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Names | |||
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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 | ||
EC Number |
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KEGG | |||
MeSH | tert-amyl+alcohol | ||
PubChem CID | |||
RTECS number |
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UNII | |||
UN number | 1105 | ||
CompTox Dashboard (EPA) | |||
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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, 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 | |||
Refractive index (nD) | 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 | ||
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: | |||
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Danger | |||
H225, H315, H332, H335 | |||
P210, P261 | |||
NFPA 704 (fire diamond) | |||
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). |
tert-Amyl alcohol (TAA) or 2-methylbutan-2-ol (2M2B), is a branched pentanol.
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.
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 produced 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.
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]
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]
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]
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]
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]
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]
In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl functional group bound to carbon. 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.
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.
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".
Cocaethylene (ethylbenzoylecgonine) is the ethyl ester of benzoylecgonine. It is structurally similar to cocaine, which is the methyl ester of benzoylecgonine. Cocaethylene is formed by the liver when cocaine and ethanol coexist in the blood. In 1885, cocaethylene was first synthesized, and in 1979, cocaethylene's side effects were discovered.
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.
To oxygenate means to impregnate, combine, or supply something with oxygen, while oxygenates are hydrocarbons containing at least one oxygen atom that are used as fuel additives to promote complete combustion in fuel mixtures. Oxygenates can also be employed to reduce air pollution by reducing carbon monoxide production and soot particle size and compounds such as aromatic hydrocarbons, polyaromatic hydrocarbons, and nitrated polyaromatic hydrocarbons that are side-products caused by incomplete combustion.
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.
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.
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.
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.
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.
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.
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.