Update to briefing note ‘Doubts about Novichoks’

The following is an update to the briefing note of 14 March 2018 from the Working Group on Syria, Propaganda and media. (Readers’ comments on this update can be made here.)

Authors: Paul McKeigue, Jake Mason and Piers Robinson

Introduction

In view of the seriousness of the rapidly worsening relations between the West and Russia, and the quickly evolving military events in the Middle East, especially Syria, we have taken the step to publish relevant evidence-based analysis with respect to the Skripal incident of 4 March 2018. This update to our earlier briefing note covers new material that has become available. We welcome comments and corrections which can be sent to piers.robinson@sheffield.ac.uk or provided in the Comments section below.

Key Points

  • There is no corroboration of Mirzayanov’s story of a secret Russian “Novichoks” programme to develop a new class of nerve agents, although the compounds described in his book in 2008 are real structures.

  • There is evidence that the US government has concealed what it knows about these compounds: specifically

    • A record in a public database showing that one of these compounds had been synthesized around 1998 by the US Army’s chemical defence lab (Edgewood) has been deleted

    • When the structures of these compounds were published in 2008 the US government sought to discourage discussions of the matter at OPCW and another international forum for chemical weapons prohibition.

  • The UK government has asserted that “No country bar Russia has combined capability, intent and motive” to carry out the Salisbury poisonings. Published studies show that these compounds can be synthesized at bench scale (sufficient for an assassination) in other countries. The UK government’s declared case therefore rests only on subjective judgements of “intent and motive”, which are open to question.

Summary

Official statements from the UK government claim that the “military grade nerve agent” detected in Salisbury was “part of a group of nerve agents known as Novichoks” that the Russian chemist Vil Mirzayanov alleged had been developed in the Soviet Union in a secret programme. The structures of these compounds, labelled A-230, A-232, A-234, A-242 and A-262, were published by Mirzayanov in a book in 2008, twelve years after he emigrated to the US.

Other than Mirzayanov’s story, there is no evidence that these compounds were ever synthesized in either the Soviet Union or Russia, or that the “Novichok” programme ever existed. The use of the term “Novichoks” to describe this A-230 series of compounds, which are real chemical structures, is therefore tendentious. An account by another Russian chemist Vladimir Uglev, often cited as corroboration of Mirzayanov’s story, appears on close examination to be about the development of a class of nerve agents denoted GV which have been studied in several countries including Czechoslovakia and the US.

The UK government has not revealed the identity of the compound detected in Salisbury, but the Russian ambassador has stated that the Foreign Secretary told him that the compound detected was A-234. Russian experts have revealed that the mass spectrometry profile of this compound was submitted to a public database by a researcher in the US Army’s Edgewood Chemical and Biological Center around 1998, indicating that Edgewood has synthesized and studied this compound.

There is also evidence that the US government has concealed what it knows about the A-230 series of compounds. Edgewood’s entry for compound A-234 in the public database has been deleted. Furthermore, US diplomatic cables from 2009 show that the US and UK governments sought to discourage discussion of Mirzayanov’s story at the OPCW and the Australia Group (an informal grouping of US-allied countries set up in 1985 to control the export of precursors for chemical weapons).

It has been suggested that the A-230 series of compounds have a different mode of action to that of classic organophosphates. To ensure that all relevant information is available to the doctors caring for the victims of the Salisbury poisoning, the UK government should without further delay reveal the identity of the compound detected, and should request urgently that all labs that have undertaken toxicity studies on such compounds make their results publicly available.

Detailed Discussion

Did a “Novichok” programme ever exist?

The word “Novichok” comes from a Russian chemist named Vil Mirzayanov, who emigrated in 1995 after alleging that a secret programme to develop a new class of nerve agents had existed in the Soviet Union and had continued in Russia. In 2008, Mirzayanov published a book containing structures of five compounds that he alleged had been developed in this programme: they were labelled A-230, A-232, A-234, A-242 and A-262. We shall refer to these as the A-230 series of compounds, without taking any position as to whether they were developed in Russia as “Novichoks”.

The UK government has added to this story with this statement from the Foreign and Commonwealth Office:-

The Foreign Secretary revealed this morning that we have information indicating that within the last decade, Russia has investigated ways of delivering nerve agents likely for assassination. And part of this programme has involved producing and stockpiling quantities of Novichok.

The wording “we have information indicating” suggests that this is raw human intelligence rather than the “finished” evaluation for use by policy makers, for which wording of the form “we have assessed” would be used.

The Russian government denies that a Novichok programme ever existed. The Russian envoy to the UN, Vasily Nebenzya stated on 15 March that:

No research, development or manufacturing of projects codenamed Novichok has ever been carried out in Russia, all CW programmes were stopped back in 1991-92_

In a television interview the Foreign Ministry spokeswoman Maria Zakharova gave a comprehensive denial:-

Never on the territory of the USSR in Soviet times or in the times of the Russian Federation on its territory have there been studies conducted under the code name Novichok. It was neither patented, nor used as a symbol or a code. Once more, as this is the key thing: the word Novichok has never been used in the USSR or in Russia as something related to chemical weapons research. This word was introduced and used for poisonous materials in the West.

