EA-3580
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EA-3580
EA-3580 is a potent anticholinergic deliriant drug with a fairly long duration of action, related to the chemical weapons, chemical warfare agent 3-Quinuclidinyl benzilate (QNB). It was developed under contract to Edgewood Arsenal experiments, Edgewood Arsenal during the 1960s as part of the United States and weapons of mass destruction#Chemical weapons, US military chemical weapons program, during research to improve upon the properties of earlier agents such as QNB. EA-3580 is closely related to the similar compound EA-3443, and has similar potency and high central to peripheral effects ratio, but with a duration of action around half as long, although effects of EA-3580 can still persist for 24 hours or more following high doses. See also * EA-3167 * N-methyl-3-piperidyl benzilate * N-ethyl-3-piperidyl benzilate * 3-Quinuclidinyl benzilate * Ditran References

Deliriants Muscarinic antagonists Incapacitating agents Piperidines Acetate esters Cyclobutyl compounds ...
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3-Quinuclidinyl Benzilate
3-Quinuclidinyl benzilate (QNB) (IUPAC name 1-azabicyclo .2.2ctan-3-yl hydroxy(diphenyl)acetate; US Army code EA-2277; NATO code BZ; Soviet code Substance 78) is an odorless and bitter-tasting military incapacitating agent.QNB: Incapacitating AgentEmergency Response Safety and Health Database National Institute for Occupational Safety and Health. Accessed April 20, 2009. BZ is an antagonist of muscarinic acetylcholine receptors whose structure is the ester of benzilic acid with an alcohol derived from quinuclidine. Physiochemical characteristics BZ is a white crystalline powder with a bitter taste. It is odorless and nonirritating with delayed symptoms several hours after contact. It is stable in most solvents, with a half-life of three to four weeks in moist air; even heat-producing munitions can disperse it. It is extremely persistent in soil and water and on most surfaces. BZ is soluble in water, soluble in dilute acids, trichloroethylene, dimethylformamide, and most organic so ...
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Edgewood Arsenal Experiments
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. Overall, about 7,000 soldiers took part in these experiments that involved exposures to more than 250 different chemicals, according to the Department of Defense (DoD). Some of the volunteers exhibited symptoms at the time of exposure to these agents but long-term follow-up was not planned as part of the DoD studies. The experiments were abruptly terminated by the Army in late 1975 amidst an atmosphere ...
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Anticholinergic
Anticholinergics (anticholinergic agents) are substances that block the action of the neurotransmitter called acetylcholine (ACh) at synapses in the central and peripheral nervous system. These agents inhibit the parasympathetic nervous system by selectively blocking the binding of ACh to its receptor in nerve cells. The nerve fibers of the parasympathetic system are responsible for the involuntary movement of smooth muscles present in the gastrointestinal tract, urinary tract, lungs, sweat glands, and many other parts of the body. In broad terms, anticholinergics are divided into two categories in accordance with their specific targets in the central and peripheral nervous system and at the neuromuscular junction: antimuscarinic agents, and antinicotinic agents ( ganglionic blockers, neuromuscular blockers). The term "anticholinergic" is typically used to refer to antimuscarinics which competitively inhibit the binding of ACh to muscarinic acetylcholine receptors; such agen ...
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Ditran
Ditran (JB-329) is an anticholinergic drug mixture, related to the chemical warfare agent 3-Quinuclidinyl benzilate (QNB). Ditran is composed of a mixture of 70% 1-ethyl-2-pyrrolidinylmethyl-alpha- phenylcyclopentylglycolate and 30% 1-ethyl-3-piperidyl-alpha-phenylcyclopentylglycolate. These compounds are structural isomers and have very similar pharmacological properties. The piperidine compound is the more potent of the two and the reason the mixture was used was because of ease of manufacture, however it is also possible to make the piperidine compound in its pure form, so there were ultimately two forms of Ditran used in research, the original 70/30 mix, and "Ditran-B", the pure piperidine compound. Ditran was developed during chemical weapons research in an attempt to produce non-lethal incapacitating agents, similar to QNB itself. The ditran mixture is more potent as an anticholinergic than the piperidyl benzilate drugs such as N-methyl-3-piperidyl benzilate, but is less po ...
