CAR-302,196

Last updated
CAR-302,196
CAR-302,196 structure.png
Identifiers
  • (1-methylpiperidin-4-yl) 2-cyclopentyl-2-hydroxypent-3-ynoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C16H25NO3
Molar mass 279.380 g·mol−1
3D model (JSmol)
  • CN1CCC(CC1)OC(=O)C(O)(C#CC)C2CCCC2
  • InChI=1S/C16H25NO3/c1-3-10-16(19,13-6-4-5-7-13)15(18)20-14-8-11-17(2)12-9-14/h13-14,19H,4-9,11-12H2,1-2H3
  • Key:GKCPDYHGDHCIJL-UHFFFAOYSA-N
   (verify)

CAR-302,196 (also known as PCMG or just by its code number 302196) 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.

CAR-302,196 was found to be only around 1/4 the potency of QNB, but its onset of action was much faster at only a few minutes, and the duration far shorter at only 2–3 hours. A fast-acting and short-lasting anticholinergic drug was felt to be more desirable for some applications. [1] [2]

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.

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

Benzilic acid is an organic compound with formula C
14
H
12
O
3
or (C
6
H
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">EA-3167</span> Anticholinergic deliriant drug

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, and a duration of 120–240 hours. However unlike QNB, EA-3167 was never weaponized or manufactured in bulk.

<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">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">Cholinergic blocking drug</span> Drug that block acetylcholine in synapses of cholinergic nervous system

Cholinergic blocking drugs are a group of drugs that block the action of acetylcholine (ACh), a neurotransmitter, in synapses of the cholinergic nervous system. They block acetylcholine from binding to cholinergic receptors, namely the nicotinic and muscarinic receptors.

<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. 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. Vol. 1. The National Academies Press. pp. 206–207. 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.