Tert-Amyl alcohol

Last updated
tert-Amyl alcohol
2-Methyl-2-butanol FormulaV1-Seite001.svg
Ball-and-stick model of 2-methyl-2-butanol 2-Methyl-2-butanol-3D-balls.png
Ball-and-stick model of 2-methyl-2-butanol
Space-filling model of the 2-methyl-2-butanol 2-Methyl-2-butanol-3D-spacefill.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-908-9
KEGG
MeSH tert-amyl+alcohol
PubChem CID
RTECS number
  • SC0175000
UNII
UN number 1105
  • InChI=1S/C5H12O/c1-4-5(2,3)6/h6H,4H2,1-3H3 Yes check.svgY
    Key: MSXVEPNJUHWQHW-UHFFFAOYSA-N Yes check.svgY
  • CCC(C)(C)O
Properties
C5H12O
Molar mass 88.150 g·mol−1
AppearanceColorless 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, benzene, chloroform, 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
Std molar
entropy (S⦵298)
229.3 J K−1 mol−1
−380.0 to −379.0 kJ mol−1
−3.3036 to −3.3026 MJ mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Danger
H225, H315, H332, H335
P210, P261
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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

Contents

Historically, TAA has been used as an anesthetic [3] and more recently as a recreational drug. [4] TAA is mostly a positive allosteric modulator for GABAA receptors in the same way as ethanol. [5] 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. [6]

TAA is a colorless liquid with a burning flavor [7] and an unpleasant odor [8] similar to paraldehyde with a hint of camphor. [9] 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. [10] [3]

Natural occurrence

Fusel alcohols like TAA are grain fermentation byproducts, and therefore trace amounts of TAA are present in many alcoholic beverages. [11] Traces of TAA have been detected in other foods, like fried bacon, [12] cassava [13] and 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 anesthetic with the contemporary name of amylene hydrate, but it was rarely used because more efficient drugs existed. [3] In the 1930s, TAA was mainly used as a solvent for the primary anesthetic tribromoethanol (TBE). Like chloroform, TBE is toxic for the liver, so the use of such solutions declined in the 1940s in humans. TBE-TAA-solutions remained in use as short-acting anesthetics for laboratory mice and rats. Such solutions are sometimes called Avertin, which was a brand name for the now discontinued TAA and TBE solution with a volume ratio of 0.5:1 made by Winthrop Laboratories. [16] TAA has emerged recently as a 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 alcohol poisoning and is a medical emergency due to the sedative/depressant properties which manifest in overdose as potentially lethal respiratory depression. Sudden loss of consciousness, simultaneous respiratory and metabolic acidosis, [18] fast heartbeat, increased blood pressure, pupil constriction, coma, respiratory depression [19] and death may follow from an overdose. The oral LD50 in rats is 1 g/kg. The 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. 2-Methyl-2-butanol oxidation.svg
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

Related Research Articles

<span class="mw-page-title-main">Alcohol (chemistry)</span> Organic compound with at least one hydroxyl (–OH) group

In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl functional group bound to a saturated carbon atom. Alcohols range from the simple, like methanol and ethanol, to complex, like sugars and cholesterol. The presence of an OH group strongly modifies the properties of hydrocarbons, conferring hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur.

<span class="mw-page-title-main">Amyl alcohol</span> Chemical compound family

Amyl alcohols are alcohols with the formula C5H11OH. Eight are known. A mixture of amyl alcohols (also called amyl alcohol) can be obtained from fusel alcohol. Amyl alcohol is used as a solvent and in esterification, by which is produced amyl acetate and other products. The name amyl alcohol without further specification applies to the normal (straight-chain) form, 1-pentanol.

Butanol (also called butyl alcohol) is a four-carbon alcohol with a formula of C4H9OH, which occurs in five isomeric structures (four structural isomers), from a straight-chain primary alcohol to a branched-chain tertiary alcohol; all are a butyl or isobutyl group linked to a hydroxyl group (sometimes represented as BuOH, sec-BuOH, i-BuOH, and t-BuOH). These are 1-butanol, two stereoisomers of sec-butyl alcohol, isobutanol and tert-butyl alcohol. Butanol is primarily used as a solvent and as an intermediate in chemical synthesis, and may be used as a fuel. Biologically produced butanol is called biobutanol, which may be n-butanol or isobutanol.

<span class="mw-page-title-main">Chloral hydrate</span> Chemical sedative and hypnotic drug

Chloral hydrate is a geminal diol with the formula Cl3C−CH(OH)2. It was first used as a sedative and hypnotic in Germany in the 1870s. Over time it was replaced by safer and more effective alternatives but it remained in usage in the United States until at least the 1970s. It sometimes finds usage as a laboratory chemical reagent and precursor. It is derived from chloral (trichloroacetaldehyde) by the addition of one equivalent of water.

