Thujone

Thujone

Thujone is a monoterpene a component of the herb grand wormwood (Artemesia absinthium).   Thujone has three chiral centers but in nature position 1 and 5 are fixed so the natural product exists only as two stereoisomers, alpha-thujone and beta-thujone, and in its chemically pure form is a colorless liquid with a menthol-like aroma. Oil of Artemesia absinthium (or wormwood oil) is approximately 40-60% thujone but it can also be found in common herbs such as Sage and Tarragon. Thujone is infamous as an ingredient in the liquor Absinthe. 

Absinthe, the Green Fairy or La Fée Verte, was a drink that has a romantic history connected to the French Impressionists, Toulouse Lautrec, Degas, Manet, and Van Gogh, and founded a culture in Paris in the Belle Epoque, the cafes of Montmartre frequented by the muse of writers from Verlaine and Rimbaud to Joyce and Hemingway.   The drink was consumed by people from all walks of life including the lower classes celebrating l'heure verte in numerous cafes and bars. Absinthe is liquor that has an emerald green color that is attributed to the extraction of wormwood although many different recipes included other herbs such as anise, fennel, coriander, hyssop, and marjoram.  Absinthe became the subject of much writing and appears in many paintings of the period as in the works of Van Gogh (Still Life with absinthe, Paris 1887).

Absinthe's height of popularity occurred during the last quarter of the 19th century and the early part of the 20th century. Absinthe was banned by the French government in 1915 as a reaction to the reported toxicity of the drink.  The alcohol content of these liquors was 47 - 80 percent which made the alcohol toxicity probably the greatest danger.  Oil of wormwood has been shown to cause convulsions in early studies published prior to 1906.  In 1997 there was a NEJM report of acute kidney failure after ingestion of oil of wormwood. (Weisbord, Soule, and Kimmel 825-27)  Research by Dettling (Dettling et al. 573-81)and others (Hold et al. 3826-31) have found thujone a GABA-a receptor antagonist, which means it inhibits GABA receptor activation. Other studies have elucidated toxicity and metabolism of the thujones.  (Hold, Sirisoma, and Casida 589-95) However all current evidence indicates the symptoms attributed to absinthe were due to the high alcohol content since the concentrations of thujone in most of the preparations were probably low based on current efforts to reproduce the production formulas.  (Lachenmeier et al. 365-77) , (Padosch, Lachenmeier, and Kroner 14).  Today the EU regulates thujone amounts to 10 mg/l in high proof beverages and 35 mg/l in beverages labeled as "bitters." (EU Commission 2003)

The history of Absinthe is replete with romantic notions and visual associations, witness the musical tribute in the recent film "Moulin Rouge", and the Internet has fanned the recent resurgence along with exporters and marketing executives interested in profit.  Many intoxicants are linked to cultural habits and have social and political implications.  Interest in Absinthe use is steeped with ritual and mystery and serves as a titillating variation to more common barroom distractions such as boasting, singing, wenching and brawling.  Click here for a video of the ritual on using absinthe. The history of Absinthe is replete with images, historical figures and the arts. Click here for more information. This mystery surrounding use of absinthe continues to this day with a recent report of absenthe involvement in missing cruise ship passenger. (Christofferson, AP 2006)

Reference List

Dettling, A. et al. "Absinthe: attention performance and mood under the influence of thujone." J.Stud.Alcohol 65.5 (2004): 573-81.

Hold, K. M., N. S. Sirisoma, and J. E. Casida. "Detoxification of alpha- and beta-Thujones (the active ingredients of absinthe): site specificity and species differences in cytochrome P450 oxidation in vitro and in vivo." Chem.Res.Toxicol. 14.5 (2001): 589-95.

Hold, K. M. et al. "Alpha-thujone (the active component of absinthe): gamma-aminobutyric acid type A receptor modulation and metabolic detoxification." Proc.Natl.Acad.Sci.U.S.A 97.8 (2000): 3826-31.

Lachenmeier, D. W. et al. "Absinthe--a review." Crit Rev.Food Sci.Nutr. 46.5 (2006): 365-77.

Padosch, S. A., D. W. Lachenmeier, and L. U. Kroner. "Absinthism: a fictitious 19th century syndrome with present impact." Subst.Abuse Treat.Prev.Policy 1.1 (2006): 14.

Weisbord, S. D., J. B. Soule, and P. L. Kimmel. "Poison on line--acute renal failure caused by oil of wormwood purchased through the Internet." N.Engl.J.Med. 337.12 (1997): 825-27.

Internet References

  1. Opinion of the Scientific Committee on Food on Thujone, European Commission. SCF/CS/FLAV/FLAVOUR/23 ADD2 Final 2003.
  2. The Shaky History of Thujone by Ari
  3. Associated Press By John Christoffersen "Banned liquor latest twist in cruise disappearance",   January 22, 2006
  4. http://www.oxygenee.com/
  5. http://www.feeverte.net/thujone.html
  6. http://en.wikipedia.org/wiki/Absinthe
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