Novichok Agent
Design objectives
Design objectives
These agents are designed to achieve three objectives:
To be undetectable using standard NATO chemical detection equipment
To defeat NATO chemical protective gear
To be safer to handle
Some of these agents are binary weapons, in which precursors for the nerve agents are mixed in a munition to produce the agent just prior to its use. Because the precursors are generally significantly less hazardous than the agents themselves, this technique makes handling and transporting the munitions a great deal simpler. Additionally, precursors to the agents are usually much easier to stabilize than the agents themselves, so this technique also made it possible to increase the shelf life of the agents. During the 1980s and 1990s, binary versions of several Soviet agents were developed and are designated as "Novichok" agents (after the Russian word for "newcomer").
Disclosure
Extremely potent third-generation chemical weapons were developed in the Soviet Union and Russia from the 1970s until the early 1990s, according to a publication by two chemists, Lev Fedorov and Vil Mirzayanov in Moskovskiye Novosti weekly in 1992. The publication appeared just on the eve of Russia's signing of the Chemical Weapons Convention. According to Mirzayanov, the Russian Military Chemical Complex (MCC) was using defense conversion money received from the West for development of a chemical warfare facility. Mirzoyanov made his disclosure out of environmental concerns. He was a head of a counter-intelligence department and performed measurements outside the chemical weapons facilities to make sure that foreign spies could not detect any traces of production. To his horror, the levels of deadly substances were 80 times greater than the maximum safe concentration. (A full account by Mirzayanov is available online.)
The existence of Novichok agents was openly admitted by Russian military industrial complex authorities when they brought a treason case against Mirzayanov. According to expert witness testimonies prepared for the KGB by three scientists, novichok and other related chemical agents had indeed been produced and therefore the disclosure by Mirzoyanov represented high treason.
Vil Mirzayanov was arrested in October 22, 1992 and sent to Lefortovo prison for divulging state secrets. He was released later because "not one of the formulas or names of poisonous substances in the Moscow News article was new to the Soviet press, nor were locations ... of testing sites revealed." According to Yevgenia Albats, "the real state secret revealed by Fyodorov and Nirzoyanov was that generals had lied and were still lying to both the international community and their fellow citizens." He now lives in the U.S.
Description of Novichok agents
The first description of these agents was provided by Mirzayanov. Dispersed in an ultra-fine powder instead of a gas or a vapor, they have unique qualities. A binary agent was then created that would mimic the same properties but would either be manufactured using materials legal under the CWT or be undetectable by treaty regime inspections. The most potent compounds from this family, novichok-5 and novichok-7, are supposedly around 5-8x more potent than VX, however the exact structures of these compounds have not been reliably verified.
One of the key manufacturing sites was a chemical research institute in what is now Uzbekistan, and small, experimental batches of the weapons may have been tested on the nearby Ustyurt plateau.
Two broad families of organophosphorus agents have been claimed to be Novichok agents. First are a group of organophosphorus compounds with an attached dihaloformaldoxime group, with the general formula shown below, where R = alkyl, alkoxy, alkylamino or fluorine and X = halogen (F, Cl, Br) or pseudohalogen such as CN. These compounds are extensively documented in Soviet literature of the time, but it is unclear whether they are in fact the potent "Novichok" compounds.
Some examples of the first group of compounds reported in the literature are shown below, but it is unknown whether any of these is novichok-5 or novichok-7.
Mirzayanov gives somewhat different structures for Novichok agents in his autobiography, as shown below. He makes clear that a large number of compounds were made, and many of the less potent derivatives reported in the open literature as new organophosphate insecticides, so that the secret chemical weapons program could be disguised as legitimate pesticide research.
Effects
As a nerve agent, Novichok belongs to organophosphate acetylcholinesterase inhibitors. These chemical compounds inhibit the enzyme acetylcholinesterase, preventing the normal breakdown of neurotransmitter acetylcholine. Acetylcholine concentrations then increase at neuromuscular junctions to cause involuntary contraction of all muscles. This then leads to respiratory and cardiac arrest and finally death. The use of a fast-acting peripheral anticholinergic drug such as Atropine could block the receptors where acetylcholine acts to prevent poisoning (as is the treatment for poisoning by other acetylcholinesterare inhibitors). This is however quite dangerous in itself.
References
^ Tucker, J. B.; War of Nerves; Anchor Books; New York; 2006; pp 232-233.
^ a b Vadim J. Birstein. The Perversion Of Knowledge: The True Story of Soviet Science. Westview Press (2004) ISBN 0-813-34280-5
^ a b c d e Yevgenia Albats and Catherine A. Fitzpatrick. The State Within a State: The KGB and Its Hold on Russia Past, Present, and Future, 1994. ISBN 0-374-18104-7 (see pages 325-328)
^ Tucker, J. B.; War of Nerves; Anchor Books; New York; 2006; pp 231.
