EA-2613

Last updated
EA-2613
EA-2613 Structure.svg
Identifiers
3D model (JSmol)
  • InChI=1S/C28H47N2O5P.2HI/c1-22(28(2,3)4)34-36(11,31)35-27-20-24(30(8,9)10)19-26(21-27)33-17-13-16-32-25-15-12-14-23(18-25)29(5,6)7;;/h12,14-15,18-22H,13,16-17H2,1-11H3;2*1H/q+2;;/p-2
    Key: PLSZUOADUSAOET-UHFFFAOYSA-L
  • [I-].[I-].CC(C)(C)C(C)OP(=O)(C)Oc1cc([N+](C)(C)C)cc(c1)OCCCOc2cccc(c2)[N+](C)(C)C
Properties
C28H47I2N2O5P
Molar mass 776.476 g·mol−1
AppearanceSolid
Melting point 124–126 °C (255–259 °F; 397–399 K)
Soluble
Solubility Soluble in alcohol, acetone and chloroform
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Extremely toxic
Lethal dose or concentration (LD, LC):
100 μg/kg (Rats, IV)
12 μg/kg (Rabbits, IV)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

EA-2613 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 irreversible acetylcholinesterase inhibitors used as poison.

<span class="mw-page-title-main">Soman</span> 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).

<span class="mw-page-title-main">VX (nerve agent)</span> 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 its pure form, VX is an oily, relatively non-volatile liquid that is amber-like in colour. 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 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.

<span class="mw-page-title-main">VG (nerve agent)</span> 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.

<span class="mw-page-title-main">GV (nerve agent)</span> Chemical compound

GV, also known as EA-5365 and GP, is an organophosphate nerve agent. GV is a part of a series of nerve agents with properties similar to the "G-series" and "V-series". It is a potent acetylcholinesterase inhibitor with properties similar to other nerve agents, being a highly poisonous vapour. Treatment for poisoning with GV involves drugs such as atropine, benactyzine, obidoxime, and HI-6.

<span class="mw-page-title-main">EA-3148</span> 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.

<span class="mw-page-title-main">EA-3990</span> 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.

<span class="mw-page-title-main">EA-4056</span> 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.

<span class="mw-page-title-main">Chlorosoman</span> Chemical compound

Chlorosoman is a chlorine analog of soman. It is a highly toxic organophosphorus compound and used as the precursor substance for soman nerve agent. Its physical properties are estimated. Soman is insoluble in water, with a boiling point of 223 degrees Celsius and a melting point of -27 degrees Celsius. Chlorosoman is at least 2.5x less toxic than its analogue.

<span class="mw-page-title-main">Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)</span> Chemical compound

Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) (4-673-745-01) is an extremely potent carbamate nerve agent. It works by inhibiting acetylcholinesterase, causing acetylcholine to accumulate. Since the agent molecule is positively charged, it does not cross the blood brain barrier very well.

<span class="mw-page-title-main">3,3,5-Trimethylcyclohexyl 3-pyridyl methylphosphonate</span> Chemical compound

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

<span class="mw-page-title-main">EA-2192</span> Chemical compound

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

<span class="mw-page-title-main">EA-2012</span> Chemical compound

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

<span class="mw-page-title-main">EA-2054</span> 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.

<span class="mw-page-title-main">EA-2098</span> Chemical compound

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

<span class="mw-page-title-main">2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate</span> 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.

<span class="mw-page-title-main">Crotylsarin</span> Chemical compound

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

<span class="mw-page-title-main">Methylfluorophosphonylcholine</span> 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 cholinesterase reactivators. MFPCh also acts directly on the acetylcholine receptors. MFPCh is a relatively unstable compound and degrades rapidly in storage, so despite its enhanced toxicity it was not deemed suitable to be weaponised for military use.

<span class="mw-page-title-main">EA-1356</span> Chemical compound

EA-1356 is an organophosphate nerve agent of the G-series. It is highly resistant to enzymatic degradation in the body. The nerve agent was tested at Edgewood Arsenal in Maryland among many other chemicals tested on humans. A novel enzyme was patented by the US Army in 2018 to break down EA-1356. It is a schedule 1 substance by the Chemical Weapons Convention standards. It is under the category of munitions of ML7.b.1.a.

References

  1. "Toxic phosphorus compounds".