|Preferred IUPAC name
|Systematic IUPAC name
|Molar mass||88.15 g·mol−1|
|Density||805 mg cm−3|
|Melting point||−9 °C; 16 °F; 264 K|
|Boiling point||101 to 103 °C; 214 to 217 °F; 374 to 376 K|
|120 g dm−3|
|Vapor pressure||1.6 kPa (at 20 °C)|
Refractive index (nD)
|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|
|GHS signal word||DANGER|
|H225, H315, H332, H335|
|EU classification||F Xn|
|R-phrases||R11, R20, R37/38|
|Flash point||19 °C (66 °F; 292 K)|
|437 °C (819 °F; 710 K)|
Except where noted otherwise, data is 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 pentanol used primarily as a pharmaceutical or pigment solvent. It is a trace component in fermentation ethanol. It is a colorless liquid with a pungent odor of camphor, and soluble with water and other organic solvents.
The oxo alcohol process is the principal commercial source of TAA. The reaction of 2-methyl-2-butene with water in the presence of an acid catalyst yields TAA. Minor quantities, mainly in Europe, are obtained from separation of fusel alcohols.
Fusel alcohols including TAA are a grain fermentation by-product and therefore present in many alcoholic beverages. Trace levels of TAA have also been detected in various foodstuffs, including fried bacon and 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 g 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 However, like other tertiary alcohol based anaesthetics (e.g. methylpentynol, ethchlorvynol) TAA was eventually superseded by safer and more effective agents. It is still occasionally used for the anaesthesia of rodents.
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 2,3-dihydroxy-2-methylbutane. 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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