|
|
| Line 1: |
Line 1: |
| − | {{Chembox new
| |
| − | | ImageFile = Chloral-hydrate-montage.png
| |
| − | | ImageSize = 250px
| |
| − | | IUPACName = 2,2,2-trichloroethane-1,1-diol
| |
| − | | OtherNames = trichloroacetaldehyde monohydrate<br/>Tradenames: Aquachloral, Novo-Chlorhydrate, Somnos, Noctec, Somnote
| |
| − | | Section1 = {{Chembox Identifiers
| |
| − | | CASNo = 302-17-0
| |
| − | | ChemSpiderID = 2606
| |
| − | | PubChem = 2707
| |
| − | | SMILES = ClC(Cl)(Cl)C(O)O
| |
| − | | InChI=1/C2H3Cl3O2/c3-2(4,5)1(6)7/h1,6-7H
| |
| − | }}
| |
| − | | Section2 = {{Chembox Properties
| |
| − | | Formula = C<sub>2</sub>H<sub>3</sub>Cl<sub>3</sub>O<sub>2</sub>
| |
| − | | MolarMass = 165.403 g/mol
| |
| − | | Appearance = Colorless solid
| |
| − | | Density = 1.91 g/cm<sup>3</sup>
| |
| − | | MeltingPtC = 57
| |
| − | | BoilingPtC = 98
| |
| − | | Solubility =
| |
| − | }}
| |
| − | | Section5 = {{Chembox Pharmacology
| |
| − | | AdminRoutes = Oral capsule/syrup, rectal [[suppository]]
| |
| − | | Bioavail = well absorbed
| |
| − | | Metabolism = converted to trichloroethanol, hepatic and renal
| |
| − | | HalfLife = 8–10 hours in plasma
| |
| − | | ProteinBound =
| |
| − | | Excretion = bile, feces, urine (various metabolites not unchanged)
| |
| − | | Legal_status =
| |
| − | | Legal_US = Schedule IV
| |
| − | | Legal_UK =
| |
| − | | Legal_AU =
| |
| − | | Legal_CA =
| |
| − | | PregCat =
| |
| − | | PregCat_AU =
| |
| − | | PregCat_US = C}}
| |
| − | | Section7 = {{Chembox Hazards
| |
| − | | ExternalMSDS = [http://www.pcl.ox.ac.uk/MSDS/CH/chloral_hydrate.html External MSDS]
| |
| − | | EUClass = Harmful ('''Xn''')
| |
| − | | MainHazards =
| |
| − | | FlashPt =
| |
| − | | Autoignition =
| |
| − | | RPhrases = {{R22}} {{R36}} {{R37}} {{R38}}
| |
| − | }}
| |
| − | | Section8 = {{Chembox Other
| |
| − | | OtherCpds = [[Chloral]], [[chlorobutanol]]}}
| |
| − | }}
| |
| | | | |
| − | '''Chloral hydrate''' is a [[sedative]] and [[hypnotic]] [[approved drug|drug]] as well as a [[chemical reagent]] and precursor. The name chloral hydrate indicates that it is formed from [[chloral]] (trichloroacetaldehyde) by the addition of one molecule of water. Its [[chemical formula]] is [[Carbon|C]]<sub>2</sub>[[Hydrogen|H]]<sub>3</sub>[[Chlorine|Cl]]<sub>3</sub>[[Oxygen|O]]<sub>2</sub>.
| |
| − |
| |
| − | This chemical is produced from [[chlorine]] and [[ethanol]] in acidic solution. In addition, it is a minor by-product of the [[chlorination]] of [[water]] in the presence of organic residues. It is soluble in both water and alcohol, readily forming concentrated solutions.
| |
| − |
| |
| − | Chloral hydrate has been used as a clearing agent of [[chitin]] (and fibers), and as a key ingredient of Hoyer's mounting medium, which is used for slide-mounted observation of organisms under the [[microscope]]. On the downside, [[ethanol|alcoholic]] drinks have sometimes been laced with chloral hydrate to incapacitate a person. In slang, this has been referred to as serving someone a "[[Mickey Finn (drugs)|Mickey Finn]]," or "slipping a mickey."
