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Revision as of 17:24, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 475920055 of page 2-Methyl-2-butanol for the Chem/Drugbox validation project (updated: 'KEGG').		Latest revision as of 10:41, 13 October 2024 edit Autspectorder (talk | contribs)365 edits Removed original research.Tag: Visual edit
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			{{DISPLAYTITLE:''tert''-Amyl alcohol}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{Chembox		{{Chembox
			| Name = ''tert''-Amyl alcohol
	| Watchedfields = changed
			| Verifiedfields = changed
	| verifiedrevid = 413111871
			| verifiedrevid = 477214097
	| Name = 2-Methyl-2-butanol
	| ImageFile = Tert-pentyl-alcohol-2D-skeletal.png		| ImageFile = 2-Methyl-2-butanol FormulaV1-Seite001.svg
	| ImageFile_Ref = {{chemboximage|correct|??}}		| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageSize = 100		| ImageSize = 150
	| ImageName = Stereo, skeletal formula of 2-methyl-2-butanol		| ImageName = Stereo, skeletal formula of 2-methyl-2-butanol
	| PIN = 2-Methyl-2-butanol{{Citation needed|date = November 2011}}		| ImageFileL2 = 2-Methyl-2-butanol-3D-balls.png
			| ImageNameL2 = Ball-and-stick model of 2-methyl-2-butanol
	| SystematicName = 2-Methylbutan-2-ol<ref>{{ Cite web | title = tert-amyl alcohol - Compound Summary | url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6405&loc=ec_rcs | work = PubChem Compound | publisher = National Center for Biotechnology Information | accessdate = 2011-12-13 | location = USA | date = 26 March 2005 | at = Identification and Related Records }}</ref>
			| ImageFileR2 = 2-Methyl-2-butanol-3D-spacefill.png
	| OtherNames = ''tert''-Amyl alcohol{{Citation needed|date = November 2011}}<br />
			| ImageNameR2 = Space-filling model of the 2-methyl-2-butanol
	Amylene hydrate{{Citation needed|date = November 2011}}<br />
			| PIN = 2-Methylbutan-2-ol
	Dimethylethylcarbinol{{Citation needed|date = November 2011}}<br />
			| OtherNames = 2-Methyl-2-butanol<br />''tert''-Amyl alcohol<br />''t''-Amylol<br />TAA<br />''tert''-Pentyl alcohol<br />2-Methyl-2-butyl alcohol<br />''t''-Pentylol<br />Amylene hydrate<br />Dimethylethylcarbinol
	''tert''-Pentyl alcohol{{Citation needed|date = November 2011}}
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| CASNo = 75-85-4		| CASNo = 75-85-4
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| PubChem = 6405		| PubChem = 6405
			| ChemSpiderID = 6165
	| PubChem_Ref = {{Pubchemcite|correct|Pubchem}}
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 6165
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 69C393R11Z
	| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 69C393R11Z		| EINECS = 200-908-9
	| EINECS = 200-908-9		| UNNumber = 1105
	| UNNumber = 1105		| KEGG = D02931
			| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = <!-- blanked - oldvalue: D02931 -->
			| MeSHName = tert-amyl+alcohol
	| KEGG_Ref = {{keggcite|correct|kegg}}
			| SMILES = CCC(C)(C)O
	| MeSHName = tert-amyl+alcohol
	| SMILES = CCC(C)(C)O		| ChEBI = 132750
	| ChEMBL = 44658		| ChEMBL = 44658
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| RTECS = SC0175000		| RTECS = SC0175000
