EA-4056
From Wikipedia, the free encyclopedia
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| Names | |
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| IUPAC name
1,9-Bis[methyl-2(3-dimethylcarbamoxypyridyl)methylamino]nonane dimethobromide | |
| Preferred IUPAC name
N1,N9-Bis({3-[(dimethylcarbamoyl)oxy]pyridin-2-yl}methyl)-N1,N1,N9,N9-tetramethylnonane-1,9-bis(aminium) dibromide | |
| Identifiers | |
3D model (JSmol) |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C31H52N6O4 · Br2 | |
| Molar mass | 732.6 g/mol |
| Appearance | crystalline solid |
| Melting point | 100–105 °C |
| Solubility | soluble in water and alcohols |
| Hazards | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
11 µg/kg for mice and 2.7 µg/kg for rabbits via IV |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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EA-4056 is a deadly carbamate nerve agent. It is lethal because it inhibits acetylcholinesterase.[1] 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 those used for breathing.[2]
Patent assigned to US Army for EA-4056 among other similar nerve agents was filed in December 7, 1967.[3] It patents derivatives with 3 to 11 carbons in the connecting alkane chain.
Carbamates like EA-4056 are well absorbed by the lungs, gastrointestinal tracts, and the skin. Signs and symptoms from exposure to such carbamates are similar to other nerve agents. In general their penetration through the blood-brain barrier is difficult due to quaternary nitrogens in these molecules.[4] Despite this, EA-4056 is claimed to be about three times more toxic than VX (another nerve agent).[1] For VX, the median lethal dose (LD50) for 70 kg men via exposure to the skin is estimated to be 10 mg, and the lethal concentration time (LCt50), measuring the concentration of the vapor per length of time exposed, is estimated to be 30–50 mg·min/m3.[5] These values for EA-4056 can be estimated to be 3.3 mg and 10–16.7 mg·min/m3 by division.
Intravenous LD50 for EA-4056 is 0.0011 mg/kg for mice and 0.0027 mg/kg for rabbits.[3]
Properties
EA-4056's CAS is 110913-96-7, mass 732.6 g/mol, melting point 100–105 °C, and it is soluble in water and alcohols. It is a crystalline solid.[1] EA-4056 evaporates slowly in to the air; thus it can be classified as being extremely persistent in the environment if any possible effects of external factors like sun light and water (air humidity) upon it are neglected. Various other salts than just bromine salts have been reported.[1]