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Chemical Compound Review

THUJONE     (1S,4R,5R)-4-methyl-1-propan- 2-yl...

Synonyms: Thujon, l-Thujone, dl-Thujone, alpha-Thujone, SureCN122447, ...
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Disease relevance of THUJONE


High impact information on THUJONE


Chemical compound and disease context of THUJONE


Biological context of THUJONE


Anatomical context of THUJONE

  • We report here unexpected site specificity and species differences in the metabolism of the thujone diastereomers in mouse, rat, and human liver microsomes and human recombinant P450 (P450 3A4), in orally treated mice and rats, and in Drosophila melanogaster [8].
  • Radioligand receptor binding assays employing membrane preparations from rat brains containing CB1 cannabinoid receptors, and human tonsils containing CB2 receptors, demonstrated that thujone displaced [3H]CP55940, a cannabinoid agonist, only at concentrations above 10 microM [9].

Associations of THUJONE with other chemical compounds


Gene context of THUJONE


  1. Absinthe: attention performance and mood under the influence of thujone. Dettling, A., Grass, H., Schuff, A., Skopp, G., Strohbeck-Kuehner, P., Haffner, H.T. J. Stud. Alcohol (2004) [Pubmed]
  2. Vincent van Gogh and the thujone connection. Arnold, W.N. JAMA (1988) [Pubmed]
  3. Alpha-thujone (the active component of absinthe): gamma-aminobutyric acid type A receptor modulation and metabolic detoxification. Höld, K.M., Sirisoma, N.S., Ikeda, T., Narahashi, T., Casida, J.E. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  4. Radical rebound mechanism in cytochrome P-450-catalyzed hydroxylation of the multifaceted radical clocks alpha- and beta-thujone. He, X., de Montellano, P.R. J. Biol. Chem. (2004) [Pubmed]
  5. Toxicity of some essential plant oils. Clinical and experimental study. Millet, Y., Jouglard, J., Steinmetz, M.D., Tognetti, P., Joanny, P., Arditti, J. Clin. Toxicol. (1981) [Pubmed]
  6. Composition of essential oil of costmary [Balsamita major (L.) Desf. ] at different growth phases. Bylaite, E., Venskutonis, R., Roozen, J.P., Posthumus, M.A. J. Agric. Food Chem. (2000) [Pubmed]
  7. Terpenoid biotransformation in mammals. V. Metabolism of (+)-citronellal, (+-)-7-hydroxycitronellal, citral, (-)-perillaldehyde, (-)-myrtenal, cuminaldehyde, thujone, and (+-)-carvone in rabbits. Ishida, T., Toyota, M., Asakawa, Y. Xenobiotica (1989) [Pubmed]
  8. 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. Höld, K.M., Sirisoma, N.S., Casida, J.E. Chem. Res. Toxicol. (2001) [Pubmed]
  9. Thujone exhibits low affinity for cannabinoid receptors but fails to evoke cannabimimetic responses. Meschler, J.P., Howlett, A.C. Pharmacol. Biochem. Behav. (1999) [Pubmed]
  10. Volatile chemicals identified in extracts from leaves of Japanese mugwort (Artemisia princeps pamp.). Umano, K., Hagi, Y., Nakahara, K., Shoji, A., Shibamoto, T. J. Agric. Food Chem. (2000) [Pubmed]
  11. Phytochemical analysis of the essential oil of Achillea millefolium L. from various European Countries. Orav, A., Arak, E., Raal, A. Nat. Prod. Res. (2006) [Pubmed]
  12. Alpha-thujone reduces 5-HT3 receptor activity by an effect on the agonist-reduced desensitization. Deiml, T., Haseneder, R., Zieglgänsberger, W., Rammes, G., Eisensamer, B., Rupprecht, R., Hapfelmeier, G. Neuropharmacology (2004) [Pubmed]
  13. alpha- and beta-Thujones (herbal medicines and food additives): synthesis and analysis of hydroxy and dehydro metabolites. Sirisoma, N.S., Höld, K.M., Casida, J.E. J. Agric. Food Chem. (2001) [Pubmed]
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