水合氯醛

Chloral Hydrate

HCID 2707CAS 302-17-0

基本信息

标准SMILES
OC(O)C(Cl)(Cl)Cl
InChIKey
RNFNDJAIBTYOQL-UHFFFAOYSA-N
分子式
C2H3Cl3O2
平均分子量
165.4 g/mol
单同位素质量
163.91986238

概述

Chloral Hydrate can cause cancer according to California Labor Code.

名称与标识

首选名称
Chloral Hydrate
IUPAC
2,2,2-trichloroethane-1,1-diol
中文名
水合氯醛
英文名
Chloral hydrate
分子式
C2H3Cl3O2
分子量
165.4

名称与别名

chloral hydrate302-17-02,2,2-Trichloroethane-1,1-diolTrichloroacetaldehyde hydrateNoctecTosylChloral monohydrateChloralduratChloralhydratePhaldroneNycotonEscre
展开更多名称
水氯醛水合氯醛含水氯醛水化氯醛水合氯乙醛三氯乙二醇水合三氯乙醛氯醛 水合物水合氯醛试液水合氯醛ARTCAHSoraLTrichloroCHLORAL HYDRATE SOLUTIONTRICHLOROACETALDEHYDE MONOHYDRATEHydral
ChloradormCohidrateFelsulesKessodrateOradrateRectulesTrawotoxDormal

数据库标识

CAS
302-17-0
PubChem CID
2707
DTXSID
DTXSID7020261
ChEMBL
CHEMBL455917
ChEBI
CHEBI:28142
UNII
418M5916WG
EC Number
206-117-5
Nikkaji
J1.517B

性质

结构计算性质

XLogP
1
极性表面积
40.5 Ų
氢键供体
2
氢键受体
2
可旋转键
0
重原子
7

实验与物化性质

Chemical Classes · 2 条

Other Classes -> Halogenated Alcohols

Carcinogens

Drugs · 6 条

DEA NFLIS-Drug Category -> Depressants and Tranquilizers

DEA Schedule IV Controlled Substance -> Depressants

Pharmaceuticals -> Antiepileptics

Pharmaceuticals

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Used in Switzerland

pH3.5-4.4 (10% soln in water)
SpringerMaterials PropertiesMoessbauer quadrupole effect
PesticidesPesticide -> EPA IRIS
LogP · 2 条

log Kow = 0.99

0.99

物理化学性质

熔点
57 °C · 57 °C(lit.)
沸点
97 °C · 97 °C
密度
1.43 g/mL · 1.43 g/mL at 20 °C
蒸气压
19.998 hPa · 19.998hPa at 25℃
折射率
1.4603 · 1.4603 (estimate)
闪点
16 °C · 16 °C

化学性质

无色单斜片状结晶。熔点53-57℃。溶于水、乙醇和醚。1ml水可溶解水合氯醛:0℃时2.4g;25℃8.3g;40℃14.3g。1g水合氯醛可溶于:1.3ml乙醇,2ml氯仿,1.5ml乙醚。

安全与法规

GHS分类

GHS Classification · 6 条

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P316, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Danger

H301 (99%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P316, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

危害信息

Regulatory Information · 6 条

Chemical: 1,1-Ethanediol, 2,2,2-trichloro-

Hazard Traits - Carcinogenicity; Neurotoxicity

DEA schedule IV controlled substance

Status: Active Update: 01-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/17704

Chloral hydrate: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison
Fire Hazards · 2 条

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

Not combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Fire PotentialCombustible when exposed to heat or flame.
Health Hazards · 1 条

SYMPTOMS: Symptoms of exposure to this compound include general anesthesia, cardiac arrythmias and blood pressure depression. Other symptoms include hemorrhagic gastritis, enteritis, central nervous system depression, coma, severe respiratory depression, ventricular tachycardia and cardiac arrest. Dermatitis, swelling of the lids, hyperemia, edema of the conjuctiva and a sensation of irritation and tearing may also occur. Exposure may result in gastric irritation, rapid circulatory collapse, kidney and liver damage, heart damage, psychosis and leukopenia. Flatulence, abdominal distension, nausea, headache, giddiness, rashes and blood dyscrasias can occur.

Hazards Summary · 1 条

A skin, eye, and respiratory tract irritant; A CNS depressant; [ICSC] A skin and mucous membrane irritant; May cause eye injury; [HSDB] A skin and eye irritant; [eChemPortal: ERMA; ESIS] An irritant; [MSDSonline] Liver injury reported after lethal doses, but not after therapeutic doses; [INCHEM: CICADS]

安全与防护

Fire Fighting · 2 条

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

In case of fire in the surroundings, use appropriate extinguishing media. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 条

Fresh air, rest. Artificial respiration may be needed. Refer immediately for medical attention.

Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention.

First Aid · 1 条

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Safe StorageSeparated from strong bases and food and feedstuffs.
Storage ConditionsChloral hydrate oral solution should be stored in tight, light-resistant containers. Chloral hydrate capsules should be stored at 15-30 °C.
Nonfire Spill Response · 1 条

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

毒理信息

Body Burden · 2 条

Chloral hydrate has been detected in /human/ ... milk ... .

Chloral hydrate and its metabolite, trichloroethanol reached 50-100% /in breast milk/ of maternal blood levels in most of 50 women given 1.3 g rectally.

Interactions · 5 条

Prolonged concurrent use /with other addictive medications especially CNS depressants with habituating potential/ may increase the risk of habituation; caution is recommended.

Concurrent use /with alcohol or other CNS depression-producing medications/ may increase the CNS depressant effect of either these medications or chloral hydrate; caution is recommended and dosage of one or both agents should be reduced.

Hypoprothrombinemic effects may be increased when these medications /coumarin- or indandione-derivative anticoagulants/ are used concurrently with chloral hydrate, particularly during the first 2 weeks of concurrent therapy, because of displacement of the anticoagulant from its plasma protein binding sites; with continued concurrent use, anticoagulant activity may return to baseline level or be decreased; frequent prothrombin-time determinations may be required, especially during initiation of chloral hydrate therapy, to determine if dosage adjustment of the anticoagulant is necessary.

Administration of chloral hydrate followed by intravenous furosemide within 24 hours may result in diaphoresis, hot flashes, and variable blood pressure, including hypertension, due to a hypermetabolic state caused by displacement of thyroxine from its bound state.

For more Interactions (Complete) data for CHLORAL HYDRATE (13 total), please visit the HSDB record page.

Target OrgansGastrointestinal
Hepatotoxicity · 1 条

Chloral hydrate has been in clinical use for many decades and has not been linked to serum enzyme elevations during therapy or instances of clinically apparent liver injury. While prospective studies of the effects of chloral hydrate on liver tests have not been done, the absence of reported instances of liver injury attributable to chloral hydrate suggests that it has little or no hepatic toxicity. Chloral hydrate has been linked to hypersensitivity reactions such as rash, fever and eosinophilia. Chloral hydrate also has major drug-drug interactions with oral anticoagulants, antidepressants and alcohol. In patients with cirrhosis and hepatic decompensation, chloral hydrate can trigger or worsen hepatic encephalopathy.

Ecotoxicity Values · 4 条

EC50; Species: Daphnia magna (Water flea); Conditions: freshwater; pH 8; Concentration: 630 mg/L for 24 hr; Effect: behavior, equilibrium /Conditions of bioassay not specified in source examined/

EC50; Species: Daphnia magna (Water flea); Conditions: freshwater; Concentration: 500 mg/L for 48 hr; Effect: intoxication, immobilization /Conditions of bioassay not specified in source examined/

LC50; Species: Daphnia magna (Water flea, age < or =24 hr); Conditions: freshwater; static, 20-22 °C, pH 7.6-7.7; Concentration: 510 mg/L for 24 hr

LC50; Species: Leuciscus idus melanotus (Carp); Conditions: freshwater; Concentration: 1720 mg/L for 48 hr /Conditions of bioassay not specified in source examined/

Environmental Fate · 3 条

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 82(SRC), determined from a log Kow of 0.99(2) and a regression-derived equation(3), indicates that chloral hydrate is expected to have high mobility in soil(SRC). Volatilization of chloral hydrate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.7X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 15 mm Hg(4), and water solubility, 7.93X10+5 mg/L(5). Chloral hydrate is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Biodegradation data for chloral hydrate were not available(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 82(SRC), determined from a log Kow of 0.99(2) and a regression-derived equation(3), indicates that chloral hydrate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 4.1X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 15 mm Hg(4), and water solubility, 7.93X10+5 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 12 days and 88 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data for chloral hydrate were not available(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chloral hydrate, which has a vapor pressure of 15 mm Hg at 25 deg(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase chloral hydrate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 8 days(SRC), calculated from its rate constant of 1.9X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). The related aldehyde chloral is readily photolyzed in sunlight based on an atmospheric half-life of 4.5-6 hours for this compound under conditions representing the solar flux during summer months(4).

法规信息

FDA Requirements · 5 条

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: chloral hydrate is included in external analgesic drug products - analgesic and anesthetic drug products.

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: chloral hydrate is included in external analgesic drug products - counter irritant drug products.

