Nerve agents

Nerve agents interfere with nerve impulse transmission. They are a class of phosphorus containing organic chemicals (organophosphates) that disrupt the mechanism by which nerves transfer messages to organs. The disruption is caused by blocking acetylcholinesterase, an enzyme that normally destroys acetylcholine, a neurotransmitter. They are related to DDT. They are the most toxic of CW agents.
Nerve agents are now divided into three series:
  1. The G-series is named because German scientists first synthesized them. G series agents are known as non-persistent, while the V series are persistent. The first nerve agent synthesised was GA (Tabun) in 1936. GB (Sarin) was discovered next in 1939, followed by GD (Soman) in 1944 and finally the more obscure GF (Cyclosarin) in 1949.
  2. The V-series were developed in the 1950s. Workers at ICI in the UK were looking for new organophosphorous pesticides. In 1954, ICI put one of them on the market under the trade name Amiton. It was subsequently withdrawn, as it was too toxic for safe use. The toxicity did not go unnoticed and some of the more toxic materials had in fact been sent to the Chemical Defence Establishment at Porton Down for evaluation. After the evaluation was complete, several members of this class of compounds became a new group of nerve agents, the V agents (depending on the source, the V stands for Victory, Venomous, or Viscous). The best known of these is probably VX, with the Russian V-gas coming a close second (Amiton is largely forgotten as VG). This class of compounds is also sometimes known as Tammelin's esters, after Lars-Erik Tammelin of the Swedish Institute of Defense Research who first synthesised a number of the agents.
  3. The Novichok  (Russian for "newcomer") agents are a series of organophosphorous compounds that were developed in the Soviet Union from the mid-1960s to the 1990s. The goal of this program was to develop and manufacture highly deadly chemical weapons that were unknown to the West. These new agents were designed to be undetectable using standard 1970s and 80s NATO chemical detection equipment; to defeat NATO chemical protective gear; to be safer to handle; and to circumvent the Chemical Weapons Convention list of controlled precursors, classes of chemical and physical form.
In addition to the newly developed "third generation" weapons, binary versions of several Soviet agents were developed and were also designated as "Novichok" agents. In the USA binary weapons were also developed. Binary agents are made up of two parts, individually they are relatively non-toxic, but when combined following discharge from a weapon, they form the active agent. Novichok agents are of such importance that on this site they warrant their own page.

Cyclohexyl methylphosphonofluoridate  [Cyclosarin, GF] - C7H14FO2P

A colorless liquid, odorless to fruity odour, possibly of peach. Cyclosarin is readily absorbed through skin, eyes, and respiratory tract with inhalation and dermal routes of exposure posing significant threats.Toxic manifestations of exposure to cyclosarin vapor or aerosols occur within seconds to minutes of inhalation, while signs and symptoms of percutaneous exposure to liquid cyclosarin may take a minute to hours.

Isopropyl methylphosphonofluoridate  [Sarin, GB] - C4H10FO2P

In the pure form a colourless, odourless liquid. Exposure is lethal even at very low concentrations, where death can occur within one-to-ten minutes after direct inhalation of a lethal dose, due to suffocation from lung muscle paralysis, unless antidotes are quickly administered. People who absorb a non-lethal dose, but do not receive immediate medical treatment, may suffer permanent neurological damage.

O-butyl S-[2-(diethylamino)ethyl] methylphosphonothioate [Chinese VX, EA-6043] - C11H26NO2PS

A structural isomer of VX. It is an organic thiophosphate that is an ester of S-[2-(diethylamino)ethyl] O hydrogen methylphosphonothioate. A toxic nerve agent developed by the Peoples' Republic of China. It has a role as a neurotoxin and an EC 3.1.1.7 (acetylcholinesterase) inhibitor. It is an organic thiophosphate and a tertiary amino compound.

O-Ethyl N,N-dimethyl phosphoramidocyanidate [Tabun, GA] - C5H11N2O2P

A clear, colourless to brownish, and tasteless liquid with a faint fruity odor. The symptoms of exposure include: nervousness/restlessness, miosis , rhinorrhea, excessive salivation, dyspnea, sweating, bradycardia, loss of consciousness, convulsions, flaccid paralysis, loss of bladder and bowel control, apnea and lung blisters. The exact symptoms of overexposure are similar to those created by all nerve agents. Tabun is toxic even in minute doses. The number and severity of symptoms which appear vary according to the amount of the agent absorbed and rate of entry of it into the body. Very small skin dosages sometimes cause local sweating and tremors accompanied with characteristically constricted pupils with few other effects. Tabun is about half as toxic as sarin by inhalation, but in very low concentrations it is more irritating to the eyes than sarin. The effects of tabun appear slowly when tabun is absorbed through the skin rather than inhaled. A victim may absorb a lethal dose quickly, although death may be delayed for one to two hours. A person's clothing can release the toxic chemical for up to 30 minutes after exposure. Inhaled lethal dosages kill in one to ten minutes, and liquid absorbed through the eyes kills almost as quickly. However, people who experience mild to moderate exposure to tabun can recover completely, if treated almost as soon as exposure occurs.