Fusel alcohols or fuselol, also sometimes called fusel oils in Europe, are mixtures of several higher alcohols produced as a by-product of alcoholic fermentation. The word Fusel is German for "bad liquor".

<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

In the liquid fuel industry, oxygenates are hydrocarbon-derived fuel additives containing at least one oxygen atom to promote complete combustion. Absent oxygenates, fuel combustion is usually incomplete, and the exhaust stream pollutes the air with carbon monoxide, soot particles, aromatic and polyaromatic hydrocarbons, and nitrated polyaromatic hydrocarbons.

<span class="mw-page-title-main">Hexobarbital</span> Chemical compound

Hexobarbital or hexobarbitone, sold both in acid and sodium salt forms as Citopan, Evipan, and Tobinal, is a barbiturate derivative having hypnotic and sedative effects. It was used in the 1940s and 1950s as an agent for inducing anesthesia for surgery, as well as a rapid-acting, short-lasting hypnotic for general use, and has a relatively fast onset of effects and short duration of action. Modern barbiturates have largely supplanted the use of hexobarbital as an anesthetic, as they allow for better control of the depth of anesthesia. Hexobarbital is still used in some scientific research.

<span class="mw-page-title-main">Ro15-4513</span> Chemical compound

Ro15-4513(IUPAC: Ethyl-8-azido-5,6-dihydro-5-methyl-6-oxo-4H-imidazo-1,4-benzodiazepine-3-carboxylate) is a weak partial inverse agonist of the benzodiazepine class of drugs, developed by Hoffmann–La Roche in the 1980s. It acts as an inverse agonist, and can therefore be an antidote to the acute impairment caused by alcohols, including ethanol, isopropanol, tert-butyl alcohol, tert-amyl alcohol, 3-methyl-3-pentanol, methylpentynol and ethchlorvynol.

The molecular formula C5H12O (molar mass: 88.15 g/mol, exact mass: 88.088815) may refer to:

The molecular formula C6H14O may refer to:

Isopropyl alcohol is a colorless, flammable organic compound with a pungent alcoholic odor.

Methylbutanol may refer to:

tert-Amyl methyl ether (TAME) is an ether used as a fuel oxygenate. TAME derives from C5 distillation fractions of naphtha. It has an ethereous odor. Unlike most ethers, it does not require a stabilizer as it does not form peroxides on storage.

<span class="mw-page-title-main">2-Pentanol</span> Chemical compound

2-Pentanol (IUPAC name: pentan-2-ol; also called sec-amyl alcohol) is an organic chemical compound. It is used as a solvent and an intermediate in the manufacturing of other chemicals. 2-Pentanol is a component of many mixtures of amyl alcohols sold industrially. 2-Pentanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-2-pentanol and (S)-(+)-2-pentanol.

<span class="mw-page-title-main">2-Methyl-2-pentanol</span> Chemical compound

2-Methyl-2-pentanol is an organic chemical compound. It can be added to a gas chromatograph to help distinguish between branched compounds, especially alcohols. Its presence in urine can be used to test for exposure to 2-methylpentane. As with many other short-chain alcohols, 2-methyl-2-pentanol can produce intoxication and sedative effects similar to those of ethanol, though it is more irritating to mucous membranes and generally more toxic to the body.

<span class="mw-page-title-main">Tribromoethanol</span> Chemical compound

2,2,2-Tribromoethanol, often called just tribromoethanol, is a chemical compound with formula Br3C−CH2OH. Its molecule can be described as that of ethanol, with the three hydrogen atoms in position 2 replaced by bromine. It is a white crystalline solid, soluble in water and other solvents, that absorbs strongly in the UV below 290 nm.

<span class="mw-page-title-main">Alcohols (medicine)</span> Alcohols used as antiseptics, disinfectants or antidotes

Alcohols, in various forms, are used medically as an antiseptic, disinfectant, and antidote. Alcohols applied to the skin are used to disinfect skin before a needle stick and before surgery. They may also be used as a hand sanitizer; to clean other areas; and in mouthwashes. Taken by mouth or injected into a vein, ethanol is used to treat methanol or ethylene glycol toxicity when fomepizole is not available.

