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'''2-Methyl-2-butanol''' (also known as '''''tert''-amyl alcohol''' or '''2M2B''') is a tertiary [[chemical class::alcohol]] substance that produces [[psychoactive class::depressant]], [[hypnotic]], and [[anxiolytic]] effects. Historically, it has been used in anesthesia as a component of avertin fluid mixed with tribromoethanol and water.<ref>{{cite journal | vauthors=((Schlaepfer, K.)) | journal=Archives of Surgery | title=AVERTIN FLUID ANESTHESIA IN SURGERY | volume=24 | issue=5 | pages=868 | date=1 May 1932 | url=http://archsurg.jamanetwork.com/article.aspx?doi=10.1001/archsurg.1932.01160170155006 | issn=0004-0010 | doi=10.1001/archsurg.1932.01160170155006}}</ref> It has a strong solvent smell reminiscent of gasoline and camphor, but with little flavor aside from a burning sensation. 2M2B's simple structure and intoxicating effects have led to its use as a recreational drug.<ref>{{Citation | title=2-Methyl-2-Butanol (also tert-amyl alcohol) : Erowid Exp: Main Index | url=https://www.erowid.org/experiences/subs/exp_2Methyl2Butanol.shtml}}</ref>
| ''[[2-methyl-2-butanol/Summary|Summary sheet: 2-methyl-2-butanol]]''
 
|}
Fusel alcohols including 2M2B are a grain fermentation by-product and therefore present in many alcoholic beverages.<ref>{{cite book | vauthors=((Gould, G. M.)) | date= 1919 | title=The Practitioner’s Medical Dictionary: Containing All the Words and Phrases Generally Used in Medicine and the Allied Sciences, with Their Proper Pronunciation, Derivation, and Definition | publisher=P. Blakiston’s}}</ref> Trace levels of 2M2B have also been detected in various food substances, including fried bacon and cassava,<ref>{{cite journal | vauthors=((Dougan, J.)), ((Robinson, J. M.)), ((Sumar, S.)), ((Howard, G. E.)), ((Coursey, D. G.)) | journal=Journal of the Science of Food and Agriculture | title=Some flavouring constituents of cassava and of processed cassava products | volume=34 | issue=8 | pages=874–884 | date= August 1983 | url=https://onlinelibrary.wiley.com/doi/10.1002/jsfa.2740340816 | issn=00225142 | doi=10.1002/jsfa.2740340816}}</ref><ref>{{cite journal | vauthors=((Ho, C. T.)), ((Lee, K. N.)), ((Jin, Q. Z.)) | journal=Journal of Agricultural and Food Chemistry | title=Isolation and identification of volatile flavor compounds in fried bacon | volume=31 | issue=2 | pages=336–342 | date= March 1983 | url=https://pubs.acs.org/doi/abs/10.1021/jf00116a038 | issn=0021-8561 | doi=10.1021/jf00116a038}}</ref> rooibos tea,<ref>{{cite journal | vauthors=((Habu, T.)), ((Flath, R. A.)), ((Mon, T. R.)), ((Morton, J. F.)) | journal=Journal of Agricultural and Food Chemistry | title=Volatile components of Rooibos tea (Aspalathus linearis) | volume=33 | issue=2 | pages=249–254 | date= March 1985 | url=https://pubs.acs.org/doi/abs/10.1021/jf00062a024 | issn=0021-8561 | doi=10.1021/jf00062a024}}</ref> and fruits (such as apple and pineapple).
'''2-methyl-2-butanol''' (also known as '''''tert''-amyl alcohol''' or '''2m2b''') is a tertiary alcohol with [[psychoactive class::depressant]], [[hypnotic]], and [[anxiolytic]] effects. Historically, it has been used in anesthesia as a component of avertin fluid mixed with tribromoethanol and water.<ref>http://archsurg.jamanetwork.com/article.aspx?articleid=540829</ref> It has a strong solvent smell reminiscent of gasoline, but with little flavor. 2m2b's simple structure and intoxicating effects have led to its use as a recreational drug.<ref>https://www.erowid.org/experiences/subs/exp_2Methyl2Butanol.shtml</ref>


