EA-3167

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EA-3167
EA-3167.svg
EA3167 27feb.gif
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.

Contents

Stereoisomers of EA-3167 have also been synthesized under the codename HL-031120. [3]

Effects

The intensity of EA-3167's effects is unparalleled among known psychoactive substances of any class. 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

Related Research Articles

3-Quinuclidinyl benzilate (QNB) is an odorless and bitter-tasting military incapacitating agent. BZ is an antagonist of muscarinic acetylcholine receptors whose structure is the ester of benzilic acid with an alcohol derived from quinuclidine.

Incapacitating agent is a chemical or biological agent which renders a person unable to harm themselves or others, regardless of consciousness.

Chemical, biological (CB) — and sometimes radiological — warfare agents were assigned what is termed a military symbol by the U.S. military until the American chemical and biological weapons programs were terminated. Military symbols applied to the CB agent fill, and not to the entire weapon. A chemical or biological weapon designation would be, for example, "Aero-14/B", which could be filled with GB, VX, TGB, or with a biological modification kit – OU, NU, UL, etc. A CB weapon is an integrated device of (1) agent, (2) dissemination means, and (3) delivery system.

<span class="mw-page-title-main">Edgewood Arsenal human experiments</span> US military chemical warfare research

From 1948 to 1975, the U.S. Army Chemical Corps conducted classified human subject research at the Edgewood Arsenal facility in Maryland. The purpose was to evaluate the impact of low-dose chemical warfare agents on military personnel and to test protective clothing, pharmaceuticals, and vaccines. A small portion of these studies were directed at psychochemical warfare and grouped under the prosaic title of the "Medical Research Volunteer Program" (1956–1975). The MRVP was also driven by intelligence requirements and the need for new and more effective interrogation techniques.

<span class="mw-page-title-main">Benzilic acid</span> Chemical compound

Benzilic acid is an organic compound with formula C
14H
12O
3 or (C
6H
5)2(HO)C(COOH). It is a white crystalline aromatic acid, soluble in many primary alcohols.

<span class="mw-page-title-main">Dimethylheptylpyran</span> Chemical compound

Dimethylheptylpyran is a synthetic analog of THC, which was invented in 1949 during attempts to elucidate the structure of Δ9-THC, one of the active components of Cannabis. DMHP is a pale yellow, viscous oil which is insoluble in water but dissolves in alcohol or non-polar solvents.

<i>N</i>-Methyl-3-piperidyl benzilate Chemical compound

N-Methyl-3-piperidyl benzilate is an anticholinergic drug related to the chemical warfare agent 3-quinuclidinyl benzilate.

<i>N</i>-Ethyl-3-piperidyl benzilate Chemical compound

N-Ethyl-3-piperidyl benzilate (JB-318) is an anticholinergic drug related to the chemical warfare agent 3-Quinuclidinyl benzilate.

<span class="mw-page-title-main">Ditran</span> Chemical compound

Ditran (JB-329) is an anticholinergic drug mixture, related to the chemical warfare agent 3-Quinuclidinyl benzilate (QNB).

<span class="mw-page-title-main">M43 BZ cluster bomb</span>

The M43 BZ cluster bomb, or simply M43 cluster bomb, was a U.S. chemical cluster bomb intended to deliver the incapacitating agent known as BZ. The weapon was produced in the early 1960s and all stocks of U.S. BZ were destroyed by 1989.

Psychochemical warfare — or "drug weapons" — involves the use of psychopharmacological agents with the intention of incapacitating an adversary through the temporary induction of hallucinations or delirium. These agents have generally been considered chemical weapons and, more narrowly, constitute a specific type of incapacitating agent. Although never developed into an effective weapons system, psychochemical warfare theory and research—along with overlapping mind control drug research—was secretly pursued in the mid-20th century by the US military and Central Intelligence Agency (CIA) in the context of the Cold War. These research programs were ended when they came to light and generated controversy in the 1970s. The degree to which the Soviet Union developed or deployed similar agents during the same period remains largely unknown.

<span class="mw-page-title-main">EA-3443</span> Chemical compound

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.

<span class="mw-page-title-main">CAR-302,196</span> Chemical compound

CAR-302,196 is a moderately potent and relatively short 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.

<span class="mw-page-title-main">EA-3580</span> Chemical compound

EA-3580 is a potent anticholinergic deliriant drug with a fairly long duration of action, 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.

<span class="mw-page-title-main">CAR-226,086</span> Chemical compound

CAR-226,086 is a potent anticholinergic deliriant drug with a fairly long duration of action, 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.

<span class="mw-page-title-main">EA-3834</span> Chemical compound

EA-3834 is a potent anticholinergic deliriant drug with a fairly long duration of action, 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.

<span class="mw-page-title-main">CAR-301,060</span> Chemical compound

CAR-301,060 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.

<span class="mw-page-title-main">CS-27349</span> Chemical compound

CS-27349, or L-2-α-tropinyl benzilate, is an experimental incapacitating agent. It acts as an antagonist to muscarinic acetylcholine receptors, causing delirium. It has 37% of the potency of the related compound 3-quinuclidinyl benzilate (BZ) in producing peripheral effects, but 85% of the potency in producing central effects. The mean dose required to incapacitate subjects was 1.2 times that of BZ. It has not been in use since the 1970s, and there have been no publications about its effects or long-term toxicology since then.

<span class="mw-page-title-main">CAR-302,282</span> Delirant drug

CAR-302,282 (302282, NSC-263548, α-(3-Methylbut-1-yn-3-enyl)mandelic acid 1-methyl-4-piperidyl ester) is an anticholinergic deliriant drug, invented under contract to Edgewood Arsenal in the 1960s. It is a potent incapacitating agent with an ED50 of 1.2μg/kg and a high central to peripheral effects ratio, and a relatively short duration of action compared to other similar drugs of around 6-10 hours. Despite its favorable properties it was relatively little researched compared to more high profile compounds from the series such as EA-3167 and EA-3580.

<span class="mw-page-title-main">CAR-302,668</span> Chemical compound

CAR-302,668 (302668, α-isopropylmandelic acid (1-methyl-1,2,3,6-tetrahydro-4-pyridyl)methyl ester) is an anticholinergic deliriant drug, invented under contract to Edgewood Arsenal in the 1960s. It is a reasonably potent incapacitating agent with an ED50 of 4μg/kg and a long duration of action of around 16-24 hours.

References

  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. 1 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.
  4. 1 2 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.


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