A recent interview with Vladimir Uglev has been often cited as corroborating Mirzayanov’s account. Uglev describes how he helped to develop a “new class of organophosphorus chemical agents”, but states that the name “Novichok” was not used for these compounds. Uglev states that one of these compounds, obtained from a military laboratory, was used to murder the banker Ivan Kivelidi and his secretary Zara Ismailova in 1995. A report in the pro-Western magazine Novaya Gazeta includes an image of a page from a document purported to be from the investigation of this murder. This document shows a reconstruction of the molecular structure of the compound from the fragments detected by mass spectrometry.   However the reconstructed structure shown is identical to that of a nerve agent known as GV (see Appendix), with what may be the mistaken substitution of an ethoxy group for a fluorine atom. If Uglev’s account is accurate and this document is genuine, this establishes that the new class of nerve agents that he helped to develop was the GV class of agents, which Russia has never denied studying. Because the A-230 series of compounds have structures that are very different from GV-like compounds, Uglev’s story does not corroborate that of Mirzayanov.   Mirzayanov’s account in 1995, in which he labels “Substance 33” (the Russian isomer of VX), as a “precursor” (possibly “forerunner” is the intended meaning as Russian VX is not a chemical precursor) of what he called “novichoks” is also consistent with these being GV-type agents. At a briefing by the Russian Ministry of Foreign Affairs on 21 March, Viktor Kholstov, Director of the Centre for Analytical Research on Chemical and Biological Weapon Conventions under the Russian Ministry of Industry and Trade, stated that “Vil Mirzayanov did not have these formulas [the structures given in his 2008 book for the A-230 series of compounds] in the early 2000s”.

In summary, there is ample evidence that the Soviet Union and other countries were developing GV-type agents up to the 1990s. However Mirzayanov’s story that the chemical structures labelled as A-230 to A-262 in his 2008 book were developed in the Soviet Union or Russia remains open to serious doubt.

Was one of the A-230 series of compounds used in the Salisbury poisoning?

The Prime Minister stated to the House of Commons on 12 March that

It is now clear that Mr Skripal and his daughter were poisoned with a military-grade nerve agent of a type developed by Russia. It is part of a group of nerve agents known as Novichok.

On 22 March, the Russian Ambassador to the UK gave a briefing:-

On 12 March, 8 days after the day of poisoning, I was summoned by Foreign Secretary Johnson, who put forward a 24-hour ultimatum to explain the Russian Government’s position by the end of the next day. The question was put like following: either the incident in Salisbury was a direct act of the Russian Government against the UK or the Russian Government had lost control of a nerve agent that the Foreign Secretary identified as A-234, and allowed it to get into the hands of others.

The UK government has not confirmed that the nerve agent was identified as A-234, or that this information was conveyed to the Ambassador by the Foreign Secretary. It is expected that the OPCW investigation will reveal the identity of the agent detected in Salisbury within the next few weeks. For now, it is reasonable to assume that the agent found was one of the A-230 series of compounds.

Scientific studies of the A-230 series of compounds

In 2016, Iranian scientists reported bench scale synthesis of a few compounds closely related to those labelled by Mirzayanov as “Novichoks”. They added the mass spectrometry signatures of these compounds studied to the OPCW’s Central Analytical Database. The structure denoted “compound 3” in their paper is similar to A-234 except that it has methyl instead of ethyl groups.

A similar study of the compound later published as A-234 had been undertaken by Dr Dennis Rohrbaugh at the US Army Chemical and Biological Defense Command’s Edgewood Research Development and Engineering Center around 1998. He added the mass spectrometry profile to the 1998-2001 version (NIST 98) of the National Institute of Standards and Technology Mass Spectral Library. This was revealed in a television interview by Professor Igor Rybalchenko, formerly the head of the Russian chemical weapon detection lab (the Laboratory of Chemical and Analytical Control of the Ministry of Defence) . Rybalchenko is a highly-respected scientist who has worked closely with western colleagues on the OPCW Scientific Advisory Board and with international agencies supervising the destruction of the former Soviet chemical weapons stockpiles.   Rybalchenko showed a slide (at 1:11:53 in the recording) and explained:-

As far back as 1998, we looked though a regular edition of the spectral database released by the US National Bureau of Standards [now the National Institute of Standards and Technology], which has spectral data on about 300,000 compounds and is regularly updated, to find an agent that caught our attention as it was an organophosphate chemical. We understood that it must have a lethal effect. Now it has turned out that, judging by the name of that agent, it was “Novichok” A-234.