Fusel alcohols including 2m2b are a grain fermentation by-product and therefore present in many alcoholic beverages.<ref>The Practitioner's Medical Dictionary | http://books.google.co.uk/books?id=XewWAAAAYAAJ&redir_esc=y</ref> Trace levels of 2m2b have also been detected in various food substances, including fried bacon and cassava,<ref>Some flavouring constituents of cassava and of processed cassava products | http://onlinelibrary.wiley.com/doi/10.1002/jsfa.2740340816/abstract;jsessionid=1200794E266855A06F6A07494E7D1B1E.f04t04</ref><ref>Isolation and identification of volatile flavor compounds in fried baconhttp://pubs.acs.org/doi/abs/10.1021/jf00116a038</ref> rooibos tea,<ref>Volatile components of Rooibos tea (Aspalathus linearis) | http://pubs.acs.org/doi/abs/10.1021/jf00062a024</ref> and fruits (such as apple and pineapple).
==Chemistry==
==Chemistry==
2-methyl-2-butanol is also known as tert-amyl-alcohol, 2m2b, or amylene hydrate. 2-methyl-2-butanol is an amyl [[chemical class::alcohol]] with the formula C5H11OH. 2-methyl-2-butanol is comprised of butane, an alkyl chain of four carbons. This chain is substituted at R<sub>2</sub> with a methyl group (CH<sub>3</sub>) and an alcohol group (OH-). It is synthesized by the reaction of 2-methyl-2-butene with water in the presence of an acid catalyst.<ref>http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+5005</ref>
2-methyl-2-butanol is also known as tert-amyl-alcohol, 2M2B, or amylene hydrate. 2-methyl-2-butanol is an [[chemical class::alcohol]] with the formula C<sub>5</sub>H<sub>11</sub>OH. 2-methyl-2-butanol is comprised of butane, an alkyl chain of four carbons. This chain is substituted at R<sub>2</sub> with a methyl group CH<sub>3</sub>- and an alcohol group OH-. It is synthesized by the reaction of 2-methyl-2-butene with water in the presence of an acid catalyst.<ref>http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+5005</ref>


==Pharmacology==
==Pharmacology==
2-methyl-2-butanol inhibits binding to a proconvulsant site on the [[GABA]] [[receptor]]<ref>http://www.ncbi.nlm.nih.gov/pubmed/11888705?dopt=Abstract</ref> which causes negatively charged chloride ions to enter neurons and increase the amount of excitation necessary to cause the neurons to fire. As it is 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.<ref>http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch15oxidationalcohols.html</ref> 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.
2-Methyl-2-butanol inhibits binding to a proconvulsant site on the [[GABA]] [[receptor]]<ref>{{cite journal | vauthors=((Martin, J. V.)), ((Bilgin, N. M.)), ((Iba, M. M.)) | journal=Toxicology Letters | title=Influence of oxygenated fuel additives and their metabolites on the binding of a convulsant ligand of the gamma-aminobutyric acid(A) (GABA(A)) receptor in rat brain membrane preparations | volume=129 | issue=3 | pages=219–226 | date=28 March 2002 | issn=0378-4274 | doi=10.1016/s0378-4274(02)00020-6}}</ref> which causes negatively charged chloride ions to enter neurons and increase the amount of excitation necessary to cause the neurons to fire. As it is 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.<ref>http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch15oxidationalcohols.html</ref> However, a consequence of this is that 2-methyl-2-butanol has an extended duration of action with effects that last up to 12 hours after its consumption.


==Subjective effects==
==Subjective effects==
The effects listed below are based upon the [[subjective effects index]] and personal experiences of [[PsychonautWiki]] [[Special:TopUsers|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.
In comparison to other depressants of a similar nature, 2M2B is comparatively closer to [[alcohol]] than [[GHB]] in terms of its subjective effects and is also considerably more sedating than alcohol but less sedating than GHB.


In comparison to other depressants of a similar nature, 2m2b is comparatively closer to [[alcohol]] than [[GHB]] in terms of its subjective effects and is also considerably more sedating than alcohol but less sedating than GHB.
{{Preamble/SubjectiveEffects}}


===Physical effects===
{{effects/base
 
|{{effects/physical|
*'''[[Effect::Sedation]]''' - In comparison to [[alcohol]],  2-methyl-2-butanol is significantly more sedating. On low to moderate doses, one may feel a lack of energy, resulting in extreme difficulty in performing basic tasks. This effect can last up to 24 hours afterwards.
*'''[[Effect::Sedation]]''' - In comparison to [[alcohol]],  2-methyl-2-butanol is significantly more sedating. On low to moderate doses, one may feel a lack of energy, resulting in extreme difficulty in performing basic tasks. This effect can last up to 24 hours afterwards.
*'''[[Effect::Muscle relaxation]]'''
*'''[[Effect::Physical euphoria]]''' - In comparison to [[alcohol]], 2-methyl-2-butanol has less pronounced physical euphoria in proportion to other effects.
*'''[[Effect::Motor control loss]]''' - In comparison to [[alcohol]], 2-methyl-2-butanol is significantly more impairing to motor control in proportion to other effects.
*'''[[Effect::Appetite enhancement]]'''
*'''[[Effect::Dizziness]]'''
*'''[[Effect::Pain relief]]'''
*'''[[Effect::Pain relief]]'''
*'''[[Effect::Muscle relaxation]]
*'''[[Effect::Motor control loss]]'''
*'''[[Effect::Dizziness]]'''
*'''[[Effect::Respiratory depression]]'''
*'''[[Effect::Respiratory depression]]'''


