DIHYDROKAWAIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H16O3
Molecular Weight	232.275
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(=O)O[C@@H](CCC2=CC=CC=C2)C1

InChI

InChIKey=VOOYTQRREPYRIW-LBPRGKRZSA-N

InChI=1S/C14H16O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-6,10,12H,7-9H2,1H3/t12-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12494336

Dihydrokavain (or DIHYDROKAWAIN) is one of the six major kavalactones found in the kava plant. It was shown that dihydrokavain might play an important role in regulation of GABAergic neurotransmission, because this compound can modulate the brainstem GABAergic mechanism.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABAergic activity 1 Target ID: GABAergic activity Sources: https://www.ncbi.nlm.nih.gov/pubmed/12494336	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Interaction of various Piper methysticum cultivars with CNS receptors in vitro.	2001 Jun	11458444
Kavalactones and dihydrokavain modulate GABAergic activity in a rat gastric-brainstem preparation.	2002 Dec	12494336
Inhibition of cytochrome P450 3A4 by extracts and kavalactones of Piper methysticum (Kava-Kava).	2002 Dec	12494328
Determination of six kavalactones in dietary supplements and selected functional foods containing Piper methysticum by isocratic liquid chromatography with internal standard.	2005 Jan-Feb	15759721
Extracts and kavalactones of Piper methysticum G. Forst (kava-kava) inhibit P-glycoprotein in vitro.	2005 Nov	16051732
Cyclodextrins as carriers for kavalactones in aqueous media: spectroscopic characterization of (S)-7,8-dihydrokavain and beta-cyclodextrin inclusion complex.	2010 Aug 1	20185265
Nutritional and herbal supplements for anxiety and anxiety-related disorders: systematic review.	2010 Oct 7	20929532
Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1.	2011 Dec	21908763

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Pretreatment with dihydrokavain (300 uM) significantly decreased the nucleus tractus solitarius (NTS) inhibitory effects induced by muscimol (30 uM), approximately from 51 % to 36 %. Dihydrokavain induced inhibitory effects was not reduced after co-application of saclofen or naloxone.

Name

Type

Language

DIHYDROKAWAIN

Common Name

English

2H-PYRAN-2-ONE, 5,6-DIHYDRO-4-METHOXY-6-(2-PHENYLETHYL)-, (6S)-

Systematic Name

English

MARINDININ

Brand Name

English

DIHYDROKAWAIN [MI]

Common Name

English

(S)-(+)-DIHYDROKAWAIN

Common Name

English

(6S)-5,6-DIHYDRO-4-METHOXY-6-(2-PHENYLETHYL)-2H-PYRAN-2-ONE

Systematic Name

English

7,8-DIHYDROKAWAIN

Common Name

English

NSC-112163

Code

English

DIHYDROKAVAIN

Common Name

English

DHK

Common Name

English

Classification Tree Code System Code

DSLD

2592 (Number of products:13)