![]() | |
![]() | |
Identifiers | |
---|---|
3D model (JSmol) | |
| |
| |
Properties | |
C32H40Br2N4O4 | |
Molar mass | 704.504 g·mol−1 |
Appearance | Solid |
Melting point | 121–125 °C (250–257 °F; 394–398 K) |
Soluble | |
Solubility | Soluble in polar solvents |
Vapor pressure | Negligible |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | Extremely toxic |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 16 μg/kg (Mice) 6 μg/kg (Rabbits) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) (4-673-745-01) is an extremely potent carbamate nerve agent. It works by inhibiting the acetylcholinesterase, causing acetylcholine to accumulate. [1] [2] Since the agent molecule is positively charged, it does not cross the blood brain barrier very well. [1]
Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) is an extremely toxic nerve agent that can be lethal even at extremely low doses. The LD50 in mice and rabbits is 16 μg/kg and 6 μg/kg, respectively. [3]
5-Hydroxyisoquinoline and dimethylcarbamoyl chloride is heated on a steam bath for 2 hours. The mixture is then cooled and treated with benzene. The resulting solid is then dissolved in water. Sodium hydroxide is added to make the solution basic. The solution is extracted with chloroform and then dried with magnesium sulfate. The solvent is evaporated and the solid residue is then recrystallized from petroleum ether. The resulting product, 5-dimethylcarbamoxyisoquinoline, is then mixed with 1,8-dibromooctane in acetonitrile and refluxed for 8 hours. After cooling, the precipitate is filtered and recrystallized from acetonitrile. The product is then dried in vacuo for 14 hours at room temperature, resulting in the final product. [3]
Bromine is a chemical element with the symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between those of chlorine and iodine. Isolated independently by two chemists, Carl Jacob Löwig and Antoine Jérôme Balard, its name was derived from the Ancient Greek βρῶμος (bromos) meaning "stench", referring to its sharp and pungent smell.
Tabun or GA is an extremely toxic synthetic organophosphorus compound. It is a clear, colorless, and tasteless liquid with a faint fruity odor. It is classified as a nerve agent because it fatally interferes with normal functioning of the mammalian nervous system. Its production is strictly controlled and stockpiling outlawed by the Chemical Weapons Convention of 1993. Tabun is the first of the G-series nerve agents along with GB (sarin), GD (soman) and GF (cyclosarin).
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.
VX is an extremely toxic synthetic chemical compound in the organophosphorus class, specifically, a thiophosphonate. In the class of nerve agents, it was developed for military use in chemical warfare after translation of earlier discoveries of organophosphate toxicity in pesticide research. In recent years, VX was found to be the agent used in the assassination of Kim Jong-nam. In its pure form, VX is an oily, relatively non-volatile liquid that is amber-like in colour. Because of its low volatility, VX persists in environments where it is dispersed.
Instant coffee is a beverage derived from brewed coffee beans that enables people to quickly prepare hot coffee by adding hot water or milk to coffee solids in powdered or crystallized form and stirring. The product was first invented in Invercargill, the largest city in Southland, New Zealand, in 1890. Instant coffee solids refers to the dehydrated and packaged solids available at retail used to make instant coffee. Instant coffee solids are commercially prepared by either freeze-drying or spray drying, after which it can be rehydrated. Instant coffee in a concentrated liquid form, as a beverage, is also manufactured.
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.
In chemistry, work-up refers to the series of manipulations required to isolate and purify the product(s) of a chemical reaction. The term is used colloquially to refer to these manipulations, which may include:
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.
EA-3167 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, 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.
EA-3148 is a "V-series" nerve agent related to the better-known compounds VX and VR. It was studied by both the US and Soviet chemical weapons programmes during the Cold War, and is notable as the only V-series organophosphate nerve agent specifically identified in public domain sources as having a higher absolute potency as an acetylcholinesterase inhibitor than VX. However, both the US and Soviet investigations of the compound concluded that despite its high potency, the physicochemical properties of the substance made it unsuitable for weaponisation, and further research was not conducted.
o-Cresolphthalein is a phthalein dye used as a pH indicator in titrations. It is insoluble in water but soluble in ethanol. Its solution is colourless below pH 8.2, and purple above 9.8. Its molecular formula is C22H18O4. It is used medically to determine calcium levels in the human body, or to synthesize polyamides or polyimides.
EA-3990 is a deadly carbamate nerve agent. It is lethal because it inhibits acetylcholinesterase. Inhibition causes an overly high accumulation of acetylcholine between the nerve and muscle cells. This paralyzes the muscles by preventing their relaxation. The paralyzed muscles include the muscles used for breathing.
EA-4056 is a deadly carbamate nerve agent. It is lethal because it inhibits acetylcholinesterase. Inhibition causes an overly high accumulation of acetylcholine between the nerve and muscle cells. This paralyzes the muscles by preventing their relaxation. The paralyzed muscles includes the muscles used for breathing.
1,8-Dibromooctane is a chemical compound used in the synthesis of the carbamate nerve agents EA-3990 and octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide).
VP, also known as EA-1511, is an extremely toxic organophosphate nerve agent of the V-series.
EA-2192 is an extremely toxic degradation product of the VX nerve agent. It is a white solid that is very soluble and stable in water.
EA-3966 is a carbamate nerve agent. It is synthesized by reacting 2-dimethylaminomethyl-3-dimethylcarbamoxypyridine with 10-bromodecyltrimethylammonium bromide.
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.
4-686-293-01, also known as Agent 1-10, is a highly potent experimental carbamate nerve agent, patented in May 1967. Due to its high molecular weight and thermal stability, it can remain embedded within various surfaces and clothes for prolonged periods of time. The agent can be decontaminated using bleach or hot caustic soda. The main effector pathway is through the inhibition and antagonization of acetylcholinesterase, achieved by the presence of quaternary ammonium groups in the structure. Perceived as one of the most potent agents in chemical warfare - it can be disseminated through aerosols, explosives or smoke generating munitions.