| |
| − |
| |
| − | == Discovery and early use ==
| |
| − |
| |
| − | Chloral hydrate was discovered through the [[Halogenation|chlorination]] of [[ethanol]] in 1832 by [[Justus von Liebig]] in [[Gießen]].<ref>{{cite journal
| |
| − | | title = Ueber die Zersetzung des Alkohols durch Chlor
| |
| − | | author = Justus Liebig
| |
| − | | journal = Annalen der Pharmacie
| |
| − | | volume = 1
| |
| − | | issue = 1
| |
| − | | pages = 31–32
| |
| − | | year = 1832
| |
| − | | url =
| |
| − | | doi = 10.1002/jlac.18320010109}}</ref><ref>{{cite journal
| |
| − | | title = Ueber die Verbindungen, welche durch die Einwirkung des Chlors auf Alkohol, Aether, ölbildendes Gas und Essiggeist entstehen
| |
| − | | author = Justus Liebig
| |
| − | | journal = Annalen der Pharmacie
| |
| − | | volume = 1
| |
| − | | issue = 2
| |
| − | | pages = 182–230
| |
| − | | year = 1832
| |
| − | | url =
| |
| − | | doi = 10.1002/jlac.18320010203}}</ref> Its [[sedative]] properties were first published in 1869 and subsequently, because of its easy synthesis, its use was widespread.<ref>{{cite book
| |
| − | | author = Liebreich, Oskar
| |
| − | | title = Das Chloralhydrat : ein neues Hypnoticum und Anaestheticum und dessen Anwendung in der Medicin ; eine Arzneimittel-Untersuchung
| |
| − | | year = 1869
| |
| − | | place Berlin
| |
| − | | publisher = Müller}}</ref>
| |
| − | It was widely [[Drug addiction|abused]] and [[Medical prescription|misprescribed]] in the late nineteenth century.
| |
| − |
| |
| − | ==Production==
| |
| − | Chloral hydrate is produced from [[chlorine]] and [[ethanol]] in acidic solution. In basic conditions the [[haloform reaction]] takes place and [[chloroform]] is produced.
| |
| − |
| |
| − | :4 Cl<sub>2</sub> + C<sub>2</sub>H<sub>5</sub>OH + H<sub>2</sub>O → Cl<sub>3</sub>CCH(OH)<sub>2</sub> + 5 HCl
| |
| − |
| |
| − | Together with [[chloroform]], chloral hydrate is a minor side-product of the [[chlorination]] of [[water]], if organic residues are present in the water. Concentrations rarely exceed 5 [[microgram]]s per [[liter]] (µg/l).
| |
| − |
| |
| − | ==Uses==
| |
| − | ===Building block===
| |
| − | Chloral hydrate is a cheaply available building block chemical. 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]].
| |
| − |
| |
| − | Notably, it is used to synthesize [[isatin]]. In this synthesis, chloral hydrate reacts with [[aniline]] and [[hydroxylamine]] to give a condensation product that cyclizes in [[sulfuric acid]] to give the target compound:<ref>{{OrgSynth | title = Isatin | author = C. S. Marvel and G. S. Hiers | collvol = 1 | collvolpages = 327 | year = 1941 | prep = cv1p0327}}</ref>
| |
| − |
| |
| − | [[Image:Synthesis of isatin.png|400px]]
| |
| − |
| |
| − | ===Sedative===
| |
| − | Chloral hydrate is used for the short-term treatment of [[insomnia]] and as a sedative before minor medical or dental treatment. It was largely displaced in the mid-20th century by [[barbiturate]]s<ref>Tariq, Syed H. and Shailaja Pulisetty; “Pharmacotherapy for Insomnia,” Clinics in Geriatric Medicine (24), 2008 p. 93-105 PMID: 18035234</ref> and subsequently by [[benzodiazepine]]s. It was also formerly used in veterinary medicine as a [[general anesthetic]]. Today, it is commonly used as an ingredient in the veterinary anesthetic [[Equithesin]]. It is also still used as a sedative prior to [[Electroencephalography|EEG]] procedures, as it is one of the few available sedatives that does not suppress [[epilepsy|epileptiform]] discharges.
