Tert-Amyl alcohol
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| Names | |
|---|---|
| IUPAC names
• 2-Methyl-2-butanol
• 2-Methylbutan-2-ol | |
| Other names
• tert-Amyl alcohol
• Dimethylethylcarbinol • t-Amyl alcohol • tert-Pentyl alcohol • Amylene hydrate | |
| Identifiers | |
| ECHA InfoCard | 100.000.827 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C5H12O | |
| Molar mass | 88.150 g·mol−1 |
| Density | 0.815 g/cm³, liquid |
| Melting point | −12 °C (10 °F; 261 K) |
| Boiling point | 102 °C (216 °F; 375 K) |
| 120 g/L | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Highly Flammable Liver damage may occur with prolonged exposure |
| NFPA 704 (fire diamond) | |
| Flash point | 19 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[1][2] 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.[3] It is active in doses of 2,000-5,000 mg, making it some 20 times more potent than regular ethanol.[4][5] Its hypnotic potency is between that of chloral hydrate and paraldehyde.[6] 2-methyl-2-butanol is similar in structure to ethchlorvynol and methylpentynol. It is a byproduct of the fermentation of grain. [7] 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.[8] Overdose produces symptoms similar to alcohol poisoning and is a medical emergency.
See also
References
- ^ 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., "Amylene hydrate, a new hypnotic." The American Practitioner and News, Vol. 5, 1888. [4]
- ^ F.A. Castle & C. Rice. The American Druggist - An illustrated monthly journal. Vol. XVII, 19 Jul 1889. [5]
- ^ George Milbry Gould & R J E Scott. "The Practitioner's Medical Dictionary", 1910
- ^ Collins, A., Sumner, S., Borghoff, S., and Medinsky, M. (1999). A physiological model for tert-amyl methyl ether and tert-amyl alcohol: Hypothesis testing of model structures. Toxicol. Sci. 49, 15–28.[6]