2M2B: Difference between revisions
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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? | '''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, but with little flavor. 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>The | 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). | ||
==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> | 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 which last up to 12 hours after its consumption. | ||
==Subjective effects== | ==Subjective effects== | ||
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{{legalStub}} | {{legalStub}} | ||
*'''Germany:''' 2M2B is a prescription medicine, according to Anlage 1 AMVV ("Amylenhydrat").<ref>https://www.gesetze-im-internet.de/amvv/BJNR363210005.html</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>Psychoactive Substances Act 2016 | *'''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== |