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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H14O3
Molecular Weight 230.2592
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of KAVAIN

SMILES

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

InChI

InChIKey=XEAQIWGXBXCYFX-GUOLPTJISA-N
InChI=1S/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-8,10,12H,9H2,1H3/b8-7+/t12-/m0/s1

HIDE SMILES / InChI

Molecular Formula C14H14O3
Molecular Weight 230.2592
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

Kavain is the main kavalactone found mostly in the roots of the kava plant. Kavain interacts with voltage-dependent Na+ and Ca2+ channels, GABAA ion channels. Kavain is found to be involved in TNF-alpha expression in human and mouse cells via regulation transcriptional factors. Kavain exhibits neuroprotective effects in models of Alzheimer's and Parkinson's diseases, and produces anxyolitic effect.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
88.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
The therapeutic efficacy of Cavain should be proved in the treatment of patients suffering from abnormal anxiety, psychosomatic complaints and psychoreactive disorder. Thus two randomized groups of patients (26 each) were treated in double-blind technique with either 2 x 200 mg daily Cavain or placebo for a period of 28 days.
Route of Administration: Oral
In Vitro Use Guide
How the excitability of neurons is affected was investigated by determining the interaction of (+/-)-kavain with epitopes (site 1, site 2) of voltage-dependent Na+ channels and the action of (+/-)-kavain on 4-aminopyridine-stimulated synaptosomes as model of repetitive firing neurons. [3H]Saxitoxin and [3H]batrachotoxin were used for radioligand-binding assays performed with synaptosomal membranes. It was shown that (+/-)-Kavain failed to compete with [3H]saxitoxin up to 400 mumol/l but dose-dependently suppressed binding of [3H]batrachotoxin with an IC50 value of 88 mumol/l (Ki = 72 mumol/l) although displacement of [3H]batrachotoxin was restricted to 33% of control at 400 mumol/l (+/-)-kavain.
Substance Class Chemical
Record UNII
W1ES06373M
Record Status Validated (UNII)
Record Version