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| Names | |
|---|---|
| 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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| |
| 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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
EA-4056 is a deadlycarbamatenerve agent. It is lethal because itinhibitsacetylcholinesterase.[1] Inhibition causes an overly high accumulation ofacetylcholine between thenerve andmuscle cells. This paralyzes the muscles by preventing their relaxation. The paralyzed muscles include those used for breathing.[2]
Patent assigned toUS 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 andsymptoms from exposure to such carbamates are similar to other nerve agents. In general their penetration through theblood-brain barrier is difficult due toquaternary nitrogens in thesemolecules.[4] Despite this, EA-4056 is claimed to be about three times more toxic thanVX (another nerve agent).[1] For VX, themedian lethal dose (LD50) for 70 kg men via exposure to the skin is estimated to be 10 mg, and thelethal concentration time (LCt50), measuring theconcentration 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 bydivision.
Intravenous LD50 for EA-4056 is 0.0011 mg/kg for mice and 0.0027 mg/kg for rabbits.[3]
EA-4056'sCAS 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 othersalts than justbromine salts have been reported.[1]
2-dimethylaminomethyl-3-dimethylcarbamoxypyridine precursor is prepared. It is made viaMannich reaction by using 3-pyridol (CAS 109-00-2),dimethylamine andformaldehyde. Resulting 2-((Dimethylamino)methyl)pyridin-3-ol (CAS 2168-13-0) is thencarbamoylated withdimethylcarbamoyl chloride. For a different product other secondaryamines than dimethylamine can be used; such as those containingmethyl,ethyl,propyl,isopropyl,butyl andbenzyl groups.[6]
2moles of 2-dimethylaminomethyl-3-dimethylcarbamoxypyridine and app. 1 molα,ω-dihaloalkane (e.g.1,9-dibromononane in this case) inacetonitrile is heated on asteam bath for 6 hours. It is then allowed to stand overnight at room temperature. The crystalline product is collected by filtration and thentriturated withacetone. If no solid separates,ethyl acetate is added toprecipitate the crude product. The product is then dissolved in hotethanol and treated with decolorizingcharcoal. Ethyl acetate is added to the filtered solution to precipitate the crystalline product. E-4056 product is then collected and dried.Yield is 95%.[3][6]
Other stable salts of EA-4056 thanbromide can be made such assulfate,nitrate,hydride,oxalate andperchlorate. Other α,ω-dihaloalkanes can be used to obtain similar molecules with different carbon chain lengths.[6]