	| Beilstein = 1361351		| Beilstein = 1361351
	| StdInChI = 1S/C5H12O/c1-4-5(2,3)6/h6H,4H2,1-3H3		| StdInChI = 1S/C5H12O/c1-4-5(2,3)6/h6H,4H2,1-3H3
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = MSXVEPNJUHWQHW-UHFFFAOYSA-N		| StdInChIKey = MSXVEPNJUHWQHW-UHFFFAOYSA-N
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C = 5		| C=5 | H=12 | O=1
			| Appearance = Colorless liquid
	| H = 12
	| O = 1		| Odor = Camphorous
			| Density = 0.805 g/cm<sup>3</sup><ref name=prop>{{Cite journal | doi = 10.1021/je800571y| title = Densities and Viscosities of Binary Liquid Mixtures of 2-Butanone with Branched Alcohols at (293.15 to 313.15) K| journal = Journal of Chemical & Engineering Data| volume = 54| pages = 127–130| year = 2009| last1 = Lomte | first1 = S.B. | last2 = Bawa | first2 = M.J. | last3 = Lande | first3 = M.K. | last4 = Arbad | first4 = B.R. }}</ref>
	| ExactMass = 88.088815006 g mol<sup>−1</sup>
			| MeltingPtK = 264
	| Appearance = Colourless liquid
			| BoilingPtK = 374 to 376
	| Odor = Camphorous, peppermint
	| Density = 805 mg cm<sup>−3</sup>		| Solubility = 120 g·dm<sup>−3</sup>
			| LogP = 1.0950.5:1 volume ratio
	| MeltingPtK = 264
			| Viscosity = 4.4740 mPa·s (at 298.15 ])<ref name=prop />
	| BoilingPtKL = 374
			| VaporPressure = 1.6 kPa (at 20 °C)
	| BoilingPtKH = 376
			| RefractIndex = 1.405
	| Solubility = 120 g dm<sup>−3</sup>
			| SolubleOther = soluble in water, ], ], ] and ]<ref name=":crc">{{Cite book|title=CRC Handbook of Chemistry and Physics, 95th Edition|last1=Haynes|first1=William M.|last2=Lide|first2=David R.|last3=Bruno|first3=Thomas J.|publisher=CRC Press|year=2014|isbn=9781482208689|edition=95th|pages=362|chapter=Section 3 - Physical Constants of Organic Compounds|oclc=908078665}}</ref>
	| LogP = 1.095
			| MagSus = {{val|-7.09e-5|u=cm<sup>3</sup>/mol}}}}
	| VaporPressure = 1.6 kPa (at 20 °C)
			|Section3={{Chembox Thermochemistry
	| RefractIndex = 1.405
			| DeltaHf = −380.0 to −379.0 kJ mol<sup>−1</sup>
			| DeltaHc = −3.3036 to −3.3026 MJ mol<sup>−1</sup>
			| Entropy = 229.3 J K<sup>−1</sup> mol<sup>−1</sup>
	}}		}}
	| Section3 = {{Chembox Thermochemistry		|Section4={{Chembox Hazards
			| ExternalSDS =
	| DeltaHf = −380.0–−379.0 kJ mol<sup>−1</sup>
			| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}}
	| DeltaHc = −3.3036–−3.3026 MJ mol<sup>−1</sup>
			| GHSSignalWord = '''DANGER'''
	| Entropy = 229.3 J K<sup>−1</sup> mol<sup>−1</sup>
			| HPhrases = {{H-phrases|225|315|332|335}}
	}}
	| Section4 = {{Chembox Hazards		| PPhrases = {{P-phrases|210|261}}
			| NFPA-H = 1
	| ExternalMSDS =
			| NFPA-F = 3
	| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}}
			| NFPA-R = 0
	| GHSSignalWord = '''DANGER'''
			| FlashPtC = 19
	| EUIndex = 603-007-00-2
			| AutoignitionPtC = 437
	| EUClass = {{Hazchem F}} {{Hazchem Xn}}
			| ExploLimits = 9%
	| HPhrases = {{H-phrases|225|315|332|335}}
	| PPhrases = {{P-phrases|210|261}}
	| RPhrases = {{R11}}, {{R20}}, {{R37/38}}
	| SPhrases = {{S2}}, {{S46}}
	| NFPA-H = 1
	| NFPA-F = 3
	| NFPA-R = 0
	| FlashPt = 19 °C
	| Autoignition = 437 °C
	| ExploLimits = 9%
	}}		}}
	}}		}}
			'''''tert''-Amyl alcohol''' ('''TAA''') or '''2-methylbutan-2-ol''' ('''2M2B'''), is a branched ].
