Examine individual changes

'{{chembox | Name = β-Thujone | ImageFileL1 = Beta-Thujone.svg | ImageSizeL1 = 150px | ImageNameL1 = Beta-thujone | ImageFileR1 = Beta-thujone-3D-balls.png | ImageSizeR1 = 170px | ImageNameR1 = Ball-and-stick model of β-thujone | IUPACName = (1''S'',4''R'',5''R'')-4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one | Section1 = {{Chembox Identifiers | CASNo = 471-15-8 | CASOther = &nbsp;(β-thujone)<br />[546-80-5], (α-thujone) | PubChem = 261491 | SMILES = C[C@@H]([C@@H](C2)[C@]2([C@@H](C)C)C1)C1=O (β-thujone) }} | Section2 = {{Chembox Properties | Formula = C₁₀H₁₆O | MolarMass = 152.23 g/mol | Density = 0.92 g/cm³ | Solubility = Insoluble | Solvent = [[ethanol]] | SolubleOther = Soluble | MeltingPt = | BoilingPtC = 201 }} }} '''Thujone''' is a [[ketone]] and a [[terpene|monoterpene]] that exists in two [[stereoisomerism|stereoisomeric]] forms: (+)-3-thujone or α-thujone and (−)-3-thujone or β-thujone. It has a [[menthol]] odor. Even though it is best known for being a chemical in [[absinthe]], recent tests show absinthe contains only small quantities of thujone, and may or may not be responsible for absinthe's reported psychedelic effects. Thujone acts on [[GABA receptors|GABA]] and 5-HT3 receptors<ref>{{cite journal | author = Deiml T, Haseneder R, Zieglgänsberger W, Rammes G, Eisensamer B, Rupprecht R, Hapfelmeier G | title = Alpha-thujone reduces 5-HT3 receptor activity by an effect on the agonist-reduced desensitization | journal = Neuropharmacology | year = 2004 | month = Feb | volume = 46 | issue = 2 | pages = 192–201}}</ref> in the brain. In many countries the amount of thujone allowed in food or drink products is regulated. ==Sources== Thujone is found in a number of plants, such as [[Thuja|arborvitae]] (genus ''Thuja'', hence the derivation of the name), [[Callitropsis nootkatensis|Nootka Cypress]], some [[juniper]]s, [[mugwort]], [[common sage]], [[tansy]] and [[Artemisia (plant)|wormwood]], most notably grand wormwood (''[[Artemisia absinthium]]''), usually as a mix of isomers in a 1:2 ratio. It is also found in various species of ''[[mentha]]'' (mint). ==Pharmacology== Based on studies that looked only at molecular shape, for many years thujone was thought to act similarly to [[Tetrahydrocannabinol|THC]] on the [[cannabinoid]] receptors.<ref name="thc">Conrad III, Barnaby; (1988). ''Absinthe History in a Bottle.'' Chronicle books. ISBN 0-8118-1650-8 p. 152</ref> Today this is known to be false because studies have shown that thujone does not activate these receptors.<ref>{{cite journal |author=Meschler JP, Howlett AC |title=Thujone exhibits low affinity for cannabinoid receptors but fails to evoke cannabimimetic responses |journal=Pharmacol. Biochem. Behav. |volume=62 |issue=3 |pages=473–80 |year=1999 |month=March |pmid=10080239 |url=http://linkinghub.elsevier.com/retrieve/pii/S0091-3057(98)00195-6}}</ref> Thujone is a [[gamma-aminobutyric acid|GABA_A]] receptor antagonist.<ref>{{cite journal |author=Olsen RW |title=Absinthe and gamma-aminobutyric acid receptors |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=97 |issue=9 |pages=4417–8 |year=2000 |month=April |pmid=10781032 |pmc=34311 |url=http://www.pnas.org/cgi/content/full/97/9/4417}}</ref> By inhibiting GABA receptor activation neurons may fire more easily which can cause muscle spasms and convulsions.<ref name="gaba">{{cite journal |author=Höld KM, Sirisoma NS, Ikeda T, Narahashi T, Casida JE |title=Alpha-thujone (the active component of absinthe): gamma-aminobutyric acid type A receptor modulation and metabolic detoxification |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=97 |issue=8 |pages=3826–31 |year=2000 |month=April |pmid=10725394 |pmc=18101 |doi=10.1073/pnas.070042397 |url=http://www.pnas.org/cgi/content/full/97/8/3826}}</ref> A toxicology study in mice of alpha-thujone, the more active of the two isomers, found that the median lethal dose, or [[LD50|LD₅₀]], is around 45&nbsp;mg/kg, with 0% mortality rate at 30&nbsp;mg/kg and 100% at 60&nbsp;mg/kg. Mice exposed to the higher dose had [[convulsions]] that led to death in 1 minute. From 30 to 45&nbsp;mg/kg the mice experienced muscle spasms in the legs which progressed to general convulsions until death or recovery. Pretreatment with [[diazepam]], [[phenobarbital]] or 1 g/kg of [[ethanol]] protected against a lethal 100&nbsp;mg/kg dose. These findings are in line with other GABA antagonists. This study also found that alpha-thujone was metabolized quickly in the liver.<ref name="gaba"/> Researchers at Rutgers University <ref>[http://www.jsad.com/jsad/article/Absinthe_Attention_Performance_and_Mood_under_the_Influence_of_Thujone/1040.html Absinthe: Attention Performance and Mood under the Influence of Thujone.] A. Dettling, H. Grass, A. Schuff, G. Skopp, P. Strohbeck-Kuehner, H.