^ Tucker, J. B.; War of Nerves; Anchor Books; New York; 2006; pp 233.
^ Tucker, J. B.; War of Nerves; Anchor Books; New York; 2006; pp 253.
^ Fedorov, Lev and Vil Mirzayanov, "Poisoned Politics," Moskovskiye Novosti weekly No. 39, 1992. Much of this information was published earlier in the newspaper "Top Secret" run by Artyom Borovik in September 1991. However the KGB did not arrest Mirzayanov earlier due to political turmoil in Russia at this time, according to a book by Yevgenia Albats.
^ a b Vil Mirzayanov "Dismantling the Soviet/Russian Chemical Weapons Complex: An Insider's View" Chemical Weapons Disarmament in Russia: Problems and Prospects (Washington, D.C.: Henry L. Stimson Center, 1995), page 21.
^ "the talk [by Mirzayanov] about binary weapons was no more than a verbal construct, an argument ex adverso, and only the MCC [Russian Military Chemical Complex] could corroborate or refute this natural assumption. By entangling V. S. Mirzayanov in investigation, the MCC confirmed the stated hypothesis, advancing it to the ranks of proven facts."
^ a b David Hoffman (August 16, 1998). [http://www.washingtonpost.com/wp-srv/inatl/longterm/coldwar/wasteside1.htm "Wastes of War: Soviets Reportedly Built Weapon Despite Pact"]. The Washington Post. http://www.washingtonpost.com/wp-srv/inatl/longterm/coldwar/wasteside1.htm. Retrieved 2007-07-20.
^ a b c Louise Hidalgo (August 9, 1999). "US dismantles chemical weapons". BBC News Online. http://news.bbc.co.uk/2/hi/asia-pacific/415742.stm. Retrieved 2007-07-20.
^ Kruglyak Yu L, Malekin SI, Martynov IV. Phosphorylated oximes. XII. Reactions of 2-halophospholanes with dichlorofluoronitrosomethane. Zhurnal Obshchei Khimii. 1972; 42(4):811-14.
^ Raevskii OA, Chapysheva NV, Ivanov AN, Sokolov VB, Martynov IV. Effect of Alkyl Substituents in Phosphorylated Oximes. Zhurnal Obshchei Khimii. 1987; 57(12):2720-2723
^ Raevskii OA, Grigor'ev V Yu, Solov'ev VP, Ivanov AN, Sokolov VB, Martynov IV. Electron-Donor Functions of Ethyl Methylchloroformimino Methylphosphonate. Zhurnal Obshchei Khimii. 1987; 57(9):2073-2078
^ Makhaeva GF, Filonenko IV, Yankovskaya VL, Fomicheva SB, Malygin VV. Comparative studies of O,O-dialkyl-O-chloromethylchloroformimino phosphates: interaction with neuropathy target esterase and acetylcholinesterase. Neurotoxicology. 1998 Aug-Oct;19(4-5):623-8. PMID 9745921
^ Raevski OA, Chistiakov VV, Agabekian RS, Sapegin AM, Zefirov NS. Formation of models of the interaction between organophosphate compound structure and their ability to inhibit cholinesterase. Bioorganicheskaia Khimiia. 1990 Nov;16(11):1509-22. PMID 2096825
^ Ivanov IuIa, Sokolov VB, Epishina TA, Martynov IV. O-substituted alkylchloroformoximes as substrates and inhibitors of cholinesterases. Doklady Akademii Nauk SSSR. 1990;310(5):1253-5. PMID 2354654
^ Malygin VV, Sokolov VB, Richardson RJ, Makhaeva GF. Quantitative structure-activity relationships predict the delayed neurotoxicity potential of a series of O-alkyl-O-methylchloroformimino phenylphosphonates. Journal of Toxicology and Environmental Health Part A. 2003 Apr 11;66(7):611-25. PMID 12746136
^ Steven L. Hoenig. Compendium of Chemical Warfare Agents. Springer New York, 2007. ISBN 978-0-387-34626-7
^ D Hank Ellison. Handbook of Chemical and Biological Warfare Agents (2nd) 2008. p37-41. ISBN 0849314348
^ Vil S Mirzayanov. State Secrets. An Insider's Chronicle of the Russian Chemical Weapons Program. (2009) pp142-145, 179-180. ISBN 9781432725662
External links
Chemical Weapons in Russia: History, Ecology, Politics by Lev Fedorov, Moscow, Center of Ecological Policy of Russia, 27 July 1994
Vil Mirzayanov "Dismantling the Soviet/Russian Chemical Weapons Complex: An Insider's View" Chemical Weapons Disarmament in Russia: Problems and Prospects (Washington, D.C.: Henry L. Stimson Center, 1995).
