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

Molecular Formula	C14H16O3
Molecular Weight	232.275
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 846

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1.	2011-12	21908763
Nutritional and herbal supplements for anxiety and anxiety-related disorders: systematic review.	2010-10-07	20929532
Cyclodextrins as carriers for kavalactones in aqueous media: spectroscopic characterization of (S)-7,8-dihydrokavain and beta-cyclodextrin inclusion complex.	2010-08-01	20185265
Identification and characterization of kava-derived compounds mediating TNF-alpha suppression.	2009-08	19538508
Efficient enantioselective hetero-Diels-Alder reaction of Brassard's diene with aliphatic aldehydes: a one-step synthesis of (R)-(+)-kavain and (S)-(+)-dihydrokavain.	2008-03-20	18303910
Inhibition of TNFalpha-induced activation of nuclear factor kappaB by kava (Piper methysticum) derivatives.	2006-04-14	16464438
Fourier transform ion cyclotron resonance mass spectrometry for the characterisation of kavalactones in the kava plant: elemental formulae confirmation by dual spray accurate mass measurement and structural confirmation by infrared multiphoton dissociation and sustained off-resonance irradiation collision induced dissociation.	2006	17057279
Extracts and kavalactones of Piper methysticum G. Forst (kava-kava) inhibit P-glycoprotein in vitro.	2005-11	16051732
Determination of six kavalactones in dietary supplements and selected functional foods containing Piper methysticum by isocratic liquid chromatography with internal standard.	2005-03-12	15759721
Determination of kava lactones in food supplements by liquid chromatography-atmospheric pressure chemical ionisation tandem mass spectrometry.	2005-03-04	15844515
Anxiolytic properties of Piper methysticum extract samples and fractions in the chick social-separation-stress procedure.	2003-03	12672148
Kavalactones and dihydrokavain modulate GABAergic activity in a rat gastric-brainstem preparation.	2002-12	12494336
Inhibition of cytochrome P450 3A4 by extracts and kavalactones of Piper methysticum (Kava-Kava).	2002-12	12494328
Interaction of various Piper methysticum cultivars with CNS receptors in vitro.	2001-06	11458444
Anxiolytic effects of kava extract and kavalactones in the chick social separation-stress paradigm.	2001-04	11374340

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:20:50 GMT 2025` Edited by `admin` on `Mon Mar 31 22:20:50 GMT 2025`
Record UNII	NW8ZGW9XRZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIHYDROKAWAIN

Common Name

English

MARINDININ

Preferred Name

English

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

Systematic 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)