2M2B: Difference between revisions

>David Hedlund
>David Hedlund
{{Experience reports|erowid_experience_substance_label=2-Methyl-2-Butanol}}
 
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{{SubstanceBox/2M2B}}
{{SubstanceBox/2M2B}}


'''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>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>
'''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>
 
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).


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 [[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>
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==
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|{{effects/physical|
|{{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]]'''


}}
}}
|{{effects/cognitive|
|{{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::Analysis suppression]]'''
*'''[[Effect::Cognitive euphoria|Euphoria]]'''
*'''[[Effect::Anxiety suppression]]'''
*'''[[Effect::Amnesia]]'''
}}
}}
}}
}}
===Experience reports===
===Experience reports===
There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here:
{{Experience reports|erowid_experience_substance_label=2-Methyl-2-Butanol}}
* [https://www.erowid.org/experiences/subs/exp_2Methyl2Butanol.shtml Erowid Experience Vaults: 2-methyl-2-butanol]


==Toxicity and harm potential==
==Toxicity and harm potential==
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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===
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==Legal status==
==Legal status==
{{legalStub}}
{{legalStub}}
*'''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>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)]
===Discussion===
*[https://www.bluelight.org/xf/threads/490389/ 2-methyl-2-butanol (2M2B) "Vodka" (Bluelight)]


==References==
==References==
<references/>
<references />
[[Category:Alcohol]]
 
[[Category:Substance]]
[[Category:Psychoactive substance]]
[[Category:Psychoactive substance]]
[[Category:Depressant]]
[[Category:Depressant]]
[[Category:Alcohol]]
{{#set:Featured=true}}
{{#set:Featured=true}}
Retrieved from "http://psy.st/wiki/2M2B"