Research Story of the Week

The Moscow Theater Hostage Crisis: Incapacitants and Chemical Warfare

Diagram
Chemical formula for fentanyl.

By Chemical and Biological Weapons Nonproliferation Program[1]

On October 23, 2002, in the middle of an evening performance at a Moscow music theater, some 50 Chechen terrorists equipped with firearms as well as large quantities of explosives suddenly seized the venue and the 800 people inside. The terrorists threatened to kill everyone inside unless Russia ended the war in Chechnya. Although the Chechen militants agreed to release some of the hostages during the first couple of days, negotiations with the Russian authorities eventually stalled. Just before dawn on October 26, Russian special police units resorted to using an incapacitating gas based on the drug fentanyl to end the crisis. All of the Chechen militants were killed, and most of the civilian captives survived. But while the operation was largely a success, at least 117 of the hostages died from the effects of the gas.[2] That so many died because of poisoning has been the source of some controversy about how the entire operation was handled. But even while acknowledging that mistakes may have been made by the police, most Russians seem to support the action taken by Moscow authorities.

Following the resolution of the hostage crisis, much has also been made of the Moscow theater incident with respect to the Chemical Weapons Convention (CWC) and even the Biological Weapons Convention (BWC). The concern is two-fold: first, did this action violate international law, and second, does possession of the agent used in this instance suggest that the Russians have been covertly pursuing chemical weapons in a manner which could be considered in breach of the CWC?

Background on Opiates and Chemical Warfare

"An incapacitating agent is an agent producing physiological or mental effects that may persist for hours or days after exposure to the agent has ceased." (U.S. Army field manual FM 3-9).[3]

Especially during the Cold War, a great deal of research was expended by the United States and the former Soviet Union on chemical substances that would not necessarily kill, but would instead merely incapacitate enemy personnel. During the heyday of the U.S. chemical warfare (CW) program (1950s-1960s), a wide number of pharmacological substances were investigated for their potential as incapacitants, including depressants, hallucinogens (e.g., LSD), belladonna drugs (scopolamine, BZ), and the opiate derivatives. The latter category refers to those drugs like morphine that fit receptors in the human brain/nervous system, as a key would fit a lock, releasing pain-killing endorphins and inducing a state of euphoria. Given the right amount, opium-based drugs can also induce sleep/unconsciousness.

Such properties of poppy-derived medicaments had been known for many centuries, and morphine had already found some use as a total anesthetic agent by the late 1800s. However, the use of morphine as a total anesthetic sometimes led to deadly complications both during and following medical procedures. In 1939, the synthesis of meperidine and its improved safety profile led to renewed interest in the use of opiates for anesthesia.[4]

But arguably the most important development in opiate drugs in medicine was the synthesis of fentanyl, its structure first patented by Janssen in France (1963). Fentanyl remains among the more often used compound in combination with other drugs, or even by itself for anesthesia. However, large doses of fentanyl have also been known to increase risks for complications, particularly in terms of respiratory depression during recovery. Recently, a number of different analogues based on fentanyl have been introduced, including sufentanil, alfentanil, and remifentanil (cr. 1996) for use in anesthesia.

If drugs like the belladonna alkaloids (atropine, BZ, etc.) could be utilized in chemical weapons, some CW specialists have wondered if opioid derivatives could also play a role in warfare or in certain tactical operations. During their own military-related chemical research, however, U.S. military chemists found that the dose of opiate-related drugs needed to cause the desired degree of incapacitation was not far from the lethal dose. In the case of the opiates, for example, it the difference between incapacitating and lethal quantities was found to be about 10-20 fold. With such a narrow margin of relative safety, there was not much rationale to include these substances as incapacitating weapons. [5] (The United States eventually weaponized BZ as its standardized incapacitant, but due to the unpredictable effects of this agent in humans, these stocks were destroyed during the 1980s.)

Table: Clinical data for fentanyl-based compounds, comparing the effective
dose (ED50), and the lethal dose (LD50) for 50% of a given population.

