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Thujone is a ketone and a monoterpene that exists in two 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 it is not responsible for absinthe's reported hallucinogenic effects. Thujone acts on the GABA receptors in the brain and does not cause hallucinations. In many countries the amount of thujone allowed in food or drink products is regulated. Image File history File links Created using MDL ISIS/DRAW and Paint Shop Pro 8 by Catbar. ...
Image File history File links Size of this preview: 699 × 600 pixel Image in higher resolution (1100 × 944 pixel, file size: 214 KB, MIME type: image/png) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Thujone ...
IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ...
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The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ...
In physics, density is mass m per unit volume V. For the common case of a homogeneous substance, it is expressed as: where, in SI units: Ï (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg V is...
Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ...
The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ...
Italic text This article is about the boiling point of liquids. ...
CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ...
The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ...
Ketone group A ketone(key tone) is either the functional group characterized by a carbonyl group (O=C) linked to two other carbon atoms or a chemical compound that contains this functional group. ...
Many terpenes are derived from conifer resins, here a pine. ...
Main article: stereochemistry Stereoisomerism is the arrangement of atoms in molecules whose connectivity remains the same but their arrangement in space is different in each isomer. ...
Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. ...
A reservoir glass filled with a naturally colored verte next to an absinthe spoon. ...
The GABA receptors are a group of receptors with γ-aminobutyric acid (GABA) as their endogenous ligand. ...
Sources Thujone is found in a number of plants, such as arborvitae (genus Thuja, hence the derivation of the name), Nootka Cypress, some junipers, mugwort, sage, tansy and wormwood, most notably grand wormwood (Artemisia absinthium), usually as a mix of isomers in a 1:2 ratio. Species Thuja koraiensis Thuja occidentalis Thuja plicata Thuja standishii Thuja sutchuenensis Thuja (pronounced Thuya) is a genus of coniferous trees in the Cupressaceae (cypress family). ...
Binomial name Callitropsis nootkatensis (D. Don) Örsted Nootka Cypress (Callitropsis nootkatensis), formerly Cupressus nootkatensis, Xanthocyparis nootkatensis or Chamaecyparis nootkatensis, is a cypress (Cupressaceae) with a chequered taxonomic and nomenclatural history. ...
Species Junipers are coniferous plants in the genus Juniperus of the cypress family Cupressaceae. ...
Binomial name Artemisia vulgaris L. Mugwort or Common Wormwood (Artemisia vulgaris) is a species from the daisy family Asteraceae. ...
Binomial name L. Sage leaves - first variety Sage leaves - second variety Common sage (Salvia officinalis) is a small evergreen subshrub, with woody stems, grayish leaves, and blue to purplish flowers native to southern Europe and the Mediterranean region. ...
Binomial name L. Illustration of a tansy Tansy (Tanacetum vulgare) is a perennial herbaceous flowering plant of the aster family that is native to temperate Europe and Asia. ...
Species See text Artemisia abrotanum (Southernwood) Artemisia absinthium (Absinth Wormwood) Artemisia alba Artemisia Powys Castle Artemisia californica (California Sagebrush) leaves Artemisia mauiensis (Maui Wormwood) Artemisia pontica (Roman Wormwood) Artemisia pycnocephala (Beach Sagewort) flowers Dried Artemisia absinthium (Absinth Wormwood) Artemisia absinthium (Absinth Wormwood) Artemisia cina (Levant Wormseed) Artemisia is a large...
Binomial name Artemisia absinthium L. Artemisia absinthium by Koehler 1887 Artemisia absinthium or Absinth Wormwood, is a wormwood. ...
Pharmacology For many years thujone was thought to act on the cannabinoid receptors similar to THC based on studies that only looked at the molecules' shapes.[1] This is known to be false today and studies show thujone does not activate these receptors[2]. Thujone is a GABAA receptor antagonist. By inhibiting GABA receptor activation neurons may fire more easily which can cause muscle spasms and convulsions.[3] Cannabinoids are a group of chemicals which activate the bodys cannabinoid receptors. ...
“THC†redirects here. ...
Gamma-aminobutyric acid (usually abbreviated to GABA) is an inhibitory neurotransmitter found in the nervous systems of widely divergent species. ...