===Cognitive effects===
}}
|{{effects/cognitive|
*'''[[Effect::Analysis suppression]]'''
*'''[[Effect::Anxiety suppression]]'''
*'''[[Effect::Cognitive euphoria]]'''
*'''[[Effect::Compulsive redosing]]'''
* [[Effect::Delusions|'''Delusions of sobriety''']] - This is the false belief that one is perfectly sober despite obvious evidence to the contrary such as severe cognitive impairment and an inability to fully communicate with others.
- Compared to alcohol, 2-methyl-2-butanol impairs motor control proportionately more than cognition, which can act to amplify delusions of sobriety if using alcohol intoxication as a reference.
*'''[[Effect::Disinhibition]]'''
*'''[[Effect::Disinhibition]]'''
*'''[[Effect::Focus suppression]]'''
*'''[[Effect::Language suppression]]'''
*'''[[Effect::Memory suppression]]'''
**'''[[Effect::Amnesia]]'''
*'''[[Effect::Thought deceleration]]'''
*'''[[Effect::Thought deceleration]]'''
*'''[[Effect::Information processing suppression]]'''
}}
*'''[[Effect::Cognitive euphoria|Euphoria]]'''
}}
*'''[[Effect::Anxiety suppression]]'''
===Experience reports===
*'''[[Effect::Amnesia]]'''
{{Experience reports|erowid_experience_substance_label=2-Methyl-2-Butanol}}


==Toxicity and harm potential==
==Toxicity and harm potential==
The toxicity and long-term health effects of recreational 2m2b use do not seem to have been studied in any scientific context and the [[Toxicity::exact toxic dosage is unknown]] although the lowest recorded fatal dose in a human is 30mL.<ref>http://www.toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+5005</ref> However, 2m2b is expected to be less toxic than ethanol as  it cannot be metabolized into aldehydes in the same way.<ref>http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch15oxidationalcohols.html</ref> Anecdotal evidence from people who have tried 2m2b within the community suggest that there do not seem to be any negative health effects attributed to simply trying this drug at low to moderate doses by itself and using it sparingly (but nothing can be completely guaranteed).  
The toxicity and long-term health effects of recreational 2M2B use do not seem to have been studied in any scientific context and the [[Toxicity::exact toxic dosage is unknown]] although the lowest recorded fatal dose in a human is 30mL.<ref>http://www.toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+5005</ref> However, 2M2B is expected to be less toxic than ethanol as  it cannot be metabolized into aldehydes in the same way.<ref>http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch15oxidationalcohols.html</ref> Anecdotal evidence from people who have tried 2M2B within the community suggest that there do not seem to be any negative health effects attributed to simply trying this drug at low to moderate doses by itself and using it sparingly (but nothing can be completely guaranteed).  


It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug.
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance.


===Tolerance and addiction potential===
===Tolerance and addiction potential===
As with any other GABA receptor agonist, repeated use and increasing tolerance will eventually result in a withdrawal syndrome upon abrupt discontinuation resembling alcohol, barbiturate, or [[Benzodiazepine#Discontinuation|benzodiazepine withdrawal]], up to and including delirium tremens ("the shakes"). The chronic use of this compound can be considered [[Addiction potential::moderately addictive with a high potential for abuse]] and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and [[withdrawal effects]] may occur if a person suddenly stops their usage.
As with any other GABA receptor agonist, repeated use and increasing tolerance will eventually result in a withdrawal syndrome upon abrupt discontinuation resembling alcohol, barbiturate, or [[Benzodiazepine#Discontinuation|benzodiazepine withdrawal]], up to and including delirium tremens ("the shakes"). The chronic use of this compound can be considered [[Addiction potential::moderately addictive with a high potential for abuse]] and is capable of causing psychological dependence among certain users. When addiction has developed, cravings and [[withdrawal effects]] may occur if a person suddenly stops their usage.


