Editing Chloral hydrate

From Wikipedia, the free encyclopedia

You are not currently logged in. Editing this way will cause your IP address to be recorded publicly in this page's edit history. If you create an account, you can conceal your IP address and be provided with many other benefits. Messages sent to your IP can be viewed on your talk page.

Please do not save test edits. If you want to experiment, please use the sandbox.

Anti-spam check. Do NOT fill this in!

{{Chembox new
| ImageFile = Chloral-hydrate-montage.png
| ImageSize = 250px
| IUPACName = 2,2,2-trichloroethane-1,1-diol
| OtherNames = trichloroacetaldehyde monohydrate 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 = C2H3Cl3O2
| MolarMass = 165.403 g/mol
| Appearance = Colorless solid
| Density = 1.91 g/cm3
| 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 = 8â€“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]]2[[Hydrogen|H]]3[[Chlorine|Cl]]3[[Oxygen|O]]2.

It was discovered through the [[Halogenation|chlorination]] of [[ethanol]] in 1832 by [[Justus von Liebig]] in [[GieÃŸen]].<ref>{{cite journal 
 | title = Ueber die Zersetzung des Alkohols durch Chlor 
 | author = Justus Liebig 
 | journal = Annalen der Pharmacie
 | volume = 1 
 | issue = 1
 | pages = 31â€“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, Ã¶lbildendes Gas und Essiggeist entstehen 
 | author = Justus Liebig 
 | journal = Annalen der Pharmacie
 | volume = 1 
 | issue = 2
 | pages = 182â€“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 = MÃ¼ller}}</ref>
It was widely [[Drug addiction|abused]] and [[Medical prescription|misprescribed]] in the late 19th century. Chloral hydrate is soluble in both water and [[Ethanol|alcohol]], readily forming concentrated solutions. A solution of chloral hydrate in [[Ethanol|alcohol]] called "knockout drops" was used to prepare a [[Mickey Finn (drugs)|Mickey Finn]]. More reputable uses of chloral hydrate include its use 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]].

It is, together with [[chloroform]], a minor side-product of the [[chlorination]] of [[water]], if organic residues are present in the water, concentrations rarely exceeding 5 [[microgram]]s per [[litre]] (Âµg/l).

==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 Cl2 + C2H5OH + H2O â†’ Cl3CCH(OH)2 + 5 HCl

==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 which cyclicizes 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; â€œPharmacotherapy for Insomniaâ€, 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]] {{Fact|date=December 2007}}.

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]] {{Fact|date=July 2008}}.

Due to the lack of availability of chloral hydrate, this so-called â€œdate-rape-drugâ€ (chloral hydrate) has now been supplanted by a new substance called '''GHB''', or [[Gamma-Hydroxybutyric acid]], a synthetic neuroprotective therapeutic drug that is illegal in the United States, and a number of countries. GHB is far more plentiful on the illicit drug market than its predecessor chloral hydrate â€“â€“ a substance that has all but been abandoned (see above note). Unfortunately GHB is far more dangerous to the victim â€“â€“ both chemically, and because the predator who administers it is likely to do more harm to the intended victim. Many states have enhanced rape penalties for offenders using GHB in the course of sexual assaults.

===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 and 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 (e.g., 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.

==See also==
*[[Jennie Bosschieter]] (1882â€“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.
*[[AndrÃ© 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, AndrÃ© and Dorothy Bussey (trans). ''If It Dieâ€¦An Autobiography''. New York: Vintage International, 2001. p105</ref>

== Chloral hydrate in fiction and film ==

* [[Bram Stoker]], "[[Dracula]]," 1897
* [[Edith Wharton]], "[[The House of Mirth]]." New York, C. Schribnerâ€™s Sons, 1905.
* [[Evelyn Waugh]], ''[[Vile Bodies]].'' London, Chapman & Hall Ltd., 1930.
* [[Margery Allingham]], "[[The Case of the Late Pig]]." Hodder & Stoughton, 1937.
* [[Agatha Christie]], "[[And Then There Were None]]." Dodd, Mead and Company, 1940.
* [[Rex Stout]], "[[The Final Deduction]]," Chapter 7. Viking Press, 1961.
* [[From Russia with Love]], Movie, 1963.
* [[Roger Zelazny]], "[[Lord of Light]]", 1967.
* [[Jimmy Breslin]], "[[The Gang That Couldn't Shoot Straight]]," 1969.
* [[Larry Gelbart]], "[[M*A*S*H*]]" TV-Series, Season 3, 1974.
* [[The Living Daylights]], Movie, 1987.
* [[Caleb Carr]], "[[The Alienist]]." Random House, 1994.
* [[Sarah Waters]], ''Affinity''. London: [[Virago Press]], 1999.
* [[Oz]], TV-Series, Multiple episodes,(Handicap used by Ryan O'Rielly)
* [[David Shore]], "[[House M.D.]]" TV-Series, Season 1, 2004.
* [[The Venture Brothers]], TV-Series, Season 1, Episode 4, 2004
* [[Taxi Driver]], [[Martin Scorsese]], Travis is offered this by gun dealer
* [[Thomas Pynchon]], [[Against the Day]], London, Vintage Books, 2007.
* [[Joanne Harris]], [[Sleep Pale Sister]], Black Swan 2004.

