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((Multiple issues|
((notability|date=September 2023))
((more citations needed|date=September 2023))
))

((Chembox
| Name           = 4-686-293-01
| ImageFile      = 4-686-293-01 2D sctruture.png
| OtherNames     = Agent 1-10
| IUPACName      = 1,10-Bis[(3-dimethylcarbamoxy-α-picolinyl)ethylamino]decane dimethobromide
| Section1       = ((Chembox Identifiers
| SMILES = [Br-].[Br-].C[N+](Cc1ncccc1OC(=O)N(C)C)(CC)CCCCCCCCCC[N+](C)(Cc1ncccc1OC(=O)N(C)C)CC
| StdInChI=1S/C34H58N6O4.2BrH/c1-9-39(7,27-29-31(21-19-23-35-29)43-33(41)37(3)4)25-17-15-13-11-12-14-16-18-26-40(8,10-2)28-30-32(22-20-24-36-30)44-34(42)38(5)6;;/h19-24H,9-18,25-28H2,1-8H3;2*1H/q+2;;/p-2
| StdInChIKey=MBJLKFXQGQFYSE-UHFFFAOYSA-L
| CASNo = 113402-82-7
| CASNo_Ref = ((cascite|correct|CAS))
  ))
| Section2       = ((Chembox Properties
| Formula = C<sub>34</sub>H<sub>58</sub>N<sub>6</sub>O<sub>4</sub> · Br<sub>2</sub>
| MeltingPtC = 173–176
| SolubleOther = soluble in water and alcohols
| MolarMass = 774.678 g/mol
| Appearance = white crystalline solid
))
| Section7       = ((Chembox Hazards
| NFPA-H = 4
| NFPA-F = 1
| NFPA-R = 1
| LD50 = 11 μg/kg (intravenous, mouse)<br>4 μg/kg (intravenous, rabbit)<br />))
))

'''4-686-293-01''', also known as '''Agent 1-10''', is a highly potent experimental [[carbamate]] [[nerve agent]], patented in May 1967.<ref name=":1">((cite patent|number=4686293|title=Chemical agents|country=US|pubdate=1987-08-11|assign1=[[Secretary of the United States Army]]|inventor1-last=Sommer|inventor1-first=Harold Z.|inventor2-last=Owens|inventor2-first=Omer O.))</ref> Due to its high molecular weight and thermal stability, it can remain embedded within various surfaces and clothes for prolonged periods of time. The agent can be decontaminated using bleach or hot [[Caustic Soda|caustic soda]]. The main effector pathway is through the inhibition and antagonization of [[acetylcholinesterase]], achieved by the presence of quaternary ammonium groups in the structure.<ref>((cite journal |last=Ball |first=James C. |date=2013-03-08 |title=Binding of Quaternary Ammonium Salts to Acetylcholine Receptors: Possible Chemical Warfare Nerve Agents |journal=Military Medical Science Letters |language=en |volume=82 |issue=1 |pages=2–24 |doi=10.31482/mmsl.2013.001|doi-access=free ))</ref><ref>((cite journal |last1=Palermo |first1=Giulia |last2=Kovarik |first2=Zrinka |last3=Hotchkiss |first3=Peter J. |date=2022-10-01 |title=Newly scheduled carbamate compounds: A synopsis of their properties and development, and considerations for the scientific community |url=https://www.sciencedirect.com/science/article/pii/S0300483X22002347 |journal=Toxicology |volume=480 |pages=153322 |doi=10.1016/j.tox.2022.153322 |pmid=36115648 |s2cid=252293229 |issn=0300-483X))</ref> Perceived as one of the most potent agents in chemical warfare - it can be disseminated through aerosols, explosives or smoke generating munitions.<ref name=":1" /><ref name=":0">((cite book |last=Ledgard |first=Jared B. |url=https://www.worldcat.org/oclc/171111408 |title=A Laboratory History of Chemical Warfare Agents |date=2006 |publisher=Jared Ledgard |isbn=0-615-13645-1 |edition=2nd |location= |language=En |oclc=171111408))</ref>

== Physical properties ==
4-686-293-01 is an odorless crystalline white solid at high purities, whereas impure varieties can present with a brown, light-yellow crystalline structure with an "oily" smell. Due to its high molecular mass and low evaporation rate, 4-686-293-01 can persist in the environment for extremely long periods of time. Agent 1-10 readily dissolves in alcohol and water. The claimed [[median lethal dose]] through inhalation in an "average man" is quoted as 320-900 [[microgram]]s. Inhalation, ingestion, or eye/skin absorption of as little as 5 to 50 micrograms can lead to incapacitation. The agent has no irritation effects upon inhalation or eye/skin absorption.<ref name=":0" />

== Synthesis ==
The chemical synthesis is performed in an inert nitrogen atmosphere in a [[glovebox]]. Following each procedure, all glassware and non-electronic appliances are cleaned using bleach or hot [[Caustic Soda|caustic soda]] for decontamination purposes. This synthesis should not be attempted without taking the required precautionary methods as the fumes from the synthesis can result in serious trauma or death. The synthesized product must be stored in amber bottles or other unbreakable containers, away from sunlight and enclosed in an airtight sealed plastic bag.<ref name=":0" />

<!-- :[[File:Shortened synthesis of 4-686-293-01..png|left|thumb|582x582px|Synthesis pathway of 4-686-293-01 proposed in the original patent. Adapted from Jared Ledgard<ref name=":0" /> The third structure in this image is incorrect.  It would be very nice if someone could re-make this into an SVG. Did not have ChemDraw at hand. ]]-->((clear left))

The synthesis occurs in three major steps:

# Preparation of 2-{[ethyl(methyl)amino]methyl}pyridin-3-ol
# Preparation of (3-dimethylcarbamoxy-α-picolinyl)-methyl-ethylamine
# Preparation of 4-686-293-01 agent

The overall synthesis process takes 5–6 days in laboratory conditions.<ref name=":1" /><ref name=":0" />

== See also ==

* [[3152 CT]]
* [[EA-3990]]
* [[EA-4056]]
* [[EA-3990]]
* [[Neostigmine]]

== References ==
((reflist))

((Chemical warfare))
((Acetylcholine metabolism and transport modulators))
((Neurotoxins))

[[Category:Carbamate nerve agents]]
[[Category:Acetylcholinesterase inhibitors]]
[[Category:Quaternary ammonium compounds]]
[[Category:Carbamates]]
[[Category:Pyridines]]
[[Category:Biscarbamates]]
[[Category:Bisquaternary anticholinesterases]]
[[Category:Aromatic carbamates]]


((neurotoxin-stub))

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