			Historically, TAA has been used as an ]<ref name="adriani" /> and more recently as a ].<ref name=":1">{{Cite journal|last1=Rusiecka|first1=Izabela|last2=Gągało|first2=Iwona|last3=Anand|first3=Jacek Sein|last4=Schetz|first4=Daria|last5=Waldman|first5=Wojciech|date=October 2016|title=Drinking "Vodka" or vodka – This is a question|journal=Toxicology in Vitro|volume=36|pages=66–70|doi=10.1016/j.tiv.2016.07.009|issn=1879-3177|pmid=27448500}}</ref> TAA is mostly a ] in the same way as ].<ref>{{Cite journal|last=Martin|first=J|title=Influence of oxygenated fuel additives and their metabolites on γ-aminobutyric acidA (GABAA) receptor function in rat brain synaptoneurosomes|journal=Toxicology Letters|volume=147|issue=3|pages=209–217|doi=10.1016/j.toxlet.2003.10.024|year=2004|pmid=15104112}}</ref> The psychotropic effects of TAA and ethanol are similar, though distinct. Impact on coordination and balance are proportionately more prominent with TAA, which is significantly more potent by weight than ethanol. Its appeal as an alternative to ethanol may stem from its lack of a hangover (due to different ]) and the fact that it is often not detected on standard drug test.<ref>{{Cite journal |last1=Syed |first1=Alia N. |last2=Leo |first2=Raphael J. |date=2022-11-22 |title=Recreational 2-Methyl-2-Butanol Use: An Emerging Wave of Misuse of an Ethanol Substitute on the Horizon? |url=https://www.psychiatrist.com/pcc/recreational-2-methyl-2-butanol-use-emerging-wave-misuse-ethanol-substitute/ |journal=The Primary Care Companion for CNS Disorders |language=English |volume=24 |issue=6 |pages=44189 |doi=10.4088/PCC.22cr03292 |pmid=36441984 |s2cid=253700629 |issn=2155-7780}}</ref>
			TAA is a colorless liquid with a burning flavor<ref>{{Cite book|title=The Merck index|date=2006|publisher=Merck|editor-last=O'Neil |editor-first=Maryadele J.|isbn=9780911910001|edition=14th|pages=1232|oclc=70882070}}</ref> and an unpleasant odor<ref name=":5" /> similar to ] with a hint of ].<ref>{{Cite journal|journal=The American Practitioner and News|last=Yandell|first=D. W.|display-authors=etal|year=1888|volume=5|pages=88–98|title=Amylene hydrate, a new hypnotic|url=https://babel.hathitrust.org/cgi/pt?id=mdp.39015070262681;view=1up;seq=106}}</ref> TAA remains liquid at room temperature, making it a useful alternative solvent to ].
