| 2-methyl-2-butanol |
| 2-methyl-2-butanol | |||||||||||||||||||||||||||||
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| Chemical Nomenclature | |||||||||||||||||||||||||||||
| Common names | 2m2b | ||||||||||||||||||||||||||||
| Systematic name | 2-methyl-2-butanol | ||||||||||||||||||||||||||||
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This article requires proofreading. As such, it likely contains incorrect grammar, spelling, and punctuation. |
2-methyl-2-butanol (Also known as tert-amyl alcohol or 2m2b) is a tertiary alcohol with sedative, hypnotic, and anxiolytic effects. Historically it has been used in anesthesia as a component of avertin fluid, mixed with tribromoethanol and water.[1] It has a strong solvent smell, reminiscent of gasoline, but little flavor. 2m2b's simple structure and intoxicating effects have led to its use as a recreational drug.[2]
Fusel alcohols including 2m2b are a grain fermentation by-product and therefore present in many alcoholic beverages.[3] Trace levels of 2m2b have also been detected in various foodstuffs, including fried bacon and cassava,[4][5] rooibos tea[6] and fruits such as apple and pineapple.
Contents
Chemistry
2-methyl-2-butanol is also known as tert-amyl-alcohol, 2m2b, or amylene hydrate. 2-methyl-2-butanol is a pentanol and an isomer of amyl alcohol. It is synthesized by the the reaction of 2-methyl-2-butene with water in the presence of an acid catalyst. [7]
Pharmacology
2-methyl-2-butanol activates GABA receptors which causes negatively charged chloride ions to enter neurons and increase the amount of excitation necessary to cause the neuron to fire. Being a tertiary alcohol, it cannot be metabolized by alcohol dehydrogenase into aldehydes which cause the hangover associated with consuming large amounts of ethanol. This makes 2m2b significantly safer than primary alcohols.[8] However, a consequence of this is that 2-methyl-2-butanol has an extended duration of action, with effects which last up to 12 hours after its consumption.
Subjective Effects
The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. The listed effects will rarely if ever occur all at once but heavier dosages will increase the chances and are more likely to induce a full range of effects.
Physical Effects
Cognitive Effects
- Disinhibition
- Thought deceleration
- Information processing suppression
- Euphoria
- Empathy, love and sociability enhancement
- Amnesia
Toxicity and harm potential
Little is known about the long-term effects of 2-methyl-2-butanol use. As it cannot be metabolized into aldehydes it is not expected to be as hepatoxic as ethanol.[9]
Lethal dosage
The lowest recorded fatal dose in a human is 30mL.[10] The oral LD50 in rats has been found to be about 1000mg/kg,[11] however this does not necessarily carry over to humans and doses large enough to induce coma may allow aspiration of vomit, which is a medical emergency.
Tolerance and addiction potential
As it cannot be oxidized to an aldehyde, tolerance occurs solely through upregulation of liver enzymes responsible for glucoronidation combined with the downregulation of GABA receptors.
Withdrawals
As with any other GABA receptor agonist, repeated use resulting in increasing tolerance will eventually result in a withdrawal syndrome upon abrupt discontinuation resembling alcohol, barbiturate, or benzodiazepine withdrawal, up to and including delirium tremens.
Interactions
2-methyl-2-butanol, being a GABA agonist, is greatly potentiated by drugs which potentiate GABA agonists such as benzodiazepines and barbiturates. Its effects are additive with other drugs which activate GABA receptors and the respiratory depression caused by opioids.
Legal issues
2-methyl-2-butanol is not known to be specifically controlled in any area. However, some jurisdictions may have catch-all laws against any substance or solvents in particular possessed with the intent to use them to become intoxicated, so it is wise to avoid any indication of it being for human consumption.
References
- ↑ http://archsurg.jamanetwork.com/article.aspx?articleid=540829
- ↑ https://www.erowid.org/experiences/subs/exp_2Methyl2Butanol.shtml
- ↑ The Practitioner's Medical Dictionary | http://books.google.co.uk/books?id=XewWAAAAYAAJ&redir_esc=y
- ↑ Some flavouring constituents of cassava and of processed cassava products | http://onlinelibrary.wiley.com/doi/10.1002/jsfa.2740340816/abstract;jsessionid=1200794E266855A06F6A07494E7D1B1E.f04t04
- ↑ Isolation and identification of volatile flavor compounds in fried baconhttp://pubs.acs.org/doi/abs/10.1021/jf00116a038
- ↑ Volatile components of Rooibos tea (Aspalathus linearis) | http://pubs.acs.org/doi/abs/10.1021/jf00062a024
- ↑ http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+5005
- ↑ http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch15oxidationalcohols.html
- ↑ http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch15oxidationalcohols.html
- ↑ http://www.toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+5005
- ↑ Soehring, K.; Frey, H. H.; Endres, G. (1955). "Relations between constitution and effect of tertiary alcohols". Arzneimittel-Forschung 5 (4): 161–165. PMID 14389140
