|Preferred IUPAC name
|Systematic IUPAC name
|Jmol interactive 3D||Image|
|Molar mass||88.15 g·mol−1|
|Density||0.805 g·cm−3 |
|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-methyl-2-butanol (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 which is miscibile with both water and 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 However, like other tertiary alcohol based anaesthetics (e.g. methylpentynol, ethchlorvynol) TAA was eventually superseded by safer and more effective agents.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 and relatively high potency of the drug. The oral LD50 in rats is 1000 mg/kg. The subcutaneous LD50 in mice is 2100 mg/kg.
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- 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 : an official journal of the Society of Toxicology 49 (1): 15–28. doi:10.1093/toxsci/49.1.15. PMID 10367338.
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