A toxicology study of alpha-thujone, the more active of the two isomers, in mice found the median lethal dose, or LD50, is around 45 mg/kg, with 0% mortality rate at 30 mg/kg and 100% at 60 mg/kg. Those exposed to the higher dose had convulsions that led to death in 1 minute. From 30 to 45 mg/kg the mice would experience muscle spasms in the legs which progressed to general convulsions until death or recovery. Pretreatment of diazepam, phenobarbital or 1 g/kg of ethanol protected against a lethal 100 mg/kg dose. These findings are inline with other GABA antagonists. This study also found alpha-thujone was quickly metabolized in the mouse's liver.[3] An LD50 test being administered In toxicology, the LD50 or colloquially semilethal dose of a particular substance is a measure of how much constitutes a lethal dose. ...
This article is about the medical condition. ...
Diazepam (IPA: ), first marketed as Valium by Hoffmann-La Roche, is a drug which is a benzodiazepine derivative. ...
Phenobarbital (INN) or phenobarbitone (former BAN) is a barbiturate, first marketed as Luminal by Farbwerke Fr. ...
Ethanol, also known as ethyl alcohol, drinking alcohol or grain alcohol, is a flammable, colorless, slightly toxic chemical compound, and is best known as the alcohol found in alcoholic beverages. ...
The LD50 dose in humans is not known; however a study in the "Journal of Studies of alcohol" tested attention performance with low, and high doses of thujone in alcohol. The researchers administered 0.28 mg/kg thujone in alcohol, 0.028 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.[4]
There is no evidence any size dose will cause hallucinations. A hallucination is a false sensory perception in the absence of an external stimulus, as distinct from an illusion, which is a misperception of an external stimulus. ...
Thujone in absinthe Thujone is most famous for being a chemical in the drink absinthe and many modern producers list their supposed thujone levels on the bottle. At one time it was estimated absinthe contained up to 260–350 mg/L thujone,[5] but this has been shown false through testing. A 2005 study recreated three 1899 high-wormwood recipes and tested them with Gas Chromatography Mass-Spectrometry (GC-MS), the highest contained 4.3 mg/L thujone. A 1930s Pernod Tarragona was also tested and contained 1.8 mg/L thujone. [6] These results match earlier findings showing a vintage 1900s bottle contained 6 mg/L.[7] GC-MS testing is important in this capacity, because gas chromatography alone may record an abnormally high reading of thujone because of other chemicals present.[8] Through these tests it has become evident absinthe contains very little thujone. A reservoir glass filled with a naturally colored verte next to an absinthe spoon. ...
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Gas-liquid chromatography (GLC), or simply gas chromatography (GC) is a type of chromatography in which the mobile phase is a carrier gas, usually an inert gas such as helium or nitrogen, and the stationary phase is a microscopic layer of liquid on an inert solid support. ...
Despite these studies, many companies still play up the myth that absinthe contains a large amount of thujone and that it will produce some sort of hallucinatory effect on the drinker.
Although it contains thujone, anyone binging on absinthe would die of alcohol poisoning long before the thujone would cause any major, i.e. life-threatening, effects.[9]
History Thujone was an unknown chemical until absinthe became popular in the mid 1800s. Dr. Valentin Magnan, who studied alcoholism, tested pure wormwood oil on animals and discovered it caused an epileptic reaction different from plain alcohol. Based on this, it was assumed that absinthe, which contains a small amount of wormwood oil, was more dangerous than ordinary alcohol. Eventually thujone was isolated as the cause of these reactions. Magnan went on to study 250 abusers of alcohol noting that those who drank absinthe had epileptic attacks and hallucinations. In light of modern evidence, these conclusions are questionable and probably based on a poor understanding of other chemicals and diseases and were clouded by Magnan's belief that alcohol and absinthe were "degenerating" the French race.[10] // Invention of the Jacquard loom in 1801. ...
Alcoholism is the consumption of, or preoccupation with, alcoholic beverages to the extent that this behavior interferes with the drinkers normal personal, family, social, or work life, and may lead to physical or mental harm. ...