Opiate Lowest effective dose, ED50 mg/kg LD50, mg/kg Relative safety index
Meperidine 6.0 29.0 4.8
Alfentanil 0.044 47.5 1,080
Fentanyl 0.011 3.1 277
Sufentanil 0.007 17.9 25,211
Lofentanil 0.0059 0.066 112
Carfentanil 0.0034 3.4 10,000

Fentanyl and Its Suggested Role in Vietnam

Although considered unfit for large scale production or weaponization, opiate-drugs like fentanyl may have had some applications in specialized warfare or covert operations. During his tenure in Southeast Asia (1966-1968), retired Major General John K. Singlaub recalls a time when the military use of fentanyl or similar drugs was considered for tactical roles in Vietnam. The U.S. Military Advisory Command (MAC) Studies and Observation Group (SOG) was tasked to do, among other things, intelligence gathering missions by capturing enemy officers for interrogation. This proved to be among the most daunting challenges that Singlaub and others faced along the Ho Chi Minh trail, where North Vietnam shuttled logistical and other support to the Viet Cong irregulars in the South. While most of the Vietnamese carrying supplies on foot or on bicycles were low-ranked soldiers--mainly peasants pressed into labor--some high-ranking NVA officers would also be present. Often, when SOG units engaged these caravans it would quickly turn into a desperate firefight, resulting in the death of the NVA officers, as well as many of those who were merely carrying supplies for the Viet Cong guerrillas. General Singlaub wondered if there was a way to temporarily knock out the isolated individuals, while scattering away the irrelevant logistical support units. They could then bring these NVA officers in for questioning. One of the plans was to utilize something along the lines of a tranquilizing dart with fentanyl or related substance. In the end, however, the science advisor to General Westmoreland did not approve of this venture, and only CS (a riot control agent) was ever approved for the Southeast theater of operations.[6]

Israeli Mossad, 1997

In October 1997, the Israeli Mossad used fentanyl in either an assassination attempt or a snatch-and-grab operation that subsequently went awry. In this case, Israeli intelligence operatives (including one physician) traveled to Jordan. There, they followed Khalid Mishal, a Jordanian-based Hamas leader in a car. The plan was to deliver fentanyl in a spray that would be absorbed through the target's ear, but Khalid Mishal was able to escape. Following the event, he was reportedly affected by the drug, requiring significant medical attention afterwards.[7]

What Chemical Was Used in the Moscow Theater Raid?

One might consider remifentanil, a related analogue to fentanyl, to be a possible candidate for the Russian version of the incapacitating agent used in the Moscow theater. Among other opiate analogues, remifentanil is rather unique and extremely potent, with relatively fast action but also short duration. Its chemical structure also allows the body to quickly metabolize the substance into non-toxic and water soluble forms.[8] It is therefore possible that this or a similar compound was chosen because of lower associated risks for both the hostage-takers and hostages. And, as is the case with other compounds, an effective antidote to opiates is widely available in the form of naloxone (Narcan). While Russian authorities insist that emergency personnel were prepared with 1,000 antidotes in anticipation of the raid, controversy continues over whether local hospitals and physicians were adequately informed about the gas used during the operation. [9]

Did the Use of This Chemical by Russian Police Contravene International Law?

Even allowing for the fact that Moscow authorities were faced with a desperate situation, some have argued that the Russian operation was conducted with inadequate attention to the safety of innocent civilians. But whether or not the use of an incapacitating gas contravened the CWC is much more difficult to discern. In general, the CWC's wording allows for the use of chemical agents for "law enforcement" purposes, as stated in Article II 9(d) ("Purposes Not Prohibited Under this Convention"). The chemicals to be used in this context, although not precisely identified, are essentially taken to represent riot control agents. A riot control agent (RCA) is defined in Article II, pt. 7 as "any chemical not listed in a Schedule, which can produce rapidly in humans sensory irritation or disabling physical effects which disappear within a short time frame following termination of exposure." This is in stark contrast to those CW agents that are explicitly named in the CWC's three Schedules, such as VX or mustard gas. (Simply stated, the CWC Schedules are compilations of chemicals that have been used in chemical weapons or their production, and are therefore of particular concern to the Convention.)

Determining where fentanyl-derivatives fall in this spectrum of lethal vs. non-lethal agents is, therefore, of utmost importance when evaluating whether the incident in question was in fact a violation of the CWC. In the final analysis, because it is not listed in any of the Schedules and is traditionally characterized by the rapid onset and short duration (15 to 30 minutes) of analgesia, fentanyl can be legally considered a riot control agent according to the definition set forth in the CWC. However, additional and binding terms in the CWC do apply. While Article VI, "Activities Not Prohibited Under this Convention," explicitly notes that a listed toxic chemical is subject to the restrictions inherent to its Schedule, such as import/export controls and production limitations, riot control agents have no similar restrictions. But the overall requirement of the Convention that each State Party declare any possession of Scheduled agents does have a parallel rule with respect to RCAs. In accordance with the terms of Article III 1(e), within 30 days of the Convention entering into force each State Party was to have specified "the chemical name, structural formula and Chemical Abstracts Service (CAS) registry number, if assigned, of each chemical it holds for riot control purposes. This declaration shall be updated not later than 30 days after any change becomes effective."