The image shows a faded printout of a record from NIST 98 for a chemical with formula C8H18FN2O2P named as N-(O-ethyl-fluorophosphoryl)-N’-N’-diethyl-acetamidine, with NIST number 226889. As Rybalchenko notes, this molecular structure corresponds to A-234

Evidence that the US and UK governments are concealing what they know about the A-230 series of compounds

The record submitted by Edgewood for a compound with formula C8H18FN2O2P no longer exists in the current version of the NIST Mass Spectral Library.   As such research is entirely legitimate, it is puzzling that this record should have been deleted.

A secret cable dated 26 March 2009 from a US delegate to OPCW reported that at a meeting of the OPCW Data Validation Group in The Hague a few weeks earlier, “representatives of several countries (Finland, Netherlands, UK) had begun discussing the Mirzayanov book on the margins of the meeting”.   The US delegate noted that

U.S. Del understands from OSD that the UK Ministry of Defense has spoken to its counterparts in the Netherlands and Finland, apprised them of the conversation, and asked each country to provide guidance to its del members not/not to raise this issue in the future

The Canadian delegate was also curious, but the US and UK delegates expressed lack of familiarity with and interest in the matter.

On March 25, in a private conversation, Canadian delegate asked U.S. and UK Delreps whether they had heard of the Mirzayanov book “State Secrets: An Insider’s View of the Russian Chemical Weapons Program.” Canadian Rep added that Mirzayanov now appeared on YouTube. UK Rep acknowledged she had heard of it, but said this was the first time she had heard of “novichoks” and thought the entire discussion was best left to experts in capital. U.S. Delrep indicated a lack of familiarity with the subject matter and indicated no interest in pursuing the discussion further.

The cable requested further “guidance as to how this issue is to be handled if raised by others” for US members of OPCW technical advisory bodies such as the Scientific Advisory Board. The cable was addressed to the CIA, the National Security Council, the Secretary of Defense and the Secretary of State, suggesting that this issue was being discussed at high levels of the US government.

A subsequent cable on 3 April 2009 from the Secretary of State Hillary Clinton instructed the US delegation to the Informal Inter-Sessional Meeting of the Australia Group (a group of US-allied countries set up in 1985 to control the export of precursors of chemical weapons) that one of five US objectives for the meeting was to:-

— Avoid any substantive discussion of the Mirazayanov book “State Secrets: An Insider’s View of the Russian Chemical Weapons Program” or so-called ‘Fourth Generation Agents.’

More detailed guidance was provided for the US delegates, echoing the description of how US and UK delegates had responded to the Canadian delegate a week earlier:-

If AG participants raise the issue of Vils Mirazayonov’s book “State Secrets: An Insider’s View of the Russian Chemical Weapons Program,” the Del should:

— Report any instances in which the book is raised.

— Not/not start or provoke conversations about the book or engage substantively if it comes up in conversation.

— Express a lack of familiarity with the issue.

— Quietly discourage substantive discussions by suggesting that the issue is ‘best left to experts in capitals.’

These cables establish that the US and UK governments sought to discourage discussion of Mirzayanov’s book in 2009. Taken together with the deletion of the record for A-234 submitted by Edgewood to the NIST Mass Spectral library, this suggests that the US and UK governments are concealing what they know about the A-230 series of compounds, for reasons that are not clear.

These cables suggest a reinterpretation of our earlier briefing in which we noted that the OPCW Scientific Advisory Board in 2013 had stated that it “has insufficient information to comment on the existence or properties of “Novichoks”. We had interpreted this as scepticism, on the part of experts who were in a position to know, about whether these compounds were really military-grade nerve agents.   From the cables cited above, however, it appears that these experts may have been following the guidance issued earlier that they should “discourage substantive discussions” of the matter.

What is known of the toxicity of the A-230 series of compounds?

Rybalchenko stated that “All that we know is that all substances of this class are very difficult to overcome in case of injuries, and the antidote therapy will hardly bring about the desired effect”. One review has stated (without citing a source) that inhibition of an enzyme known as neuropathy target esterase, which can cause delayed nerve damage, “is of primary concern for the Novichok agent”. The consultant treating the victims of the Salisbury poisoning reported on 22 March that they were “heavily sedated following injury by a nerve agent” and unable to communicate. This prolonged paralysis is not typical of acute poisoning by standard organophosphate agents. To ensure that all available toxicological and medical expertise can be mobilized to help the Salisbury doctors manage the victims, the identity of the agent should be made public without delay. Edgewood and any other laboratories that have studied this compound should reveal the results of any toxicity studies they have done.

Appendix – technical points

This appendix explains some technical points on which there has been confusion.

Why is it necessary to synthesize a new compound before it can be detected by mass spectrometry?

Mass spectrometry identifies compounds by the mass-charge ratio of the ions produced by fragmentation of the compound. These mass-charge ratios, combined with separation by another method such as gas chromatography, are a unique “signature” for the compound. To determine this signature for a new compound, it has to be synthesized and analysed by mass spectrometry to measure the mass-charge ratios, which are then added to databases so that the compound can be detected in future by matching the observed mass-charge ratios with the records in the database.

Is it feasible to synthesize these compounds at bench scale?

