tert-Amyl alcohol

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tert-Amyl alcohol
Stereo, skeletal formula of 2-methyl-2-butanol
Ball-and-stick model of 2-methyl-2-butanol
Space-filling model of the 2-methyl-2-butanol
Names
Preferred IUPAC name
2-Methyl-2-butanol[1]
Systematic IUPAC name
2-Methylbutan-2-ol[1]
Other names
tert-Amyl alcohol, t-Amylol, t-AmOH, TAA[1]

tert-Pentyl alcohol, 2m2bOH, 2-methyl-2-butyl alcohol, t-Pentylol,[1]
Amylene hydrate[1]

Dimethylethylcarbinol[1]
Identifiers
1361351
75-85-4 YesY
ChEMBL ChEMBL44658 YesY
ChemSpider 6165 YesY
EC number 200-908-9
Jmol-3D images Image
KEGG D02931 YesY
MeSH tert-amyl+alcohol
PubChem 6405
RTECS number SC0175000
UNII 69C393R11Z YesY
UN number 1105
Properties
C5H12O
Molar mass 88.15 g·mol−1
Appearance Colorless liquid
Odor Camphorous
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
log P 1.095
Vapor pressure 1.6 kPa (at 20 °C)
1.405
Thermochemistry
229.3 J K−1 mol−1
−380.0–−379.0 kJ mol−1
−3.3036–−3.3026 MJ mol−1
Hazards
MSDS hazard.com
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H225, H315, H332, H335
P210, P261
EU Index 603-007-00-2
EU classification Highly Flammable F Harmful Xn
R-phrases R11, R20, R37/38
S-phrases (S2), S46
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 19 °C (66 °F; 292 K)
437 °C (819 °F; 710 K)
Explosive limits 9%
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

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.

Industrial production[edit]

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.[2][3] Minor quantities, mainly in Europe, are obtained from separation of fusel alcohols.[citation needed]

Natural occurrence[edit]

Fusel alcohols including TAA are a grain fermentation by-product and therefore present in many alcoholic beverages.[4] Trace levels of TAA have also been detected in various foodstuffs, including fried bacon and cassava,[5][6] rooibos tea[7] and fruits such as apple and pineapple.

Pharmacology[edit]

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.[3]

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.[8] 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.[citation needed]

TAA produces euphoria, sedative, hypnotic, and anticonvulsant effects similar to ethanol through ingestion or inhalation.[9] It is active in doses of 2,000–4,000 mg, making it 20 times more potent than ethanol.[10][11] Its hypnotic potency is between chloral hydrate and paraldehyde[12] 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,[13] though older sources suggest it is excreted unchanged.[3]

2-Methyl-2-butanol oxidation.svg

TAA's simple structure and intoxicating effects have led to its use as a recreational drug.[14]

Overdose and toxicity[edit]

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.[15]

See also[edit]

References[edit]

  1. ^ a b c d e f "tert-Amyl alcohol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 2011-12-13. 
  2. ^ 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
  3. ^ a b c Adriani, John (1962). The Chemistry and Physics of Anesthesia. Second Edition. Illinois: Thomas Books. p. 273-274. ISBN 9780398000110.  edit
  4. ^ George Milbry Gould; Richard John Ernst Scott (1919). The Practitioner's Medical Dictionary: Containing All the Words and Phrases Generally Used in Medicine and the Allied Sciences, with Their Proper Pronunciation, Derivation, and Definition. P. Blakiston's. p. 50. Retrieved February 7, 2013. 
  5. ^ Dougan, J.; Robinson, J. M.; Sumar, S.; Howard, G. E.; Coursey, D. G. (1983). "Some flavouring constituents of cassava and of processed cassava products". Journal of the Science of Food and Agriculture 34 (8): 874. doi:10.1002/jsfa.2740340816.  edit
  6. ^ 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.  edit
  7. ^ Habu, Tsutomu; Flath, Robert A.; Mon, T. Richard; Morton, Julia F. (1 March 1985). "Volatile components of Rooibos tea (Aspalathus linearis)". Journal of Agricultural and Food Chemistry 33 (2): 249–254. doi:10.1021/jf00062a024. 
  8. ^ Carey, Francis. Organic Chemistry (4 ed.). ISBN 0072905018. Retrieved 2013-02-05. 
  9. ^ Robert A. Lewis (1998). Lewis' Dictionary of Toxicology. CRC Press. p. 45. ISBN 1-56670-223-2. 
  10. ^ Hans Brandenberger & Robert A. A. Maes, ed. (1997). Analytical Toxicology for Clinical, Forensic and Pharmaceutical Chemists. p. 401. ISBN 3-11-010731-7. 
  11. ^ 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. 
  12. ^ F. A. Castle & C. Rice (March 1888). "Amylene and amylene hydrate". The American Druggist 17 (3): 58–59. 
  13. ^ 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.  edit
  14. ^ "2-Methyl-2-Butanol Reports". Erowid. Retrieved 1 July 2014. 
  15. ^ Soehring, K.; Frey, H. H.; Endres, G. (1955). "Relations between constitution and effect of tertiary alcohols". Arzneimittel-Forschung 5 (4): 161–165. PMID 14389140.  edit