| |
| − |
| |
| − | In therapeutic doses for insomnia chloral hydrate is effective within sixty [[minute]]s, it is [[Metabolism|metabolized]] within 4 minutes into [[trichloroethanol]] by erythrocytes and plasma esterases and many hours later into [[trichloroacetic acid]]. Higher doses can depress [[Respiration (physiology)|respiration]] and [[blood pressure]]. An [[overdose]] is marked by confusion, [[convulsion]]s, [[nausea]] and [[vomiting]], severe drowsiness, slow and irregular breathing, [[cardiac arrhythmia]] and weakness. It may also cause [[liver]] damage and is moderately [[addictive]], as [[chronic (medicine)|chronic]] use is known to cause [[Chemical dependency|dependency]] and [[withdrawal]] symptoms. The chemical can potentiate various [[anticoagulant]]s and is weakly [[mutagen]]ic [[in vitro]] and [[in vivo]].
| |
| − |
| |
| − | Chloral hydrate is now illegal in the United States without a prescription. Chloral hydrate is a [[Schedule IV (US)|schedule IV]] [[controlled substance]] in the [[United States]]. Its properties have sometimes led to its use as a [[date rape drug]].
| |
| − |
| |
| − | ===Hoyer's Mounting Medium===
| |
| − | Chloral hydrate is also an ingredient used for Hoyer's solution, a slide-mounting medium for microscopic observation of diverse organisms such as bryophytes, ferns, seeds, and small arthropods (especially mites). One recipe for making Hoyer's is dissolving gum arabic (30.0 g) in water (50.0 ml), then adding chloral hydrate (200.0 g), and then finally adding glycerol (16.0 ml). An advantage of this medium include an excellent refraction index and clearing (macerating) properties of the small specimens (especially advantageous if specimens require observation with Nomarski optics). The major disadvantage of Hoyer's is its susceptibility to the effects of hydration, which causes the mountant to crystallize, threatening the slide to become unusable. It is therefore absolutely necessary, after drying a mounted specimen, to thoroughly ring (2 layers are best) cover slips with a protective coating (such as insulating Glyptol), which prevents rehydration and mountant deterioration. Chloral hydrate reportedly does not effectively clear larger specimens, or arthropods that are more heavily sclerotized (e.g., larger insects). These should first be cleared with another product (e.g.,10% KCl), and then mounted in Hoyer's. Other disadvantages of Hoyer's (principally due to chloral hydrate) include toxicity (see above), and procurement problems due to chloral hydrate being a controlled substance.
| |
| − |
| |
| − | == Specific instances of chloral hydrate abuse ==
| |
| − | *[[Jennie Bosschieter]] (1882–1900) who was murdered in [[Paterson, New Jersey]] on October 19, 1900.
| |
| − | *[[John Tyndall]] (1820-1893) who died of an accidental overdose.
| |
| − | *[[Anna Nicole Smith]] (1967-2007) who died of an accidental<ref>[http://www.thesmokinggun.com/archive/years/2007/0326074report14.html Anna Nicole Smith Autopsy Report. XI. Manner of death. A. The Exclusion of Homicide] The Smoking Gun</ref> combination of chloral hydrate with three [[benzodiazepine]]s, as announced by forensic pathologist Dr. [[Joshua Perper]] on 26 March 2007. Chloral hydrate was the major factor, but none of these drugs would have been sufficient by itself to cause her death.<ref>[http://www.thesmokinggun.com/archive/years/2007/0326071anna1.html Anna Nicole Smith Autopsy Released. Coroner: Ex-Playmate died from accidental sedative overdose] The Smoking Gun</ref>
| |
| − | *[[Marilyn Monroe]] had chloral hydrate in her possession, and it has been speculated that it contributed to her death.<ref>[http://www.crimelibrary.com/notorious_murders/celebrity/marilyn_monroe/9.html Marily Monroe. Theories] Crime Library</ref>
| |
| − | *[[Hank Williams]] came under the spell of a man calling himself "Doctor" Toby Marshall (actually a paroled forger), who often supplied him with prescriptions and injections of chloral hydrate, which Marshall claimed was a pain reliever.<ref>[http://www.bookrags.com/Hank_Williams Hank Williams summary] Book Rags</ref>
| |
| − | *[[William S. Burroughs]] was expelled from school for experimenting with chloral hydrate along with another pupil. The incident is detailed in the writer's foreword to [[Junkie (novel)|Junkie]].
