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EA-3167

From Wikipedia, the free encyclopedia
Anticholinergic deliriant drug

Pharmaceutical compound
EA-3167
Identifiers
  • 1-Azabicyclo[2.2.2]octan-8-yl 2-cyclopentyl-2-hydroxy-2-phenylethanoate
CAS Number
PubChemCID
ChemSpider
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC20H27NO3
Molar mass329.440 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-lastinganticholinergicdeliriant drug, related to thechemical warfare agent3-quinuclidinyl benzilate (QNB) and to thebronchodilator drugtiotropium bromide. It was developed under contract toEdgewood Arsenal during the 1960s as part of theUS military chemical weapons program, in an attempt to develop non-lethalincapacitating 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).[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]

Effects

[edit]

Incapacitating effects can last anywhere from 5-10 days, sometimes manifesting as a full 3-day peak of vivid hallucinations, along with prolonged confusion, amnesia, and inhibition of speech and cognition.[4] Some subjects exposed to the drug would not fully recover for almost 20 days.[2] Even six months after exposure, a few subjects demonstrated significant increases in the scores on thehypochondriasis, depression, hysteria,psychasthenia,schizophrenia, andmania scales.[5] The drug's potency caught the attention of the military, which considered weaponizing EA-3167 for topical use, potentially even through a handshake.[4] However, weaponization and further studies were eventually abandoned, possibly due to the extreme nature of its effects and the strain on available study resources caused by conducting human studies for extended periods.[6]

See also

[edit]

References

[edit]
  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. ^abKetchum 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.
  4. ^abRichelson JT (2001).The Wizards Of Langley: Inside The Cia's Directorate Of Science And Technology.Westview Press.ISBN 978-0-8133-6699-9.
  5. ^National Research Council (US) Panel on Anticholinesterase Chemicals, National Research Council (US) Panel on Anticholinergic Chemicals (1982)."Possible Long-Term Health Effects of Short-Term Exposure to Chemical Agents".National Research Council.1.doi:10.17226/740.ISBN 978-0-309-07759-0.PMID 25032448.
  6. ^Hornblum AM (1999).Acres of Skin: Human Experiments at Holmesburg Prison (1 ed.).Routledge.ISBN 978-0-415-92336-1.
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