The Iranian paper confirms that compounds similar to A-234 can be synthesized at bench scale in any modern university lab. Synthesis at industrial scale for military use would be a different matter, but an assassination would require only bench scale quantities.

Did Porton Down make a definite identification of the agent?

In Mr Justice Williams’s court judgement on 22 March, the statement from witness CC, described as “Porton Down chemical and biological analyst” was summarized as follows:-

Blood samples from Sergei Skripal and Yulia Skripal were analysed and the findings indicated exposure to a nerve agent or related compound. The samples tested positive for the presence of a Novichok class nerve agent or closely related agent.

This is similar to the form of words that OPCW has used to report positive blood tests for sarin exposure: “sarin, or a sarin-like substance”. This wording is used because blood tests for nerve agent detect only what is left of the molecule after it has bound to the receptor. The “leaving group” (the rest of the molecule) cannot be identified. For sarin (and presumably for A-234) the leaving group is a fluorine atom, and for VX the leaving group is a thiol.

Although it is possible that the blood test would not be able to identify definitively a molecular structure such as A-234. this inability to determine the leaving group applies only to physiological samples. If environmental samples have tested positive, Porton Down should have been able to identify the original molecule precisely.   As noted above, to use the word “Novichoks” for the A-230 series of compounds is tendentious.

The GV agents studied in several countries are not the “Novichoks” described by Mirzayanov

In his authoritative review, Dr Robin Black, former head of the detection laboratory at Porton Down, makes clear that the development of a class of “intermediate volatility agents” (IVAs), designated “GV agents” by the Czechoslovak chemists Ivan Masek and Jiri Matousek is distinct from Mirzayanov’s unconfirmed story about “Novichoks”:-

Two additional series of nerve agents are worthy of mention. Research on IVAs in several countries led to the analogue known as GV, O-(2-dimethylaminoethyl) N,N-dimethyl phosphoramidofluoridate (Scheme 1.7). The name GV was coined by Czech chemists to indicate properties of both G and V agents65 The US military designator was GP. GV is a hybrid structure incorporating structural features of tabun, sarin and V agent. GV had true intermediate volatility properties (bp 226 °C, volatility 527 mg m−3 at 25 °C),66 producing sufficient vapour to cause an inhalation hazard, and possessing percutaneous toxicity approaching that of the V agents. GV might have become an important threat agent had it not had very poor storage stability. It has been suggested that a binary version might be feasible.

In recent years, there has been much speculation that a fourth generation of nerve agents, ‘Novichoks’ (newcomer), was developed in Russia, beginning in the 1970s as part of the ‘Foliant’ programme, with the aim of finding agents that would compromise defensive countermeasures.67,68 Information on these compounds has been sparse in the public domain,30,68–70 mostly originating from a dissident Russian military chemist, Vil Mirzayanov.69 No independent confirmation of the structures or the properties of such compounds has been published.

A-264 image NIST

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82 Responses to Update to briefing note ‘Doubts about Novichoks’

  1. i’m wondering why you did not include the testimony of Leonard Rink, who was given a one year suspended sentence for supplying a nerve agent poison to the alleged murderer of a Moscow banker, Ivan Kivelidi in 1995. He recently spoke to the Russian media about the so-called “Novichok”/Foliant program after Uglev made his allegations.

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  4. Paul McKeigue says:

    Rink’s story is described in the linked article in Novaya Gazeta. He does not add much to Uglev’s account except that he apparently confessed to supplying (for a fee of $1800) the nerve agent used to murder Kivelidi. The most relevant information in the Novaya Gazeta article is the document from the investigation showing a reconstruction of the molecular structure of the agent from the fragments detected by mass spectrometry. The structure is similar to that of GV, with what may be the mistaken substitution of an ethoxy group for a fluorine atom. The GosNIIOKhT expert commented that the structure should have a fluorine atom.

    If this document is genuine, the agent used in this murder was not one of the A-230 series of compounds for which the structures were given by Mirzayanov in 2008, and Uglev’s account does not corroborate Mirzayanov’s story of a secret programme to develop a fourth generation of nerve agents but confirms only that USSR and Russia were studying GV agents at bench scale, as were other countries including Czechoslovakia and the US.

    • Your analysis is simplistic to say the least, and your dismissal of Rink’s statements (“He does not add much to Uglev’s account “) is strange. The precise formula was declared at the time of the trial by the state prosecutor to be a State Secret and thus unpublished until Mirzayanov published it more than a decade later in his book. The formula declared at the trial was obviously not the correct formula as it was not permitted to publish it. As you say “If this document is genuine,”.

      • causticlogic says:

        Good point that maybe the document isn’t genuine. That should be considered. But it does say if, so all’s good. There’s also Mirzayanov ’95 account of the genesis of “Novichoks” that suggests the same thing – GV class, like the diagram shows (see article). So unless both points are incorrect, there’s a good case for the formula having been changed sometime between ’98 and 2008.

        So what else did Rink add to the picture besides bearing witness to a transfer of what he called “novichok”? Any other molecular details given in connection with this? What is it “strange” to “dismiss” here?