| |
| − | *[[Mary Todd Lincoln]] was given chloral hydrate for sleep problems. See ''Mary Todd Lincoln'' by Jean Baker and ''Mary: Mrs. A. Lincoln'', by Janis Cooke Newman.
| |
| − | *[[André Gide]] (1869-1951) was also given chloral hydrate as a boy for sleep problems by a quack doctor named Lizart. Gide states in his autobiography, ''If It Die...'' that "all my later weaknesses of will or memory I attribute to him."<ref>Gide, André and Dorothy Bussey (trans). ''If It Die…An Autobiography''. New York: Vintage International, 2001. p105</ref>
| |
| − |
| |
| − | == See also ==
| |
| − |
| |
| − | * [[Alkane]]
| |
| − | * [[Chlorine]]
| |
| − | * [[Chloroform]]
| |
| − | * [[Organic chemistry]]
| |
| − |
| |
| − | == Notes ==
| |
| − | <references/>
| |
| − |
| |
| − | ==References==
| |
| − |
| |
| − | * Benson, R. 2000. ''Chloral hydrate.'' Geneva: World Health Organization. ISBN 9241530251
| |
| − | * Carson-DeWitt, Rosalyn. 2001. ''Encyclopedia of Drugs, Alcohol & Addictive Behavior'', 2nd ed. New York: Macmillan Reference USA. ISBN 0028655419
| |
| − | * McMurry, John. 2004. ''Organic Chemistry'', 6th ed. Belmont, CA: Brooks/Cole. ISBN 0534420052
| |
| − | * Solomons, T.W. Graham, and Craig B. Fryhle. 2004. ''Organic Chemistry'', 8th ed. Hoboken, NJ: John Wiley. ISBN 0471417998
| |
| − | * Thackery, Ellen, and Madeline Harris. 2003. ''The Gale Encyclopedia of Mental Disorders.'' Detroit, Mich: Gale Group. ISBN 0787657689
| |
| − | * Zumdahl, Steven S. 2005. ''Chemical Principles''. New York, NY: Houghton Mifflin. ISBN 0618372067
| |
| − |
| |
| − | == External links ==
| |
| − |
| |
| − | * [http://drugs.uta.edu/chloral.html Chloral hydrate]. Retrieved December 10, 2008.
| |
| − |
| |
| − | * [http://www.medicinenet.com/chloral_hydrate-oral/article.htm Generic Name: Chloral hydrate - Oral]. MedicineNet.com. Retrieved December 10, 2008.
| |
| − |
| |
| − | * [http://www.webmd.com/drugs/drug-8629-Chloral+Hydrate+Oral.aspx?drugid=8629&drugname=Chloral+Hydrate+Oral Chloral Hydrate Oral]. WebMD. Retrieved December 10, 2008.
| |
| − |
| |
| − | * [http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc02/icsc0234.htm Chloral hydrate, International Chemical Safety Card 0234]. International Occupational Safety and Health Information Centre (CIS). Retrieved December 10, 2008.
| |
| − |
| |
| − | * [http://webbook.nist.gov/cgi/cbook.cgi?Name=chloral+hydrate&Units=SI Chloral hydrate]. NIST Chemistry WebBook. Retrieved December 10, 2008.
| |
| − |
| |
| − | ----
| |
| − | {{Sedative}}
| |
| − |
| |
| − | [[Category:Physical sciences]]
| |
| − | [[Category:Chemistry]]
| |
| − | [[Category:Organic chemistry]]
| |
| − |
| |
| − | {{credit|255443576}}
| |
