Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Nverify (what is YN ?)
Infobox references
Chemical compound
This article includes inline links to audio files. If you have trouble playing the files, see Wikipedia Media help.
Thujone (/ˈθuːdʒoʊn/ⓘ[2]) is a ketone and a monoterpene that occurs predominantly in two diastereomeric (epimeric) forms: (−)-α-thujone and (+)-β-thujone.[3][4]
Though it is best known as a chemical compound in the spirit absinthe, it is unlikely to be responsible for absinthe's alleged stimulant and psychoactive effects due to the small quantities present.[5][6][7]
Thujone acts on the GABAA receptor as an antagonist. As a competitive antagonist of GABAA receptor, thujone alone is considered to be convulsant,[8] though by interfering with the inhibitory transmitter GABA, it may convey stimulating, mood-elevating effects at low doses.[citation needed] It is also found in perfumery as a component of several essential oils.[citation needed]
In addition to the naturally occurring (−)-α-thujone and (+)-β-thujone, two other forms are possible: (+)-α-thujone and (−)-β-thujone. In 2016, they were found in nature as well,[9] in Salvia officinalis.
(−)-α-thujone
(+)-α-thujone
(+)-β-thujone
(−)-β-thujone
^Richert, Clemens; Krupp, Felix; Frey, Wolfgang (2020). "Absolute Configuration of Small Molecules by Co-Crystallization". Angew. Chem. Int. Ed.59 (37): 15875–15879. doi:10.1002/anie.202004992. PMC 7540501. PMID 32441841.
^Derived from the Ancient Greek θυία, thuj(a), a kind of cedar + -ωνη, -one, feminine patronymic for a chemical relative of acetone
^Perry NB, Anderson RE, Brennan NJ, Douglas MH, Heaney AJ, McGimpsey JA, Smallfield BM (1999). "Essential Oils from Dalmatian Sage (Salvia officinalis L.): Variations among Individuals, Plant Parts, Seasons, and Sites". J. Agric. Food Chem.47 (5): 2048–2054. doi:10.1021/jf981170m. PMID 10552494.
^Oppolzer W, Pimm A, Stammen B, Hume WE (1997). "Palladium-Catalysed Intramolecular Cyclisations of Olefinic Propargylic Carbonates and application to the diastereoselective synthesis of enantiomerically pure (−)-α-thujone". Helv. Chim. Acta. 80 (3): 623–639. doi:10.1002/hlca.19970800302.
^Dettling A, Grass H, Schuff A, Skopp G, Strohbeck-Kuehner P, Haffner HT (2004). "Absinthe: attention performance and mood under the influence of thujone". J. Stud. Alcohol. 65 (5): 573–81. doi:10.15288/jsa.2004.65.573. PMID 15536765.
^Absinthe Myths Finally Laid To Rest
^Chemical Composition of Vintage Preban Absinthe with Special Reference to Thujone, Fenchone, Pinocamphone, Methanol, Copper, and Antimony Concentrations
^Olsen, Richard W. (2000-04-25). "Absinthe and γ-aminobutyric acid receptors". Proceedings of the National Academy of Sciences of the United States of America. 97 (9): 4417–4418. Bibcode:2000PNAS...97.4417O. doi:10.1073/pnas.97.9.4417. ISSN 0027-8424. PMC 34311. PMID 10781032.
^Williams, Jack D.; Yazarians, Jessica A.; Almeyda, Chelcie C.; Anderson, Kristin A.; Boyce, Gregory R. (23 May 2016). "Detection of the Previously Unobserved Stereoisomers of Thujone in the Essential Oil and Consumable Products of Sage (Salvia officinalis L.) Using Headspace Solid-Phase Microextraction–Gas Chromatography–Mass Spectrometry". Journal of Agricultural and Food Chemistry. 64 (21): 4319–4326. doi:10.1021/acs.jafc.6b01065. PMID 27181395.
nature as well, in Salvia officinalis. (−)-α-thujone (+)-α-thujone (+)-β-thujone (−)-β-thujoneThujone is found in a number of plants, such as arborvitae...
long before thujone could become a factor. In documented cases of acute thujone poisoning as a result of oral ingestion, the source of thujone was not commercial...
chemotypes of A. absinthium contain (−)-α- and/or (+)-β-thujone, though some do not. (−)-α-Thujone by itself is a GABAA receptor antagonist that can cause...
large quantities; the volatile oil contains toxic compounds including thujone, which can cause convulsions and liver and brain damage. Some insects,...
its harvest. Its main components can include camphor, cineole, α- and β-thujone, artemisia ketone (CAS: 546-49-6), borneol and bornyl acetate as well as...
essential oil includes the chemicals thujone and phenol, which give it antiseptic properties. Its high concentrations of thujone and chemicals that stimulate...
liquid with a warm camphoraceous, thujone-like odor and sharp and bitter taste. The main components of the oil are thujone (50%), camphor, pinene, and cineol...
Native American canoes.[citation needed] Oil of Thuja contains the terpene thujone which has been studied for its GABA receptor antagonizing effects, with...
minor amounts of β-thujone, t-dihydrocarvone, c-dihydrocarvone, dihydrocarveol isomer, c-carveol, and t-carveol. Levels of β-thujone, a toxic ketone, were...
preliminary research for their potential effects on human brain function. The thujone present in Salvia extracts may be neurotoxic. In favourable conditions...
loose panicles at stem tips. The essential oil contains cineol, camphor, thujone, and borneol among other components. It is said to be less bitter than...
4-Decadienal Fenchone (S)-Ipsdienol Myrtenol Perillyl alcohol Piperitone Pulegone Thujone Verbenol This set index page lists chemical structure articles associated...
β-thujene (or 2-thujene). Another double-bond isomer is known as sabinene. Thujone Umbellulone, a thujene derivative L. Tschugaeff (1900). "Ueber das Thujen...
crises in his last two years were brought about by the additional effect of thujone poisoning from his consumption of absinthe. Arnold has suggested the association...
chromatography) which are typical of extracts of the genus Artemisia: α-thujone 52.9% β-thujone 15.07% 1,8 cineole 10.66% camphor 5.72% germacrene 1.60% δ-cadinene...
dreaming. This supposed oneirogenic effect is reported to be due to the thujone contained in the plant. A. vulgaris is a tall, herbaceous, perennial plant...
the winter of 1535–1536. Due to the presence of the neurotoxic compound thujone, internal use can be harmful if used for prolonged periods or while pregnant...