			==Production==
			TAA is primarily made by the hydration of ] in the presence of an acidic ].<ref name=":4">{{cite book|last1=Papa|first1=Anthony J.|title=Kirk–Othmer Encyclopedia of Chemical Technology|date=2004|publisher=Wiley-Interscience|location=Hoboken, N.J.|isbn=9780471238966|edition=5th|chapter=Amyl Alcohols|doi=10.1002/0471238961.0113251216011601.a01.pub2}}</ref><ref name="adriani">{{cite book | isbn = 9780398000110 | title = The Chemistry and Physics of Anesthesia | edition = 2nd | last1 = Adriani | first1 = John | year = 1962 | publisher = Thomas Books | location = Illinois | pages = 273–274 }}</ref>
			==Natural occurrence==
			]s like TAA are grain fermentation byproducts, and therefore trace amounts of TAA are present in ].<ref name="GouldScott1919">{{cite book|first1=George M. |last1=Gould|author-link1=George M. Gould|first2=Richard J. E. |last2=Scott|title=The Practitioner's Medical Dictionary|url=https://archive.org/stream/practitionersmed00goul/practitionersmed00goul#page/50/mode/1up|access-date=2018-07-27|year=1919|publisher=P. Blakiston's|page=50}}</ref> Traces of TAA have been detected in other foods, like fried ],<ref>{{Cite journal|last1=Ho|first1=C.-T.|last2=Lee|first2=K.-N.|last3=Jin|first3=Q.-Z.|year=1983|title=Isolation and identification of volatile flavor compounds in fried bacon|journal=Journal of Agricultural and Food Chemistry|volume=31|issue=2|pages=336|doi=10.1021/jf00116a038|issn=0021-8561}}</ref> ]<ref>{{Cite journal|last1=Dougan|first1=J.|last2=Robinson|first2=J. M.|last3=Sumar|first3=S.|last4=Howard|first4=G. E.|last5=Coursey|first5=D. G.|year=1983|title=Some flavouring constituents of cassava and of processed cassava products|journal=Journal of the Science of Food and Agriculture|volume=34|issue=8|pages=874|doi=10.1002/jsfa.2740340816|bibcode=1983JSFA...34..874D |issn=1097-0010}}</ref> and ].<ref>{{cite journal|last1=Habu|first1=Tsutomu|last2=Flath|first2=Robert A.|last3=Mon|first3=T. Richard|last4=Morton|first4=Julia F.|date=1 March 1985|title=Volatile components of Rooibos tea (''Aspalathus linearis'')|journal=Journal of Agricultural and Food Chemistry|volume=33|issue=2|pages=249–254|doi=10.1021/jf00062a024|issn=0021-8561}}</ref>
			TAA is also present in ] ] and seems to play a role in ]-inducing suckling in the newborn rabbit.<ref>{{cite journal|journal=Nature|last1=Benoist|first1=Schaal|last2=Gérard|first2=Coureaud|first3=Dominique|last3=Langlois|first4=Christian|last4=Giniès|first5=Etienne|last5=Sémon|first6=Guy|last6=Perrier|date=2003|title=Chemical and behavioural characterization of the rabbit mammary pheromone|volume=424 |issue=6944 |page=68 |doi=10.1038/nature01739 |bibcode=2003Natur.424...68S |s2cid=4428155 }}</ref>
			==History==
			From about the 1880s to the 1950s, TAA was used as an ] with the contemporary name of ''amylene hydrate'', but it was rarely used because more efficient drugs existed.<ref name="adriani" /> In the 1930s, TAA was mainly used as a solvent for the primary anesthetic ] (TBE). Like ], TBE is toxic for the liver, so the use of such solutions declined in the 1940s in humans. TBE-TAA-solutions remained in use as short-acting anesthetics for ] and ]. Such solutions are sometimes called ''Avertin'', which was a brand name for the now discontinued TAA and TBE solution with a volume ratio of 0.5:1 made by ].<ref name=":0">{{Cite journal|last1=Meyer|first1=Robert E.|last2=Fish|first2=Richard E.|date=November 2005|title=A review of tribromoethanol anesthesia for production of genetically engineered mice and rats|journal=Lab Animal|volume=34|issue=10|pages=47–52|doi=10.1038/laban1105-47|issn=0093-7355|pmid=16261153|s2cid=21759580}}</ref> TAA has emerged recently as a ].<ref name=":1" />