Russian chemical weapons and [by Federation of American Scientists
Vil Mirzayanov, a scientist honored by the AAAS Science and Human Rights Program in 1995
The Chemical Weapons Coverup, by J. Michael Waller, The Wall Street Journal, February 13, 1997
http://www.nbcdefence.net/nore/novi_1.htm
vde
Chemical agents
Blood
Cyanogen chloride (CK) Hydrogen cyanide (AC)
Blister
Ethyldichloroarsine (ED) Methyldichloroarsine (MD) Phenyldichloroarsine (PD) Lewisite (L) Sulfur mustard gas (HD H HT HL HQ) Nitrogen mustard gas (HN1 HN2 HN3)
Nerve
G-agents
Tabun (GA) Sarin (GB) Soman (GD) Cyclosarin (GF) GV
V-agents
EA-3148 VE VG VM VR VX
Novichok agents
Pulmonary
Chlorine Chloropicrin (PS) Phosgene (CG) Diphosgene (DP)
Incapacitating
Agent 15 (BZ) EA-3167 Kolokol-1
Riot control
Pepper spray (OC) CS gas CN gas (mace) CR gas
vde
Cholinergics
Receptor
Ligands
mAChR
Agonists: 77-LH-28-1 AC-42 AC-260,584 Aceclidine Acetylcholine AF30 AF150(S) AF267B AFDX-384 Alvameline AQRA-741 Arecoline Bethanechol Butyrylcholine Carbachol CDD-0034 CDD-0078 CDD-0097 CDD-0098 CDD-0102 Cevimeline cis-Dioxolane Ethoxysebacylcholine LY-593,039 L-689,660 LY-2,033,298 McNA343 Methacholine Milameline Muscarine NGX-267 Ocvimeline Oxotremorine PD-151,832 Pilocarpine RS86 Sabcomeline SDZ 210-086 Sebacylcholine Suberylcholine Talsaclidine Thiopilocarpine Vedaclidine VU-0029767 VU-0090157 VU-0152099 VU-0152100 VU-0238429 WAY-132,983 Xanomeline YM-796
Antagonists: 3-Quinuclidinyl Benzilate 4-DAMP Anisodamine Anisodine Atropine Atropine Methonitrate Benactyzine Benzatropine (Benztropine) Benzydamine BIBN 99 Biperiden Bornaprine CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin DAU-5884 Dimethindene Dexetimide DIBD Dicyclomine (Dicycloverine) Ditran EA-3167 EA-3443 EA-3580 EA-3834 Elemicin Etanautine Etybenzatropine (Ethylbenztropine) Flavoxate Himbacine HL-031,120 Ipratropium J-104,129 Hyoscyamine Mamba Toxin 3 Mamba Toxin 7 Mazaticol Mebeverine Methoctramine Metixene Myristicin N-Ethyl-3-Piperidyl Benzilate N-Methyl-3-Piperidyl Benzilate Orphenadrine Otenzepad Oxybutynin PBID PD-102,807 Phenglutarimide Phenyltoloxamine Pirenzepine Piroheptine Procyclidine Profenamine RU-47,213 SCH-57,790 SCH-72,788 SCH-217,443 Scopolamine (Hyoscine) Solifenacin Telenzepine Tiotropium Tolterodine Trihexyphenidyl Tripitamine Tropatepine Tropicamide WIN-2299 Zamifenacin; Others: 1st Generation Antihistamines (Brompheniramine Chlorpheniramine, Cyclizine, Cyproheptadine, Dimenhydrinate, Diphenhydramine, Doxylamine, Hydroxyzine, Meclizine, Mepyramine/Pyrilamine, Phenindamine, Pheniramine, Tripelennamine, Triprolidine, etc) Tricyclic Antidepressants (Amitriptyline, Doxepin, Trimipramine, etc) Tetracyclic Antidepressants (Amoxapine, Maprotiline, etc) Typical Antipsychotics (Chlorpromazine, Thioridazine, etc) Atypical Antipsychotics (Clozapine, Olanzapine, Quetiapine, etc)
nAChR
Agonists: 5-HIAA A-84,543 A-366,833 A-582,941 A-867,744 ABT-202 ABT-418 ABT-560 ABT-894 Acetylcholine Altinicline Anabasine AR-R17779 Butyrylcholine Carbachol Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium Epibatidine Epiboxidine Ethoxysebacylcholine EVP-4473 EVP-6124 Galantamine GTS-21 Ispronicline Lobeline MEM-63,908 (RG-3487) Nicotine NS-1738 PHA-543,613 PHA-709,829 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A Sebacylcholine SIB-1508Y SIB-1553A SSR-180,711 Suberylcholine TC-1698 TC-1734 TC-1827 TC-2216 TC-5214 TC-5619 TC-6683 Tebanicline Tropisetron UB-165 Varenicline XY-4083
