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

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27332705 | https://www.ncbi.nlm.nih.gov/pubmed/26918116 | https://www.ncbi.nlm.nih.gov/pubmed/18334601 | https://www.ncbi.nlm.nih.gov/pubmed/12357387

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The efficacy of Cavain in patients suffering from anxiety.
1989 Nov
Influence of genuine kavapyrone enantiomers on the GABA-A binding site.
1998 Aug
Neuroprotective effects of (+/-)-kavain in the MPTP mouse model of Parkinson's disease.
2001 Apr
Kava extract for treating anxiety.
2002
Kavalactones protect neural cells against amyloid beta peptide-induced neurotoxicity via extracellular signal-regulated kinase 1/2-dependent nuclear factor erythroid 2-related factor 2 activation.
2008 Jun
Kavain, the Major Constituent of the Anxiolytic Kava Extract, Potentiates GABAA Receptors: Functional Characteristics and Molecular Mechanism.
2016
Kavain Inhibition of LPS-Induced TNF-α via ERK/LITAF.
2016 Jan 1
Patents

Sample Use Guides

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
Created
by admin
on Sat Dec 16 02:49:11 UTC 2023
Edited
by admin
on Sat Dec 16 02:49:11 UTC 2023
Record UNII
W1ES06373M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
KAVAIN
Common Name English
NSC-112162
Code English
(+)-KAWAIN
Common Name English
KAWAIN [MI]
Common Name English
KAWAIN
MI   USP-RS   WHO-DD  
Common Name English
Kawain [WHO-DD]
Common Name English
D-KAWAIN
Common Name English
KAWAIN [USP-RS]
Common Name English
2H-PYRAN-2-ONE, 5,6-DIHYDRO-4-METHOXY-6-((1E)-2-PHENYLETHENYL)-, (6R)-
Systematic Name English
Classification Tree Code System Code
DSLD 2592 (Number of products:13)
Created by admin on Sat Dec 16 02:49:11 UTC 2023 , Edited by admin on Sat Dec 16 02:49:11 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
207-907-2
Created by admin on Sat Dec 16 02:49:11 UTC 2023 , Edited by admin on Sat Dec 16 02:49:11 UTC 2023
PRIMARY
NSC
112162
Created by admin on Sat Dec 16 02:49:11 UTC 2023 , Edited by admin on Sat Dec 16 02:49:11 UTC 2023
PRIMARY
EVMPD
SUB22114
Created by admin on Sat Dec 16 02:49:11 UTC 2023 , Edited by admin on Sat Dec 16 02:49:11 UTC 2023
PRIMARY
MERCK INDEX
m6605
Created by admin on Sat Dec 16 02:49:11 UTC 2023 , Edited by admin on Sat Dec 16 02:49:11 UTC 2023
PRIMARY Merck Index
RS_ITEM_NUM
1355753
Created by admin on Sat Dec 16 02:49:11 UTC 2023 , Edited by admin on Sat Dec 16 02:49:11 UTC 2023
PRIMARY
EPA CompTox
DTXSID5033595
Created by admin on Sat Dec 16 02:49:11 UTC 2023 , Edited by admin on Sat Dec 16 02:49:11 UTC 2023
PRIMARY
PUBCHEM
5281565
Created by admin on Sat Dec 16 02:49:11 UTC 2023 , Edited by admin on Sat Dec 16 02:49:11 UTC 2023
PRIMARY
WIKIPEDIA
KAVAIN
Created by admin on Sat Dec 16 02:49:11 UTC 2023 , Edited by admin on Sat Dec 16 02:49:11 UTC 2023
PRIMARY
FDA UNII
W1ES06373M
Created by admin on Sat Dec 16 02:49:11 UTC 2023 , Edited by admin on Sat Dec 16 02:49:11 UTC 2023
PRIMARY
SMS_ID
100000088941
Created by admin on Sat Dec 16 02:49:11 UTC 2023 , Edited by admin on Sat Dec 16 02:49:11 UTC 2023
PRIMARY
CAS
500-64-1
Created by admin on Sat Dec 16 02:49:11 UTC 2023 , Edited by admin on Sat Dec 16 02:49:11 UTC 2023
PRIMARY
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