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Names | |
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IUPAC name 4-Methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one | |
Other names Dihydrokawain Marindinin | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C14H16O3 | |
Molar mass | 232.27 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Dihydrokavain is one of the six major kavalactones found in the kava plant. [1] It appears to contribute significantly to the anxiolytic effects of kava, based on a study in chicks. [2]
Dihydrokavain bears some structural similarity to the strobilurins and has some fungicidal activity. [3]
An analogue of the molecule was also shown to improve glycemic control by modulating AMPK target genes expression in fruit flies. [4]
Kava or kava kava is a crop of the Pacific Islands. The name kava is from Tongan and Marquesan, meaning 'bitter'; other names for kava include ʻawa (Hawaiʻi), ʻava (Samoa), yaqona or yagona (Fiji), sakau (Pohnpei), seka (Kosrae), and malok or malogu. Kava is consumed for its sedating effects throughout the Pacific Ocean cultures of Polynesia, including Hawaii and Vanuatu, Melanesia, some parts of Micronesia, such as Pohnpei and Kosrae, and the Philippines.
Strobilurins are a group of natural products and their synthetic analogs. A number of strobilurins are used in agriculture as fungicides. They are part of the larger group of QoIs, which act to inhibit the respiratory chain at the level of Complex III.
Kavalactones are a class of lactone compounds found in kava roots and Alpinia zerumbet. Kavalactones are under research for potential to have various psychotropic effects, including anxiolytic and sedative/hypnotic activities.
Depressants, or central depressants, are drugs that lower neurotransmission levels, which is to depress or reduce arousal or stimulation in various areas of the brain. Depressants are also colloquially referred to as "downers" as they lower the level of arousal when taken. Stimulants, or "uppers," increase mental or physical function, hence the opposite drug class from depressants is stimulants, not antidepressants.
5-HT receptors, 5-hydroxytryptamine receptors, or serotonin receptors, are a group of G protein-coupled receptor and ligand-gated ion channels found in the central and peripheral nervous systems. They mediate both excitatory and inhibitory neurotransmission. The serotonin receptors are activated by the neurotransmitter serotonin, which acts as their natural ligand.
Tianeptine, sold under the brand names Stablon, Tatinol, and Coaxil among others, is an atypical tricyclic antidepressant which is used mainly in the treatment of major depressive disorder, although it may also be used to treat anxiety, asthma, and irritable bowel syndrome.
Alpidem, sold under the brand name Ananxyl, is a nonbenzodiazepine anxiolytic medication which was briefly used to treat anxiety disorders but is no longer marketed. It was previously marketed in France, but was discontinued due to liver toxicity. Alpidem is taken by mouth.
Nociceptin/orphanin FQ (N/OFQ), a 17-amino acid neuropeptide, is the endogenous ligand for the nociceptin receptor. Nociceptin acts as a potent anti-analgesic, effectively counteracting the effect of pain-relievers; it's activation is associated with brain functions such as pain sensation and fear learning.
Etizolam is a thienodiazepine derivative which is a benzodiazepine analog. The etizolam molecule differs from a benzodiazepine in that the benzene ring has been replaced by a thiophene ring and triazole ring has been fused, making the drug a thienotriazolodiazepine.
Fenobam is an imidazole derivative developed by McNeil Laboratories in the late 1970s as a novel anxiolytic drug with an at-the-time-unidentified molecular target in the brain. Subsequently, it was determined that fenobam acts as a potent and selective negative allosteric modulator of the metabotropic glutamate receptor subtype mGluR5, and it has been used as a lead compound for the development of a range of newer mGluR5 antagonists.
Siramesine is a sigma receptor agonist, selective for the σ2 subtype. In animal studies, siramesine has been shown to produce anxiolytic and antidepressant effects. It was developed by the pharmaceutical company H Lundbeck for the treatment of anxiety, although development was discontinued after clinical trials showed a lack of efficacy in humans.
Etifoxine, sold under the brand name Stresam among others, is a nonbenzodiazepine anxiolytic medication which is used in the short-term treatment of adjustment disorder with anxiety, for instance stress-related anxiety. It is taken by mouth.
Serine/threonine kinase 11 (STK11) also known as liver kinase B1 (LKB1) or renal carcinoma antigen NY-REN-19 is a protein kinase that in humans is encoded by the STK11 gene.
L-838,417 is an anxiolytic drug used in scientific research. It has similar effects to benzodiazepine drugs, but is structurally distinct and so is classed as a nonbenzodiazepine anxiolytic. The compound was developed by Merck, Sharp and Dohme.
Kavain is the main kavalactone found mostly in the roots of the kava plant.
3α-Androstanediol also known as 5α-androstane-3α,17β-diol and sometimes shortened in the literature to 3α-diol, is an endogenous steroid hormone and neurosteroid and a metabolite of androgens like dihydrotestosterone (DHT).
Yangonin is one of the six major kavalactones found in the kava plant. It has been shown to possess binding affinity for the cannabinoid receptor CB1 (Ki = 0.72 μM), and selectivity vs. the CB2 receptor (Ki >10 μM) where it behaves as an agonist. The CB1 receptor affinity of yangonin suggests that the endocannabinoid system might contribute to the complex human psychopharmacology of the traditional kava drink and the anxiolytic preparations obtained from the kava plant.
Dihydromethysticin is one of the six major kavalactones found in the kava plant.
Methysticin is one of the six major kavalactones found in the kava plant. Research suggests that methysticin and the related compound dihydromethysticin have CYP1A1 inducing effects which may be responsible for their toxicity. Additionally, methysticin has been shown to potentiate GABAA receptor activity, contributing to the overall anxiolytic profile of the kava plant.
PNU-99,194(A) (or U-99,194(A)) is a drug which acts as a moderately selective D3 receptor antagonist with ~15-30-fold preference for D3 over the D2 subtype. Though it has substantially greater preference for D3 over D2, the latter receptor does still play some role in its effects, as evidenced by the fact that PNU-99,194 weakly stimulates both prolactin secretion and striatal dopamine synthesis, actions it does not share with the more selective (100-fold) D3 receptor antagonists S-14,297 and GR-103,691.