EA-3966

EA-3966
Names

Preferred IUPAC name N¹-({3-[(Dimethylcarbamoyl)oxy]pyridin-2-yl}methyl)-N¹,N¹,N¹⁰,N¹⁰,N¹⁰-pentamethyldecane-1,10-bis(aminium) dibromide
Identifiers
CAS Number	110913-86-5^Y
3D model (JSmol)	Interactive image
CompTox Dashboard (EPA)	DTXSID201336456
InChI InChI=1S/C24H46N4O2.2BrH/c1-26(2)24(29)30-23-17-16-18-25-22(23)21-28(6,7)20-15-13-11-9-8-10-12-14-19-27(3,4)5;;/h16-18H,8-15,19-21H2,1-7H3;2*1H/q+2;;/p-2 Key: SMYJBWHIVMYSPG-UHFFFAOYSA-L
SMILES [Br-].[Br-].CN(C)C(=O)Oc1cccnc1C[N+](C)(C)CCCCCCCCCC[N+](C)(C)C
Properties
Chemical formula	C₂₄H₄₆Br₂N₄O₂
Molar mass	582.466 g·mol⁻¹
Appearance	Crystalline solid
Melting point	139–143 °C (282–289 °F; 412–416 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

EA-3966 is a carbamate nerve agent.^[1] It is synthesized by reacting 2-dimethylaminomethyl-3-dimethylcarbamoxypyridine with 10-bromodecyltrimethylammonium bromide.^[2]

References

^ Handbook of chemical and biological warfare agents (2nd ed.). CRC Press. 24 August 2007. ISBN 9780849314346.
^ "Chemical agents".

Agents used in chemical warfare
incapacitation
riot control

Blood agents

Blister agents

Arsenicals	Ethyldichloroarsine (ED) Methyldichloroarsine (MD) Phenyldichloroarsine (PD) Lewisite (L) Lewisite 2 (L2) Lewisite 3 (L3)
Sulfur mustards	Levinstein mustard (EA-229) T Q CEES
Nitrogen mustards	HN1 HN2 HN3 TL-301
Nettle agents	Phosgene oxime (CX)
Other	KB-16 Dibutylchloromethyltin chloride Selenium oxychloride

Nerve agents

G-agents	Tabun (GA) Sarin (GB) Chlorosarin (ClGB) Thiosarin (SGB) Soman (GD) Chlorosoman (ClGD) Ethylsarin (GE) GH Cyclosarin (GF) GP Fluorotabun EA-1356 EA-4352 Crotylsarin
V-agents	EA-2192 EA-3148 VE VG VM VP VR VS VX EA-1763 Chinese VX V-sub x (GD-7)
GV agents	GV (EA-5365)
Novichok agents	A-208 A-232 A-234 A-242 A-262 C01-A035 C01-A039 C01-A042
Carbamates	Dimethylcarbamoyl fluoride EA-3887 EA-3887A EA-3966 EA-3990 EA-4056 T-1123 T-1152 T-1194 Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) TL-599 TL-1238 TL-1299 TL-1317 Miotine (AR-28/T-1843) 3152 CT 4-686-293-01 (Agent 1-10)
Other	Diisopropyl fluorophosphate Dicyclohexyl phosphorofluoridate EA-2012 EA-2054 EA-2098 EA-2613 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Neopentylene fluorophosphate Selenophos Phospholine R-16661 Ro 3-0422 Methanesulfonyl fluoride Dimefox (TL-792) MSPI
Precursors	Acetonitrile AT ATO AlP A.P.C. complex Chlorosarin Chlorosoman Cyclohexanol 1,8-Dibromooctane N,N-Diisopropylaminoethanol (KB) EA-1250 DIHP ZS DEHP EA-1224 Dimethylamidophosphoric dichloride Dimethylamidophosphoric dicyanide DMHP Ethylphosphonoselenoic dichloride Formaldoxime Nital 4-Hydroxycoumarin Isopropyl alcohol (TB) Methyldichlorophosphine (SW) Methylphosphonyl difluoride (difluoro) (DF) Methylphosphonyl dichloride (dichloro) Nitromethane OPA mixture Phosphoryl chloride Phosphorus pentachloride Phosphorus trichloride (TH) Pinacolone Pinacolyl alcohol Phenacyl chloride QL 2,4,5-Trichlorophenol 3,3,5-Trimethylcyclohexanol Triethyl phosphite Trimethyl phosphite TC TG

Neurotoxins

Anatoxin-a
Saxitoxin (TZ)
Bungarotoxin
Botulinum toxin (BTX)
Tetanospasmin (TeNT)
Ryanodine
Ciguatoxin (CTX)
Guanitoxin (GTX)
Chlorophenylsilatrane
Palytoxin (PTX)
Maitotoxin (MTX)
Tetrodotoxin
Aconitine
Brevetoxin (PbTX)
Strychnine
Antillatoxin (ATX)
Tetraethyllead
Dimethylmercury
HN1 hydrochloride
HN2 hydrochloride
HN3 hydrochloride
A-8564
Picrotoxin
Sulfuryl fluoride
Tremorine
Oxotremorine
Batrachotoxin
Tetramethylenedisulfotetramine (TETS)
Bicyclic phosphates
- IPTBO
- TBPO
- TBPS
Cloflubicyne
Trimethylolpropane phosphite
Domoic acid

