EA-3167

EA-3167
Identifiers
  • 1-Azabicyclo[2.2.2]octan-8-yl 2-cyclopentyl-2-hydroxy-2-phenylethanoate
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H29NO3
Molar mass331.456 g·mol−1
3D model (JSmol)
  • C1CCC(C1)C(C2=CC=CC=C2)(C(=O)OC3CN4CCC3CC4)O
  • InChI=1S/C20H27NO3/c22-19(24-18-14-21-12-10-15(18)11-13-21)20(23,17-8-4-5-9-17)16-6-2-1-3-7-16/h1-3,6-7,15,17-18,23H,4-5,8-14H2
  • Key:RFXCNPOWSCFJCD-UHFFFAOYSA-N
  (verify)

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, 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).[1][2] 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.[3]

  1. ^ Wills H (1982). "Appendix I: Digest Report -- Anticholinergic Chemicals". In National Research Council (U.S.). Committee on Toxicology (ed.). Possible Long-Term Health Effects of Short-Term Exposure to Chemical Agents. Vol. 1. Washington, D.C.: National Academies Press. pp. 195–196. doi:10.17226/740. ISBN 978-0-309-07759-0. OCLC 35472774. PMID 25032448.
  2. ^ Ketchum JS (2006). Chemical Warfare Secrets Almost Forgotten. A Personal Story of Medical Testing of Army Volunteers with Incapacitating Chemical Agents During the Cold War. ChemBooks. ISBN 978-1-4243-0080-8.
  3. ^ Liu YM, Liu H, Zhong BH, Liu KL (2006). "Stereoselective Synthesis of the Optical Isomers of a New Muscarinic Receptor Antagonist, HL-031120". Synthetic Communications. 36 (13): 1815–1822. doi:10.1080/00397910600602453. S2CID 96011273.