938:
4933:
4923:
4908:
4849:
4844:
4655:
4515:
4500:
4470:
4445:
4420:
4375:
4370:
4360:
4330:
4300:
4164:
4154:
4099:
4094:
4065:
4042:
4008:
3973:
3958:
3923:
3898:
3752:
3580:
3575:
3555:
3550:
3535:
3530:
3443:
3438:
3414:
3238:
3223:
3218:
3163:
3158:
2840:
2721:
2680:
2674:
2658:
2641:
2635:
2602:
2594:
2535:
2329:
2101:
2007:
1996:
1818:
1812:
900:
887:
727:
655:
628:
477:
345:
151:
1018:
765:
761:
757:
753:
5216:
5100:
5049:
4958:
4953:
4943:
4785:
4720:
4715:
4705:
4660:
4630:
4625:
4610:
4595:
4565:
4530:
4520:
4425:
4305:
4295:
4285:
4255:
4250:
4245:
4169:
4144:
4109:
4038:
4013:
3983:
3943:
3893:
3748:
3675:
3625:
3600:
3590:
3515:
3243:
3233:
3228:
3148:
3128:
3102:
3087:
3025:
2972:
2731:
2669:
2652:
2630:
2607:
2344:
2185:
1978:
1842:
1781:
1707:
731:
699:
498:
Except where otherwise noted, data are given for materials in their
5383:
5085:
5018:
4973:
4903:
4871:
4770:
4750:
4740:
4605:
4525:
4455:
4440:
4325:
4320:
4225:
4159:
4104:
4028:
3978:
3908:
3888:
3684:
3585:
3494:
3459:
3364:
3278:
3188:
3138:
3021:
3010:
2987:
2977:
2957:
2852:
2819:
2813:
2803:
2203:
2175:
2170:
2165:
1806:
1665:
867:
752:
was determined by Millard et al. in 1999 by X-ray crystallography:
687:
443:
119:
5120:
5028:
4993:
4765:
4665:
4635:
4620:
4570:
4465:
4410:
4405:
4400:
4395:
4390:
4385:
4380:
4355:
4310:
4204:
4199:
4119:
4114:
3988:
3433:
3428:
3143:
3133:
3123:
3118:
2808:
2436:
2354:
2339:
2314:
2309:
2304:
2299:
2268:
2263:
2258:
2253:
2248:
2218:
2213:
2208:
2198:
2106:
2096:
2056:
2051:
2028:
2023:
1757:
639:
366:
172:
1533:
United States Senate, 103d Congress, 2d Session (May 25, 1994).
1184:
4645:
4435:
4194:
4189:
4184:
4179:
3993:
3767:
3651:
3314:
3309:
3097:
2243:
2233:
2228:
2223:
1885:
1687:
945:
914:
131:
5023:
4735:
4585:
4480:
3830:
3595:
3510:
3469:
2756:
2160:
2155:
2145:
1967:
1920:
711:
671:
624:
109:
4175:
Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)
2239:
Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)
222:
5288:
5201:
4221:
2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate
2766:
2761:
2320:
2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate
1135:
643:
607:
is strictly controlled, and stockpiling is outlawed by the
5257:
3153:
2706:
1228:
1004:
571:, interfering with normal functioning of the mammalian
1363:
741:
Producing or stockpiling soman was banned by the 1993
262:
InChI=1S/C7H16FO2P/c1-6(7(2,3)4)10-11(5,8)9/h6H,1-5H3
272:
InChI=1/C7H16FO2P/c1-6(7(2,3)4)10-11(5,8)9/h6H,1-5H3
710:. This discovery was followed by the isolation of
3785:
1486:
1392:
5426:
184:
62:3,3-Dimethylbutan-2-yl methylphosphonofluoridate
690:were used as chemical warfare agents, the 1925
459:
95:
5130:Many of the other AChE inhibitors listed above
1058:. Centers for Disease Control and Prevention.
748:The crystal structure of soman complexed with
5070:
3734:
1617:
5409:Muscarinic acetylcholine receptor modulators
3866:
1594:https://somantoxicologia.wixsite.com/meusite
5414:Nicotinic acetylcholine receptor modulators
5293:Tooltip Vesicle-associated membrane protein
5206:Tooltip Vesicular acetylcholine transporter
5160:
1082:Journal of the History of the Neurosciences
771:
5262:Tooltip Synaptosomal-associated protein 25
3741:
3727:
1624:
1610:
804:from the sarin processes is replaced with
237:
159:
1320:
1274:
619:nerve agents to be discovered along with
204:
1079:
944:dose is where the first effects appear.
924:
899:
810:
775:
4366:Dimethyl 4-(methylthio)phenyl phosphate
1131:
1129:
1127:
838:
615:. Soman was the third of the so-called
233:
5427:
2505:Methylphosphonyl dichloride (dichloro)
2499:Methylphosphonyl difluoride (difluoro)
1433:
1398:
1136:Lukey, Brian J., Salem, Harry (2007).
391:198 °C (388 °F; 471 K)
381:−42 °C (−44 °F; 231 K)
4556:Methylfluorophosphonylcholine (MFPCh)
3806:2-(α-Naphthoyl)ethyltrimethylammonium
3722:
2747:Tetramethylenedisulfotetramine (TETS)
1605:
1316:
1314:
955:
908:
738:. It was never used in World War II.
651:for soman is 70 mg·min/m in humans.
265:Key: GRXKLBBBQUKJJZ-UHFFFAOYSA-N
139:
5455:German inventions of the Nazi period
5440:Cold War weapons of the Soviet Union
1270:
1268:
1124:
1046:
1044:
611:of 1993 where it is classified as a
5353:
3856:N,N-Dimethylaminoethylchloroacetate
2836:Dimethyl(trifluoromethylthio)arsine
1188:Toxicology and Applied Pharmacology
275:Key: GRXKLBBBQUKJJZ-UHFFFAOYAY
175:
13:
2452:Dimethylamidophosphoric dichloride
1311:
455:
338:
14:
5481:
3790:Tooltip Choline acetyltransferase
2467:Ethylphosphonoselenoic dichloride
2457:Dimethylamidophosphoric dicyanide
1527:
1265:
1041:
819:Soman is synthesized by reacting
4850:Fasciculins (green mamba toxins)
4341:Dicyclohexyl phosphorofluoridate
2295:Dicyclohexyl phosphorofluoridate
1738:2,3,7,8-Tetrachlorodibenzodioxin
784:Soman (C(±)P(±)-soman) has four
682:After World War I, during which
506:
329:
323:
43:
34:
5470:Soviet chemical weapons program
5450:German chemical weapons program
5435:Acetylcholinesterase inhibitors
4781:Tetraethyl pyrophosphate (TEPP)
4506:Hexaethyl tetraphosphate (HETP)
3703:List of chemical warfare agents
1926:Dibutylchloromethyltin chloride
1480:
1470:
1427:
1357:
1062:from the original on 2017-12-22
502:(at 25 °C , 100 kPa).
16:Chemical compound (nerve agent)
3851:N,N-Dimethylaminoethylacrylate
1549:AChE inhibitors and substrates
1222:
1178:
1154:
1073:
998:
980:
662:; its precursor chemicals are
425:Occupational safety and health
332:
317:
1:
5404:Receptor/signaling modulators
5176:Hemicholinium-3 (hemicholine)
5075:Tooltip Butyrylcholinesterase
1378:10.1016/S0272-0590(81)80050-4
1289:10.1016/s0300-483x(01)00463-2
1140:. CRC Press. pp. 10–13.