What does this mean? If it is conceded that fentanyl was utilized as a riot control agent for law enforcement purposes. A final legal hurdle still remains, namely, that fentanyl and its delivery systems should have been declared by Russia under the terms of the Convention. As far as open sources are concerned, the analysis effectively ends here; however, because Article III declarations are generally not available in the public domain, and whether such a declaration was made by the Russians for fentanyl-like compounds--or any other chemical agent--cannot be determined here. This last point does leave at least some question as to whether the Russians were in fact in strict compliance with the CWC.

In this case, however, not only is it apparent that the use of the opiate gas was legitimate given the circumstances, the decision to do so appears in the end to have been morally justified from the perspective of the Russians. Ultimately, as this issue is debated over the coming weeks the overall intent in possessing this form of RCA and delivery system may prove to be the key: This fentanyl-like drug was not intended to serve as either a lethal or incapacitating agent on a battlefield. Russian officials believed it to be the most humane solution to a volatile hostage situation.

Conclusion

The terrorist group that seized the hostages at the Moscow Dubrovka Theatre Center was a particularly extreme and violent group. Its leader, Movsar Barayev, was the son of a murdered Chechen guerrilla leader named Abdi Barayev, whose own fighters were notorious for their brutal and bloodthirsty behavior (as was reflected in their murder and beheading of three Britons and one New Zealander in 1998). Movsar Barayev's hostage takers vehemently rejected Russian offers of safe passage in exchange for releasing the hostages, and repeatedly boasted of their willingness to "punish the sinners" if the Russians attacked the theater or failed to begin withdrawing from Chechnya. The latter was clearly an impossible demand that the Russian government would never meet, and all the while the terrorists were making it clear that they were on a "martyrdom" mission and were willing to kill both the hostages and themselves. In such a context, the Russians were facing a "no-win" situation and were therefore probably right to act when and as they did. Knowing the extreme nature of Barayev and his followers--as well as other fanatical Islamist groups that share similar goals and tactics, both in Chechnya and elsewhere--it is difficult to envision any response that could have ended this takeover without resulting in significant numbers of casualties.

Structural chemical formulas for fentanyl and remifentanil

Fentanyl
Diagram


Remifentanil
Diagram



[1] The Chemical and Biological Weapons Nonproliferation Program (CBWNP) would like to thank Mark Gorwitz of the Defense Technical Information Center (DTIC) for his generous assistance with open source data and his very helpful advice.
[2] Susan B. Glasser and Peter Baker, "Russia Confirms West's Suspicions about Deadly Gas," Washington Post, October 31, 2002, p. 15.
[3] Quoted in James A.F. Compton, Military Chemical and Biological Agents (Caldwell, NJ: The Telford Press, 1987), p. 254.
[4] Peter L. Bailey, Talmage D. Egan, and Theodore H. Stanely, "Intravenous Opioid Anesthetics," in Ronald D. Miller, ed., Anesthesia, 5th edition (Philadelphia: Churchill Livingstone, 2000), p. 274.
[5] James S. Ketchum and Frederick R. Sidell, "Incapacitating Agents," in Frederick R. Sidell, Ernest T. Takafuji, and David R. Franz, eds., Medical Aspects of Chemical and Biological Warfare (Washington, DC: Borden Institute, 1997), p. 293.
[6] Interview with General Singlaub, August 13, 1998.
[7] "Physician Member of Hit Team, Paper Says," Canadian Medical Association Journal, Vol. 157, No. 11, December 1997, p. 1504; Lisa Beyer, "Don't Try This at Home--Or in Aman," Time, Vol. 150, No. 17, October 27, 1997, p. 27.
[8] Donald R. Stanski, "Monitoring Depth of Anesthesia," in Ronald D. Miller, ed., Anesthesia, 5th edition (Philadelphia: Churchill Livingstone, 2000), pp. 1103-4.
[9] Susan B. Glasser and Peter Baker, "Russia Confirms West's Suspicions about Deadly Gas," Washington Post, October 31, 2002, p. 15.


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Author(s): CBWNP
Related Resources: NIS, CBW, Weekly Story
Date Created: November 4, 2002
Date Updated: -NA-
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