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: chloral hydrate is included in external analgesic drug products - fever blister and cold sore treatment drug products.

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: chloral hydrate is included in external analgesic drug products - poison ivy, poison oak, and poison sumac drug products.

For more FDA Requirements (Complete) data for CHLORAL HYDRATE (8 total), please visit the HSDB record page.

State Drinking Water Guidelines(ME) MAINE 70 ug/l
Federal Drinking Water GuidelinesEPA 60 ug/l

安全数据

wgk
2
tsca
TSCA listed
毒性
LD50 oral in rat: 479mg/kg
RTECS号
FM8750000
包装类别
III
危险等级
6.1(b)

毒性防护

急性毒性口服-大鼠 LD50: 479 毫克/公斤; 口服-小鼠 LD50: 1100 毫克/

包装储运 · 3 条

可燃性危险特性遇热, 明火燃烧; 热分解排出有毒氯化物烟雾

储运特性库房低温通风干燥; 防明火, 高温, 与食品原料, 氧化剂分开存放

灭火剂二氧化碳, 泡沫, 干粉

化学与工业

药理信息

ATC Code · 2 条

N - Nervous system

QN - Nervous system

Mechanism of Action · 1 条

Chloral hydrate has CNS depressant effects similar to those of paraldehyde and the barbiturates. The mechanism of action of the drug is not completely known. The CNS depressant effect of chloral hydrate is believed to result mainly from its metabolite, trichloroethanol, although some animal studies have indicated that the rapid onset of sedation and hypnosis that chloral hydrate produces may be due to chloral hydrate itself and that the prolonged duration of action may be due to trichloroethanol.

Biological Half-Life · 4 条

The plasma half-life of trichloroethanol, the active metabolite, is about 7 to 10 hours.

The average half-life of trichloroethanol glucuronide was 6.7 hr. The average plasma half-life for chloral hydrate metabolites was 8.2 hr; the half-life of the third chloral hydrate metabolite, trichloroacetic acid, was about four days, as it binds extensively to plasma proteins.

The plasma half-life for therapeutic doses of chloral hydrate is 4 to 5 min, whereas for trichloroethanol /a metabolite/ is 8 to 12 hr and for trichloroacetic acid /a metabolite/, 67 hr.

This study was designed to characterize the kinetics of chloral hydrate (CH) metabolism, and the formation and elimination of trichloroacetate (TCA), dichloroacetate (DCA), trichloroethanol (TCOH), and trichloroethanol glucuronide (TCOG) in male B6C3F1 mice. Mice were dosed with 67.8, 678, and 2034 umol/kg of CH through the tail vein. ... After intravenous administration, CH rapidly disappeared from blood with a terminal half-life ranging from 5 to 24 min. ... The terminal half-lives of TCOH and TCOG were similar, ranging from 0.2 to 0.7 hr. ...

Metabolism/Metabolites · 6 条

Metabolized by the liver and erythrocytes to form trichloroethanol, an active metabolite. This reaction is catalyzed by alcohol dehydrogenase and other enzymes. Oxidation of chloral hydrate and trichloroethanol to trichloroacetic acid in the liver and kidneys also occurs to a lesser extent. Trichloroethanol also undergoes glucuronidation to produce an inactive metabolism.

/Chloral hydrate/ biotransformation to trichloroethanol must be rapid, since no parent compound could be detected in even the first samples taken 10 min after administration of 15 mg/kg bw to volunteers.

Chloral hydrate is metabolized by the liver and erythrocytes to form trichloroethanol (an active metabolite). The reduction of chloral hydrate to trichloroethanol (the major metabolite) is catalyzed by alcohol dehydrogenase and other enzymes. ... A small but variable amount of chloral hydrate and a larger portion of trichloroethanol are oxidized to trichloroacetic acid (an inactive metabolite), mainly in the liver and kidneys. Trichloroethanol may also be conjugated with glucuronic acid to form trichloroethanol glucuronide (urochloralic acid), an inactive metabolite. ... The quantities of metabolites excreted in the urine appear to be quite variable not only between different individuals but may even vary in the same individual on different days.

In mammalian species, chloral hydrate is rapidly reduced to trichloroethanol, the metabolite that appears to be responsible for the hypnotic properties of the drug. ... In rodents, a slightly different metabolic pattern is seen, as chloral hydrate is oxidized directly to trichloroacetic acid, and the oxidative pathway from trichloroethanol to trichloroacetate that is observed in humans seems to be absent.

As < 50% of an administered dose of chloral hydrate was recovered as metabolites in urine, yet unknown biotransformation reactions may exist for chloral hydrate in humans.

