Jump to content
Wikipedia The Free Encyclopedia

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
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C20H29NO3
Molar mass 331.456 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]

Effects

[edit ]

The intensity of EA-3167's effects is unparalleled among known psychoactive substances of any class.[dubiousdiscuss ] 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 the hypochondriasis, depression, hysteria, psychasthenia, schizophrenia, and mania 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. ^ a b 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.
  4. ^ a b Richelson 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.
Blood agents
Blister agents
Arsenicals
Sulfur mustards
Nitrogen mustards
Nettle agents
Other
Nerve agents
G-agents
V-agents
GV agents
Novichok agents
Carbamates
Other
Precursors
Neurotoxins
Pulmonary/
choking agents
Vomiting agents
Incapacitating
agents
Lachrymatory
agents
Malodorant agents
Cornea-clouding agents
Biological toxins
Other
Psychedelics
(5-HT2A
agonists)
Benzofurans
Lyserg‐
amides
Phenethyl‐
amines
2C-x
25x-NBx
25x-NB
25x-NB3OMe
25x-NB4OMe
25x-NBF
25x-NBMD
25x-NBOH
25x-NBOMe
Atypical structures
25x-NMx
N-(2C)-fentanyl
3C-x
4C-x
DOx
HOT-x
MDxx
Mescaline (subst.)
TMAs
  • TMA
  • TMA-2
  • TMA-3
  • TMA-4
  • TMA-5
  • TMA-6
Others
Piperazines
Tryptamines
alpha-alkyltryptamines
x-DALT
x-DET
x-DiPT
x-DMT
x-DPT
Ibogaine-related
x-MET
x-MiPT
Others
Others
Dissociatives
(NMDAR
antagonists)
Arylcyclo‐
hexylamines
Ketamine-related
PCP-related
Others
Adamantanes
Diarylethylamines
Morphinans
Others
Deliriants
(mAChR
antagonists)
Others
Cannabinoids
(CB1 agonists)
Natural
Synthetic
AM-x
CP x
HU-x
JWH-x
Misc. designer cannabinoids
D2 agonists
GABAA
enhancers
Inhalants
(Mixed MOA)
κOR agonists
Oneirogens
Others
mAChRs Tooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
(and prodrugs)


Stub icon

This hallucinogen-related article is a stub. You can help Wikipedia by expanding it.

AltStyle によって変換されたページ (->オリジナル) /