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EA-3167
Sign in to saveEA-3167 is a potent and long-lasting anticholinergic deliriant drug, related to the chemical warfare agent 3-quinuclidinyl benzilate (QNB) and to the bronchodilator drug tiotropium bromide. It was developed under contract to Edgewood Arsenal during the 1960s as part of the US military chemical weapons program, in an attempt to develop non-lethal incapacitating agents. EA-3167 has identical effects to QNB (EA-2277), but is even more potent and longer-lasting, with an effective dose when administered by injection of as little as 2.5 μg/kg (i.e. 0.2 milligrams for an 80 kg person), and a dur
In the Vinony graph
Vinony's link graph records 722 inbound references to EA-3167, and connects out to cannabinoids, T-1123 and lysergic acid diethylamide.
It sits within the topics 3-Quinuclidinyl esters, Acetate esters and Chemical pages without DrugBank identifier.
Vinony links it to 7 Wikipedia language editions.
Chemical data
- Formula
- C20H27NO3
- Molecular weight
- 329.4 g/mol
- IUPAC name
- 1-azabicyclo[2.2.2]octan-3-yl 2-cyclopentyl-2-hydroxy-2-phenylacetate
- SMILES
- C1CCC(C1)C(C2=CC=CC=C2)(C(=O)OC3CN4CCC3CC4)O
- InChIKey
- RFXCNPOWSCFJCD-UHFFFAOYSA-N
- XLogP
- 3.4
- Polar surface area
- 49.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 329.199094
- Has use
- chemical weapon
Show 3 more facts
- chemical formula
- C₂₀H₂₇NO₃
- canonical SMILES
- C1CCC(C1)C(C2=CC=CC=C2)(C(=O)OC3CN4CCC3CC4)O
- Commons category
- EA-3167
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- Effects
- See also
- References
EA-3167 is a potent and long-lasting anticholinergic deliriant drug, related to the chemical warfare agent 3-quinuclidinyl benzilate (QNB) and to the bronchodilator drug tiotropium bromide. It was developed under contract to Edgewood Arsenal during the 1960s as part of the US military chemical weapons program, in an attempt to develop non-lethal incapacitating agents. EA-3167 has identical effects to QNB (EA-2277), but is even more potent and longer-lasting, with an effective dose when administered by injection of as little as 2.5 μg/kg (i.e. 0.2 milligrams for an 80 kg person), and a duration of 120–240 hours (5–10 days). However unlike QNB, EA-3167 was never weaponized or manufactured in bulk.
Stereoisomers of EA-3167 have also been synthesized under the codename HL-031120.
Excerpted from Wikipedia’s “EA-3167” article, available under the CC BY-SA 4.0 licence.