After absinthe was banned, research dropped off until the 1970s when Nature magazine published an article comparing the molecular shape of thujone to THC, and hypothesized it would act the same way on the brain, sparking the myth that thujone is a cannabinoid.[1] The acronym THC has several possible meanings: Teens Hate Chains, a Japanese singing group Tetrahydrocannabinol, the main active ingredient in Cannabis Tetrahydrocurcuminoids, extracted from Turmeric as an active ingredient in cosmetics Texas Historical Commission Therapeutic Humane Cannabis Act Thermohaline circulation The History Channel Terminal Handling Charges This page concerning a...
More recently, following the European Council Directive No. 88/388 [1] allowing certain levels of thujone in foodstuffs in the EU, the studies described above were conducted and found only minute levels of thujone in absinthe. A reservoir glass filled with a naturally colored verte next to an absinthe spoon. ...
Regulations
European Union Maximum thujone levels in the EU are: [11] - 0.5 mg/kg in food not prepared with sage and non alcoholic beverages.
- 5 mg/kg in alcoholic beverages with 25% or less ABV.
- 10 mg/kg in alcoholic beverages with more than 25% ABV.
- 25 mg/kg in food prepared with sage.
- 35 mg/kg in alcohol labeled as bitters.
Binomial name L. Sage leaves - first variety Sage leaves - second variety Common sage (Salvia officinalis) is a small evergreen subshrub, with woody stems, grayish leaves, and blue to purplish flowers native to southern Europe and the Mediterranean region. ...
Alcohol by volume (ABV) is an indication of how much alcohol (expressed as a percentage) is included in an alcoholic beverage. ...
Binomial name L. Sage leaves - first variety Sage leaves - second variety Common sage (Salvia officinalis) is a small evergreen subshrub, with woody stems, grayish leaves, and blue to purplish flowers native to southern Europe and the Mediterranean region. ...
bitter An antique (probably 1880s) bitters bottle from Germany that sold for $1240. ...
United States Foods or beverages that contain Artemisia species, White Cedar, oak moss, tansy or Yarrow must be thujone-free.[12] Other herbs that contain thujone have no restrictions. For example, sage and sage oil (which can be 50%+ thujone) are on the Food and Drug Administration's list of substances generally recognized as safe. [13] Species See text Artemisia abrotanum (Southernwood) Artemisia absinthium (Absinth Wormwood) Artemisia alba Artemisia Powys Castle Artemisia californica (California Sagebrush) leaves Artemisia mauiensis (Maui Wormwood) Artemisia pontica (Roman Wormwood) Artemisia pycnocephala (Beach Sagewort) flowers Dried Artemisia absinthium (Absinth Wormwood) Artemisia absinthium (Absinth Wormwood) Artemisia cina (Levant Wormseed) Artemisia is a large...
Binomial name Thuja occidentalis L. Thuja occidentalis, a species of thuja, is an evergreen coniferous tree in the cypress family Cupressaceae, native to the northeastern US and southeastern Canada, from central Saskatchewan east to New Brunswick, and south to eastern Tennessee in the Appalachian Mountains. ...
Binomial name Evernia prunastri (L.) Ach. ...
Binomial name L. Illustration of a tansy Tansy (Tanacetum vulgare) is a perennial herbaceous flowering plant of the aster family that is native to temperate Europe and Asia. ...
Binomial name Achillea millefolium L. Yarrow (Achillea millefolium) is a flowering plant in the family Asteraceae, native to the Northern Hemisphere. ...
Binomial name L. Sage leaves - first variety Sage leaves - second variety Common sage (Salvia officinalis) is a small evergreen subshrub, with woody stems, grayish leaves, and blue to purplish flowers native to southern Europe and the Mediterranean region. ...
Sage oil is the essential oil made from the culinary herb sage, Salvia officinalis. ...
hi “FDA†redirects here. ...
Generally Recognized as Safe (GRAS) is an FDA designation that a chemical or substance (including certain pesticides) added to food is considered safe by experts, and so is exempted from the usual FFDCA food additive tolerance requirements. ...
