CAR-302,196
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CAR-302,196
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. See also * CAR-302,282 * EA-3167 * N-methyl-3-piperidyl benzilate * N-ethyl-3-piperidyl benzilate * 3-Quinuclidinyl benzilate * Ditran Ditran (JB-329) is an anticholinergic drug mixture, related to the chemical warfare agent 3-Quinuclidinyl benzilate (QNB). Ditran is composed of ...
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CAR-302,282
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 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, Ed .... See also * CAR-226,086 * CAR-301,060 * CAR-302,196 References Deliriants Muscarinic antagonists Incapacitating agents Piperidines Carboxylate esters Alkyne deriva ...
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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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Alkyne Derivatives
\ce \ce Acetylene \ce \ce \ce Propyne \ce \ce \ce \ce 1-Butyne In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula . Alkynes are traditionally known as acetylenes, although the name ''acetylene'' also refers specifically to , known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic. Structure and bonding In acetylene, the H–C≡C bond angles are 180°. By virtue of this bond angle, alkynes are rod-like. Correspondingly, cyclic alkynes are rare. Benzyne cannot be isolated. The C≡C bond distance of 121 picometers is much shorter than the C=C distance in alkenes (134 pm) or the C–C bond in alkanes (153 pm). : The triple bond is very strong with a bond strength of 839 kJ/mol. The sigma bond contributes ...
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Carboxylate Esters
In organic chemistry, a carboxylate is the conjugate base of a carboxylic acid, (or ). It is an ion with negative charge. Carboxylate salts are salts that have the general formula , where M is a metal and ''n'' is 1, 2,...; ''carboxylate esters'' have the general formula (or ). R and R′ are organic groups; R′ ≠ H. Synthesis Carboxylate ions can be formed by deprotonation of carboxylic acids. Such acids typically have p''K''a of less than 5, meaning that they can be deprotonated by many bases, such as sodium hydroxide or sodium bicarbonate. :RCOOH + NaOH -> RCOONa + H2O Resonance stabilization of the carboxylate ion Carboxylic acids easily dissociate into a carboxylate anion and a positively charged hydrogen ion (proton), much more readily than alcohols do (into an alkoxide ion and a proton), because the carboxylate ion is stabilized by resonance. The negative charge that is left after deprotonation of the carboxyl group is delocalized between the ...
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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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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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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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