973:
866:Soman can also bind to other
853:
579:. It is an inhibitor of both
3871:Tooltip Acetylcholinesterase
2779:Trimethylolpropane phosphite
2325:Neopentylene fluorophosphate
1335:10.1016/j.toxlet.2009.03.017
1243:10.1016/0006-2952(88)90279-1
795:
7:
5165:Tooltip Choline transporter
5111:Profenamine (ethopropazine)
4351:Diisopropyl fluorophosphate
3816:4-(1-Naphthylvinyl)pyridine
3801:1-(-Benzoylethyl)pyridinium
2561:3,3,5-Trimethylcyclohexanol
2421:N,N-Diisopropylaminoethanol
2290:Diisopropyl fluorophosphate
1501:10.1093/toxsci/4.2part2.195
825:methylphosphonyl difluoride
780:The stereoisomers of soman.
743:Chemical Weapons Convention
664:methylphosphonyl difluoride
609:Chemical Weapons Convention
10:
5486:
5460:Methylphosphonofluoridates
5014:Dimethylcarbamoyl fluoride
3821:Acetylseco hemicholinium-3
3400:Hexamethylene diisocyanate
2868:Phenylcarbylamine chloride
2194:Dimethylcarbamoyl fluoride
1545:). Retrieved Nov. 6, 2004.
677:
593:weapon of mass destruction
575:by inhibiting the enzyme
20:
5396:
5342:
5246:
5229:
5199:
5158:
5141:
5068:
3864:
3783:
3766:
3698:
3658:Fluoroethyl fluoroacetate
3639:
3503:
3452:
3413:
3277:
3054:
3001:
2863:Perchloromethyl mercaptan
2792:
2593:
2368:
2282:
2274:4-686-293-01 (Agent 1-10)
2184:
2131:
2115:
2042:
1952:
1943:
1913:
1894:
1861:
1827:
1780:
1771:
1656:
1448:10.3109/15563657408987971
1413:10.3109/15563657408987971
1094:10.1080/09647040600658229
1052:"CDC | Facts About Soman"
815:The synthesis of agent GD
496:
422:
417:
304:
284:
249:
79:
68:
56:
51:
42:
33:
4884:Methanesulfonyl fluoride
3375:Chloroacetophenone oxime
3360:Bromomethyl ethyl ketone
2968:Trifluoroacetyl chloride
2878:Tetrachlorodinitroethane
2525:Phosphorus pentachloride
2350:Methanesulfonyl fluoride
1231:Biochemical Pharmacology
904:The metabolism of soman.
772:Structure and reactivity
591:, it is classified as a
4061:+glycopyrronium bromide
3654:(variants and mixtures)
2923:Trichloronitrosomethane
2918:Trifluoronitrosomethane
2493:Methyldichlorophosphine
3811:3-Chloro-4-stillbazole
3453:Cornea-clouding agents
2948:Phosphorus trichloride
2530:Phosphorus trichloride
2264:Miotine (AR-28/T-1843)
1718:Phosphorus trifluoride
1489:Toxicological Sciences
1200:10.1006/taap.1998.8451
905:
845:acetylcholine esterase
816:
781:
660:binary chemical weapon
634:When pure, soman is a
466:
296:FP(=O)(OC(C)C(C)(C)C)C
23:Soman (disambiguation)
5445:G-series nerve agents
2847:Disulfur decafluoride
2648:Chlorophenylsilatrane
2556:2,4,5-Trichlorophenol
1366:Fundam. Appl. Toxicol
925:Toxicity and efficacy
903:
884:methylphosphonic acid
814:
779:
585:butyrylcholinesterase
465:
5372:Atracotoxins (e.g.,
4999:Tetrahydrocannabinol
4346:Diisopropylphosphate
3647:Methyl fluoroacetate
3475:Methyl cyanoacrylate
3395:Allyl isothiocyanate
2983:Uranium hexafluoride
2938:Dinitrogen tetroxide
2883:Chlorine trifluoride
1931:Selenium oxychloride
1801:Phenyldichloroarsine
1795:Methyldichloroarsine
1733:Nickel tetracarbonyl
839:Mechanisms of action
750:acetylcholinesterase
702:in Germany isolated
613:Schedule 1 substance
581:acetylcholinesterase
448:(fire diamond)
58:Preferred IUPAC name
21:For other uses, see
5358:Tooltip Latrophilin
5060:Trimedoxime bromide
4989:Stercuronium iodide
4806:Tricresyl phosphate
4281:Chlorpyrifos-methyl
3340:Bromobenzyl cyanide
3108:Dimethylheptylpyran
3036:Diphenylcyanoarsine
3031:Diphenylchlorarsine
2963:Methyl vinyl ketone
2888:Perchloryl fluoride
2752:Bicyclic phosphates
2571:Trimethyl phosphite
2520:Phosphoryl chloride
1789:Ethyldichloroarsine
1763:Chloral cyanohydrin
1753:Acetone cyanohydrin
1723:Methyl cyanoformate
1495:(2part2): 195–208.
1436:Clinical Toxicology
1401:Clinical Toxicology
563:, systematic name:
398:Solubility in water
353: g·mol
30:
4877:Onchidella binneyi
4219:Organophosphates:
3708:CB military symbol
3566:Enterotoxin type B
3521:Cyclopiazonic acid
3480:N-Methylmorpholine
3380:Ethyl bromoacetate
2858:Ethyl bromoacetate
2825:Perfluoroisobutene
2566:Triethyl phosphite
1837:Levinstein mustard
1728:Iron pentacarbonyl
1541:2013-09-12 at the
1323:Toxicology Letters
991:2013-09-12 at the
956:Effects on animals
909:Signs and symptoms
906:
817:
782:
529:Infobox references
467:
413:0.40 mmHg (53 Pa)
28:
5422:
5421:
5392:
5391:
5240:
5225:
5224:
5152:
5137:
5136:
4776:Tetrachlorvinphos
4651:Pirimiphos-methyl
4601:Oxydemeton-methyl
4551:Methyl phenkapton
3777:
3716:
3715:
3526:Histrionicotoxins
3504:Biological toxins
3385:Ethyl iodoacetate
2953:Methyl isocyanate
2913:Selenoyl fluoride
2903:Mercuric chloride
2873:Tetranitromethane
2727:Sulfuryl fluoride
2712:HN3 hydrochloride
2707:HN2 hydrochloride
2702:HN1 hydrochloride
2589:
2588:
2546:Phenacyl chloride
2541:Pinacolyl alcohol
2487:Isopropyl alcohol
2482:4-Hydroxycoumarin
2416:1,8-Dibromooctane
1939:
1938:
1863:Nitrogen mustards
1676:Cyanogen chloride
1237:(15): 2939–2948.