For more Metabolism/Metabolites (Complete) data for CHLORAL HYDRATE (10 total), please visit the HSDB record page.

MeSH Pharmacological ClassificationDrugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
Absorption, Distribution and Excretion · 6 条

Rapidly absorbed in the GI tract following oral or rectal administration. Chloral hydrate and its active metabolite, trichloroethanol, have been detected in CSF, umbilical cord blood, fetal blood, and amniotic fluid.

Trichloroethanol, trichloroethanol glucuronide, and trichloroacetic acid are excreted in the urine. Some trichloroethanol glucuronide may be secreted into bile and excreted in the feces.

Following therapeutic doses of chloral hydrate, only small, clinically insignificant amounts of the active metabolite are distributed into milk.

Chloral hydrate is rapidly absorbed from the GI tract following oral or rectal administration. Plasma concentrations of chloral hydrate (or the major metabolite, trichloroethanol) required for sedative or hypnotic effects are unknown. Following administration of a single chloral hydrate dose of 15 mg/kg, peak plasma concentrations of trichloroethanol ranged from 7-10 ug/mL in one study.

After oral administration, chloral hydrate is rapidly absorbed from the gastrointestinal tract. Peak levels of trichloroethanol and trichloroethanol glucuronide were reached within 20- 60 min after oral administration of aqueous solutions.

The volume of distribution of chloral hydrate is 0.6 L/kg.

用途与制造

Uses · 6 条

Used as a drug (sedative and hypnotic), a rubefacient and liniment, a glue peptizing agent, and a chemical intermediate; [HSDB] Formed as by-product of drinking water chlorination; [IPCS]

Working with Glues and Adhesives [Category: Other]

As glue peptizing agent

Manufacture of DDT

Medicine (sedative), manufacture of DDT, linaments.

Hypnotic ... possesses anticonvulsant and muscle relaxant activities.

U.S. Imports · 4 条

(1972) 2.83X10+7 G

(1975) 4.8X10+7 G

(1984) 5.41X10+6 g

(1986) 1.03X10+5 lb

U.S. Production · 2 条

(1972) 1.14X10+10 G (ANHYDROUS CHLORAL)

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#846]

Methods of Manufacturing · 3 条

Made by adding required amt of water to trichloroacetaldehyde.

Insoluble chloral hydrate forms from the reaction of chloral with water.

Chloral hydrate is formed by adding one molecule of water to the carbonyl group of chloral (2,2,2-trichloroacetaldehyde).

Formulations/Preparations · 5 条

Dosage Forms-Capsules: 250 and 500 mg, and 1 g; Elixir: 500 mg/5 mL; Suppositories: 325, 500, and 650 mg. Syrup: 250 and 500 mg/5 mL.

Noctec capsules contain 500 mg chloral hydrate per capsule, Noctec syrup contains 500 mg chloral hydrate per 5 mL

Grade: Technical, USP

Chloropent injection; Intravenous anesthetic; Each mL contains: chloral hydrate 42.5 mg; magnesium sulfate 21.2 mg; pentobarbital 8.86 mg; ethyl alcohol 14.25%; propylene glycol 33.8%; purified water, qs (for cattle & horses)

For more Formulations/Preparations (Complete) data for CHLORAL HYDRATE (7 total), please visit the HSDB record page.

Use ClassificationAnimal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
应用领域 · 4 条

用途催眠药。DDT的中间体。

用途水合氯醛可用于银的检定和测定;有机合成;制造三氯乙酸、DDT等;镀镍光亮剂及晶粒细化剂。

用途用作镀镍中间体,也用作医药和农药中间体,用于制作敌百虫,除草剂等多种农药的中间体。用于半光镍光亮剂, 调节光亮镍 与半光亮镍之间的电位差。水合氯醛可以做催眠药和抗惊厥药,用于失眠烦躁不安及惊厥。

用途用作农药、医药中间体,也用于制备氯仿、三氯乙醛等

制备方法

生产方法将三氯乙醛、对苯二酚、碳酸钠和碳酸钙一起搅拌,加热至90℃。减压蒸馏,收集30℃(5.32-10.64kPa)馏分,得精制三氯乙醛。搅拌下缓缓加入0.182倍量的水,至反应液成粥状,静置结晶。过滤,低温干燥,得水合氯醛。

试剂价格

23247 · 2.5kg
水合氯醛Chloral hydrate, 98.5%, Thermo Scientific Chemicals — 8050元
C0073 · 25G
水合三氯乙醛Chloral Hydrate — 230元

供应商50 家

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
武汉博莱特化工有限公司+86-027-85583407 +86-13554014698 · [email protected]

相关反应

212 条

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