- Product Name:
- Chloral hydrate
- 2,2,2-TRICHLOROETHANE-1,1-DIOL HYDRATE
- TRICHLOROACETALDEHYDE HYDRATE
- TRICHLOROACETALDEHYDE MONOHYDRATE
- CHLORAL HYDRATE, CRYSTALLIZED
- CHLORAL HYDRATE SOLUTION (1 G/ML) REAG. DAB
- Product Categories:
- Method 551EPA
- Method 8240
- 500 Series Drinking Water Methods
- 8000 Series Solidwaste Methods
- Bioactive Small Molecules
- Building Blocks
- C1 to C6
- Carbonyl Compounds
- Cell Biology
- Chemical Synthesis
- Organic Building Blocks
- Mol File:
Chloral hydrate Chemical Properties
- Melting point:
- 57 °C(lit.)
- Boiling point:
- 97 °C
- 1.43 g/mL at 20 °C
- refractive index
- 1.4603 (estimate)
- Flash point:
- 16 °C
- storage temp.
- Very soluble in water, freely soluble in ethanol (96 per cent).
- 10(at 25℃)
- Specific Gravity
- 3.5-5.5 (20℃, 10%)
- Water Solubility
- 660 g/100 mL
- Stable, but may be air or light sensitive. Incompatible with alcohols, cyanides, iodine, strong bases, carbonates.
- CAS DataBase Reference
- 302-17-0(CAS DataBase Reference)
- NIST Chemistry Reference
- Chloral hydrate(302-17-0)
- 2A (Vol. 63, 84, 106) 2014
- EPA Substance Registry System
- Chloral hydrate (302-17-0)
- Hazard Codes
- Risk Statements
- Safety Statements
- UN 3286 3/PG 2
- WGK Germany
- HS Code
- Hazardous Substances Data
- 302-17-0(Hazardous Substances Data)
- LD50 oral in rat: 479mg/kg
Chloral hydrate Usage And Synthesis
Chloral hydrate was first synthesized in 1832 by Justus von Liebig and was the first synthetic central nervous system (CNS) depressant. It was used to treat delirium tremens, insomnia, and anxiety, although it is considered an unapproved drug by the US Food and Drug Administration. Initially considered to be a safer alternative to opium, it was noted to produce rapid unconsciousness when combined with ethanol. Physical dependence can occur with chronic use.
colourless crystals with a pentrating odour
Chloral is a combustible, oily liquid with a pungent irritating odor.
Trichloroacetaldehyde Hydrate is a useful chemical reagent used as a sedative/hypnotic agent for the short-term treatment of insomnia. First developed in 1832, chloral hydrate is the oldest sleep medication still in use today. This medication is also used to calm you just before surgery or other procedures. It works by affecting certain parts of the brain to cause calmness.
Studies have shown that when used in pediatric sedation side effects such as hallucination, excessive sleep and seizures were observed. Drowsiness and trouble waking up in the morning, nausea, vomiting, stomach pain, diarrhea, and headache may occur. Stomach problems can be reduced by taking chloral hydrate with a full glass of water. It is sometimes administered to patients being treated with cyclophosphamide and it is known to inhibit some aldehyde dehydrogenases.
Besides, Chloral hydrate is a starting point for the synthesis of other organic compounds. It is the starting material for the production of chloral, which is produced by the distillation of a mixture of chloral hydrate and sulfuric acid, which serves as the desiccant.
The sedative–hypnotic action of chloral hydrate should be explained by the formation of trichloroethanol, which is synthesized as a result of its reduction in tissues. Despite the fact that the precise mechanism of action of chloral hydrate is not known, it evidently acts analogous to ethanol on the CNS by increasing membrane permeability, which leads to sedation or sleep. Chloral hydrate can be used for insomnia as an alternative to benzodiazepines.
Chloral hydrate is used as a sedative hypnotic, more commonly in pediatrics. With the advent of newer sedative hypnotics, its use has significantly decreased. It is also a drug of abuse, particularly in combination with ethanol to produce an amnestic effect in an individual who ingests it unknowingly.
ChEBI: An organochlorine compound that is the hydrate of trichloroacetaldehyde.
Chloral hydrate (Noctec, Somnos) was developed in the late 1800s and is still used as a sedative–hypnotic agent. It is a hydrated aldehyde with a disagreeable smell and taste that is rapidly reduced in vivo to trichloroethanol, which is considered to be the active metabolite. It produces a high incidence of gastric irritation and allergic responses, occasionally causes cardiac arrhythmias, and is unreliable in patients with liver damage.
Chloral hydrate, trichloroacetaldehydemonohydrate, CCl3CH(OH)2 (Noctec), is analdehyde hydrate stable enough to be isolated. The relativestability of this gem-diol is largely a result of an unfavorabledipole–dipole repulsion between the trichloromethyl carbonand the carbonyl carbon present in the parent carbonylcompound.