Pulmonary/
choking agents

Vomiting agents

Incapacitating
agents

Lachrymatory
agents

Malodorant agents

Cornea-clouding agents

Biological toxins

Other

Methyl fluoroacetate
Napalm (variants and mixtures)
Fluoroethyl fluoroacetate
Depleted uranium
- post-combustion uranium oxides
Plutonium and its compounds
Polonium
White phosphorus

Acetylcholine metabolism and transport modulators

Enzyme
(modulators)

ChATTooltip Choline acetyltransferase	Inhibitors: 1-(-Benzoylethyl)pyridinium 2-(α-Naphthoyl)ethyltrimethylammonium 3-Chloro-4-stillbazole 4-(1-Naphthylvinyl)pyridine Acetylseco hemicholinium-3 Acryloylcholine AF64A B115 BETA CM-54,903 N,N-Dimethylaminoethylacrylate N,N-Dimethylaminoethylchloroacetate
AChETooltip Acetylcholinesterase	Inhibitors: Reversible: Carbamates: Aldicarb Aminocarb Bendiocarb Bufencarb Carbaryl Carbendazim Carbetamide Carbofuran Carbosulfan Chlorbufam Chloropropham Dimetilan Ethienocarb Ethiofencarb Fenobucarb Formetanate Formparanate Methiocarb Methomyl Metolcarb Miotine Oxamyl Phenmedipham Pinmicarb Pirimicarb Promecarb Propamocarb Propham Propoxur Thiodicarb Thiofanox; Stigmines: Distigmine Eptastigmine Ganstigmine Neostigmine +glycopyrronium bromide Phenserine Physostigmine Pyridostigmine Quilostigmine Rivastigmine Terestigmine; Others: Acotiamide Ambenonium Caffeine Donepezil EA-3990 EA-4056 Edrophonium Galantamine Huperzine A Huprine W Huprine X Huprine Y Ipidacrine Itopride Ladostigil Minaprine Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) T-1123 T-1152 T-1194 TL-599 TL-1238 Tacrine Zanapezil Irreversible: Organophosphates: 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Acephate Armine Azinphos-ethyl Azinphos-methyl BAY-29952 Bensulide Cadusafos Carbophenothion Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Crotylsarin Cyanophos Cyclosarin (GF) Demephion Demeton Demeton-S-methyl Dialifor Diazinon Dichlorvos Dicrotophos Dicyclohexyl phosphorofluoridate Diisopropylphosphate Diisopropyl fluorophosphate Dimefox Dimethoate Dimethyl 4-(methylthio)phenyl phosphate Dioxathion Disulfoton EA-2012 EA-2054 EA-2098 EA-2192 EA-2613 EA-3148 EA-4352 Echothiophate Ethylsarin (GE) Endothion EPN Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fluorotabun Fonofos Formothion Fosthiazate GD-42 GH GT-45 GV Guanitoxin Hexaethyl tetraphosphate (HETP) Isofluorophate Isoxathion Leptophos Malaoxon Malathion Mazidox Methamidophos Methidathion Methyl phenkapton Methylfluorophosphonylcholine (MFPCh) Metrifonate Mevinphos Mipafox Monocrotophos MSPI Naled Novichok agent Omethoate Oxydemeton-methyl Paraoxon Parathion Parathion-methyl Phorate Phosalone Phosfolan Phosmet Phosphamidon Phoxim Pirimiphos-methyl Profenofos Prothoate R-16661 Ro 3-0340 Ro 3-0346 Ro 3-0347 Ro 3-0351 Ro 3-0352 Ro 3-0397 Ro 3-0411 Ro 3-0412 Ro 3-0417 Ro 3-0419 Ro 3-0422 Ro 3-0433 Ronnel Sarin (GB) Schradan Soman (GD) Sulfotep (TEDP) Tabun (GA) Tebupirimfos Temefos Terbufos Tetrachlorvinphos Tetraethyl pyrophosphate (TEPP) Triazofos Tribufos Trichlorfon Trichloronate Tricresyl phosphate VE VG VM VP VS VR VX; Others: Demecarium Fasciculins (green mamba toxins) (1, 2, 3, 4) Onchidal (Onchidella binneyi) Methanesulfonyl fluoride Unsorted: α-Pinene α-Viniferin Affinine Affinisine Arisugacin A Bulbocapnine Conodurine Coronaridine Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol Ungeremine Ungiminorine Dimethylcarbamoyl fluoride BW284C51 TMTFA 3152 CT Reactivators: Asoxime chloride Methoxime Obidoxime Pralidoxime Trimedoxime bromide
BChETooltip Butyrylcholinesterase	Inhibitors: Affinine Affinisine Conodurine Cymserine Ladostigil Profenamine (ethopropazine) Rivastigmine Tacrine ZINC-12613047 Many of the other AChE inhibitors listed above

Transporter
(modulators)

CHTTooltip Choline transporter	Inhibitors: Hemicholinium-3 (hemicholine) Triethylcholine Enhancers: Coluracetam
VAChTTooltip Vesicular acetylcholine transporter	Inhibitors: Vesamicol

Release
(modulators)

Inhibitors	SNAP-25Tooltip Synaptosomal-associated protein 25 inactivators: Botulinum toxin (A, C, E) VAMPTooltip Vesicle-associated membrane protein inactivators: Botulinum toxin (B, D, F, G) Others: Bungarotoxins (β-bungarotoxin, γ-bungarotoxin)
Enhancers	LPHNTooltip Latrophilin agonists: α-Latrotoxin Others: Atracotoxins (e.g., robustoxin, versutoxin) Crotoxin