  5. Istvan Ujvary says:

    Actually, there is at least one publication in a Russian agrochemical journal that describes such Novichok-related compounds:
    Neklesova, ID, Alimov, PI, Kudrina, MA, Iraidova, IS (1966) [Relation between chemical structure of some ester amides and imides of phosphoric acid and their toxicity]. Khim. v Sel’sk. Khoz. 4(6), 422-426.
    Synthesis and bioactivity of compounds similar to those described by Mirzayanov though lacking the P-F bond which could be important for toxicity, are given. A series of (EtO)2P(:O)N:C(R)(R1) was tested against insect and mouse LD50 values, ranging from 85 to 150 mg/kg, were also determined.

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  7. Neil says:

    As regards the term “sarin or sarin like substance” in OPCW reports on Syria. I wondered if anyone with suitable expertise, could explain why a biomedical results table from OPCW would use that phrase instead of a chemical designation/identifier for any Sarin-like molecules found. Also, why would there be a discrepency between that vague term being used for blood sample results, whilst the urine sample and other results were identified definitely as isopropylmethylphosphonic acid in the OPCW report on Khan Sheikhoun. Is there a biomedical reason for this difference between what would be found in blood and urine results (if an individual was genuinely exposed to sarin)? https://www.opcw.org/fileadmin/OPCW/Fact_Finding_Mission/s-1497-2017_e_.pdf Table 3 page 38

    • Neil says:

      5.89 The team noted that the blood of person reference numbers 131814, 131820, and 131825 tested negative for sarin or sarin-like substances, yet other biomedical specimens from the same people tested positive for isopropyl methylphosphonate. https://www.opcw.org/fileadmin/OPCW/Fact_Finding_Mission/s-1510-2017_e_.pdf

      Although isopropyl methylphosphanate is a degradation product of Sarin and its presence can be taken to indicate Sarin exposure, it is also commercially available.
      ———————————————————————————-
      Isopropyl Methylphosphonic Acid
      Retail Price: $ 135.00
      Quantity:
      Add To Cart
      Or call 1-800-LAB-SPEXPayment
      1000ug/mL Isopropyl Methylphosphonic Acid in MeOH
      Components CAS# Concentration
      Isopropyl Methylphosphonic Acid 1832-54-8 1000 µg/mL
      SPEX CertiPrep Organic Certified Reference Materials are manufactured for GC, GC/MS, LC and LC/MS for a wide range of applications including: volatiles, semi-VOAs, pesticides, petrochemical, biofuel, drinking water, wine, phthalates, pharmaceutical and residual solvents. Over 4,000 organic single-component standards are available and sold in 1 mL ampules that are supplied with a pre-labeled “transfer/storage vial.”

      We also offer custom blends with quick turnaround based on your individual needs.
      ——————————————————————————————————–
      This and other irregularites – most notably the time of arrivals in hospital were – had a blind eye turned to them by the OPCW-JIM report. https://drive.google.com/file/d/0ByLPNZ-eSjJdcGZUb0hqalFOa0hhdEZ3WlBvZmRnajFRV3pr/view

      The use of samples gathered by NGO’s of dubious impartiality was at odds with previous OPCW statements:

      “The OPCW would never get involved in testing samples that our own inspectors don’t gather in the field because we need to maintain chain of custody of samples from the field to the lab to ensure their integrity,” MIchael Luhan April 2013
      https://www.reuters.com/article/us-syria-crisis-chemical-weapons/evidence-of-syria-chemical-weapons-use-not-up-to-u-n-standard-idUSBRE93P0UG20130426

      • causticlogic says:

        My understanding is “sarin-like” comes from the fluoride ion reactivation test (names vary). It means only the “leaving group” is unknown, but the rest of the molecule can be identified. The option are sarin, clorosarin, an obscure VX derivative, nothing seemingly relevant (phosphine, VX, chlorine, “novichok”, etc.). It’s best read as “sarin,” small footnote.

        Why the phrase then? Maybe to be pedantic, maybe to give us a false lead to chase, maybe other or no good reason. They might have given a reason somewhere, but it might not be true anyway…

        The fluoride test is done on blood samples, and can be done some time after the fact – on samples. Would have to review how fresh samples would test weeks later. Extremely small doses one can’t even feel will register as positive for “sarin-like” (and OPCW only looks for positive, not quantitative, results). So if a blood sample tests negative, I THINK it really means there’s like none at all. But if urine tests for IMPA, I’m not a real expert but to me, I suspect the person ingested IMPA. For the others, it’s easy to fake real sarin exposure with a token dose.

        As for the rule changes on chain of custody: hey… this is, like, a special case, or something.

      • Neil says:

        Thanks causticlogic. I also wonder why urine results where people had positive blood tests for.sarin or sarin like would only come up positive for IMPA

      • DDTea says:

        Isopropyl methylphosphonic acid (IPMA) is a CWC-scheduled precursor. Aldrich ships only to bonafide labs. A rando in Syria could not possibly order it. Moreover, I have a collaborator in Lebanon, and he tells me it takes *months* to receive chemicals from Aldrich where he is.

