EA-3443

Chemical compound
EA-3443
Identifiers
  • (1-methylpiperidin-4-yl) 2-cyclopentyl-2-hydroxy-2-phenylacetate
CAS Number
  • 37830-21-0
PubChem CID
  • 37838
ChemSpider
  • 34695
UNII
  • 90H2V46IP4
CompTox Dashboard (EPA)
  • DTXSID50958860 Edit this at Wikidata
ECHA InfoCard100.110.337 Edit this at Wikidata
Chemical and physical data
FormulaC19H27NO3
Molar mass317.429 g·mol−1
3D model (JSmol)
  • Interactive image
  • C1CN(C)CCC1OC(=O)C(O)(C3CCCC3)c2ccccc2
InChI
  • InChI=1S/C19H27NO3/c1-20-13-11-17(12-14-20)23-18(21)19(22,16-9-5-6-10-16)15-7-3-2-4-8-15/h2-4,7-8,16-17,22H,5-6,9-14H2,1H3
  • Key:DZFJGXMHIMAYMW-UHFFFAOYSA-N
  (verify)

EA-3443 is a potent and long lasting anticholinergic deliriant drug, related to the chemical warfare agent 3-Quinuclidinyl benzilate (QNB). It was developed under contract to Edgewood Arsenal during the 1960s as part of the US military chemical weapons program, during research to improve upon the properties of earlier agents such as QNB.

The main advantages of EA-3443 were not only increased potency over QNB, but also a significantly improved central to peripheral effects ratio. Anticholinergic drugs produce both incapacitating deliriant effects through action in the brain, and a variety of distinctive physical symptoms such as dry mouth, dilated pupils, blurred vision and hot flushed skin, all of which together comprise the "anticholinergic syndrome" which is generally easy for doctors to diagnose. EA-3443 however is mainly selective for the brain, and when administered in a narrow dose range of around 0.3 mg can produce the central effects of confusion, hallucinations and amnesia, but without producing significant physical symptoms, which was predicted to make poisoning with EA-3443 much more difficult to diagnose and treat. However, despite these advantages, EA-3443 was never researched to the same extent as QNB or manufactured in bulk, and research into EA-3443 was discontinued along with the rest of the US chemical weapons program in the mid-1970s.[1][2]

See also

References

  1. ^ Commission on Life Sciences (1982). "N-Methyl-4-piperidinyl-(phenylcyclopentyl)-glycolate (EA-3443)". Possible Long-Term Health Effects of Short-Term Exposure to Chemical Agents. Vol. 1. The National Academies Press. pp. 189–191. doi:10.17226/740. ISBN 978-0-309-07759-0. 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 Inc. ISBN 978-1-4243-0080-8.
  • v
  • t
  • e
Blood agentsBlister agents
Arsenicals
Sulfur mustards
Nitrogen mustards
Nettle agents
Other
Nerve agents
G-agents
V-agents
GV agents
  • GV (EA-5365)
Novichok agents
Carbamates
Other
Precursors
NeurotoxinsPulmonary/
choking agentsVomiting agentsIncapacitating
agentsLachrymatory
agentsMalodorant agentsCornea-clouding agentsBiological toxinsOther
  • v
  • t
  • e
Psychedelics
(5-HT2A
agonists)
Benzofurans
Lyserg‐
amides
Phenethyl‐
amines
2C-x
25x-NBx
25x-NB
25x-NB3OMe
  • 25B-NB3OMe
  • 25C-NB3OMe
  • 25D-NB3OMe
  • 25E-NB3OMe
  • 25H-NB3OMe
  • 25I-NB3OMe
  • 25N-NB3OMe
  • 25P-NB3OMe
  • 25T2-NB3OMe
  • 25T4-NB3OMe
  • 25T7-NB3OMe
  • 25TFM-NB3OMe
25x-NB4OMe
  • 25B-NB4OMe
  • 25C-NB4OMe
  • 25D-NB4OMe
  • 25E-NB4OMe
  • 25H-NB4OMe
  • 25I-NB4OMe
  • 25N-NB4OMe
  • 25P-NB4OMe
  • 25T2-NB4OMe
  • 25T4-NB4OMe
  • 25T7-NB4OMe
  • 25TFM-NB4OMe
25x-NBF
25x-NBMD
  • 25B-NBMD
  • 25C-NBMD
  • 25D-NBMD
  • 25E-NBMD
  • 25F-NBMD
  • 25H-NBMD
  • 25I-NBMD
  • 25P-NBMD
  • 25T2-NBMD
  • 25T7-NBMD
  • 25TFM-NBMD
25x-NBOH
25x-NBOMe
Atypical structures
25x-NMx
  • 25B-NMe7BF
  • 25B-NMe7BT
  • 25B-NMe7Bim
  • 25B-NMe7Box
  • 25B-NMe7DHBF
  • 25B-NMe7Ind
  • 25B-NMe7Indz
  • 25B-NMePyr
  • 25I-NMe7DHBF
  • 25I-NMeFur
  • 25I-NMeTHF
  • 25I-NMeTh
N-(2C)-fentanyl
  • N-(2C-B) fentanyl
  • N-(2C-C) fentanyl
  • N-(2C-D) fentanyl
  • N-(2C-E) fentanyl
  • N-(2C-G) fentanyl
  • N-(2C-H) fentanyl
  • N-(2C-I) fentanyl
  • N-(2C-IP) fentanyl
  • N-(2C-N) fentanyl
  • N-(2C-P) fentanyl
  • N-(2C-T) fentanyl
  • N-(2C-T-2) fentanyl
  • N-(2C-T-4) fentanyl
  • N-(2C-T-7) fentanyl
  • N-(2C-TFM) 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
  • v
  • t
  • e
mAChRsTooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
(and prodrugs)
See also
Receptor/signaling modulators
Nicotinic acetylcholine receptor modulators
Acetylcholine metabolism/transport modulators


Stub icon

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

  • v
  • t
  • e