- 2-Methyl-2-butanol
-
2-Methyl-2-butanol 
2-Methyl-2-butanol[citation needed]Systematic name2-Methylbutan-2-ol[1]Other namestert-Amyl alcohol[citation needed]
Amylene hydrate[citation needed]
tert-Pentyl alcohol[citation needed]
Dimethylethylcarbinol[citation needed]Identifiers CAS number 75-85-4 
PubChem 6405 ChemSpider 6165 UNII 69C393R11Z EC number 200-908-9 UN number 1105 KEGG D02931 MeSH tert-amyl+alcohol ChEMBL CHEMBL44658 RTECS number SC0175000 Beilstein Reference 1361351 Jmol-3D images Image 1 - CCC(C)(C)O
- InChI=1S/C5H12O/c1-4-5(2,3)6/h6H,4H2,1-3H3
Key: MSXVEPNJUHWQHW-UHFFFAOYSA-N
Properties Molecular formula C5H12O Molar mass 88.15 g mol−1 Exact mass 88.088815006 g mol−1 Appearance Colourless liquid Odor Camphorous, peppermint Density 805 mg cm−1 Melting point -9 °C, 264 K, 16 °F
Boiling point 101-103 °C, 374-376 K, 214-217 °F
Solubility in water 120 g dm−3 log P 1.095 Vapor pressure 1.6 kPa (at 20 °C) Refractive index (nD) 1.405 Thermochemistry Std enthalpy of
formation ΔfHo298−380.0–−379.0 kJ mol−1 Std enthalpy of
combustion ΔcHo298−3.3036–−3.3026 MJ mol−1 Standard molar
entropy So298229.3 J K−1 mol−1 Hazards MSDS hazard.com GHS pictograms 
GHS signal word DANGER GHS hazard statements H225, H315, H332, H335 GHS precautionary statements P210, P261 EU Index 603-007-00-2 EU classification 
F 
XnR-phrases R11, R20, R37/38 S-phrases (S2), S46 NFPA 704 
310Flash point 19 °C Autoignition
temperature437 °C Explosive limits 9% 
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)Infobox references 2-Methyl-2-butanol, also known as tert-amyl alcohol or amylene hydrate, is one of the isomers of amyl alcohol. It is a clear, colorless liquid with a strong odor of peppermint or camphor.[2][3] In humans it possesses sedative, hypnotic, and anticonvulsant effects similar to ethanol through ingestion or inhalation, and was previously used in medicine for this purpose.[4] It is active in doses of 2,000-5,000 mg, making it some 20 times more potent than regular ethanol.[5][6] Its hypnotic potency is between that of chloral hydrate and paraldehyde.[7] 2-methyl-2-butanol is similar in structure to ethchlorvynol and methylpentynol. It is a byproduct of the fermentation of grain. [8] It is also present in hops. In humans, 2-methyl-2-butanol is metabolized primarily via gluconoridation and oxidation to 2,3-dihydroxy-2-methylbutane.[9] Overdose produces symptoms similar to alcohol poisoning and is a medical emergency.
See also
- Ethanol
- Chloral hydrate
- Methylpentynol
- 2-Methyl-1-butanol
References
- ^ "tert-amyl alcohol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6405&loc=ec_rcs. Retrieved 12 November 2011.
- ^ Coblentz, Virgil. The Newer Remedies: A reference manual for physicians, pharmacists, and students. 1899. [1]
- ^ H.C. Wood & R.M. Smith. Therapeutic Gazette - A monthly journal of physiological and clinical therapeutics. Vol 3, 1887. [2]
- ^ Robert A. Lewis. Lewis' Dictionary of Toxicology, 1998
- ^ Hans Brandenberger & Robert A. A. Maes. Analytical Toxicology for Clinical, Forensic and Pharmaceutical Chemists, 1997 [3]
- ^ D.W. Yandell et al. (1888). "Amylene hydrate, a new hypnotic". The American Practitioner and News 5. http://books.google.com/books?id=Ra5YAAAAMAAJ&pg=PA88#v=onepage.
- ^ F.A. Castle & C. Rice (March 1888). "Amylene and amylene hydrate". The American Druggist 17 (3): 58. http://books.google.com/books?id=gNIAAAAAYAAJ&lpg=PA58&ots=CjKZ2BtKrR&dq=amylene%20hydrate%20potency&pg=PA58#v=onepage&q=&f=false.
- ^ Gould, G.M. (1910). The Practitioner's Medical Dictionary. Blakiston's Son & Co..
- ^ Collins, A. S.; Sumner, S. C.; Borghoff, S. J.; Medinsky, M. A. (1999). "A physiological model for tert-amyl methyl ether and tert-amyl alcohol: Hypothesis testing of model structures". Toxicological sciences : an official journal of the Society of Toxicology 49 (1): 15–28. doi:10.1093/toxsci/49.1.15. PMID 10367338.
GABAergics Receptor
ligandsAgonists: Main site: Bamaluzole • Gaboxadol • Ibotenic acid • Isoguvacine • Isonipecotic acid • Muscimol (Amanita Muscaria) • Progabide • SL 75102 • Thiomuscimol • Tolgabide; Positive allosteric modulators: Barbiturates • Benzodiazepines • Carbamates • Chlormezanone • Clomethiazole • Ethanol (Alcohol) • Etomidate • Kavalactones (Kava) • Loreclezole • Metomidate • Neuroactive steroids • Nonbenzodiazepines (β-Carbolines, Cyclopyrrolones, Imidazopyridines, Pyrazolopyrimidines, etc.) • Phenols • Piperidinediones • Propanidid • Pyrazolopyridines • Quinazolinones • ROD-188 • Skullcap • Stiripentol • Valerenic acid (Valerian)
Antagonists: Main site: Bicuculline • Gabazine • Pitrazepin; Negative allosteric modulators: α5IA • Bilobalide • Cicutoxin • Cyclothiazide • DMCM • Flumazenil • Flurothyl • Furosemide • L-655,708 • Oenanthotoxin • Penicillin • Pentylenetetrazol • Picrotoxin • PWZ-029 • Ro15-4513 • Sarmazenil • Suritozole • Thujone (Absinthe) • Thiocolchicoside • ZK-93426
* See Template:GABAAergics for a full list of GABAA positive allosteric modulators.Agonists: Main site: CACA • CAMP • GABOB • N(4)-chloroacetylcytosine arabinoside • Progabide • Tolgabide
Antagonists: Main site: Bilobalide • TPMPAReuptake
inhibitorsPlasmalemmalGAT inhibitorsCI-966 • Deramciclane • EF-1502 • Gabaculine • Guvacine • Nipecotic acid • NNC 05-2090 • SKF-89976A • SNAP-5114 • TiagabineEnzyme
inhibitorsGAD inhibitorsAllylglycineGABA-T inhibitors3-Hydrazinopropionic acid • Aminooxyacetic acid • Gabaculine • Isoniazid • Phenelzine • Phenylethylidenehydrazine • Sodium valproate • Valnoctamide • Valproate pivoxil • Valproate semisodium (Divalproex sodium) • Valproic acid • Valpromide • VigabatrinOthers Glutamate • GlutamineOthersCategories:- Alcohols
- Sedatives
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