Tert-Amyl alcohol
chemical compound
tert-Amyl alcohol (TAA) or 2-methylbutan-2-ol (2M2B), is a branched pentanol.
Historically, TAA has been used as an anesthetic and more recently as a recreational drug. TAA is mostly a positive allosteric modulator for GABAA receptors in the same way as ethanol. 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 metabolic pathways) and the fact that it is often not detected on standard drug test.
TAA is a colorless liquid with a burning flavor and an unpleasant odor similar to paraldehyde with a hint of camphor. TAA remains liquid at room temperature, making it a useful alternative solvent to tert-butyl alcohol.
Production
TAA is primarily made by the hydration of 2-methyl-2-butene in the presence of an acidic catalyst.
Natural occurrence
Fusel alcohols like TAA are grain fermentation byproducts, and therefore trace amounts of TAA are present in many alcoholic beverages.
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