        Also, IPMA does not bind strongly to acetylcholinesterase. It’s water soluble, and would be washed out with urine. It does not bioaccumulate to any appreciable degree. So it’s difficult to imagine this giving a positive result in the enzyme reactivation test.

        The last reasonable thing to imagine is that the Khan Sheikhoun victims were somehow dosed with Sarin metabolites. A far more likely explanation is unintended cross contamination of samples.

  8. Istvan Ujvary says:

    Only my picture C8H18FN2O2P was inserted. My comment not.
    Reason?

  9. Steve McIntyre says:

    there are two different definitions of A-234: Mirzajanov vs Hoenig/Ellison. https://t.co/VLSDsX6VOI

    A234_Mirzajanov is almost certainly the same as the Rohrbauch’s NIST98 molecule and fits within Ellison’s (Handbook of Chemical and Biological Warfare Agents, 2007) definition of GV series. A234_Hoenig fits within Ellison’s definition of novichok (carbonimidic phosphorohalides).

    At present, seems to me that there is some unnecessary shadow boxing unless one distinguishes the two molecules, since assertions about A234_Hoenig do not necessarily apply to A234_Mirzajanov and vice versa.

    I claim no expertise in this field. The descriptions by Hoenig and Ellison are much more thorough than those by Mirzajanov, who does not appear to have been involved in the chemistry itself (as compared to, say, Uglev).

    • Paul McKeigue says:

      This story
      in the Washington Times on 4 February 1997
      purports to quotes from a leaked US military intelligence report which asserts that “the Russians can produce A-232 and its ethyl analog A-234”. This is consistent with the structures of these compounds published by Mirzayanov in 2008, in which A-234 differs from A-232 only by the substitution of an ethyl group for a methyl group. I have not checked the original of Hoenig’s 2007 book, but the structure for A-234 quoted elsewhere as that given in his book has no ethyl group.
      Whether or not the Washington Times story that the Russians could produce these compounds was true, this article corroborates the structures given for A-232 and A-234 by Mirzayanov in 2008 as consistent with labels used by the US military eleven years earlier.

      The structure for A-234 published by Hoenig has a dihaloformaldoxime group. Does the
      book give a source for this? . The earliest source I can identify for “Novichok” structures with dihaloformaldoxime groups is a post on the sciencemadness.org discussion board in 2004 by DDTea, an organic chemist who has commented on this blog in relation to alleged chemical attacks in Syria. On 16 March 2004 DDTea posted an edited version of a book review that had originally been posted on Amazon on 16 November 2003 under the name Anatoly Kuntsevich,. The structure
      given by Hoenig for A-232 in 2007 is similar to structures given for two Novichok compounds in DDTea’s edited version of the book review.

      The book review is no longer on Amazon’s site, and the identity used to post it was clearly fake as the real Anatoly Kuntsevich (a retired Soviet-era general alleged to have had responsibility for the Novichok programme) had died in April 2002. I am not sure what to make of this. The release of structures for purported Novichoks in 2004 and the encouragement on an amateur chemistry forum of discussions on how to synthesize them
      may have been part of an disinformation operation, or possibly a honeypot operation to entrap likely terrorists.

      • causticlogic says:

        This is a wrinkle. An alleged book from the alleged head of the Novichok program, published after his death … after the alleged scrubbing of the NIST entry (as of 2001?) … seems to be the source for … another allegedly alleged molecular structure?

        I hope this is, has been, will be sorted out. Is Steve wrong then to say “A234_Mirzajanov is almost certainly the same as the Rohrbauch’s NIST98 molecule and fits within Ellison’s (Handbook of Chemical and Biological Warfare Agents, 2007) definition of GV series.” ? Or is the GV classification wrong? Or is there not a clash there as it was seeming?

      • Paul McKeigue says:

        Steve is correct to say that A234_Mirzajanov is almost certainly the same as the Rohrbauch’s NIST98 molecule. I don’t know what Ellison defined as a GV agent (maybe their structures had not been published then) but we now have a canonical source for the generic structure of GV agents in the 2015 paper by Masek et al (linked in the post) It was Masek and Matousek who named these compounds GV to indicate that they had structural features of both G series (sarin-like) and V series (VX-like) compounds.

      • DDTea says:

        Hey Paul,

        Sorry for the delay in replying to this.

        Life is really weird sometimes, and that book review ranks among the strangest things I’ve seen in my life. Doubly so now that it is being read 14 years down the road. I feel as if I’m sharing a homework essay from my junior high English class.