==References==
{{reflist}}

[[Category:Aldehydes]]
[[Category:Hydrates]]
[[Category:Hypnotics]]
[[Category:Sedatives]]

[[de:Chloralhydrat]]
[[es:Hidrato de cloral]]
[[fr:Hydrate de chloral]]
[[it:Cloralio]]
[[nl:Chloraalhydraat]]
[[ja:æŠ±æ°´ã‚¯ãƒãƒ©ãƒ¼ãƒ«]]
[[pl:Wodzian chloralu]]
[[pt:Hidrato de cloral]]
[[ru:Ð¥Ð»Ð¾Ñ€Ð°Ð»Ð³Ð¸Ð´Ñ€Ð°Ñ‚]]
[[fi:Kloraalihydraatti]]
[[sv:Kloralhydrat]]
[[tr:Kloralhidrat]]

Content that violates any copyright will be deleted. Encyclopedic content must be verifiable. You irrevocably agree to release your contributions under the terms of the GFDL^*.

Edit summary (Briefly describe the changes you have made):

Cancel | Editing help (opens in new window)

Do not copy text from other websites without a GFDL-compatible license. It will be deleted.

Copy and paste: â€“ â€” â€¦ â€˜ â€œ â€™ â€ Â° â€³ â€² â‰ˆ â‰ â‰¤ â‰¥ Â± âˆ’ Ã— Ã· â† â†’ Â· Â§ Sign your posts on talk pages: ~~~~

{{}} {{{}}} | [] [[]] [[Category:]] #REDIRECT [[]]   <s></s> <code></code> <blockquote></blockquote> <ref></ref> {{Reflist}} <references/> <includeonly></includeonly> <noinclude></noinclude> {{DEFAULTSORT:}} <nowiki></nowiki>