1056:emergency.cdc.gov
1019:10.1021/bi982678l
880:carboxylesterases
833:hydrofluoric acid
829:hydrogen fluoride
821:pinacolyl alcohol
806:pinacolyl alcohol
668:pinacolyl alcohol
666:and a mixture of
601:UN Resolution 687
537:Chemical compound
535:
534:
218:CompTox Dashboard
121:Interactive image
74:
5477:
5465:Pinacolyl esters
5359:
5355:
5294:
5290:
5263:
5259:
5244:
5243:
5234:
5207:
5203:
5166:
5162:
5156:
5155:
5146:
5076:
5072:
5040:Asoxime chloride
4616:Parathion-methyl
4316:Demeton-S-methyl
3872:
3868:
3791:
3787:
3781:
3780:
3771:
3743:
3736:
3729:
3720:
3719:
3690:White phosphorus
3667:post-combustion
3663:Depleted uranium
3490:Osmium tetroxide
3370:Phenacyl bromide
2933:Nitrogen dioxide
2908:Selenium dioxide
2898:Cadmium chloride
2355:Dimefox (TL-792)
1950:
1949:
1778:
1777:
1703:Hydrogen sulfide
1682:Hydrogen cyanide
1671:Cyanogen bromide
1637:chemical warfare
1626:
1619:
1612:
1603:
1602:
1598:
1521:
1520:
1484:
1478:
1474:
1468:
1467:
1431:
1425:
1424:
1396:
1390:
1389:
1361:
1355:
1354:
1318:
1309:
1308:
1272:
1263:
1262:
1226:
1220:
1219:
1182:
1176:
1175:
1173:
1172:
1166:
1158:
1152:
1151:
1133:
1122:
1121:
1077:
1071:
1070:
1068:
1067:
1048:
1039:
1038:
1002:
996:
984:
696:Gerhard Schrader
648:
519:
513:
510:
509:
487:
480:
473:
458:
352:
340:
334:
331:
325:
319:
312:Chemical formula
242:
241:
226:
224:
208:
188:
177:
163:
143:
123:
99:
71:
47:
38:
31:
27:
5485:
5484:
5480:
5479:
5478:
5476:
5475:
5474:
5425:
5424:
5423:
5418:
5388:
5357:
5338:
5298:Botulinum toxin
5292:
5267:Botulinum toxin
5261:
5233:
5221:
5205:
5195:
5181:Triethylcholine
5164:
5145:
5133:
5074:
5064:
4984:Rosmarinic acid
4751:Sulfotep (TEDP)
4421:Ethylsarin (GE)
4301:Cyclosarin (GF)
4271:Chlorfenvinphos
4261:Carbophenothion
4241:Azinphos-methyl
3870:
3860:
3826:Acryloylcholine
3789:
3770:
3762:
3747:
3717:
3712:
3694:
3635:
3546:Botulinum toxin
3499:
3448:
3409:
3325:Benzyl chloride
3280:
3273:
3057:
3050:
3041:Cacodyl cyanide
3003:Vomiting agents
2997:
2795:
2788:
2697:Dimethylmercury
2619:Botulinum toxin
2585:
2364:
2278:
2180:
2133:Novichok agents
2127:
2111:
2038:
1935:
1909:
1890:
1857:
1829:Sulfur mustards
1823:
1767:
1713:Carbon monoxide
1693:Cacodyl cyanide
1652:
1651:
1635:Agents used in
1630:
1597:(in Portuguese)
1596:
1543:Wayback Machine
1530:
1525:
1524:
1485:
1481:
1475:
1471:
1432:
1428:
1397:
1393:
1362:
1358:
1319:
1312:
1273:
1266:
1227:
1223:
1183:
1179:
1170:
1168:
1164:
1160:
1159:
1155:
1148:
1134:
1125:
1078:
1074:
1065:
1063:
1050:
1049:
1042:
1003:
999:
993:Wayback Machine
985:
981:
976:
964:
958:
951:
943:
939:
934:
927:
911:
856:
841:
798:
774:
692:Geneva Protocol
680:
649:
646:
589:chemical weapon
538:
531:
526:
525:
524: ?)
515:
511:
507:
503:
492:
491:
490:
489:
482:
475:
468:
464:
456:
435:
400:
350:
337:
328:
322:
314:
300:
297:
292:
291:
280:
277:
276:
273:
267:
266:
263:
257:
256:
245:
227:
220:
211:
191:
178:
166:
146:
126:
113:
102:
89:
75:
64:
63:
26:
17:
12:
11:
5:
5483:
5473:
5472:
5467:
5462:
5457:
5452:
5447:
5442:
5437:
5420:
5419:
5417:
5416:
5411:
5406:
5401:
5397:
5394:
5393:
5390:
5389:
5387:
5386:
5381:
5366:
5365:
5348:
5346:
5340:
5339:
5337:
5336:
5333:γ-bungarotoxin
5329:β-bungarotoxin
5318:
5317:
5283:
5282:
5252:
5250:
5241:
5227:
5226:
5223:
5222:
5220:
5219:
5210:
5208:
5197:
5196:
5194:
5193:
5184:
5183:
5178:
5169:
5167:
5153:
5139:
5138:
5135:
5134:
5132:
5131:
5128:
5123:
5118:
5113:
5108:
5103:
5098:
5093:
5088:
5079:
5077:
5066:
5065:
5063:
5062:
5057:
5052:
5047:
5042:
5032:
5031:
5026:
5021:
5016:
5011:
5006:
5001:
4996:
4991:
4986:
4981:
4976:
4971:
4966:
4961:
4956:
4951:
4946:
4941:
4936:
4931:
4926:
4921:
4916:
4911:
4906:
4901:
4896:
4887:
4886:
4881:
4869:
4847:
4838:
4833:
4828:
4823:
4818:
4813:
4808:
4803:
4798:
4793:
4788:
4783:
4778:
4773:
4768:
4763:
4758:
4753:
4748:
4743:
4738:
4733:
4728:
4723:
4718:
4713:
4708:
4703:
4698:
4693:
4688:
4683:
4678:
4673:
4668:
4663:
4658:
4653:
4648:
4643:
4638:
4633:
4628:
4623:
4618:
4613:
4608:
4603:
4598:
4593:
4591:Novichok agent
4588:
4583:
4578:
4573:
4568:
4563:
4558:
4553:
4548:
4543:
4538:
4533:
4528:
4523:
4518:
4513:
4511:Isofluorophate
4508:
4503:
4498:
4493:
4488:
4483:
4478:
4473:
4468:
4463:
4458:
4453:
4448:
4443:
4438:
4433:
4428:
4423:
4418:
4413:
4408:
4403:
4398:
4393:
4388:
4383:
4378:
4373:
4368:
4363:
4358:
4353:
4348:
4343:
4338:
4333:
4328:
4323:
4318:
4313:
4308:
4303:
4298:
4293:
4288:
4283:
4278:
4273:
4268:
4266:Chlorethoxyfos
4263:
4258:
4253:
4248:
4243:
4238:
4236:Azinphos-ethyl
4233:
4228:
4223:
4213:
4212:
4207:
4202:
4197:
4192:
4187:
4182:
4177:
4172:
4167:
4162:
4157:
4152:
4147:
4142:
4137:
4132:
4127:
4122:
4117:
4112:
4107:
4102:
4097:
4088:
4083:
4078:
4076:Pyridostigmine
4073:
4068:
4063:
4055:
4050:
4045:
4036:
4031:
4026:
4021:
4016:
4011:
4006:
4001:
3996:
3991:
3986:
3981:
3976:
3971:
3966:
3961:
3956:
3951:
3946:
3941:
3936:
3931:
3926:
3921:
3916:
3911:
3906:
3901:
3896:
3891:
3875:
3873:
3862:
3861:
3859:
3858:
3853:
3848:
3843:
3838:
3833:
3828:
3823:
3818:
3813:
3808:
3803:
3794:
3792:
3778:
3764:
3763:
3746:
3745:
3738:
3731:
3723:
3714:
3713:
3711:
3710:
3705:
3699:
3696:
3695:
3693:
3692:
3687:
3682:
3673:
3672:
3671:
3669:uranium oxides
3660:
3655:
3649:
3643:
3641:
3637:
3636:
3634:
3633:
3628:
3623:
3618:
3613:
3608:
3603:
3598:
3593:
3588:
3583:
3578:
3573:
3568:
3563:
3558:
3553:
3548:
3543:
3538:
3533:
3528:
3523:
3518:
3513:
3507:
3505:
3501:
3500:
3498:
3497:
3492:
3487:
3482:
3477:
3472:
3467:
3462:
3456:
3454:
3450:
3449:
3447:
3446:
3441:
3436:
3431:
3426:
3420:
3418:
3411:
3410:
3408:
3407:
3405:Crotonaldehyde
3402:
3397:
3392:
3387:
3382:
3377:
3372:
3367:
3362:
3357:
3352:
3347:
3342:
3337:
3332:
3330:Benzyl bromide
3327:
3322:
3317:
3312:
3307:
3302:
3297:
3291:
3285:
3283:
3275:
3274:
3272:
3271:
3269:Chlorpromazine
3266:
3261:
3256:
3251:
3246:
3241:
3236:
3231:
3226:
3221:
3216:
3211:
3206:
3201:
3196:
3191:
3186:
3181:
3176:
3171:
3166:
3161:
3156:
3151:
3146:
3141:
3136:
3131:
3126:
3121:
3116:
3111:
3105:
3100:
3095:
3090:
3085:
3079:
3074:
3069:
3062:
3060:
3056:Incapacitating
3052:
3051:
3049:
3048:
3043:
3038:
3033:
3028:
3019:
3014:
3007:
3005:
2999:
2998:
2996:
2995:
2990:
2985:
2980:
2975:
2970:
2965:
2960:
2955:
2950:
2945:
2943:Sulfur dioxide
2940:
2935:
2930:
2925:
2920:
2915:
2910:
2905:
2900:
2895:
2890:
2885:
2880:
2875:
2870:
2865:
2860:
2855:
2850:
2844:
2838:
2833:
2827:
2822:
2817:
2811:
2806:
2800:
2798:
2796:choking agents
2790:
2789:
2787:
2786:
2781:
2776:
2771:
2770:
2769:
2764:
2759:
2749:
2744:
2739:
2734:
2729:
2724:
2719:
2714:
2709:
2704:
2699:
2694:
2692:Tetraethyllead
2689:
2683:
2678:
2672:
2667:
2662:
2656:
2650:
2645:
2639:
2633:
2628:
2622:
2616:
2611:
2605:
2599:
2597:
2591:
2590:
2587:
2586:
2584:
2583:
2578:
2573:
2568:
2563:
2558:
2553:
2548:
2543:
2538:
2533:
2527:
2522:
2517:
2512:
2507:
2502:
2496:
2490:
2484:
2479:
2474:
2469:
2464:
2459:
2454:
2449:
2444:
2439:
2434:
2429:
2424:
2418:
2413:
2408:
2403:
2398:
2396:A.P.C. complex
2393:
2388:
2383:
2378:
2372:
2370:
2366:
2365:
2363:
2362:
2357:
2352:
2347:
2342:
2337:
2332:
2327:
2322:
2317:
2312:
2307:
2302:
2297:
2292:
2286:
2284:
2280:
2279:
2277:
2276:
2271:
2266:
2261:
2256:
2251:
2246:
2241:
2236:
2231:
2226:
2221:
2216:
2211:
2206:
2201:
2196:
2190:
2188:
2182:
2181:
2179:
2178:
2173:
2168:
2163:
2158:
2153:
2148:
2143:
2137:
2135:
2129:
2128:
2126:
2125:
2119:
2117:
2113:
2112:
2110:
2109:
2107:V-sub x (GD-7)
2104:
2099:
2094:
2089:
2084:
2079:
2074:
2069:
2064:
2059:
2054:
2048:
2046:
2040:
2039:
2037:
2036:
2031:
2026:
2021:
2016:
2011:
2005:
2000:
1994:
1988:
1982:
1976:
1970:
1965:
1958:
1956:
1947:
1941:
1940:
1937:
1936:
1934:
1933:
1928:
1923:
1917:
1915:
1911:
1910:
1908:
1907:
1904:Phosgene oxime
1900:
1898:
1892:
1891:
1889:
1888:
1883:
1878:
1873:
1867:
1865:
1859:
1858:
1856:
1855:
1850:
1845:
1840:
1833:
1831:
1825:
1824:
1822:
1816:
1810:
1804:
1798:
1792:
1786:
1784:
1775:
1773:Blister agents
1769:
1768:
1766:
1765:
1760:
1755:
1750:
1745:
1743:Glycolonitrile
1740:
1735:
1730:
1725:
1720:
1715:
1710:
1705:
1700:
1695:
1690:
1685:
1679:
1673:
1668:
1662:
1660:
1654:
1653:
1650:
1649:
1644:
1642:incapacitation
1639:
1632:
1629:
1628:
1621:
1614:
1606:
1600:
1599:
1591:
1582:
1573:
1564:
1555:
1546:
1529:
1528:External links
1526:
1523:
1522:
1479:
1469:
1426:
1391:
1372:(2): 143–147.
1356:
1310:
1283:(3): 139–160.
1264:
1221:
1177:
1153:
1146:
1123:
1088:(3): 186–209.
1072:
1040:
1013:(22): 7032–9.
997:
978:
977:
975:
972:
962:
957:
954:
949:
941:
937:
932:
926:
923:
910:
907:
876:cholinesterase
855:
852:
840:
837:
797:
794:
773:
770:
722:together with
679:
676:
645:
631:(cyclosarin).