Antagonists: 18-Methoxycoronaridine -Bungarotoxin -Conotoxin Alcuronium Anatruxonium Atracurium Bupropion (Amfebutamone) Chandonium Chlorisondamine Cisatracurium Coclaurine Coronaridine Dacuronium Decamethonium Dextromethorphan Dextropropoxyphene Dextrorphan Diadonium DHE Dimethyltubocurarine (Metocurine) Dipyrandium Dizocilpine (MK-801) Doxacurium Duador Esketamine Fazadinium Gallamine Hexafluronium Hexamethonium (Benzohexonium) Ibogaine Ketamine Kynurenic Acid Levacetylmethadol Malouetine Mecamylamine Memantine Methadone Methorphan (Racemethorphan) Methyllycaconitine Metocurine Mivacurium Morphanol (Racemorphanol) Neramexane Pancuronium Pempidine Pentamine Pentolinium Phencyclidine Pipecuronium Radafaxine Rapacuronium Rocuronium Surugatoxin Suxamethonium (Succinylcholine) Toxiferine Trimethaphan Tropeinium Tubocurarine Vecuronium
Reuptake
Inhibitors
Plasmalemmal
CHT Inhibitors
Hemicholinium-3 (Hemicholine)
Vesicular
VAChT Inhibitors
Vesamicol
Enzyme
Inhibitors
Anabolism
ChAT Inhibitors
1-(-Benzoylethyl)pyridinium 2-(-Naphthoyl)ethyltrimethylammonium 3-Chloro-4-stillbazole 4-(1-Naphthylvinyl)pyridine Acetylseco Hemicholinium-3 Acryloylcholine AF64A B115 BETA CM-54,903 N,N-Dimethylaminoethylacrylate N,N-Dimethylaminoethylchloroacetate
Catabolism
AChE Inhibitors
Reversible: Carbamates: Aldicarb Bendiocarb Bufencarb Carbaryl Carbendazim Carbetamide Carbofuran Chlorbufam Chloropropham Ethienocarb Ethiofencarb Fenobucarb Fenoxycarb Formetanate Furadan Ladostigil Methiocarb Methomyl Miotine Oxamyl Phenmedipham Pinmicarb Pirimicarb Propamocarb Propham Propoxur; Stigmines: Ganstigmine Neostigmine Phenserine Physostigmine Pyridostigmine Rivastigmine; Others: Ambenonium Donepezil Edrophonium Galantamine Huperzine A (Huperzia Serrata) Minaprine Tacrine Zanapezil
Irreversible: Organophosphates: Acephate Azinphos-Methyl Bensulide Cadusafos Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-Methyl Coumaphos Cyclosarin (GF) Demeton Demeton-S-Methyl Diazinon Dichlorvos Dicrotophos Diisopropyl Fluorophosphate (Guthion) Diisopropylphosphate Dimethoate Dioxathion Disulfoton EA-3148 Echothiophate Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fosthiazate GV Isofluorophate Isoxathion Malaoxon Malathion Methamidophos Methidathion Metrifonate Mevinphos Monocrotophos Naled Novichok Agent Omethoate Oxydemeton-Methyl Paraoxon Parathion Parathion-Methyl Phorate Phosalone Phosmet Phostebupirim Phoxim Pirimiphos-Methyl Sarin (GB) Soman (GD) Tabun (GA) Temefos Terbufos Tetrachlorvinphos Tribufos Trichlorfon VE VG VM VR VX; Others: Demecarium Onchidal (Onchidella Binneyi)
BChE Inhibitors
Many of the acetylcholinesterase inhibitors listed above act as butyrylcholinesterase inhibitors.
Others
Precursors
Choline (Lecithin) Citicoline Dimethylethanolamine Glycerophosphocholine Phosphatidylcholine Phosphatidylethanolamine Phosphorylcholine
Cofactors
Acetic Acid Acetyl-L-Carnitine Acetyl-Coenzyme A Vitamin B5 (Pantothenic Acid, Pantethine, Pantetheine, Panthenol)
Others
Acetylcholine Releasing Agents: -Latrotoxin -Bungarotoxin; Acetylcholine Release Inhibitors: Botulinum Toxin (Botox); Acetylcholinesterase Reactivators: Pralidoxime obidoxime
Categories: Nerve agents | Organophosphates | Anticholinesterases | Cold War weapons of the Soviet Union | Science and technology in the Soviet Union | Soviet inventionsHidden categories: Articles needing cleanup from November 2007 | All pages needing cleanup
Novichok Agent
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