EA-2098

Last updated
EA-2098
EA-2098 estrutura em esqueleto.png
Names
Preferred IUPAC name
N,N,N-Trimethyl-3-{[ethoxy(methylphosphonoyl)]oxy}-5-{3-[3-(trimethylazaniumyl)phenoxy]propoxy}anilinium bis(tetraphenylboranuide)
Identifiers
3D model (JSmol)
  • InChI=1S/2C24H20B.C24H39N2O5P/c2*1-5-13-21(14-6-1)25(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24;1-9-30-32(8,27)31-24-18-21(26(5,6)7)17-23(19-24)29-15-11-14-28-22-13-10-12-20(16-22)25(2,3)4/h2*1-20H;10,12-13,16-19H,9,11,14-15H2,1-8H3/q2*-1;+2
    Key: YXQOCWJQISOFRQ-UHFFFAOYSA-N
  • [B-](c1ccccc1)(c2ccccc2)(c3ccccc3)c4ccccc4.[B-](c1ccccc1)(c2ccccc2)(c3ccccc3)c4ccccc4.CCOP(=O)(C)Oc5cc([N+](C)(C)C)cc(c5)OCCCOc6cccc(c6)[N+](C)(C)C
Properties
C72H79B2N2O5P
Molar mass 1105.03 g·mol−1
AppearanceSolid
Melting point 108–111 °C (226–232 °F; 381–384 K)
Insoluble
Solubility Soluble in acetone
Hazards
Main hazards Extremely toxic
Lethal dose or concentration (LD, LC):
20 μg/kg (Rats, IV)
6.7 μg/kg (Rabbits, IV)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

EA-2098 is an extremely toxic organophosphate nerve agent. It is an extremely potent acetylcholinesterase inhibitor that is resistant to atropine and oxime treatment. [1]

See also

Related Research Articles

Nerve agents, sometimes also called nerve gases, are a class of organic chemicals that disrupt the mechanisms by which nerves transfer messages to organs. The disruption is caused by the blocking of acetylcholinesterase (AChE), an enzyme that catalyzes the breakdown of acetylcholine, a neurotransmitter. Nerve agents are acetylcholinesterase inhibitors used as poison.

Tabun (nerve agent) Chemical compound

Tabun or GA is an extremely toxic chemical substance. It is a clear, colorless, and tasteless liquid with a faint fruity odor. It is classified as a nerve agent because it fatally interferes with normal functioning of the mammalian nervous system. Its production is strictly controlled and stockpiling outlawed by the Chemical Weapons Convention of 1993. Tabun is the first of the G-series nerve agents along with GB (sarin), GD (soman) and GF (cyclosarin).

Soman Chemical compound (nerve agent)

Soman is an extremely toxic chemical substance. It is a nerve agent, interfering with normal functioning of the mammalian nervous system by inhibiting the enzyme cholinesterase. It is an inhibitor of both acetylcholinesterase and butyrylcholinesterase. As a chemical weapon, it is classified as a weapon of mass destruction by the United Nations according to UN Resolution 687. Its production is strictly controlled, and stockpiling is outlawed by the Chemical Weapons Convention of 1993 where it is classified as a Schedule 1 substance. Soman was the third of the so-called G-series nerve agents to be discovered along with GA (tabun), GB (sarin), and GF (cyclosarin).

VX (nerve agent) Chemical compound and chemical warfare nerve agent

VX is an extremely toxic synthetic chemical compound in the organophosphorus class, specifically, a thiophosphonate. In the class of nerve agents, it was developed for military use in chemical warfare after translation of earlier discoveries of organophosphate toxicity in pesticide research. In recent years, VX was found to be the agent used in the assassination of Kim Jong-nam. In its pure form, VX is an oily, relatively non-volatile, liquid that is amber-like in color. Because of its low volatility, VX persists in environments where it is dispersed.

Cyclosarin or GF is an extremely toxic substance used as a chemical weapon. It is a member of the G-series family of nerve agents, a group of chemical weapons discovered and synthesized by a German team led by Dr. Gerhard Schrader. The major nerve gases are the G agents, sarin (GB), soman (GD), tabun (GA), and the V agents such as VX. The original agent, tabun, was discovered in Germany in 1936 in the process of work on organophosphorus insecticides. Next came sarin, soman and finally, cyclosarin, a product of commercial insecticide laboratories prior to World War II.

VG (nerve agent) Chemical compound

VG is a "V-series" nerve agent chemically similar to the better-known VX nerve agent. Tetram is the common Russian name for the substance. Amiton was the trade name for the substance when it was marketed as an insecticide by ICI in the mid-1950s.