-Th. Haffner. Retrieved Mar. 26, 2008.</ref> tested attention performance with low, and high doses of thujone in alcohol. The researchers administered 0.28&nbsp;mg/kg in alcohol, 0.028&nbsp;mg/kg in alcohol and just alcohol to their subjects. The high dose had a short term negative effect on attention performance. The lower dose showed no noticeable effect.<ref>[http://www.thujone.info/thujone-absinthe-5.html Absinthe: Attention Performance and Mood under the Influence of Thujone.] DETTLING, A., GRASS, H., SCHUFF, A., SKOPP, G., STROHBECK-KUEHNER, P. AND HAFFNER, H.-TH. (2004) Retrieved Oct. 28, 2006.</ref> Thujone is reported to be toxic to both brain and liver cells and could cause [[convulsions]] if used in too high a dose. Other thujone-containing plants such as the tree ''[[Arbor vitae]]'' (''Thuja occidentalis'') are used in herbal medicine, mainly for their immune-system stimulating effects. Side-effects from the [[essential oil]] of this plant include anxiety and sleeplessness, which confirms the central nervous system effects of thujone.<ref>Naser B, Bodinet C, Tegtmeier M, Lindequist U. Thuja occidentalis (Arbor vitae): A Review of its Pharmaceutical, Pharmacological and Clinical Properties. ''Evidence Based Complementary and Alternative Medicine''. 2005 Mar;2(1):69–78.</ref> ==Thujone in absinthe== IT MEANS BRANDON LOVES BIG BOOTY MEN... YEAH THATS RIGHT.. BIG BOOTY MEN! ==Regulations== ===European Union=== '''COLE IS A JEW''' ===United States=== Foods or beverages that contain [[Artemisia (plant)|Artemisia]] species, [[White Cedar]], [[oak moss]], [[tansy]] or [[Yarrow]] must be thujone-free.<ref>[http://www.cfsan.fda.gov/~lrd/FCF172.html FDA Regulation 21 CFR 172.510 - Food Additives Permitted for Direct Addition to Food for Human Consumption.] Food and Drug Administration (2003). Retrieved Oct 28, 2006.</ref> Other herbs that contain thujone have no restrictions. For example, [[Common sage|sage]] and [[sage oil]] (which can be up to 50% thujone) are on the [[Food and Drug Administration]]'s list of substances [[generally recognized as safe]].<ref>[http://www.cfsan.fda.gov/~lrd/fcf182.html Substances generally recognized as safe.] Food and Drug Administration (2003). Retrieved Oct 28, 2006.</ref> Absinthe offered for sale in the United States must be "thujone-free", which is interpreted as containing less than 10&nbsp;mg/kg .<ref>[http://www.ttb.gov/industry_circulars/archives/2007/2007_05.html Department of the Treasury Alcohol and Tobacco Tax and Trade Bureau Industry Circular 2007-5] October 17, 2007. Retrieved May 5, 2009</ref> There are now therefore a number of thujone-containing absinthes that can be legally imported.<ref>http://drinklucid.com/faq.cfm Retrieved Nov. 29, 2007.</ref> ===Canada=== In [[Canada]], liquor laws are the domain of the provincial governments. [[British Columbia]] has no limits on thujone content; [[Alberta]], [[Ontario]] and [[Nova Scotia]] allow 10&nbsp;mg/kg thujone; [[Québec]] allows 5&nbsp;mg per kg {{Citation needed|date=April 2007}}; [[Manitoba]] allows 6–8&nbsp;mg thujone per litre; and all other provinces do not allow the sale of absinthe containing thujone{{Citation needed|date=January 2009}}<!--... I have 4 varieties at my local liquor store in alberta...--> (although, in [[Saskatchewan]], one can purchase any liquor available in the world upon the purchase of a minimum of one case, usually twelve 750-mL bottles or 9L). The individual liquor boards must approve each product before it may be sold on shelves. ==References== {{reflist}} {{refbegin}} {{refend}} ==External links== *[http://cerncourier.com/cws/article/cern/34928 Absinthe absolved], ''Cern Courier'', July 8, 2008 *[http://www.thujone.info Thujone.Info] — Databank of peer reviewed articles on thujone, absinthe, absinthism, and independent thujone ratings of some commercial brands. *[http://www.wormwoodsociety.org/index.php?option=com_content&task=view&id=1&Itemid=85 The Shaky History of Thujone] - Wormwood Society article on thujone and its history. *{{cite journal |author=Lachenmeier DW, Nathan-Maister D, Breaux TA, Sohnius EM, Schoeberl K, Kuballa T |title=Chemical composition of vintage preban absinthe with special reference to thujone, fenchone, pinocamphone, methanol, copper, and antimony concentrations |journal=J. Agric. Food Chem. |volume=56 |issue=9 |pages=3073–81 |year=2008 |month=May |pmid=18419128 |doi=10.1021/jf703568f10.1021/jf703568f}} {{GABAergics}} [[Category:Ketones]] [[Category:Terpenes and terpenoids]] [[Category:Absinthe]] [[Category:GABA antagonists]] [[Category:Convulsants]] [[cs:Thujon]] [[de:Thujon]] [[es:Tujona]] [[fr:Thuyone]] [[it:Tujone]] [[hu:Tujon]] [[nl:Thujon]] [[ja:ツジョン]] [[no:Tujon]] [[pl:Tujon]] [[pt:Tujona]] [[ru:Туйон]] [[fi:Tujoni]] [[sv:Tujon]]'