			== Use and effects ==
			Ingestion or inhalation of TAA causes ], ], ], and ] effects similar to ].<ref>{{Cite book|title=Lewisʼ Dictionary of Toxicology|last=Lewis|first=Robert Alan|date=1998|publisher=CRC Press|isbn=978-1566702232|location=Boca Raton, Florida|pages=|oclc=35269968|url=https://archive.org/details/lewisdictionaryo0000lewi/page/45}}</ref> When ingested, the effects of TAA may begin in about 30 minutes and can last up to 1–2 days.<ref name=":3">{{Cite web|url=https://www.toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+5005|title=2-METHYL-2-BUTANOL - National Library of Medicine HSDB Database|website=www.toxnet.nlm.nih.gov|archive-url=https://web.archive.org/web/20180308103247/https://www.toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+5005|archive-date=2018-03-08|url-status=live|access-date=2018-04-08}}</ref> 2–4 grams of TAA is sufficient to produce a hypnotic effect. About 100&nbsp;g of ethanol induces a similar level of sedation.<ref name=":5">{{Cite book|title=Analytical Toxicology for Clinical, Forensic, and Pharmaceutical Chemists|last1=Brandenberger|first1=Hans|last2=Maes|first2=Robert A. A.|date=1997|publisher=W. de Gruyter|isbn=978-3110107319|location=Berlin|pages=400–401|oclc=815506841}}</ref>
			== Overdose and toxicity ==
			The smallest known dose of TAA that has killed a person is 30&nbsp;mL.<ref name=":3" />
			An overdose produces symptoms similar to ] and is a medical emergency due to the sedative/depressant properties which manifest in overdose as potentially lethal ]. Sudden loss of consciousness, simultaneous ] and ],<ref name=":3" /> ], ], ], ], respiratory depression<ref name=":2">{{Cite journal|last1=Anand|first1=Jacek Sein|last2=Gieroń|first2=Joanna|last3=Lechowicz|first3=Wojciech|last4=Schetz|first4=Daria|last5=Kała|first5=Maria|last6=Waldman|first6=Wojciech|date=September 2014|title=Acute intoxication due to ''tert''-amyl alcohol—a case report|journal=Forensic Science International|volume=242|pages=e31–e33|doi=10.1016/j.forsciint.2014.07.020|issn=1872-6283|pmid=25112153}}</ref> and death may follow from an overdose. The oral {{LD50}} in rats is 1&nbsp;g/kg. The ] LD<sub>50</sub> in mice is 2.1&nbsp;g/kg.<ref>{{Cite journal
			| last1 = Soehring | first1 = K.
			| last2 = Frey | first2 = H.H.
			| last3 = Endres | first3 = G.
			| title = Relations between constitution and effect of tertiary alcohols
			| journal = Arzneimittel-Forschung
			| volume = 5
			| issue = 4
			| pages = 161–165
			| year = 1955
			| pmid = 14389140
			}}</ref>
			== Metabolism ==
			In rats, TAA is primarily ] via ], as well as by oxidation to ]. It is likely that the same path is followed in humans,<ref name="pmid10367338">{{Cite journal
			| last1 = Collins | first1 = A. S.
			| last2 = Sumner | first2 = S. C.
			| last3 = Borghoff | first3 = S. J.
			| last4 = Medinsky | first4 = M. A.
			| title = A physiological model for ''tert''-amyl methyl ether and ''tert''-amyl alcohol: Hypothesis testing of model structures
			| journal = Toxicological Sciences
			| volume = 49
			| issue = 1
			| pages = 15–28
			| year = 1999
			| pmid = 10367338
			| doi = 10.1093/toxsci/49.1.15
			| doi-access = free
			}}</ref> though older sources suggest TAA is excreted unchanged.<ref name= adriani/>
			]
			The use of TAA cannot be detected with general ethanol tests or other ordinary drug tests. Its use can be detected from a blood or a urine sample by using ] for up to 48 hours after consumption.<ref name=":2" />
			== See also ==
			* ]
			* ]
			* ]
			* ]
			* ]
			* ]
			* ]
			* ]
			* ]
			* ]
			== References ==
			<references />
			{{Alcohols}}
			{{Sedatives}}
			{{GABAAR PAMs}}
			{{DEFAULTSORT:Amyl alcohol, tert-}}
			]
			]
			]
			]
			]
			]