        Thankfully, others stole the show from my silly copy & paste job (the structures I drew were wrong, by the way). Fritz (sciencemadness) and Megalomania (of Roguesci) did a much better literature survey. Sauron, in the sciencemadness thread that I started, offered the best public commentary on the chemistry of Novichok syntheses, showing how they bypass CWC controls. SimplyRED undertook some light computational studies to model the interaction of some FOLIANT program compounds with acetylcholinesterase, and was able to identify a particularly potent compound in the series. As for me? I feel like I pushed the start button of a Rube Goldberg machine, and have just been a spectator. Since the Skripal case, I’ve been reviewing this topic myself. It’s the last thing I thought I’d think of again. Even Sauron admitted he found it all rather boring, since Novichoks are “old news” and the current series of NATO chemical warfare protection (MOPP suits) protects against them.

        I have no way of knowing whether every detail in the book review was truthful and accurate. However, the names and references (searching by I.V. Martynov and his coauthors) that were offered certainly lead to a mountain of literature, some of which includes structures identified by Mirzayanov and others as “Novichok” agents. And frankly, that’s what matters. At this point, the book review itself is irrelevant next to what else has been openly discussed.

        It’s disappointing that you see an “information operation” here. I see some excellent amateur science–albeit in the form of library research, interviews, and calculations. To the best of my knowledge, there was no encouragement of this discussion. I never had any. In fact, there was active *discouragement.*

  10. The main question – if it was a chemical warfare agent, why all survived and are getting better ?!
    The military poisonous substance was created in order to kill quickly and for sure.
    Remember how the brother of the leader of North Korea was killed. One wave of cloth in front of his nose and all, he died after a few seconds.

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  13. rogerglewis says:

    Reblogged this on MUSO MUSINGS ON FATHERHOOD THEORY AND STUFF and commented:

  14. Pingback: Novichock, The Good Stuff, Media Filter Buster Courtesy of Vanessa Beely https://www.youtube.com/watch?v=4wzmY43Luaw | MUSO MUSINGS ON FATHERHOOD THEORY AND STUFF

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  17. arclight2011part2 says:

    I thought I might add this USA based chemists thread forum here that is discussing the Novichok series (mentions 4 types) from about 2004..;
    http://www.sciencemadness.org/talk/viewthread.php?tid=7639
    and I made some notes based on the thread. I also pointed out that a random country such as Ukraine could have produced such a compound (It had motive and the ability but I state there is no definitive proof) and has a soft border with the EU;
    https://nuclear-news.net/2018/03/29/novochok-a234-the-facts-exclusive-to-nuclear-news-net/
    Great breakdown and research Tim and everybody!

  18. arclight2011part2 says:

    Reblogged this on nuclear-news and commented:
    Interesting article and comments on this topic here

  19. Pingback: Video – Novichok info and how the governments stop you from seeing it! « nuclear-news

  20. Brendan says:

    This week, the Porton Down chief Gary Aitkenhead used imprecise wording that was similar to that in the court judgement.
    Aitkenhead: “we’ve been able to establish that it’s Novichok or from that family.”

    The use of the description “Novichok class nerve agent or closely related agent” in the court judgement last month was understandable, since that was limited to the substance found in blood samples, which cannot be identified exactly (because the “leaving group” part is missing from the molecules in physiological samples, if I understand the article correctly). That case only involved an application to hand over the blood samples to the OPCW without the Skripals’ consent.

    However, Porton Down also has environmental samples, which should enable an exact identification of the molecular structure, according to the authors. The police were able to say last week “Specialists have identified the highest concentration of the nerve agent, to-date, as being on the front door of the address.”

    If Aitkenhead was confident enough, he could have just said “Novichok” because that would cover a family of molecules, possibly numbering more than a hundred. That would have been enough for him to say even if he wanted to keep his cards close to his chest and not give the Russians too many details.

    Maybe I’m reading too much into his words, but their vagueness makes me wonder if he’s hiding something. Maybe “Novichok or from that family” includes GV agents?

    • Brendan says:

      Or maybe the poison in Porton Down’s environmental samples was too small in quantity or too contaminated for it to be identified? Only a miniscule amount of nerve agent is necessary to kill within minutes, but it took at least two and a half hours to have any effect at all in Salisbury, if we believe the official story. And nobody has died.

      Also, much of the nerve agent would have been washed away by rain (it was reported that passers-by held up their umbrellas to keep the rain off the Skripals and the medics treating them).

      The fact that it took more than three weeks for the police investigators to announce their conclusion – that the nerve agent was placed on the handle of Sergei Scripal’s front door – also suggests that they lacked confidence in this theory. During that time, all kinds of theories were reported in the media, the most popular being that the nerve agent was placed as a dust in the ventilation system of Sergei’s car.

      If the “door handle” story is really correct, why didn’t they reach that conclusion much earlier by looking at the results for the environmental samples? It’s hard to believe that the tests took weeks to conclude.

  21. Pingback: Les mensonges des gouvernements démasqués sur l’affaire Skripal – brunobertez

  22. Steve H says:

    The appendix headed “Why is it necessary to synthesize a new compound before it can be detected by mass spectrometry?” is somewhat misleading: it’s quite feasible, for a trained chemist, to determine the structure of an unknown molecule, particularly those with simple structures, as these nerve agents have, from the gc-ms data alone; such problem-solving exercises are routinely given to undergraduate chemistry students, and are routine in organic chemistry research.