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 mg/kg thujone; Québec allows 15 mg per kg (according to the SAQ)[citation needed]; and all other provinces do not allow the sale of absinthe containing thujone (although, in Saskatchewan, one can purchase any liquor available in the world upon the purchase of a minimum of one case, usually 12 bottles x 750ml or 8 x 1L). The individual liquor boards must approve each product before it may be sold on shelves. Motto: Splendor Sine Occasu (Latin: Splendour without diminishment) Capital Victoria Largest city Vancouver Official languages English Government - Lieutenant-Governor Iona Campagnolo - Premier Gordon Campbell (BC Liberal) Federal representation in Canadian Parliament - House seats 36 - Senate seats 6 Confederation July 20, 1871 (6th province) Area Ranked 4th - Total 944,735 km...
Motto: Fortis et liber(Latin) Strong and free Capital Edmonton Largest city Calgary Official languages English (see below) Government - Lieutenant-Governor Norman Kwong - Premier Ed Stelmach (PC) Federal representation in Canadian Parliament - House seats 28 - Senate seats 6 Confederation September 1, 1905 (split from Northwest Territories) (8th [Province]) Area Ranked...
Motto: Ut Incepit Fidelis Sic Permanet (Latin: Loyal she began, loyal she remains) Capital Toronto Largest city Toronto Official languages English Government - Lieutenant-Governor James K. Bartleman - Premier Dalton McGuinty (Liberal) Federal representation in Canadian Parliament - House seats 106 - Senate seats 24 Confederation July 1, 1867 (1st) Area [1] Ranked...
Motto: Munit Haec et Altera Vincit(Latin) One defends and the other conquers Capital Halifax Largest city Halifax Regional Municipality Official languages English Government - Lieutenant-Governor Mayann E. Francis - Premier Rodney MacDonald (PC) Federal representation in Canadian Parliament - House seats 11 - Senate seats 10 Confederation July 1, 1867 (1st) Area...
During the 1960s, a terrorist group known as the Front de libération du Québec (FLQ) launched a decade of bombings, robberies and attacks on government offices. ...
Motto: Multis E Gentibus Vires (Latin: The Strength of Many Peoples) Capital Regina Largest city Saskatoon Official languages English Government - Lieutenant-Governor Gordon Barnhart - Premier Lorne Calvert (NDP) Federal representation in Canadian Parliament - House seats 14 - Senate seats 6 Confederation September 1, 1905 (Split from NWT) (9th (province)) Area Ranked...
References - ^ a b Conrad III, Barnaby; (1988). Absinthe History in a Bottle. Chronicle books. ISBN 0-8118-1650-8 p. 152
- ^ Thujone exhibits low affinity for cannabinoid receptors but fails to evoke cannabimimetic responses., Meschler JP, Howlett AC. Retrieved 5, July, 2007.
- ^ a b Thujone Gamma-Aminobutyric acid type A receptor modulation and metabolic detoxification. Hold K.,Sirisoma N., Ikeda T., Narahashi T. and Casida J. (2000). Retrieved Oct.28, 2006
- ^ 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.
- ^ Absinthism: a fictitious 19th century syndrome with present impact, Padosch et al. Retrieved Oct. 28, 2006.
- ^ Thujone—Cause of absinthism? Lachenmeier, Emmert et al. Retrieved Oct. 28, 2006.
- ^ Thujone Separating Myth from Reality Ian Hutton Retrieved Oct. 28, 2006.
- ^ Determination of a-/b-Thujone and Related Terpenes in Absinthe using Solid Phase Extraction and Gas Chromatography, Emmert et al. Retrieved Oct. 28, 2006.
- ^ http://home.howstuffworks.com/absinthe.htm
- ^ Conrad III, Barnaby; (1988). Absinthe History in a Bottle. Chronicle books. ISBN 0-8118-1650-8 Pg. 101-105
- ^ Opinion of the Scientific Committee on Food on Thujone Scientific Committee on Food (2003) Retrieved Oct 28, 2006.
- ^ Food Additives Permitted for Direct Addition to Food for Human Consumption. Food and Drug Administration (2003). Retrieved Oct 28, 2006.
- ^ Substances generally recognized as safe. Food and Drug Administration (2003). Retrieved Oct 28, 2006.
External links - Thujone.Info — Databank of peer reviewed articles on thujone, absinthe, absinthism, and independent thujone ratings of some commercial brands.
- The Shaky History of Thujone - Wormwood Society article on thujone and its history.
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