| Preferred IUPAC name
| Other names
|3D model (Jmol)||Interactive image|
|Molar mass||88.15 g·mol−1|
|Melting point||−9 °C; 16 °F; 264 K|
|Boiling point||101 to 103 °C; 214 to 217 °F; 374 to 376 K|
|Vapor pressure||1.6 kPa (at 20 °C)|
Refractive index (nD)
|Viscosity||4.4740 mPa·s (at 298.15 K)|
|229.3 J K−1 mol−1|
Std enthalpy of
|−380.0–−379.0 kJ mol−1|
Std enthalpy of
|−3.3036–−3.3026 MJ mol−1|
|Safety data sheet||hazard.com|
|GHS signal word||DANGER|
|H225, H315, H332, H335|
EU classification (DSD)
|R-phrases||R11, R20, R37/38|
|Flash point||19 °C (66 °F; 292 K)|
|437 °C (819 °F; 710 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|(what is ?)|
tert-Amyl alcohol (TAA), systematic name: 2-methylbutan-2-ol (2M2B), is a branched pentanol used primarily as a pharmaceutical or pigment solvent. It remains liquid at room temperature making it a useful alternative to tert-butyl alcohol. It is a colorless liquid with a pungent odor of camphor. It is slightly soluble in water and miscibile organic solvents. Although it can be produced naturally, by the fermentation of ethanol, it is primarily produced synthetically via hydroformylation.
Fusel alcohols including TAA are grain fermentation by-products and therefore trace amounts of TAA are present in many alcoholic beverages. Trace levels of TAA have also been detected in various foodstuffs, including fried bacon, cassava, rooibos tea and fruits such as apple and pineapple.
Between about 1880–1950, it was used as an anesthetic, with the contemporary name of amylene hydrate. It was mainly used as a solvent for tribromoethanol, forming "avertin fluid" at a 0.5 : 1 ratio of TAA to TBE. TAA was rarely used as a sole hypnotic because of the existence of more efficient drugs.
Tertiary alcohols like TAA cannot be oxidised to aldehyde or carboxylic acid metabolites, which are often toxic; this makes them safer drugs than primary alcohols. However, like other tertiary alcohol based anaesthetics (e.g. methylpentynol, ethchlorvynol) TAA was eventually superseded by safer and more effective agents.
TAA produces euphoria, sedative, hypnotic, and anticonvulsant effects similar to ethanol through ingestion or inhalation. It is active in doses of 2,000–4,000 mg, making it 20 times more potent than ethanol. Its hypnotic potency is between chloral hydrate and paraldehyde and between benzodiazepines and ethanol.
In rats, TAA is primarily metabolized via glucuronidation, as well as by oxidation to 2-methyl-2,3-butanediol. It is likely that the same path is followed in humans, though older sources suggest it is excreted unchanged.
Overdose and toxicity
An overdose produces symptoms similar to alcohol poisoning and is a medical emergency due to the sedative/depressant properties. The oral LD50 in rats is 1000 mg/kg. The subcutaneous LD50 in mice is 2100 mg/kg.
- Lomte, S. B.; Bawa, M. J.; Lande, M. K.; Arbad, B. R. (2009). "Densities and Viscosities of Binary Liquid Mixtures of 2-Butanone with Branched Alcohols at (293.15 to 313.15) K". Journal of Chemical & Engineering Data. 54: 127. doi:10.1021/je800571y.
- Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V2: 716. http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+5005
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- Ho, C. T.; Lee, K. N.; Jin, Q. Z. (1983). "Isolation and identification of volatile flavor compounds in fried bacon". Journal of Agricultural and Food Chemistry. 31 (2): 336. doi:10.1021/jf00116a038.
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- Robert A. Lewis (1998). Lewis' Dictionary of Toxicology. CRC Press. p. 45. ISBN 1-56670-223-2.
- Hans Brandenberger & Robert A. A. Maes, ed. (1997). Analytical Toxicology for Clinical, Forensic and Pharmaceutical Chemists. p. 401. ISBN 3-11-010731-7.
- D. W. Yandell; et al. (1888). "Amylene hydrate, a new hypnotic". The American Practitioner and News. Lousville KY: John P. Morton & Co. 5: 88–89.
- F. A. Castle & C. Rice (March 1888). "Amylene and amylene hydrate". The American Druggist. 17 (3): 58–59.
- 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. 49 (1): 15–28. doi:10.1093/toxsci/49.1.15. PMID 10367338.
- Soehring, K.; Frey, H. H.; Endres, G. (1955). "Relations between constitution and effect of tertiary alcohols". Arzneimittel-Forschung. 5 (4): 161–165. PMID 14389140.