    • DDTea says:

      I’ve done a number of those problem-solving exercises in my undergraduate and graduate spectroscopy courses. But I quickly found that in real world research problems, the spectra I encounter are never as clean as the ones I encountered in my courses. They contain mixtures of compounds: reaction byproducts, side products, degradation compounds, random impurities… Environmental analysis is even messier, as you have to deal with difficult “matrices” (matrix = everything besides the compound of interest).

      In practice, structure determinations are messy affairs. The published structures of “novichok” agents are not expected to be environmentally stable. Reactive groups such as P-F bonds or dihaloformaldoximes are not going to persist for long.

      Sometimes, the only way to really be sure is to synthesize a reference material and compare its spectral data to those of the suspect compound.

  23. Pingback: Skripal / Kelly cases? – Dr. David Kelly. “Suicided” after testifying against Blair – aladdinsmiraclelamp

  24. Pingback: Big surprise: UK govt lies about Novichok, covers it up, lies some more | Silvia's Boinnk!!!

  25. Pingback: The Skripal case and UK’s flagrant misuse of ‘intelligence’ – By Alexander Mercouris The Duran(Sott) – winstonclose

  26. Pingback: Doubts About Novichok – Viralmount

  27. Pingback: The Skripal case and the misuse of ‘intelligence’ | OffGuardian

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  35. Pingback: Updates und Untermauerungen zur „Novichok“ – Affäre. Nebst Anatomie einer Gefangennahme. | Themen & Essays

  36. Pingback: Le Foreign Office du Royaume-Uni tente de couvrir la trace de ses mensonges -- Moon of Alabama – Le Monde...

  37. Neil says:

    As this Moon Of Alabama article says http://www.moonofalabama.org/2018/04/the-best-explanation-for-the-skripal-drama-is-food-poisoning.html#more

    Saxitoxin which can be produced in shell fish has similar effects as nerve agents https://emergency.cdc.gov/agent/nerve/tsd.asp

    Considered in syndromal or functional terms it could therefore be considered a ‘closely related agent’ to an organophosphate based nerve agent. It is listed alongside OP agents as a nervous system agent here: https://onlinelibrary.wiley.com/doi/full/10.1002/ana.21072

    Also see here https://emergency.cdc.gov/agent/saxitoxin/casedef.aspCase
    Definition: Saxitoxin
    Clinical description
    . In severe poisoning, illness typically progresses rapidly and may include gastrointestinal (nausea, vomiting) and neurological (cranial nerve dysfunction, a floating sensation, headache, muscle weakness, parasthesias and vertigo) signs and symptoms. Respiratory failure and death can occur from paralysis (1-5).

    So accordingly, shellfish poisoning could be consistent with this: “The samples tested positive for the presence of a Novichok class nerve agent or closely related agent.”
    When ‘closely related agent’ is understood as pertaining to a syndromal classification rather than a chemical group.

  38. Jonathan Heswald-Beswick Gruddlestone Esq says:

    The US applied for (in 2008) and gained (15 September 2015) a US patent for treating the effects of Novichok nerve agents.

    Click to access 9132135.pdf

  39. Pingback: Why the Russian Double-Agent Skripal Could Not Have Been Poisoned with “Novichok”

  40. Ed says:

    The #Novichok formula in a study of treating organophosphorous poisoning funded by the #Pentagon in 2005. https://twitter.com/dgaytandzhieva/status/982476128379076608

  41. Pingback: Why the Russian Double-Agent Skripal Could Not Have Been Poisoned with “Novichok” | williambowles.info

  42. Pingback: Why the Russian Double-Agent Skripal Could Not Have Been Poisoned with “Novichok” – Viralmount

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  45. Pingback: Did a “Novichok” programme ever exist? | Intel Today

  46. Pingback: The Best Explanation For The Skripal Drama Is Still … Food Poisoning | williambowles.info

  47. Pingback: Did a “Novichok” programme ever exist? | Worldtruth

  48. Neil says:

    Analysis for Biomedical exposure to OPs “As the leaving group of the agent is lost when binding to AChE or BChE, this analysis can not reveal the identity of the used agent (the same is true for flouride regeneration and any other analysis that does not identify the intact agent). For example an adduct that is identical to the one produced upon exposure to Sarin might actually come from an agent that features a leaving group similar to that of VX” Section 7 of this OPCW poster below concerning testing protein adducts. https://www.opcw.org/fileadmin/OPCW/Science_Technology/Diplomats_Programme/S_T_Biomed_Analysis_Poster.pdf

    Could someone please tell me if positive indications of Sarin exposure from protein adducts in old blood samples could be the result of exposure to other methy phosphonic compounds. The laboratory procedures used by OPCW arent specified in their results, as far as I can tell.

  49. Pingback: Le Foreign Office du Royaume-Uni tente de couvrir la trace de ses mensonges | Ombre43

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