tert-Amyl alcohol

From Wikipedia, the free encyclopedia
Jump to: navigation, search
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
Identifiers
CAS number 75-85-4 YesY
PubChem 6405
ChemSpider 6165 YesY
UNII 69C393R11Z YesY
EC number 200-908-9
UN number 1105
KEGG D02931 YesY
MeSH tert-amyl+alcohol
ChEMBL CHEMBL44658 YesY
RTECS number SC0175000
Beilstein Reference 1361351
Jmol-3D images Image 1
Properties
Molecular formula 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
Solubility in water 120 g dm−3
log P 1.095
Vapor pressure 1.6 kPa (at 20 °C)
Refractive index (nD) 1.405
Thermochemistry
Std molar
entropy
So298
229.3 J K−1 mol−1
Std enthalpy of
formation
ΔfHo298
−380.0–−379.0 kJ mol−1
Std enthalpy of
combustion
ΔcHo298
−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
GHS hazard statements H225, H315, H332, H335
GHS precautionary statements 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)
Explosive limits 9%
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/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