EA-3148 Chemical compound

EA-3148 is a "V-series" nerve agent related to the better-known compounds VX and VR. It was studied by both the US and Soviet chemical weapons programmes during the Cold War, and is notable as the only V-series organophosphate nerve agent specifically identified in public domain sources as having a higher absolute potency as an acetylcholinesterase inhibitor than VX. However, both the US and Soviet investigations of the compound concluded that despite its high potency, the physicochemical properties of the substance made it unsuitable for weaponisation, and further research was not conducted. The chemical structure of EA-3148 falls within the scope of compounds designated "Toxic chemicals" under Schedule 1 of the Chemical Weapons Convention and so it is illegal throughout the world under international law and may only be used for certain types of scientific and medical research.

EA-3990 Chemical compound

EA-3990 is a deadly carbamate nerve agent. It is lethal because it inhibits acetylcholinesterase. Inhibition causes an overly high accumulation of acetylcholine between the nerve and muscle cells. This paralyzes the muscles by preventing their relaxation. The paralyzed muscles include the muscles used for breathing.

EA-4056 Chemical compound

EA-4056 is a deadly carbamate nerve agent. It is lethal because it inhibits acetylcholinesterase. Inhibition causes an overly high accumulation of acetylcholine between the nerve and muscle cells. This paralyzes the muscles by preventing their relaxation. The paralyzed muscles includes the muscles used for breathing.

Methyldichlorophosphine Chemical compound

Methyldichlorophosphine (alternatively known as dichloro(methyl)phosphane and methyl phosphonous dichloride) is an organophosphorus compound with the chemical formula CH3Cl2P. It is a colorless, corrosive, flammable, and highly reactive liquid with a pungent odor. It is also extremely toxic if inhaled, can cause burns upon contact with the skin and eyes, and releases fumes of hydrochloric acid in moist environments.

Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) Chemical compound

Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) is an extremely potent carbamate nerve agent. It works by inhibiting the acetylcholinesterase, causing acetylcholine to accumulate. Since the agent molecule is positively charged, it does not cross the blood brain barrier very well.

3,3,5-Trimethylcyclohexyl 3-pyridyl methylphosphonate Chemical compound

VP, also known as EA-1511, is an extremely toxic organophosphate nerve agent of the V-series.

EA-2192 Chemical compound

EA-2192 is an extremely toxic degradation product of the VX nerve agent. It is a white solid that is very soluble and stable in water.

EA-2613 Chemical compound

EA-2613 is an extremely toxic organophosphate nerve agent. It's an extremely potent acetylcholinesterase inhibitor that is resistant to atropine and oxime treatment.

EA-2012 Chemical compound

EA-2012 is an extremely toxic organophosphate nerve agent. It's an extremely potent acetylcholinesterase inhibitor that is resistant to atropine and oxime treatment.

EA-2054 Chemical compound

EA-2054 is an extremely toxic organophosphate nerve agent. It is an extremely potent acetylcholinesterase inhibitor that is resistant to atropine and oxime treatment.

2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Chemical compound

2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate is an extremely toxic organophosphate nerve agent. It is the cyclohexyl methylphosphonate ester of ethyl acetoacetate. The compound has two isomers, the cis isomer and trans isomer, with the trans isomer being more toxic.

Crotylsarin Chemical compound

Crotylsarin (CRS) is an extremely toxic organophosphate nerve agent of the G-series. Like other nerve agents, CRS irreversibly inhibits the acetylcholinesterase. However, since the inhibited enzyme ages so rapidly, the inhibited enzyme can't be reactivated by oxime reactivators.

Methylfluorophosphonylcholine Chemical compound

Methylfluorophosphonylcholine (MFPCh) is an extremely toxic chemical compound related to the G-series nerve agents. It is an extremely potent acetylcholinesterase inhibitor which is around 100 times more potent than sarin at inhibiting acetylcholinesterase in vitro, and around 10 times more potent in vivo, depending on route of administration and animal species tested. MFPCh is resistant to oxime reactivators, meaning the acetylcholinesterase inhibited by MFPCh can't be reactivated by oxime reactivators. MFPCh also acts directly on the acetylcholine receptors. However, despite its high toxicity, methylfluorophosphonylcholine is a relatively unstable compound and degrades rapidly in storage, so it was not deemed suitable to be weaponised for military use.

A-230 Chemical compound

A-230 is an organophosphate nerve agent. It was developed in the Soviet Union under the FOLIANT program and is one of the group of compounds referred to as Novichok agents that were revealed by Vil Mirzayanov. A-230 is possibly the most potent nerve agent for which specific toxicity figures have been published, with a human lethal dose estimated to be less than 0.1mg. However it was felt to be less suitable for weaponisation than other agents such as A-232 and A-234, due to issues with the liquid agent exhibiting low volatility and solidifying at low temperatures, as well as poor stability in the presence of water.

References

  1. "Toxic phosphorus compounds".