A kavalactone with diverse biological activities
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Dihydromethysticin

Item No. 27644

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(6S)-6-[2-(1,3-benzodioxol-5-yl)ethyl]-5,6-dihydro-4-methoxy-2H-pyran-2-one
CAS Number
19902-91-1
Synonyms
  • DHM
  • 7,8-dihydro Methysticin
  • NSC 112159
Molecular Formula
C15H16O5
Formula Weight
276.3
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: solubleMethanol: soluble
SMILES
O=C1O[C@@H](CCC2=CC=C(OCO3)C3=C2)CC(OC)=C1
InChi Code
InChI=1S/C15H16O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h3,5-6,8,11H,2,4,7,9H2,1H3/t11-/m0/s1
InChi Key
RSIWXFIBHXYNFM-NSHDSACASA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $197

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    10 mg

    $374

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    Product Description

    Dihydromethysticin is a kavalactone originally isolated from P. methysticum (kava-kava) that has diverse biological activities, including efflux transporter inhibitory, antinociceptive, and neuroprotective properties.1,2 Dihydromethysticin is a P-glycoprotein (P-gp) inhibitor that increases uptake of the P-gp substrate calcein AM (Item No. 14948) by 50% in P388 mouse leukemia cancer cells overexpressing P-gp when used at a concentration of 54.6 μM.3 Dihydromethysticin (275 mg/kg) has analgesic activity, increasing the latency to tail withdrawal in the tail-flick assay in mice.1 It also decreases the infarct size in a mouse model of ischemia induced by microbipolar coagulation of the left middle cerebral artery (MCA) when administered at a dose of 10 mg/kg.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jamieson, D.D., and Duffield, P.H. The antinociceptive actions of kava components in mice. Clin. Exp. Pharmacol. Physiol. 17(7), 495-507 (1990).

    2. Backhauβ, C., and Krieglstein, J. Extract of kava (Piper methysticum) and its methysticin constituents protect brain tissue against ischemic damage in rodent. Eur. J. Pharmacol. 215(2-3), 265-269 (1992).

    3. Weiss, J., Sauer, A., Frank, A., et al. Extracts and kavalactones of Piper methysticum G. Forst (kava-kava) inhibit P-glycoprotein in vitro. Drug Metab. Dispos. 33(11), 1580-1583 (2005).