O-Ethyl S-2-diisopropylaminoethyl methyl phosphonothiolate [Methylphosphonothioic acid, VX] - C11H26NO2PS 

A clear, amber-colored odorless, oily liquid. People exposed to a low or moderate dose of VX by inhalation, ingestion (swallowing), or skin absorption may experience some or all of the following symptoms within seconds to hours of exposure: abnormally low or high blood pressure, blurred vision, chest tightness, confusion, cough, diarrhea, drooling, excessive sweating, drowsiness, eye pain, headache, increased urination, nausea, vomiting, abdominal pain, tachypnea, rhinitis, bradycardia, tachycardia, miosis, lachrymation, weakness. Even a tiny drop of nerve agent on the skin can cause sweating and muscle twitching where the agent touched the skin.

Exposure to a large dose of VX by any route may result in these additional health effects: convulsions, loss of consciousness, paralysis, respiratory failure possibly leading to death.

O-(iso-Butyl) S-(2-diethylaminoethyl) methylphosphonothiolate [VR, Russian VX, VR is an isomer of VX] -  C11H26NO2PS 

VR has similar lethal dose levels to VX. Acute exposure to a lethal dose of VR has been shown to cause cholinergic hyperfunction, incapacitation, seizures, convulsions, cardiorespiratory depression and death.

O-Pinacolyl methylphosphonofluoridate [Soman, GD] - C7H16FO2

A volatile, corrosive, and colorless liquid with a faint odor like that of mothballs or rotten fruit. In the impure form it has a yellow to brown colour and has a strong odour described as similar to camphor.  It is both more lethal and more persistent than sarin or tabun, but less so than cyclosarin.

O,O-diethyl S-[2-(diethylamino)ethyl] phosphorothioate [VG, Amiton, Tetram] - C10H24NO3PS 

VG has a toxicity of about 1/10 that of VX, i.e. similar to that of sarin.

O-cyclopentyl S-(2-diethylaminoethyl) methylphosphonothiolate [EA-3148, Substance 100A] - C12H26NO2PS

Probably too unstable to be weaponise.

Propan-2-yl ethylphosphonofluoridate  [Ethyl sarin, E1209, GE] C5H12FO

Odourless and colourless to yellow-brown liquid. The effect of exposure to Ethyl sarin depends on the amount of the agent, route and duration of the exposure. The symptoms will appear within a few seconds after inhalation exposure to the vapour form and from a few minutes to 18 hours after exposure to the liquid form. Ethyl sarin may be absorbed quickly and easily. When dispersed as a vapour or aerosol, or absorbed on dust, it is readily absorbed through the respiratory tract and conjunctivae. Absorption is most rapid and complete through the respiratory tract. Aerosols and liquids are also absorbed through skin. Vapours may be absorbed through skin if at very high concentrations.  Liquid droplets or even vapor may persist in a victim's clothes after minutes to hours of exposure which may lead to cross-contamination of others.

Following local exposure, symptoms may include: rhinorrhoea and hyperaemia of nasal mucosal membranes, miosis -  sometimes unequal, hyperaemia of conjunctivae, excessive sweating at site of exposure, frontal headache, eye pain on focusing, slight dimness of vision, occasional nausea and vomiting, tightness of chest, sometimes with prolonged wheezing, expiration suggestive of bronchoconstriction or increased secretion and cough. Fasciculations (muscle twitching) at site of exposure to liquid.


Following systemic absorption: tightness in chest with prolonged wheezing expiration suggestive of bronchoconstriction or increased secretion,  dyspnoea, slight pain in chest,  increased bronchial secretion,  cough, pulmonary oedema,  cyanosis, anorexia, nausea, vomiting, abdominal cramps, epigastric and substernal tightness with heartburn and eructation, diarrhoea, tenesmus; involuntary defaecation, increased/excessive sweating, increased/excessive salivation, increased/excessive lacrimation, bradycardia, slight miosis occasionally unequal, blurring of vision, involuntary urination, easy fatigue, mild weakness, muscular twitching, fasciculations, cramps, generalized weakness, including muscles of respiration, with dyspnoea and cyanosis

S-[2-(Diethylamino)ethyl] O-ethyl methylphosphonothioate [Edemo, VM], C9H22NO2PS

Similar lethal dose levels to VX (between 10 and 50 mg) and have similar symptoms and method of action to other nerve agents.

energy
Fig.1 -Nerve Agents, Molecular Structures