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Acetate Esters
An acetate is a salt formed by the combination of acetic acid with a base (e.g. alkaline, earthy, metallic, nonmetallic or radical base). "Acetate" also describes the conjugate base or ion (specifically, the negatively charged ion called an anion) typically found in aqueous solution and written with the chemical formula . The neutral molecules formed by the combination of the acetate ion and a ''positive'' ion (called a cation) are also commonly called "acetates" (hence, ''acetate of lead'', ''acetate of aluminum'', etc.). The simplest of these is hydrogen acetate (called acetic acid) with corresponding salts, esters, and the polyatomic anion , or . Most of the approximately 5 billion kilograms of acetic acid produced annually in industry are used in the production of acetates, which usually take the form of polymers. In nature, acetate is the most common building block for biosynthesis. Nomenclature and common formula When part of a salt, the formula of the acetate ion ...
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Piperidines
Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, and typical of amines. The name comes from the genus name ''Piper'', which is the Latin word for pepper. Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids, such as natural-occurring solenopsins. Production Piperidine was first reported in 1850 by the Scottish chemist Thomas Anderson and again, independently, in 1852 by the French chemist Auguste Cahours, who named it. Both of them obtained piperidine by reacting piperine with nitric acid. Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst: : C5H5N + 3 H2 → C5H10NH Pyridine can also be reduce ...
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Muscarinic Antagonists
A muscarinic receptor antagonist (MRA) is a type of anticholinergic agent that blocks the activity of the muscarinic acetylcholine receptor. The muscarinic receptor is a protein involved in the transmission of signals through certain parts of the nervous system, and muscarinic receptor antagonists work to prevent this transmission from occurring. Notably, muscarinic antagonists reduce the activation of the parasympathetic nervous system. The normal function of the parasympathetic system is often summarised as "rest-and-digest", and includes slowing of the heart, an increased rate of digestion, narrowing of the airways, promotion of urination, and sexual arousal. Muscarinic antagonists counter this parasympathetic "rest-and-digest" response, and also work elsewhere in both the central and peripheral nervous systems. Drugs with muscarinic antagonist activity are widely used in medicine, in the treatment of low heart rate, overactive bladder, respiratory problems such as asthma and ...
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Deliriants
Deliriants are a subclass of hallucinogen. The term was coined in the early 1980s to distinguish these drugs from psychedelics and dissociatives such as LSD and ketamine, respectively, due to their primary effect of causing delirium, as opposed to the more lucid and less disturbed states produced by other types of hallucinogens.Duncan, D. F., and Gold, R. S. (1982). Drugs and the Whole Person. New York: John Wiley & Sons The term generally refers to anticholinergic drugs, which are substances that inhibit the function of the neurotransmitter acetylcholine. Common examples of deliriants include plants of the genera ''Datura'' and ''Brugmansia'' (both containing scopolamine) as well as higher than recommended dosages of diphenhydramine (Benadryl). A number of plant deliriants such as that of the Solanaceae family, particularly in the Americas have been used by some indigenous cultures to reach delirious and altered states for traditions or rituals, such as rites of passage, divin ...
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N-methyl-3-piperidyl Benzilate
''N''-Methyl-3-piperidyl benzilate (JB-336 or LBJ) is an anticholinergic drug related to the chemical warfare agent 3-quinuclidinyl benzilate. ''N''-methyl-3-piperidyl benzilate is less potent and shorter acting than 3-quinuclidyl benzilate, but like 3-QNB its effects on the central nervous system predominate over peripheral effects. It produces deliriant and hallucinogenic effects similar to those of plants such as datura and may be used recreationally at low doses; however, unpleasant side effects such as dysphoria, nausea and vomiting, dizziness and extreme dry mouth tend to make abuse of drugs of this kind uncommon. Both the N-methyl and N-ethyl analogues of 3-piperidyl benzilate are, however, Schedule I controlled drugs. Radiolabelled versions of this drug are used in scientific research to map the distribution of muscarinic acetylcholine receptors in the brain. Methylation of JB-336 gives the quat salt, Mepenzolate bromide. See also * N-ethyl-3-piperidyl benzilat ...
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Deliriant
Deliriants are a subclass of hallucinogen. The term was coined in the early 1980s to distinguish these drugs from psychedelics and dissociatives such as LSD and ketamine, respectively, due to their primary effect of causing delirium, as opposed to the more lucid and less disturbed states produced by other types of hallucinogens.Duncan, D. F., and Gold, R. S. (1982). Drugs and the Whole Person. New York: John Wiley & Sons The term generally refers to anticholinergic drugs, which are substances that inhibit the function of the neurotransmitter acetylcholine. Common examples of deliriants include plants of the genera ''Datura'' and ''Brugmansia'' (both containing scopolamine) as well as higher than recommended dosages of diphenhydramine (Benadryl). A number of plant deliriants such as that of the Solanaceae family, particularly in the Americas have been used by some indigenous cultures to reach delirious and altered states for traditions or rituals, such as rites of passage, divin ...
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