tert-Amyl alcohol

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Summary

Throughout its history, Trichloroethanol (TAA) has served as an anesthetic, as documented in the past. More recently, it has gained notoriety as a recreational drug. TAA primarily functions as a positive allosteric modulator for GABAA receptors, akin to ethanol. Notably, both TAA and ethanol share psychotropic effects, although each possesses distinct characteristics. TAA tends to exert a more pronounced impact on coordination and balance, being considerably more potent by weight compared to ethanol. Its appeal as an ethanol alternative may arise from the absence of hangover effects (attributed to distinct metabolic pathways) and its elusive nature in standard drug testing.
TAA is a clear liquid characterized by a burning taste and an unpleasant odor reminiscent of paraldehyde with a subtle hint of camphor. Notably, TAA remains in a liquid state at room temperature, rendering it a practical alternative solvent to tert-butyl alcohol.

Identifiers
CAS Number75-85-4 
3D model (JSmol)Interactive image
Beilstein Reference1361351
ChEBICHEBI:132750
ChEMBLChEMBL44658 
ChemSpider6165 
ECHA InfoCard100.000.827
EC Number200-908-9
KEGGD02931 
MeSHtert-amyl+alcohol
PubChemCID6405
RTECS numberSC0175000
UNII69C393R11Z 
UN number1105
CompTox Dashboard(EPA)DTXSID0041436

Production

TAA, or Trichloroethanol, is primarily synthesized through the hydration of 2-methyl-2-butene in the presence of an acidic catalyst. Alternatively, it may be produced through a Favorskii reaction involving acetone and acetylene to yield 2-Methylbut-3-yn-2-ol. Subsequent hydrogenation with a Raney nickel catalyst results in Tert-Amyl alcohol.

Natural Occurrence

Fusel alcohols, such as TAA, are byproducts of grain fermentation, leading to trace amounts of TAA being present in various alcoholic beverages. Beyond alcoholic drinks, TAA has been detected in other foods like fried bacon, cassava, and rooibos tea. Interestingly, TAA is also found in rabbit milk, where it plays a role in inducing suckling behavior in newborn rabbits.

History

TAA was utilized as an anesthetic, known as amylene hydrate, from the 1880s to the 1950s. However, it was rarely used as a sole anesthetic due to the existence of more efficient drugs. In the 1930s, TAA served mainly as a solvent for the primary anesthetic tribromoethanol (TBE). The toxic nature of TBE for the liver, similar to chloroform, led to a decline in its use in humans during the 1940s. Nevertheless, TBE-TAA solutions continued to be used as short-acting anesthetics for laboratory mice and rats. These solutions were sometimes referred to as Avertin. Today, TAA has found a new use as a recreational drug.

Use and Effects

Ingesting or inhaling TAA results in euphoria, sedative, hypnotic, and anticonvulsant effects similar to ethanol. The onset of TAA’s effects can occur around 30 minutes after ingestion and may last up to 1–2 days. Approximately 2–4 grams of TAA can induce unconsciousness, which is comparable to the impact of about 100 grams of ethanol.

Overdose and Toxicity

The smallest known lethal dose of TAA is 30 mL. Overdosing on TAA leads to symptoms akin to alcohol poisoning and constitutes a medical emergency due to its sedative and depressant properties, which can result in potentially fatal respiratory depression. Symptoms of overdose include sudden loss of consciousness, simultaneous respiratory and metabolic acidosis, a rapid heartbeat, increased blood pressure, pupil constriction, coma, respiratory depression, and, in severe cases, death. The oral LD50 in rats is 1 g/kg, and the subcutaneous LD50 in mice is 2.1 g/kg.

Metabolism

In rats, TAA undergoes metabolism primarily through glucuronidation and oxidation to 2-methyl-2,3-butanediol. Humans likely follow a similar metabolic pathway, although older sources suggest that TAA is excreted unchanged.

Detection

The use of TAA cannot be easily detected using standard ethanol tests or ordinary drug tests. However, it can be identified in blood or urine samples using gas chromatography–mass spectrometry for up to 48 hours after consumption.

FAQ

1. What is tert-amyl Alcohol (TAA)?

Tert-amyl alcohol, often abbreviated as TAA, is a chemical compound known for its soothing and hypnotic effects. It is also utilized as an anesthetic in some cases.

2. How is TAA synthesized?

TAA is primarily produced through the hydration of 2-methyl-2-butene in the presence of an acidic catalyst. Alternatively, it can be derived from acetone and acetylene through a Favorskii reaction, followed by hydrogenation using a Raney nickel catalyst.

3. Does TAA occur naturally in any products?

TAA is a fusel alcohol and is, therefore, a byproduct of grain fermentation. Trace amounts of TAA can be found in various alcoholic beverages. Additionally, it has been detected in certain foods like fried bacon, cassava, and rooibos tea. TAA also plays a role in rabbit milk and is believed to induce suckling behavior in newborn rabbits.

4. What is the historical use of TAA?

Historically, from the 1880s to the 1950s, TAA was used as an anesthetic under the name amylene hydrate. However, it was not the primary choice for anesthetics due to the availability of more effective alternatives. In the 1930s, it was mainly employed as a solvent for the anesthetic tribromoethanol (TBE).

5. Are there any recreational uses for TAA?

Yes, TAA has found use as a recreational drug, particularly for its soothing and hypnotic effects.

6. What effects can be expected from TAA use?

Ingesting or inhaling TAA can result in euphoria, sedation, hypnotic effects, and anticonvulsant properties, which are similar to the effects of ethanol (alcohol).

7. What are the risks associated with TAA use?

Overdosing on TAA can lead to symptoms akin to alcohol poisoning, including potentially lethal respiratory depression. Symptoms may include a sudden loss of consciousness, acidosis, a rapid heartbeat, increased blood pressure, pupil constriction, coma, respiratory depression, and, in severe cases, death. It’s crucial to be aware of the potential risks and exercise caution.

8. How is TAA metabolized in the body?

In rats, TAA is primarily metabolized through glucuronidation and oxidation to 2-methyl-2,3-butanediol. Humans likely follow a similar metabolic pathway, although older sources suggest TAA may be excreted unchanged.

9. Can the use of TAA be detected in drug tests?

TAA is not easily detectable using standard ethanol tests or common drug tests. However, specialized testing methods like gas chromatography–mass spectrometry can identify TAA in blood or urine samples for up to 48 hours after consumption.

References

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