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
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/12076477Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12076477
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27332705 |
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Target ID: CHEMBL1075094 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18334601 |
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Target ID: CHEMBL2095229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12357387 |
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Target ID: CHEMBL2331043 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9690349 |
88.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Neuroprotective effects of (+/-)-kavain in the MPTP mouse model of Parkinson's disease. | 2001 Apr |
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Kava extract for treating anxiety. | 2002 |
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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 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2575765
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8960869
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.
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2592 (Number of products:13)
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112162
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SUB22114
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KAVAIN
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500-64-1
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ACTIVE MOIETY