597:United Nations
577:cholinesterase
573:nervous system
536:
533:
532:
527:
505:
504:
500:standard state
497:
494:
493:
483:
476:
469:
454:
453:
452:
451:
449:
440:
439:
436:
433:
430:
429:
420:
419:
415:
414:
411:
409:Vapor pressure
405:
404:
401:
396:
393:
392:
389:
383:
382:
379:
373:
372:
369:
363:
362:
359:
355:
354:
348:
342:
341:
335:
326:
320:
315:
310:
307:
306:
302:
301:
299:
298:
295:
287:
286:
285:
282:
281:
279:
278:
274:
271:
270:
268:
264:
261:
260:
252:
251:
250:
247:
246:
244:
243:
230:
228:
216:
213:
212:
210:
209:
201:
199:
193:
192:
190:
189:
181:
179:
171:
168:
167:
165:
164:
156:
154:
148:
147:
145:
144:
136:
134:
128:
127:
125:
124:
116:
114:
107:
104:
103:
101:
100:
92:
90:
85:
82:
81:
77:
76:
70:
66:
65:
61:
60:
54:
53:
49:
48:
40:
39:
15:
9:
6:
4:
3:
2:
5482:
5471:
5468:
5466:
5463:
5461:
5458:
5456:
5453:
5451:
5448:
5446:
5443:
5441:
5438:
5436:
5433:
5432:
5430:
5415:
5412:
5410:
5407:
5405:
5402:
5399:
5398:
5395:
5385:
5382:
5379:
5375:
5371:
5368:
5367:
5364:
5361:
5356:
5350:
5349:
5347:
5345:
5341:
5334:
5330:
5326:
5325:Bungarotoxins
5323:
5320:
5319:
5315:
5311:
5307:
5303:
5299:
5296:
5295:inactivators:
5291:
5285:
5284:
5280:
5276:
5272:
5268:
5265:
5264:inactivators:
5260:
5254:
5253:
5251:
5249:
5245:
5242:
5238:
5232:
5228:
5218:
5215:
5212:
5211:
5209:
5204:
5198:
5192:
5189:
5186:
5185:
5182:
5179:
5177:
5174:
5171:
5170:
5168:
5163:
5157:
5154:
5150:
5144:
5140:
5129:
5127:
5126:ZINC-12613047
5124:
5122:
5119:
5117:
5114:
5112:
5109:
5107:
5104:
5102:
5099:
5097:
5094:
5092:
5089:
5087:
5084:
5081:
5080:
5078:
5073:
5067:
5061:
5058:
5056:
5053:
5051:
5048:
5046:
5043:
5041:
5037:
5034:
5033:
5030:
5027:
5025:
5022:
5020:
5017:
5015:
5012:
5010:
5007:
5005:
5002:
5000:
4997:
4995:
4992:
4990:
4987:
4985:
4982:
4980:
4977:
4975:
4972:
4970:
4969:Lactucopicrin
4967:
4965:
4962:
4960:
4957:
4955:
4952:
4950:
4947:
4945:
4942:
4940:
4937:
4935:
4932:
4930:
4927:
4925:
4922:
4920:
4917:
4915:
4912:
4910:
4907:
4905:
4902:
4900:
4897:
4895:
4892:
4889:
4888:
4885:
4882:
4879:
4878:
4873:
4870:
4867:
4863:
4859:
4855:
4851:
4848:
4846:
4842:
4839:
4837:
4834:
4832:
4829:
4827:
4824:
4822:
4819:
4817:
4814:
4812:
4809:
4807:
4804:
4802:
4801:Trichloronate
4799:
4797:
4794:
4792:
4789:
4787:
4784:
4782:
4779:
4777:
4774:
4772:
4769:
4767:
4764:
4762:
4759:
4757:
4754:
4752:
4749:
4747:
4744:
4742:
4739:
4737:
4734:
4732:
4729:
4727:
4724:
4722:
4719:
4717:
4714:
4712:
4709:
4707:
4704:
4702:
4699:
4697:
4694:
4692:
4689:
4687:
4684:
4682:
4679:
4677:
4674:
4672:
4669:
4667:
4664:
4662:
4659:
4657:
4654:
4652:
4649:
4647:
4644:
4642:
4639:
4637:
4634:
4632:
4629:
4627:
4624:
4622:
4619:
4617:
4614:
4612:
4609:
4607:
4604:
4602:
4599:
4597:
4594:
4592:
4589:
4587:
4584:
4582:
4579:
4577:
4576:Monocrotophos
4574:
4572:
4569:
4567:
4564:
4562:
4559:
4557:
4554:
4552:
4549:
4547:
4544:
4542:
4541:Methamidophos
4539:
4537:
4534:
4532:
4529:
4527:
4524:
4522:
4519:
4517:
4514:
4512:
4509:
4507:
4504:
4502:
4499:
4497:
4494:
4492:
4489:
4487:
4484:
4482:
4479:
4477:
4474:
4472:
4469:
4467:
4464:
4462:
4459:
4457:
4454:
4452:
4449:
4447:
4444:
4442:
4439:
4437:
4434:
4432:
4429:
4427:
4424:
4422:
4419:
4417:
4416:Echothiophate
4414:
4412:
4409:
4407:
4404:
4402:
4399:
4397:
4394:
4392:
4389:
4387:
4384:
4382:
4379:
4377:
4374:
4372:
4369:
4367:
4364:
4362:
4359:
4357:
4354:
4352:
4349:
4347:
4344:
4342:
4339:
4337:
4334:
4332:
4329:
4327:
4324:
4322:
4319:
4317:
4314:
4312:
4309:
4307:
4304:
4302:
4299:
4297:
4294:
4292:
4289:
4287:
4284:
4282:
4279:
4277:
4274:
4272:
4269:
4267:
4264:
4262:
4259:
4257:
4254:
4252:
4249:
4247:
4244:
4242:
4239:
4237:
4234:
4232:
4229:
4227:
4224:
4222:
4218:
4217:Irreversible:
4215:
4214:
4211:
4208:
4206:
4203:
4201:
4198:
4196:
4193:
4191:
4188:
4186:
4183:
4181:
4178:
4176:
4173:
4171:
4168:
4166:
4163:
4161:
4158:
4156:
4153:
4151:
4148:
4146:
4143:
4141:
4138:
4136:
4133:
4131:
4128:
4126:
4123:
4121:
4118:
4116:
4113:
4111:
4108:
4106:
4103:
4101:
4098:
4096:
4092:
4089:
4087:
4084:
4082:
4081:Quilostigmine
4079:
4077:
4074:
4072:
4071:Physostigmine
4069:
4067:
4064:
4062:
4059:
4056:
4054:
4051:
4049:
4046:
4044:
4041:; Stigmines:
4040:
4037:
4035:
4032:
4030:
4027:
4025:
4022:
4020:
4017:
4015:
4012:
4010:
4007:
4005:
4002:
4000:
3997:
3995:
3992:
3990:
3987:
3985:
3982:
3980:
3977:
3975:
3972:
3970:
3967:
3965:
3962:
3960:
3957:
3955:
3952:
3950:
3947:
3945:
3942:
3940:
3939:Chloropropham
3937:
3935:
3932:
3930:
3927:
3925:
3922:
3920:
3917:
3915:
3912:
3910:
3907:
3905:
3902:
3900:
3897:
3895:
3892:
3890:
3886:
3883:
3881:
3877:
3876:
3874:
3869:
3863:
3857:
3854:
3852:
3849:
3847:
3844:
3842:
3839:
3837:
3834:
3832:
3829:
3827:
3824:
3822:
3819:
3817:
3814:
3812:
3809:
3807:
3804:
3802:
3799:
3796:
3795:
3793:
3788:
3782:
3779:
3775:
3769:
3765:
3761:
3758:
3754:
3751:
3750:Acetylcholine
3744:
3739:
3737:
3732:
3730:
3725:
3724:
3721:
3709:
3706:
3704:
3701:
3700:
3697:
3691:
3688:
3686:
3683:
3681:
3680:its compounds
3677:
3674:
3670:
3666:
3665:
3664:
3661:
3659:
3656:
3653:
3650:
3648:
3645:
3644:
3642:
3638:
3632:
3629:
3627:
3624:
3622:
3619:
3617:
3616:Tetanospasmin
3614:
3612:
3611:T-2 mycotoxin
3609:
3607:
3604:
3602:
3599:
3597:
3594:
3592:
3589:
3587:
3584:
3582:
3579:
3577:
3574:
3572:
3569:
3567:
3564:
3562:
3559:
3557:
3554:
3552:
3549:
3547:
3544:
3542:
3541:Batrachotoxin
3539:
3537:
3534:
3532:
3529:
3527:
3524:
3522:
3519:
3517:
3514:
3512:
3509:
3508:
3506:
3502:
3496:
3493:
3491:
3488:
3486:
3485:Allyl alcohol
3483:
3481:
3478:
3476:
3473:
3471:
3468:
3466:
3463:
3461:
3458:
3457:
3455:
3451:
3445:
3442:
3440:
3437:
3435:
3432:
3430:
3427:
3425:
3422:
3421:
3419:
3416:
3412:
3406:
3403:
3401:
3398:
3396:
3393:
3391:
3388:
3386:
3383:
3381:
3378:
3376:
3373:
3371:
3368:
3366:
3363:
3361:
3358:
3356:
3353:
3351:
3350:Chloroacetone
3348:
3346:
3343:
3341:
3338:
3336:
3335:Benzyl iodide
3333:
3331:
3328:
3326:
3323:
3321:
3318:
3316:
3313:
3311:
3308:
3306:
3303:
3301:
3298:
3295:
3292:
3290:
3289:Xylyl bromide
3287:
3286:
3284:
3282:
3276:
3270:
3267:
3265:
3262:
3260:
3257:
3255:
3252:
3250:
3247:
3245:
3242:
3240:
3237:
3235:
3232:
3230:
3227:
3225:
3222:
3220:
3217:
3215:
3212:
3210:
3207:
3205:
3202:
3200:
3197:
3195:
3192:
3190:
3187:
3185:
3182:
3180:
3177:
3175:
3172:
3170:
3167:
3165:
3162:
3160:
3157:
3155:
3152:
3150:
3147:
3145:
3142:
3140:
3137:
3135:
3132:
3130:
3127:
3125:
3122:
3120:
3117:
3115:
3112:
3109:
3106:
3104:
3101:
3099:
3096:
3094:
3091:
3089:
3086:
3083:
3080:
3078:
3077:Butyrophenone
3075:
3073:
3070:
3067:
3064:
3063:
3061:
3059:
3053:
3047:
3046:o-Dianisidine
3044:
3042:
3039:
3037:
3034:
3032:
3029:
3027:
3023:
3020:
3018:
3015:
3012:
3009:
3008:
3006:
3004:
3000:
2994:
2991:
2989:
2986:
2984:
2981:
2979:
2976:
2974:
2971:
2969:
2966:
2964:
2961:
2959:
2956:
2954:
2951:
2949:
2946:
2944:
2941:
2939:
2936:
2934:
2931:
2929:
2926:
2924:
2921:
2919:
2916:
2914:
2911:
2909:
2906:
2904:
2901:
2899:
2896:
2894:
2893:Cadmium oxide
2891:
2889:
2886:
2884:
2881:
2879:
2876:
2874:
2871:
2869:
2866:
2864:
2861:
2859:
2856:
2854:
2851:
2848:
2845:
2842:
2839:
2837:
2834:
2831:
2828:
2826:
2823:
2821:
2818:
2815:
2812:
2810:
2807:
2805:
2802:
2801:
2799:
2797:
2791:
2785:
2782:
2780:
2777:
2775:
2772:
2768:
2765:
2763:
2760:
2758:
2755:
2754:
2753:
2750:
2748:
2745:
2743:
2742:Batrachotoxin
2740:
2738:
2735:
2733:
2730:
2728:
2725:
2723:
2720:
2718:
2715:
2713:
2710:
2708:
2705:
2703:
2700:
2698:
2695:
2693:
2690:
2687:
2684:
2682:
2679:
2676:
2673:
2671:
2668:
2666:
2663:
2660:
2657:
2654:
2651:
2649:
2646:
2643:
2640:
2637:
2634:
2632:
2629:
2626:
2625:Tetanospasmin
2623:
2620:
2617:
2615:
2612:
2609:
2606:
2604:
2601:
2600:
2598:
2596:
2592:
2582:
2579:
2577:
2574:
2572:
2569:
2567:
2564:
2562:
2559:
2557:
2554:
2552:
2549:
2547:
2544:
2542:
2539:
2537:
2534:
2531:
2528:
2526:
2523:
2521:
2518:
2516:
2513:
2511:
2508:
2506:
2503:
2500:
2497:
2494:
2491:
2488:
2485:
2483:
2480:
2478:
2475:
2473:
2470:
2468:
2465:
2463:
2460:
2458:
2455:
2453:
2450:
2448:
2445:
2443:
2440:
2438:
2435:
2433:
2430:
2428:
2425:
2422:
2419:
2417:
2414:
2412:
2409:
2407:
2404:
2402:
2399:
2397:
2394:
2392:
2389:
2387:
2384:
2382:
2379:
2377:
2374:
2373:
2371:
2367:
2361:
2358:
2356:
2353:
2351:
2348:
2346:
2343:
2341:
2338:
2336:
2333:
2331:
2328:
2326:
2323:
2321:
2318:
2316:
2313:
2311:
2308:
2306:
2303:
2301:
2298:
2296:
2293:
2291:
2288:
2287:
2285:
2281:
2275:
2272:
2270:
2267:
2265:
2262:
2260:
2257:
2255:
2252:
2250:
2247:
2245:
2242:
2240:
2237:
2235:
2232:
2230:
2227:
2225:
2222:
2220:
2217:
2215:
2212:
2210:
2207:
2205:
2202:
2200:
2197:
2195:
2192:
2191:
2189:
2187:
2183:
2177:
2174:
2172:
2169:
2167:
2164:
2162:
2159:
2157:
2154:
2152:
2149:
2147:
2144:
2142:
2139:
2138:
2136:
2134:
2130:
2124:
2121:
2120:
2118:
2114:
2108:
2105:
2103:
2100:
2098:
2095:
2093:
2090:
2088:
2085:
2083:
2080:
2078:
2075:
2073:
2070:
2068:
2065:
2063:
2060:
2058:
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1896:Nettle agents
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1699:
1698:Cacodyl oxide
1696:
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1197:
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1189:
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1163:
1157:
1149:
1147:9781420046618
1143:
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1128:
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869:
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836:
834:
830:
826:
822:
813:
809:
807:
803:
793:
789:
787:
786:stereoisomers
778:
769:
767:
763:
759:
755:
751:
746:
744:
739:
737:
733:
729:
725:
724:Konrad Henkel
721:
715:
713:
709:
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697:
693:
689:
685:
675:
673:
669:
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657:
652:
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637:
632:
630:
627:(sarin), and
626:
622:
618:
614:
610:
606:
602:
599:according to
598:
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586:
582:
578:
574:
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566:
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546:
542:
530:
523:
518:
501:
495:
488:
481:
474:
450:
447:
446:
442:
441:
438:Highly Toxic
437:
432:
431:
427:
426:
421:
416:
412:
410:
407:
406:
402:
399:
395:
394:
390:
388:
387:Boiling point
385:
384:
380:
378:
377:Melting point
375:
374:
370:
368:
365:
364:
360:
357:
356:
349:
347:
344:
343:
316:
313:
309:
308:
303:
294:
293:
290:
283:
269:
259:
258:
255:
248:
240:
236:
235:DTXSID2031906
232:
231:
229:
219:
215:
214:
207:
203:
202:
200:
198:
195:
194:
187:
183:
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158:
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118:
117:
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111:
106:
105:
98:
94:
93:
91:
88:
84:
83:
78:
67:
59:
55:
50:
46:
41:
37:
32:
24:
19:
5369:
5363:α-Latrotoxin
5351:
5321:
5286:
5255:
5213:
5187:
5172:
5116:Rivastigmine
5082:
5036:Reactivators
5009:Ungiminorine
4964:Kobophenol A
4929:Coronaridine
4919:Bulbocapnine
4914:Arisugacin A
4890:
4875:
4761:Tebupirimfos
4745:
4641:Phosphamidon
4546:Methidathion
4451:Fenitrothion
4276:Chlorpyrifos
4216:
4091:Terestigmine
4086:Rivastigmine
4048:Eptastigmine
3999:Phenmedipham
3969:Formparanate
3954:Ethiofencarb
3887:Carbamates:
3884:
3878:
3797:
3621:Tetrodotoxin
3571:Grayanotoxin
3355:Bromoacetone
3345:Thiophosgene
3300:Mace (spray)
3294:Pepper spray
3279:Lachrymatory
3264:Fluphenazine
3259:Procarbazine
3169:Sleeping gas
3017:Chloropicrin
2928:Nitric oxide
2830:Chloropicrin
2774:Cloflubicyne
2737:Oxotremorine
2686:Antillatoxin
2665:Tetrodotoxin
2614:Bungarotoxin
2510:Nitromethane
2472:Formaldoxime
2411:Cyclohexanol
2376:Acetonitrile
2123:GV (EA-5365)
1984:
1945:Nerve agents
1748:Lactonitrile
1658:Blood agents
1647:riot control
1492:
1488:
1482:
1472:
1439:
1435:
1429:
1404:
1400:
1394:
1369:
1365:
1359:
1326:
1322:
1280:
1276:
1234:
1230:
1224:
1194:(1): 79–87.
