tert-Amyl alcohol

Source: Wikipedia, the free encyclopedia.
tert-Amyl alcohol
Stereo, skeletal formula of 2-methyl-2-butanol
Ball-and-stick model of 2-methyl-2-butanol
Ball-and-stick model of 2-methyl-2-butanol
Space-filling model of the 2-methyl-2-butanol
Space-filling model of the 2-methyl-2-butanol
Names
Preferred IUPAC name
2-Methylbutan-2-ol
Other names
2-Methyl-2-butanol
tert-Amyl alcohol
t-Amylol
TAA
tert-Pentyl alcohol
2-Methyl-2-butyl alcohol
t-Pentylol
Amylene hydrate
Dimethylethylcarbinol
Identifiers
3D model (
JSmol
)
1361351
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.000.827 Edit this at Wikidata
EC Number
  • 200-908-9
KEGG
MeSH tert-amyl+alcohol
RTECS number
  • SC0175000
UNII
UN number 1105
  • InChI=1S/C5H12O/c1-4-5(2,3)6/h6H,4H2,1-3H3 checkY
    Key: MSXVEPNJUHWQHW-UHFFFAOYSA-N checkY
  • CCC(C)(C)O
Properties
C5H12O
Molar mass 88.150 g·mol−1
Appearance Colorless liquid
Odor Camphorous
Density 0.805 g/cm3[1]
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
Solubility soluble in water,
diethylether and ethanol[2]
log P 1.0950.5:1 volume ratio
Vapor pressure 1.6 kPa (at 20 °C)
−7.09×10−5 cm3/mol
1.405
Viscosity 4.4740 mPa·s (at 298.15 K)[1]
Thermochemistry
229.3 J K−1 mol−1
Std enthalpy of
formation
(ΔfH⦵298)
 −380.0 to −379.0 kJ mol−1
Std enthalpy of
combustion
(ΔcH⦵298)
 −3.3036 to −3.3026 MJ mol−1
Hazards
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark
Danger
H225, H315, H332, H335
P210, P261
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 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. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
3
0
Flash point 19 °C (66 °F; 292 K)
437 °C (819 °F; 710 K)
Explosive limits
 9%
Safety data sheet (SDS) hazard.com
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

tert-Amyl alcohol (TAA) or 2-methylbutan-2-ol (2M2B), is a branched

pentanol
.

Historically, TAA has been used as an

metabolic pathways) and the fact that it is often not detected on standard drug test.[6]

TAA is a colorless liquid with a burning flavor

tert-butyl alcohol
.

Production

TAA is primarily made by the hydration of

2-methyl-2-butene in the presence of an acidic catalyst.[10][3]
On the other hand, it could[original research?] be product from acetone and acetylene by Favorskii reaction to give 2-Methylbut-3-yn-2-ol, then hydrogenation with Raney nickel catalyst to give Tert-Amyl alcohol.

Natural occurrence

rooibos tea.[14]
TAA is also present in rabbit milk and seems to play a role in pheromone-inducing suckling in the newborn rabbit.[15]

History

From about the 1880s to the 1950s, TAA was used as an

recreational drug.[4]

Use and effects

Ingestion or inhalation of TAA causes euphoria, sedative, hypnotic, and anticonvulsant effects similar to ethanol.[17] When ingested, the effects of TAA may begin in about 30 minutes and can last up to 1–2 days.[18] 2–4 grams of TAA is sufficient to produce a hypnotic effect. About 100 g of ethanol induces a similar level of sedation.[8]

Overdose and toxicity

The smallest known dose of TAA that has killed a person is 30 mL.[18]

An overdose produces symptoms similar to

subcutaneous LD50 in mice is 2.1 g/kg.[20]

Metabolism

In rats, TAA is primarily metabolized via glucuronidation, as well as by oxidation to 2-methyl-2,3-butanediol. It is likely that the same path is followed in humans,[21] though older sources suggest TAA is excreted unchanged.[3]

TAA oxidises to 2-methyl-2,3-butanediol.

The use of TAA cannot be detected with general ethanol tests or other ordinary drug tests. Its use can be detected from a blood or a urine sample by using gas chromatography–mass spectrometry for up to 48 hours after consumption.[19]

See also

References

  1. ^
    doi:10.1021/je800571y
    .
  2. OCLC 908078665
    .
  3. ^
    ISBN 9780398000110
    .
  4. ^
    PMID 27448500
    .
  5. PMID 15104112
    .
  6. S2CID 253700629
    .
  7. OCLC 70882070
    .
  8. ^
    OCLC 815506841
    .
  9. ^ Yandell, D. W.; et al. (1888). "Amylene hydrate, a new hypnotic". The American Practitioner and News. 5: 88–98.
  10. ISBN 9780471238966
    .
  11. ^ Gould, George M.; Scott, Richard J. E. (1919). The Practitioner's Medical Dictionary. P. Blakiston's. p. 50. Retrieved 2018-07-27.
  12. ISSN 0021-8561
    .
  13. ISSN 1097-0010
    .
  14. ISSN 0021-8561
    .
  15. S2CID 4428155
    .
  16. S2CID 21759580
    .
  17. OCLC 35269968
    .
  18. ^ a b c "2-METHYL-2-BUTANOL - National Library of Medicine HSDB Database". www.toxnet.nlm.nih.gov. Archived from the original on 2018-03-08. Retrieved 2018-04-08.
  19. ^
    PMID 25112153
    .
  20. PMID 14389140
    .
  21. PMID 10367338
    .
Retrieved from "https://en.wikipedia.org/w/index.php?title=Tert-Amyl_alcohol&oldid=1219409096"