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Chloral hydrate information


Chloral hydrate
  Carbon, C
  Chlorine, Cl
  Oxygen, O
  Hydrogen, H
Names
Preferred IUPAC name
2,2,2-Trichloroethane-1,1-diol
Other names
  • Trichloroacetaldehyde monohydrate
  • Tradenames:
  • Aquachloral
  • Chloradorm
  • Chloratol[1]
  • Noctec
  • Novo-Chlorhydrate
  • Somnos
  • Somnote
Identifiers
CAS Number
  • 302-17-0 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
1698497
ChEBI
  • CHEBI:28142 checkY
ChEMBL
  • ChEMBL455917 checkY
ChemSpider
  • 2606 checkY
DrugBank
  • DB01563 checkY
ECHA InfoCard 100.005.562 Edit this at Wikidata
EC Number
  • 206-117-5
Gmelin Reference
101369
KEGG
  • D00265 checkY
PubChem CID
  • 2707
RTECS number
  • FM875000
UNII
  • 418M5916WG checkY
UN number 2811
CompTox Dashboard (EPA)
  • DTXSID7020261 Edit this at Wikidata
InChI
  • InChI=1S/C2H3Cl3O2/c3-2(4,5)1(6)7/h1,6-7H checkY
    Key: RNFNDJAIBTYOQL-UHFFFAOYSA-N checkY
  • InChI=1/C2H3Cl3O2/c3-2(4,5)1(6)7/h1,6-7H
    Key: RNFNDJAIBTYOQL-UHFFFAOYAY
SMILES
  • ClC(Cl)(Cl)C(O)O
Properties[3]
Chemical formula
CCl3CH(OH)2
Molar mass 165.39 g·mol−1
Appearance Colorless solid
Odor Aromatic, slightly acrid
Density 1.9081 g/cm3
Melting point 57 °C (135 °F; 330 K)
Boiling point 98 °C (208 °F; 371 K) (decomposes)
Solubility in water
660 g/(100 ml)
Solubility Very soluble in benzene, ethyl ether, ethanol
log P 0.99
Acidity (pKa) 9.66, 11.0[2]
Structure
Crystal structure
Monoclinic
Pharmacology
ATC code
N05CC01 (WHO)
Routes of
administration
Oral syrup, rectal suppository
Pharmacokinetics:
Bioavailability
Well absorbed
Metabolism
Hepatic and renal (converted to trichloroethanol)
Biological half-life
8–10 hours
Excretion
Bile, feces, urine (various metabolites not unchanged)
Legal status
  • BR: Class C1 (Other controlled substances)
  • CA: Unscheduled
  • US: Schedule IV
Hazards
GHS labelling:
Pictograms
GHS06: ToxicGHS07: Exclamation mark
Signal word
Danger
Hazard statements
H301, H315, H319
Precautionary statements
P264, P270, P280, P301+P310, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, P405, P501
Lethal dose or concentration (LD, LC):
LD50 (median dose)
1100 mg/kg (oral)
Safety data sheet (SDS) External MSDS[dead link]
Related compounds
Related compounds
Chloral, chlorobutanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Chloral hydrate is a geminal diol with the formula Cl3C−CH(OH)2. It was first used as a sedative and hypnotic in Germany in the 1870s. Over time it was replaced by safer and more effective alternatives but it remained in usage in the United States until at least the 1970s.[4] It sometimes finds usage as a laboratory chemical reagent and precursor. It is derived from chloral (trichloroacetaldehyde) by the addition of one equivalent of water.

  1. ^ Vardanyan, R.S.; Hruby, V.J. (2006). "Soporific Agents (Hypnotics and Sedative Drugs)". Synthesis of Essential Drugs. pp. 57–68. doi:10.1016/B978-044452166-8/50004-2. ISBN 978-0-444-52166-8.
  2. ^ Gawron, O.; Draus, F. (1958). "Kinetic Evidence for Reaction of Chloralate Ion with p-Nitrophenyl Acetate in Aqueous Solution". Journal of the American Chemical Society. 80 (20): 5392–5394. doi:10.1021/ja01553a018.
  3. ^ Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (85th ed.). CRC Press. pp. 3–98. ISBN 978-0-8493-0484-2.
  4. ^ Kales, Anthony (1 September 1970). "Hypnotic Drugs and Their Effectiveness: All-night EEG Studies of Insomniac Subjects". Archives of General Psychiatry. 23 (3): 226–232. doi:10.1001/archpsyc.1970.01750030034006. PMID 4318151.

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Chloral hydrate

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Hydrate

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sulfuric acid. Another example is chloral hydrate, CCl3−CH(OH)2, which can be formed by reaction of water with chloral, CCl3−CH=O. Many organic molecules...

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solvents. It reacts with water to form chloral hydrate, a once widely used sedative and hypnotic substance. Chloral was first prepared, and named, by the...

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Jean Tatlock

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died of "combined drug intoxication" with the sleeping medication chloral hydrate as the "major component". No illegal drugs were found in her system...

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conjunction with other anesthetics, such as ketamine, barbiturates, chloral hydrate, and halothane in order to provide reliable anesthesia effects. The...

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century. Treatment for insomnia in psychiatry dates back to 1869, when chloral hydrate was first used as a soporific. Barbiturates emerged as the first class...

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Jennie Bosschieter

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on October 19, 1900. She was an early victim of the date rape drug chloral hydrate which caused her death. Her death received national news coverage and...

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betaine complex of trimethylglycine with chloral hydrate, which acts as an extended-acting formulation of chloral hydrate which is then metabolized into trichloroethanol...

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Trichloroethylene

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isomerises to trichloroacetaldehyde (chloral). Chloral hydrates to chloral hydrate in the body. Chloral hydrate is either reduced to 2,2,2-trichloroethanol...

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Benzodiazepine

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amphetamine, mescaline, lysergic acid diethylamide (LSD), cannabis, chloral hydrate, theophylline, IBMX and others, can have strong effects on certain...

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Hydroxyzine (Atarax, Vistaril) Promethazine (Phenergan) General anaesthetics Chloral hydrate Chlorobutanol Chloroform Cyclopropane Desflurane Diethyl ether Enflurane...

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Sodium thiopental

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Methaqualone

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Chlorobutanol

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sedative, hypnotic and weak local anesthetic similar in nature to chloral hydrate. It has antibacterial and antifungal properties. Chlorobutanol is typically...

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Clonazepam

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Midazolam

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