Names | |
---|---|
IUPAC name 3,3,5-trimethylcyclohexan-1-ol | |
Other names Homomenthol | |
Identifiers | |
3D model (JSmol) | |
2203314 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.748 |
EC Number | 204-122-7 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C9H18O | |
Molar mass | 142.242 g·mol−1 |
Density | 0.878 at 20 °C |
Melting point | 37.0 °C (98.6 °F; 310.1 K) |
Boiling point | 198 °C (388 °F; 471 K) |
Hazards | |
GHS pictograms | |
GHS signal word | Warning |
H315, H319, H412 | |
P264, P273, P280, P302+352, P305+351+338, P321, P332+313, P337+313, P362, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
3,3,5-Trimethylcyclohexanol is a precursor to the vasodilator cyclandelate, the sunscreen component homosalate and the VP nerve agent. [1] [2] It can be synthesized by hydrogenation of isophorone. [3] It has a mint flavour.
Cyclandelate is a vasodilator used in the treatment of claudication, arteriosclerosis and Raynaud's disease. It is also used to treat nighttime leg cramps, and has been investigated for its effect against migraine. It is orally administered.
Homosalate is an organic compound used in some sunscreens. It is made by the Fischer–Speier esterification of salicylic acid and 3,3,5-trimethylcyclohexanol, the latter being a hydrogenated derivative of isophorone. Contained in 45% of U.S. sunscreens, it is used as a chemical UV filter. The salicylic acid portion of the molecule absorbs ultraviolet rays with a wavelength from 295 nm to 315 nm, protecting the skin from sun damage. The hydrophobic trimethyl cyclohexane functional group provides greasiness that prevents it from dissolving in water.
Nerve agents, sometimes also called nerve gases, are a class of organic chemicals that disrupt the mechanisms by which nerves transfer messages to organs. The disruption is caused by the blocking of acetylcholinesterase, an enzyme that catalyzes the breakdown of acetylcholine, a neurotransmitter.
Sarin, is an extremely toxic synthetic organophosphorus compound. A colorless, odorless liquid, it is used as a chemical weapon due to its extreme potency as a nerve agent. Exposure is lethal even at very low concentrations, where death can occur within one to ten minutes after direct inhalation of a lethal dose, due to suffocation from lung muscle paralysis, unless antidotes are quickly administered. People who absorb a non-lethal dose, but do not receive immediate medical treatment, may suffer permanent neurological damage.
Soman is an extremely toxic chemical substance. It is a nerve agent, interfering with normal functioning of the mammalian nervous system by inhibiting the enzyme cholinesterase. It is an inhibitor of both acetylcholinesterase and butyrylcholinesterase. As a chemical weapon, it is classified as a weapon of mass destruction by the United Nations according to UN Resolution 687. Its production is strictly controlled, and stockpiling is outlawed by the Chemical Weapons Convention of 1993 where it is classified as a Schedule 1 substance. Soman was the third of the so-called G-series nerve agents to be discovered along with GA (tabun), GB (sarin), and GF (cyclosarin).
A local anesthetic (LA) is a medication that causes absence of pain sensation. When it is used on specific nerve pathways, paralysis also can be achieved.
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 its pure form, VX is an oily, relatively non-volatile, liquid that is amber-like in color. Because of its low volatility, VX persists in environments where it is dispersed.
An oxime is a chemical compound belonging to the imines, with the general formula RR'C=NOH, where R is an organic side-chain and R' may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted oximes form a closely related family of compounds. Amidoximes are oximes of amides with general structure R1C(=NOH)NR2R3.
An anticholinergic agent is a substance that blocks the neurotransmitter acetylcholine in the central and the peripheral nervous system. These agents inhibit parasympathetic nerve impulses by selectively blocking the binding of the neurotransmitter acetylcholine 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, and many other parts of the body. Anticholinergics are divided into three categories in accordance with their specific targets in the central and peripheral nervous system: antimuscarinic agents, ganglionic blockers, and neuromuscular blockers.
VM (Edemo) is a "V-series" nerve agent closely related to the better-known VX nerve agent.
The Newport Chemical Depot, previously known as the Wabash River Ordnance Works and the Newport Army Ammunition Plant, was a 6,990-acre (28.3 km2) bulk chemical storage and destruction facility that was operated by the United States Army. It is located near Newport, in west central Indiana, thirty-two miles north of Terre Haute. The site was used as a production site for the solid explosives trinitrotoluene and RDX, as well as for heavy water. It also served as the production site for all of the U.S. military's nerve agent VX, when it was in use. All VX nerve agent at the site was neutralized by August 8, 2008. It was the third of the Army's nine chemical depots to completely destroy its stockpile.
Novichok is a series of binary chemical weapons developed by the Soviet Union and Russia between 1971 and 1993. Russian scientists who developed the nerve agents claim they are the deadliest ever made, with some variants possibly five to eight times more potent than VX, and others up to ten times more potent than soman.
VP stands for vice president, an officer in government or business below a president in rank.
Pleconaril (Picovir) is an antiviral drug that was being developed by Schering-Plough for prevention of asthma exacerbations and common cold symptoms in patients exposed to picornavirus respiratory infections. Pleconaril, administered either orally or intranasally, is active against viruses in the Picornaviridae family, including Enterovirus and Rhinovirus. It has shown useful activity against the dangerous strain enterovirus D68.
Butyrylcholinesterase, also known as BChE, BuChE, pseudocholinesterase, or plasma (cholin)esterase, is a nonspecific cholinesterase enzyme that hydrolyses many different choline-based esters. In humans, it is made in the liver, found mainly in blood plasma, and encoded by the BCHE gene.
Guanadrel is an antihypertensive agent. It is used in the form of its sulfate.
A-234 is an organophosphate nerve agent. It was developed in the Soviet Union under the Foliant program, and is one of the group of compounds referred to as Novichok agents, that were revealed by Vil Mirzayanov. In March 2018, the Russian ambassador to the UK, Alexander Yakovenko, claimed to have been informed by British authorities that A-234 had been identified as the agent used in the poisoning of Sergei and Yulia Skripal. Vladimir Uglev, one of the inventors of the Novichok series of compounds, said he was "99 per cent sure that it was A-234" in relation to the 2018 Amesbury poisonings, noting its unusually high persistence in the environment.
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 includes the muscles used for breathing.
Chinese VX (CVX) is an organophosphate nerve agent of the V-series. It is the structural isomer of VX.
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's a white solid that is very soluble and stable in water.
Crotylsarin (CRS) is an extremely toxic organophosphate nerve agent of the G-series. Like other nerve agents, CRS irreversibly inhibits the acetylcholinesterase. However, since the inhibited enzyme ages so rapidly, the inhibited enzyme can't be reactivated by oxime reactivators.
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