Chloral hydrate is unstable in alkaline solutions, undergoingthe last step of the haloform reaction to yield chloroformand formate ion. In hydroalcoholic solutions, it formsthe hemiacetal with ethanol. Whether or not this compoundis the basis for the notorious and potentially lethal effect of the combination of ethanol and chloral hydrate (the “MickeyFinn”) is controversial. Synergism between two differentCNS depressants also could be involved. Additionally,ethanol, by increasing the concentration of nicotinamideadenine dinucleotide (NADH), enhances the reduction ofchloral to the more active metabolite trichloroethanol, andchloral can inhibit the metabolism of alcohol because it inhibitsalcohol dehydrogenase. Chloral hydrate is a weak acidbecause its CCl3 group is very strong electron withdrawing.A 10% aqueous solution of chloral hydrate has pH 3.5 to4.4, which makes it irritating to mucous membranes in thestomach. As a result, GI upset commonly occurs for thedrug if undiluted or taken on an empty stomach. Chloral hydrateas a capsule, syrup, or suppository is currently available.
Transparent colorless crystals or white crystalline solid. Aromatic penetrating slightly acrid odor and a slightly bitter caustic taste. Alcoholic solution (1 in 20) does not at once redden moistened blue litmus paper.
Air & Water Reactions
Chloral hydrate is incompatible with alkalis, alkaline earth metals, alkali carbonates and soluble barbiturates. Chloral hydrate is decomposed by sodium hydroxide. Chloral hydrate reduces ammoniacal silver nitrate. Chloral hydrate liquefies when triturated with an equal quantity of menthol, camphor or thymol. . Reaction of Chloral hydrate with hydroxylamine produces toxic hydrogen cyanide gas, Org. Synth., 1941, Vol. 1, 377.
Overdose toxic, hypnotic drug, dangerous to eyes. Probable carcinogen.
Flash point data for Chloral hydrate are not available; however, Chloral hydrate is probably combustible.
Although it is suggested that chloral hydrate per semay act as a hypnotic,chloral hydrate is very quickly convertedto trichloroethanol, which is generally assumed toaccount for almost all of the hypnotic effect. Thetrichloroethanol is metabolized by oxidation to chloral andthen to the inactive metabolite, trichloracetic acid, which is also extensively metabolized to acylglucuronidesvia conjugation with glucuronic acid. It appears tohave potent barbiturate-like binding to GABAAreceptors.Although an old drug, it still finds use as a sedative in nonoperatingroom procedures for the pediatric patient.
A human poison by ingestion and possibly other routes. Poison experimentally by ingestion, intravenous, and rectal routes. Moderately toxic by subcutaneous, parenteral, and intraperitoneal routes, Experimental reproductive effects. Human systemic effects by ingestion: general anesthetic, cardiac arrhythmias, blood pressure depression, eye effects, coma, pulse rate increase, arrhythmias. Human mutation data reported. Questionable carcinogen with experimental carcinogenic and tumorigenic data by skin contact. A sedative, anesthetic, and narcotic. Combustible when exposed to heat or flame. When heated to decomposition it emits toxic fumes of Cl-.
Chloral hydrate, 2,2,2-trichloro-1,1-ethandiol (4.3.1), is synthesized either by chlorination of ethanol or chlorination of acetaldehyde and the subsequent addition of water molecules to the resulting trichloroacetic aldehyde .
Chloral is used as an intermediate in the manufacture of such pesticides as DDT, methoxychlor, DDVP, naled, trichlorfon, and TCA. Chloral is also used in the production of chloral hydrate; used as a therapeutic agent with hypnotic, sedative, and narcotic effects; used in a time prior to the introduction of barbiturates
Chloral hydrate has not been adequately tested for teratogenicity, reproductive effects, or chronic toxicity. Similarly, no histological evaluations have been conducted.
Chloral hydrate is a CNS depressant, but its mechanism of action is not well known. Coingestion with ethanol produces enhanced effects by several mechanisms. First, ethanol competes for alcohol and aldehyde dehydrogenase, which then prolongs the half-life of ethanol. The metabolism of ethanol generates the reduced form of NADH, which is a cofactor for the metabolism of chloral hydrate to its active metabolite trichloroethanol. Finally, ethanol inhibits the conjugation of trichloroethanol to its inactive form urochloralic acid. This results in enhanced CNS depression.
UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
Chloral hydrate has been detected at 5 mg l-1 in the US drinking water supply. Although chloral hydrate does not exist naturally, it can be produced as a by-product of chlorination of water at water treatment facilities, specifically in exposed water with high amounts of humic and fulvic substances.
Chloral hydrate reacts with strong bases forming chloroform. Contact with acids, or exposure to light may cause polymerization. Reacts with water, forming chloral hydrate. Reacts with oxidizers, with a risk of fire or explosions.
Incineration after mixing with another combustible fuel; care must be taken to assure complete combustion to prevent phosgene formation; an acid scrubber is necessary to remove the halo acids produced.
Chloral hydrate Preparation Products And Raw materials
- Poly(ethylene glycol)
- Iron chloride hexahydrate
- hydrazine hydrate
- Citric acid monohydrate
- Ethylene glycol diacetate
- Trichloroisocyanuric acid
- Ethylene glycol
- Chloral hydrate
- 2-Butoxyethyl acetate