Symbols: ~ | Â¡ Â¿ â€ â€¡ â†” â†‘ â†“ â€¢ Â¶ # Â½ â…“ â…” Â¼ Â¾ â…› â…œ â… â…ž âˆž â€˜ â€œ â€™ â€ Â«Â» Â¤ â‚³ à¸¿ â‚µ Â¢ â‚¡ â‚¢ $ â‚« â‚¯ â‚¬ â‚ â‚£ Æ’ â‚´ â‚ â‚¤ â„³ â‚¥ â‚¦ â„– â‚§ â‚° Â£ áŸ› â‚¨ â‚ª à§³ â‚® â‚© Â¥ â™ â™£ â™¥ â™¦ mÂ² mÂ³
Characters: Ã Ã¡ Ä† Ä‡ Ã‰ Ã© Ã Ã Ä¹ Äº Åƒ Å„ Ã“ Ã³ Å” Å• Åš Å› Ãš Ãº Ã Ã½ Å¹ Åº Ã€ Ã Ãˆ Ã¨ ÃŒ Ã¬ Ã’ Ã² Ã™ Ã¹ Ã‚ Ã¢ Äˆ Ä‰ ÃŠ Ãª Äœ Ä Ä¤ Ä¥ ÃŽ Ã® Ä´ Äµ Ã” Ã´ Åœ Å Ã› Ã» Å´ Åµ Å¶ Å· Ã„ Ã¤ Ã‹ Ã« Ã Ã¯ Ã– Ã¶ Ãœ Ã¼ Å¸ Ã¿ ÃŸ Ãƒ Ã£ áº¼ áº½ Ä¨ Ä© Ã‘ Ã± Ã• Ãµ Å¨ Å© á»¸ á»¹ Ã‡ Ã§ Ä¢ Ä£ Ä¶ Ä· Ä» Ä¼ Å… Å† Å– Å— Åž ÅŸ Å¢ Å£ Ä Ä‘ Å® Å¯ Ç ÇŽ ÄŒ Ä ÄŽ Ä Äš Ä› Ç Ç Ä½ Ä¾ Å‡ Åˆ Ç‘ Ç’ Å˜ Å™ Å Å¡ Å¤ Å¥ Ç“ Ç” Å½ Å¾ Ä€ Ä Ä’ Ä“ Äª Ä« ÅŒ Å Åª Å« È² È³ Ç¢ Ç£ Ç– Ç˜ Çš Çœ Ä‚ Äƒ Ä” Ä• Äž ÄŸ Ä¬ Ä ÅŽ Å Å¬ Å ÄŠ Ä‹ Ä– Ä— Ä Ä¡ Ä° Ä± Å» Å¼ Ä„ Ä… Ä˜ Ä™ Ä® Ä¯ Çª Ç« Å² Å³ á¸Œ á¸ á¸¤ á¸¥ á¸¶ á¸· á¸¸ á¸¹ á¹‚ á¹ƒ á¹† á¹‡ á¹š á¹› á¹œ á¹ á¹¢ á¹£ á¹¬ á¹ Å Å‚ Å Å‘ Å° Å± Ä¿ Å€ Ä¦ Ä§ Ã Ã° Ãž Ã¾ Å’ Å“ Ã† Ã¦ Ã˜ Ã¸ Ã… Ã¥ Æ É™ {{Unicode|}}
Greek: Î† Î¬ Îˆ Î Î‰ Î® ÎŠ Î¯ ÎŒ ÏŒ ÎŽ Ï Î ÏŽ Î‘ Î± Î’ Î² Î“ Î³ Î” Î´ Î• Îµ Î– Î¶ Î— Î· Î˜ Î¸ Î™ Î¹ Îš Îº Î› Î» Îœ Î¼ Î Î½ Îž Î¾ ÎŸ Î¿ Î Ï€ Î¡ Ï Î£ Ïƒ Ï‚ Î¤ Ï„ Î¥ Ï… Î¦ Ï† Î§ Ï‡ Î¨ Ïˆ Î© Ï‰ {{Polytonic|}}
Cyrillic: Ð Ð° Ð‘ Ð± Ð’ Ð² Ð“ Ð³ Ò Ò‘ Ðƒ Ñ“ Ð” Ð´ Ð‚ Ñ’ Ð• Ðµ Ð Ñ‘ Ð„ Ñ” Ð– Ð¶ Ð— Ð· Ð… Ñ• Ð˜ Ð¸ Ð† Ñ– Ð‡ Ñ— Ð™ Ð¹ Ðˆ Ñ˜ Ðš Ðº ÐŒ Ñœ Ð› Ð» Ð‰ Ñ™ Ðœ Ð¼ Ð Ð½ ÐŠ Ñš Ðž Ð¾ ÐŸ Ð¿ Ð Ñ€ Ð¡ Ñ Ð¢ Ñ‚ Ð‹ Ñ› Ð£ Ñƒ ÐŽ Ñž Ð¤ Ñ„ Ð¥ Ñ… Ð¦ Ñ† Ð§ Ñ‡ Ð ÑŸ Ð¨ Ñˆ Ð© Ñ‰ Ðª ÑŠ Ð« Ñ‹ Ð¬ ÑŒ Ð Ñ Ð® ÑŽ Ð¯ Ñ
IPA: tÌª dÌª Êˆ É– ÉŸ É¡ É¢ Ê¡ Ê” É¸ Êƒ Ê’ É• Ê‘ Ê‚ Ê Ê É£ Ê Ê• Êœ Ê¢ É¦ É± É³ É² Å‹ É´ Ê‹ É¹ É» É° Ê™ Ê€ É¾ É½ É« É¬ É® Éº É ÊŽ ÊŸ É¥ Ê É§ É“ É— Ê„ É Ê› Ê˜ Ç€ Çƒ Ç‚ Ç É¨ Ê‰ É¯ Éª Ê ÊŠ É˜ Éµ É¤ É™ Éš É› Éœ É Éž ÊŒ É” É É¶ É‘ É’ Ê° Ê· Ê² Ë Ë¤ â¿ Ë¡ Ëˆ ËŒ Ë Ë‘ Ìª {{IPA|}}

Once you click the Save button, your changes will be visible immediately.

For testing, please use the sandbox instead.

Please note:

If you don't want your writing to be edited mercilessly or redistributed for profit by others, do not submit it. Only public domain resources can be copied without permission—this does not include most web pages or images. See our policies and guidelines for more information on editing.

^ GNU Free Documentation License, Version 1.2 or any later version published by the Free Software Foundation; with no Invariant Sections, with no Front-Cover Texts, and with no Back-Cover Texts.

Pages transcluded onto the current version of this page:

This page is a member of 3 hidden categories:

Category:All articles with unsourced statements Category:Articles with unsourced statements since December 2007 Category:Articles with unsourced statements since July 2008

Retrieved from "http://en.wikipedia.org/wiki/Chloral_hydrate"

Editing Chloral hydrate

From Wikipedia, the free encyclopedia

Views

Personal tools

Navigation

Search

Interaction

Toolbox