A monoterpene ketone with diverse biological activities
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(−)-α-Thujone

Item No. 39792

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S,4R,5R)-4-methyl-1-(1-methylethyl)-bicyclo[3.1.0]hexan-3-one
CAS Number
546-80-5
Synonyms
  • Thujone
  • NSC 93742
Molecular Formula
C10H16O
Formula Weight
152.2
Purity
≥95%
Formulation (Request formulation change)
A liquid
Solubility(Learn about Variance in Solubility)
Methanol: Soluble
SMILES
CC([C@]12[C@]([C@H](C(C2)=O)C)([H])C1)C
InChi Code
InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8-,10+/m1/s1
InChi Key
USMNOWBWPHYOEA-MRTMQBJTSA-N
Origin
Plant/Unidentified sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $55

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    5 mg

    $251

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    10 mg

    $495

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    25 mg

    $1,032

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    Product Description

    (–)-α-Thujone is a monoterpene ketone and a major component of absinthe and has diverse biological activities.1,2,3,4 It inhibits currents induced by acetylcholine (ACh) in Xenopus oocytes expressing human α7 nicotinic acetylcholine receptors (nAChRs; IC50 = 27 µM).1 (–)-α-Thujone (100 and 300 µM) reduces GABA-induced current amplitude in HEK293 cells expressing α1β2δ subunit-containing GABA receptors.2 It reduces levels of the Norovirus surrogates feline calcivirus-F9 (FCV-F9) and murine norovirus 1 (MNV-1) in a plaque formation assay when used at a concentration of 25 mM.3 In vivo, (–)-α-thujone (1.25 mg/kg, i.p.) impairs nicotine-induced enhancement of long-term potentiation in the dentate gyrus, a marker of learning and memory, in rats.1 It also inhibits lung metastasis and increases survival in a B16/F10 murine melanoma model when administered at a dose of 1 mg/kg.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sultan, A., Yang, K.S., Isaev, D., et al. Thujone inhibits the function of α7-nicotinic acetylcholine receptors and impairs nicotine-induced memory enhancement in one-trial passive avoidance paradigm. Toxicology 384, 23-32 (2017).

    2. Czyzewska, M.M., and Mozrzymas, J.W. Monoterpene α-thujone exerts a differential inhibitory action on GABAA receptors implicated in phasic and tonic GABAergic inhibition. Eur. J. Pharmacol. 702(1-3), 38-43 (2013).

    3. Chung, M.S. Antiviral activities of Artemisia princeps var. orientalis essential oil and its α-thujone against norovirus surrogates. Food Sci. Biotechnol. 26(5), 1457-1461 (2017).

    4. Siveen, K.S., and Kuttan, G. Thujone inhibits lung metastasis induced by B16F-10 melanoma cells in C57BL/6 mice. Can. J. Physiol. Pharmacol. 89(10), 89(10) (2011).