DIHYDROMETHYSTICIN Chemical Properties

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly), Pyridine (Slightly)

Boiling point:

476.1±45.0 °C(Predicted)

Density 

1.28±0.1 g/cm3(Predicted)

Melting point:

117-118 °C

form 

Solid

color 

White to Off-White

BRN 

91699

Stability:

Hygroscopic

InChI

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

InChIKey

RSIWXFIBHXYNFM-NSHDSACASA-N

SMILES

C1(=O)O[C@@H](CCC2=CC=C3OCOC3=C2)CC(OC)=C1

LogP

1.810 (est)

Safety Information

WGK Germany 

3

DIHYDROMETHYSTICIN Usage And Synthesis

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. Dihydromethysticin is a P-glycoprotein (P-gp) inhibitor that increases uptake of the P-gp substrate calcein AM by 50% in P388 mouse leukemia cancer cells overexpressing P-gp when used at a concentration of 54.6 μM. Dihydromethysticin (275 mg/kg) has analgesic activity, increasing the latency to tail withdrawal in the tail-flick assay in mice. 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.

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from the rhizome of Pipermethysticum Forst.

Uses

(6S)-6-[2-(1,3-Benzodioxol-5-yl)ethyl]-5,6-dihydro-4-methoxy-2H-pyran-2-one, is used in toxicity studies through in vitro analysis. This complex is found in the roots of kava plant.

Definition

ChEBI: Dihydromethysticin is a member of 2-pyranones and an aromatic ether.

IC 50

CYP3

References

[1] D. D. JAMIESON  P. H D. THE ANTINOCICEPTIVE ACTIONS OF KAVA COMPONENTS IN MICE[J]. Clinical and Experimental Pharmacology and Physiology, 1990, 17 7: 495-507. DOI: 10.1111/j.1440-1681.1990.tb01349.x
[2] CORD BACKHAUΒ  Josef K. Extract of kava (Piper methysticum) and its methysticin constituents protect brain tissue against ischemic damage in rodents[J]. European journal of pharmacology, 1992, 215 2: Pages 265-269. DOI: 10.1016/0014-2999(92)90037-5
[3] JOHANNA WEISS. Extracts and kavalactones of Piper methysticum G. Forst (kava-kava) inhibit P-glycoprotein in vitro.[J]. Drug Metabolism and Disposition, 2005, 33 11: 1580-1583. DOI: 10.1124/dmd.105.005892

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