1191:
1187:
1180:
1169:. Retrieved
1156:
1137:
1085:
1081:
1075:
1064:. Retrieved
1055:
1010:
1007:Biochemistry
1006:
1000:
982:
968:
959:
928:
919:
912:
892:
865:
861:
857:
849:
842:
818:
799:
790:
783:
747:
740:
736:Ludwigshafen
720:Richard Kuhn
716:
708:insecticides
681:
653:
633:
616:
564:
560:
556:
552:
548:
544:
540:
539:
444:
434:Main hazards
423:
80:Identifiers
69:Other names
18:
5214:Inhibitors:
5191:Coluracetam
5173:Inhibitors:
5143:Transporter
5083:Inhibitors:
5055:Pralidoxime
4949:Cyclanoline
4899:α-Viniferin
4796:Trichlorfon
4561:Metrifonate
4476:Fosthiazate
4461:Fluorotabun
4336:Dicrotophos
4291:Crotylsarin
4135:Huperzine A
4130:Galantamine
4125:Edrophonium
4058:Neostigmine
4053:Ganstigmine
4019:Propamocarb
3964:Formetanate
3949:Ethienocarb
3929:Carbosulfan
3919:Carbetamide
3914:Carbendazim
3885:Reversible:
3798:Inhibitors:
3631:Veratridine
3606:Shiga toxin
3561:Domoic acid
3424:Thioacetone
3390:Iodoacetone
3254:Pentazocine
3249:Sevoflurane
3214:CAR-302,668
3209:CAR-302,282
3204:CAR-302,196
3199:CAR-301,060
3194:CAR-226,086
3174:Carfentanil
3072:Apomorphine
2993:Green Cross
2784:Domoic acid
2595:Neurotoxins
2515:OPA mixture
2406:Chlorosoman
2401:Chlorosarin
2335:Phospholine
2034:Crotylsarin
2019:Fluorotabun
1991:Chlorosoman
1973:Chlorosarin
1589:Proteopedia
1580:Proteopedia
1571:Proteopedia
1562:Proteopedia
1553:Proteopedia
1442:(1): 1–17.
1407:(1): 1–17.
1329:(1): 1–10.
888:hydrolysing
802:isopropanol
734:factory in
684:mustard gas
569:nerve agent
428:(OHS/OSH):
371:1.022 g/cm
358:Appearance
305:Properties
141:ChEMBL15910
5429:Categories
5378:versutoxin
5374:robustoxin
5248:Inhibitors
5237:modulators
5188:Enhancers:
5149:modulators
5106:Ladostigil
5096:Conodurine
5091:Affinisine
5004:Ungeremine
4979:Phosacetim
4939:Corynoline
4934:Corydaline
4924:Conodurine
4909:Affinisine
4845:Demecarium
4843:; Others:
4756:Tabun (GA)
4746:Soman (GD)
4736:Sarin (GB)
4656:Profenofos
4516:Isoxathion
4501:Guanitoxin
4471:Formothion
4446:Fenamiphos
4376:Disulfoton
4371:Dioxathion
4361:Dimethoate
4331:Dichlorvos
4165:Ladostigil
4155:Ipidacrine
4100:Ambenonium
4095:Acotiamide
4093:; Others:
4066:Phenserine
4043:Distigmine
4034:Thiodicarb
4009:Pirimicarb
3974:Methiocarb
3959:Fenobucarb
3934:Chlorbufam
3924:Carbofuran
3899:Bendiocarb
3880:Inhibitors
3774:modulators
3760:modulators
3753:metabolism
3581:Maitotoxin
3576:Guanitoxin
3556:Ciguatoxin
3551:Brevetoxin
3536:Anatoxin-a
3531:Aflatoxins
3444:Putrescine
3439:Cadaverine
3415:Malodorant
3239:Isoflurane
3224:Desflurane
3219:Benperidol
3164:Psilocybin
3159:PAVA spray
2841:Diphosgene
2794:Pulmonary/
2722:Picrotoxin
2681:Strychnine
2675:Brevetoxin
2659:Maitotoxin
2642:Guanitoxin
2636:Ciguatoxin
2603:Anatoxin-a
2536:Pinacolone
2369:Precursors
2330:Selenophos
2186:Carbamates
2102:Chinese VX
2008:Cyclosarin
1997:Ethylsarin
1968:Sarin (GB)
1819:Lewisite 3
1813:Lewisite 2
1782:Arsenicals
1277:Toxicology
1171:2024-02-09
1066:2018-03-20
974:References
878:(ChE) and
854:Metabolism
728:Heidelberg
654:GD can be
605:production
346:Molar mass
206:3OF3WXB67Q
152:ChemSpider
108:3D model (
87:CAS Number
5360:agonists:
5344:Enhancers
5217:Vesamicol
5101:Cymserine
5050:Obidoxime
5045:Methoxime
4959:Harmaline
4954:Cymserine
4944:Crimidine
4891:Unsorted:
4786:Triazofos
4726:Ro 3-0433
4721:Ro 3-0422
4716:Ro 3-0419
4711:Ro 3-0417
4706:Ro 3-0412
4701:Ro 3-0411
4696:Ro 3-0397
4691:Ro 3-0352
4686:Ro 3-0351
4681:Ro 3-0347
4676:Ro 3-0346
4671:Ro 3-0340
4661:Prothoate
4631:Phosfolan
4626:Phosalone
4611:Parathion
4596:Omethoate
4566:Mevinphos
4531:Malathion
4521:Leptophos
4426:Endothion
4306:Demephion
4296:Cyanophos
4286:Coumaphos
4256:Cadusafos
4251:Bensulide
4246:BAY-29952
4210:Zanapezil
4170:Minaprine
4150:Huprine Y
4145:Huprine X
4140:Huprine W
4110:Donepezil
4039:Thiofanox
4014:Promecarb
4004:Pinmicarb
3984:Metolcarb
3944:Dimetilan
3904:Bufencarb
3894:Aminocarb
3846:CM-54,903
3757:transport
3676:Plutonium
3626:Volkensin
3601:Saxitoxin
3591:Palytoxin
3516:Aconitine
3244:Halothane
3234:Bufotenin
3229:Enflurane
3149:Kolokol-1
3129:Pethidine
3103:Etoxadrol
3088:Etorphine
3084:(CS-4640)
3068:(CS-4030)
3026:glycerine
2973:Salcomine
2732:Tremorine
2670:Aconitine
2653:Palytoxin
2631:Ryanodine
2608:Saxitoxin
2345:Ro 3-0422
2116:GV agents
1979:Thiosarin
1708:Phosphine
1509:1096-6080