References

  1. 1 2 Lomte, S.B.; Bawa, M.J.; Lande, M.K.; Arbad, B.R. (2009). "Densities and Viscosities of Binary Liquid Mixtures of 2-Butanone with Branched Alcohols at (293.15 to 313.15) K". Journal of Chemical & Engineering Data. 54: 127–130. doi:10.1021/je800571y.
  2. ↑ Haynes, William M.; Lide, David R.; Bruno, Thomas J. (2014). "Section 3 - Physical Constants of Organic Compounds". CRC Handbook of Chemistry and Physics, 95th Edition (95th ed.). CRC Press. p. 362. ISBN   9781482208689. OCLC   908078665.
  3. 1 2 3 4 Adriani, John (1962). The Chemistry and Physics of Anesthesia (2nd ed.). Illinois: Thomas Books. pp. 273–274. ISBN   9780398000110.
  4. 1 2 Rusiecka, Izabela; Gągało, Iwona; Anand, Jacek Sein; Schetz, Daria; Waldman, Wojciech (October 2016). "Drinking "Vodka" or vodka – This is a question". Toxicology in Vitro. 36: 66–70. doi:10.1016/j.tiv.2016.07.009. ISSN   1879-3177. PMID   27448500.
  5. ↑ Martin, J (2004). "Influence of oxygenated fuel additives and their metabolites on γ-aminobutyric acidA (GABAA) receptor function in rat brain synaptoneurosomes". Toxicology Letters. 147 (3): 209–217. doi:10.1016/j.toxlet.2003.10.024. PMID   15104112.
  6. ↑ Syed, Alia N.; Leo, Raphael J. (2022-11-22). "Recreational 2-Methyl-2-Butanol Use: An Emerging Wave of Misuse of an Ethanol Substitute on the Horizon?". The Primary Care Companion for CNS Disorders. 24 (6): 44189. doi:10.4088/PCC.22cr03292. ISSN   2155-7780. PMID   36441984. S2CID   253700629.
  7. ↑ O'Neil, Maryadele J., ed. (2006). The Merck index (14th ed.). Merck. p. 1232. ISBN   9780911910001. OCLC   70882070.
  8. 1 2 Brandenberger, Hans; Maes, Robert A. A. (1997). Analytical Toxicology for Clinical, Forensic, and Pharmaceutical Chemists. Berlin: W. de Gruyter. pp. 400–401. ISBN   978-3110107319. OCLC   815506841.
  9. ↑ Yandell, D. W.; et al. (1888). "Amylene hydrate, a new hypnotic". The American Practitioner and News. 5: 88–98.
  10. ↑ Papa, Anthony J. (2004). "Amyl Alcohols". Kirk–Othmer Encyclopedia of Chemical Technology (5th ed.). Hoboken, N.J.: Wiley-Interscience. doi:10.1002/0471238961.0113251216011601.a01.pub2. 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. ↑ 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. ISSN   0021-8561.
  13. ↑ 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. Bibcode:1983JSFA...34..874D. doi:10.1002/jsfa.2740340816. ISSN   1097-0010.
  14. ↑ 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. ISSN   0021-8561.
  15. ↑ Benoist, Schaal; Gérard, Coureaud; Langlois, Dominique; Giniès, Christian; Sémon, Etienne; Perrier, Guy (2003). "Chemical and behavioural characterization of the rabbit mammary pheromone". Nature. 424 (6944): 68. Bibcode:2003Natur.424...68S. doi:10.1038/nature01739. S2CID   4428155.
  16. ↑ Meyer, Robert E.; Fish, Richard E. (November 2005). "A review of tribromoethanol anesthesia for production of genetically engineered mice and rats". Lab Animal. 34 (10): 47–52. doi:10.1038/laban1105-47. ISSN   0093-7355. PMID   16261153. S2CID   21759580.
  17. ↑ Lewis, Robert Alan (1998). Lewisʼ Dictionary of Toxicology. Boca Raton, Florida: CRC Press. pp.  45. ISBN   978-1566702232. OCLC   35269968.
  18. 1 2 3 "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. 1 2 Anand, Jacek Sein; Gieroń, Joanna; Lechowicz, Wojciech; Schetz, Daria; Kała, Maria; Waldman, Wojciech (September 2014). "Acute intoxication due to tert-amyl alcohol—a case report". Forensic Science International. 242: e31–e33. doi:10.1016/j.forsciint.2014.07.020. ISSN   1872-6283. PMID   25112153.
  20. ↑ Soehring, K.; Frey, H.H.; Endres, G. (1955). "Relations between constitution and effect of tertiary alcohols". Arzneimittel-Forschung. 5 (4): 161–165. PMID   14389140.
  21. ↑ 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. 49 (1): 15–28. doi: 10.1093/toxsci/49.1.15 . PMID   10367338.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.