Tolerance to many of the effects of 2m2b [[Time to full tolerance::develops with prolonged and repeated use]]. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about [[Time to half tolerance::3 - 7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::1 - 2 weeks]] to be back at baseline (in the absence of further consumption). 2m2b presents cross-tolerance with [[Cross-tolerance::all [[GABA]]genic [[depressants]]]], meaning that after the consumption of 2m2b all [[depressant]]ss will have a reduced effect.
Tolerance to many of the effects of 2M2B [[Time to full tolerance::develops with prolonged and repeated use]]. This results in users having to administer increasingly large doses to achieve the same effects. After that, it takes about [[Time to half tolerance::3 - 7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::1 - 2 weeks]] to be back at baseline (in the absence of further consumption). 2M2B presents cross-tolerance with [[Cross-tolerance::all [[GABA]]genic [[depressants]]]], meaning that after the consumption of 2M2B all [[depressant]]s will have a reduced effect.


===Dangerous interactions===
===Dangerous interactions===
Although many drugs are safe on their own, they can become dangerous and even life-threatening when combined with other substances. The list below contains some common potentially dangerous combinations, but may not include all of them. Certain combinations may be safe in low doses of each but still increase the potential risk of death. [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.
{{DangerousInteractions/Intro}}
*'''[[Depressants]]''' (''[[1,4-Butanediol]], [[alcohol]], [[barbiturates]], [[benzodiazepines]], [[GHB]]/[[GBL]], [[methaqualone]], [[opioids]]'') - This combination can result in dangerous or even fatal levels of [[respiratory depression]]. These substances potentiate the [[muscle relaxation]], [[sedation]] and [[amnesia]] caused by one another and can lead to unexpected loss of consciousness at high doses. There is also an increased risk of vomiting during unconsciousness and death from the resulting suffocation. If this occurs, users should attempt to fall asleep in the [https://www.youtube.com/watch?v=uCDa-AhrjHo recovery position] or have a friend move them into it.
{{DangerousInteractions/Depressants}}
*'''[[Dissociatives]]''' - This combination can result in an increased risk of vomiting during unconsciousness and death from the resulting suffocation. If this occurs, users should attempt to fall asleep in the [https://www.youtube.com/watch?v=uCDa-AhrjHo recovery position] or have a friend move them into it.
*'''[[Stimulants]]''' -  It is dangerous to combine 2m2b, a [[depressant]], with [[stimulant]]s due to the risk of excessive intoxication. Stimulants decrease the [[sedation|sedative]] effect of 2m2b, which is the main factor most people consider when determining their level of intoxication. Once the stimulant wears off, the effects of 2m2b will be significantly increased, leading to intensified [[disinhibition]] as well as [[2-methyl-2-butanol#Subjective effects|other effects]]. If combined, one should strictly limit themselves to only drinking a certain amount of 2m2b per hour.


==Legal issues==
==Legal status==
{{legalStub}}
{{legalStub}}
*'''United Kingdom''' - This drug is illegal under the Psychoactive Substance Act, which came into effect on May 26th, 2016.<ref>Psychoactive Substances Act 2016 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted</ref>
 
*'''Germany:''' 2M2B is a prescription medicine, according to Anlage 1 AMVV ("Amylenhydrat").<ref>{{Citation | title=AMVV - Verordnung über die Verschreibungspflicht von Arzneimitteln | url=https://www.gesetze-im-internet.de/amvv/BJNR363210005.html}}</ref>
*'''United Kingdom:''' It is illegal to produce, supply, or import this drug under the Psychoactive Substance Act, which came into effect on May 26th, 2016.<ref>{{Citation | title=Psychoactive Substances Act 2016 | url=https://www.legislation.gov.uk/ukpga/2016/2/contents/enacted}}</ref>


==See also==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Depressant]]
*[[Depressant]]
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*[[GHB]]
*[[GHB]]
*[[GBL]]
*[[GBL]]
==External links==
==External links==
*[https://en.wikipedia.org/wiki/Tert-Amyl_alcohol 2-methyl-2-butanol (Wikipedia)]
*[https://en.wikipedia.org/wiki/Tert-Amyl_alcohol 2-methyl-2-butanol (Wikipedia)]
*[https://www.erowid.org/experiences/subs/exp_2Methyl2Butanol.shtml 2-methyl-2-butanol experiences (Erowid)]
 
===Discussion===
 
*[https://www.bluelight.org/xf/threads/490389/ 2-methyl-2-butanol (2M2B) "Vodka" (Bluelight)]


==References==
==References==
<references/>
<references />
 
[[Category:Substance]]
[[Category:Psychoactive substance]]
[[Category:Psychoactive substance]]
[[Category:Depressant]]
[[Category:Depressant]]
[[Category:Substance]]
[[Category:Alcohol]]
 
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