1477:1046–1057
1456:0009-9309
1343:1879-3169
1297:0300-483X
1251:0006-2952
1208:0041-008X
1102:0964-704X
868:esterases
796:Synthesis
732:IG Farben
700:IG Farben
656:thickened
623:(tabun),
403:Moderate
5400:See also
5384:Crotoxin
5086:Affinine
5019:BW284C51
4974:Lycorine
4904:Affinine
4894:α-Pinene
4872:Onchidal
4791:Tribufos
4771:Terbufos
4741:Schradan
4606:Paraoxon
4526:Malaoxon
4456:Fenthion
4441:Ethoprop
4326:Diazinon
4321:Dialifor
4226:Acephate
4160:Itopride
4105:Caffeine
4029:Propoxur
3979:Methomyl
3909:Carbaryl
3889:Aldicarb
3685:Polonium
3586:Modeccin
3495:Acrolein
3460:Lewisite
3365:Acrolein
3189:CS-27349
3139:Ibogaine
3022:Litharge
3011:Adamsite
2988:Diborane
2978:Fluomine
2958:Ethenone
2853:Acrolein
2820:Fluorine
2814:Phosgene
2804:Chlorine
2204:EA-3887A
2176:C01-A042
2171:C01-A039
2166:C01-A035
2044:V-agents
1954:G-agents
1839:(EA-229)
1807:Lewisite
1666:Cyanogen
1539:Archived
1351:19433263
1305:11543910
1118:46250604
1110:16887760
1060:Archived
1035:11744952
1027:10353814
989:Archived
870:, e.g.,
688:phosgene
636:volatile
617:G-series
445:NFPA 704
418:Hazards
5370:Others:
5322:Others:
5258:SNAP-25
5231:Release
5121:Tacrine
5029:3152 CT
4994:Taspine
4766:Temefos
4666:R-16661
4636:Phosmet
4621:Phorate
4571:Mipafox
4536:Mazidox
4466:Fonofos
4411:EA-4352
4406:EA-3148
4401:EA-2613
4396:EA-2192
4391:EA-2098
4386:EA-2054
4381:EA-2012
4356:Dimefox
4311:Demeton
4205:Tacrine
4200:TL-1238
4120:EA-4056
4115:EA-3990
4024:Propham
3989:Miotine
3434:Skatole
3429:Allicin
3144:EA-3834
3134:EA-3580
3124:EA-3443
3119:EA-3167
3114:EA-2148
3098:CS-4297
3093:EA-2092
3082:EA-4941
2809:Bromine
2447:EA-1224
2427:EA-1250
2340:R-16661
2315:EA-2613
2310:EA-2098
2305:EA-2054
2300:EA-2012
2269:3152 CT
2259:TL-1317
2254:TL-1299
2249:TL-1238
2219:EA-4056
2214:EA-3990
2209:EA-3966
2199:EA-3887
2097:EA-1763
2057:EA-3148
2052:EA-2192
2029:EA-4352
2024:EA-1356
1758:Stibine
1517:6724212
1464:4838227
1421:4838227
1386:7184780
1259:3395367
1216:9705889
678:History
670:and an
640:camphor
595:by the
587:. As a
549:EA 1210
522:what is
520: (
367:Density
351:182.175
173:PubChem
97:96-64-0
4731:Ronnel
4646:Phoxim
4436:Ethion
4231:Armine
4195:TL-599
4190:T-1194
4185:T-1152
4180:T-1123
3994:Oxamyl
3768:Enzyme
3652:Napalm
3417:agents
3281:agents
3184:JB-336
3179:JB-318
3154:LSD-25
3110:(DMHP)
3058:agents
2717:A-8564
2677:(PbTX)
2627:(TeNT)
2244:TL-599
2234:T-1194
2229:T-1152
2224:T-1123
1993:(ClGD)
1975:(ClGB)
1886:TL-301
1688:Arsine
1515:
1507:
1462:
1454:
1419:
1384:
1349:
1341:
1303:
1295:
1257:
1249:
1214:
1206:
1144:
1116:
1108:
1100:
1033:
1025:
946:Miosis
915:miosis
642:. The
603:. Its
517:verify
514:
289:SMILES
132:ChEMBL
52:Names
29:Soman
5202:VAChT
5024:TMTFA
4586:Naled
4491:GT-45
4481:GD-42
3831:AF64A
3640:Other
3596:Ricin
3511:Abrin
3470:KB-16
2757:IPTBO
2688:(ATX)
2661:(MTX)
2655:(PTX)
2644:(GTX)
2638:(CTX)
2621:(BTX)
2477:Nital
2283:Other
2161:A-262
2156:A-242
2151:A-234
2146:A-232
2141:A-208
1985:Soman
1981:(SGB)
1962:Tabun
1921:KB-16
1914:Other
1165:(PDF)
1114:S2CID
1031:S2CID
823:with
712:sarin
704:tabun
672:amine
561:A-255
553:Zoman
541:Soman
254:InChI
110:JSmol
5354:LPHN
5289:VAMP
5071:BChE
4581:MSPI
3867:AChE
3841:BETA
3836:B115
3786:ChAT
3755:and
3678:and
3296:(OC)
3013:(DM)
2843:(DP)
2832:(PS)
2816:(CG)
2767:TBPS
2762:TBPO
2610:(TZ)
2532:(TH)
2501:(DF)
2495:(SW)
2489:(TB)
2462:DMHP
2442:DEHP
2432:DIHP
2423:(KB)
2360:MSPI
2010:(GF)
1999:(GE)
1987:(GD)
1964:(GA)
1906:(CX)
1853:CEES
1821:(L3)
1815:(L2)
1803:(PD)
1797:(MD)
1791:(ED)
1684:(AC)
1678:(CK)
1585:1som
1576:2wg1
1567:2wg0
1558:2wfz
1513:PMID
1505:ISSN
1460:PMID
1452:ISSN
1417:PMID
1382:PMID
1347:PMID
1339:ISSN
1301:PMID
1293:ISSN
1255:PMID
1247:ISSN
1212:PMID
1204:ISSN
1142:ISBN
1106:PMID
1098:ISSN
1023:PMID
929:The
895:LD50
872:AChE
766:2wg1
764:and
762:2wg0
758:2wfz
754:1som
686:and
583:and
557:PFMP
543:(or
197:UNII
186:7305
161:7032
5161:CHT
4431:EPN
3320:CNS
2849:(Z)
2391:AlP
2386:ATO
1881:HN3
1876:HN2
1871:HN1
1809:(L)
1587:in
1578:in
1569:in
1560:in
1551:in
1497:doi
1444:doi
1409:doi
1374:doi
1331:doi
1327:188
1285:doi
1281:166
1239:doi
1196:doi
1192:151
1090:doi
1015:doi
698:of
644:LCt
223:EPA
176:CID
5431::
5376:,
5331:,
5312:,
5308:,
5304:,
5277:,
5273:,
5038::
4864:,
4860:,
4856:,
4841:VX
4836:VR
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