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Synonym name: Kawain
Catalogue No.: BP0829
Cas No.: 500-64-1
Formula: C14H14O3
Mol Weight: 230.263
Botanical Source: Occurs in Root of Piper methysticum
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams.
For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.
Description:
Kavain has anticonvulsive properties, attenuating vascular smooth muscle contraction through interactions with voltage-dependent Na+ and Ca2+ channels. Kawain is advanced glycation endproduct inhibitors, can increase the mean life span of Caenorhabditis elegans exposed to high glucose.
References:
Prog Neuropsychopharmacol Biol Psychiatry. 1997 May;21(4):697-706.
Effects of kawain and dihydromethysticin on field potential changes in the hippocampus.
1. The kava-pyrones Kawain and dihydromethysticin are constituents of Piper methysticum which exert anticonvulsant, analgesic and anxiolytic properties.
METHODS AND RESULTS:
3. Kawain and dihydromethysticin reduced reversibly the frequency of occurrence of fp in a concentration range from 5 to 40 mumol/l and 10 to 40 mumol/l, respectively. 4. Reduction of the fp frequency after addition of subthreshold concentrations of 5 mumol/l Kawain and 10 mumol/l dihydromethysticin indicated additive actions of both drugs. 5. Since the serotonin-1A agonist ipsapirone also exerts anxiolytic effects, subthreshold concentrations of Kawain or dihydromethysticin were combined with a subthreshold concentration of ipsapirone in another set of experiments. Combining Kawain and ipsapirone or dihydromethysticin and ipsapirone caused a reduction of the rate of fp to 0.76 and 0.81 of the baseline value, respectively.
CONCLUSIONS:
6. The findings suggest that (i) single constituents of Piper methysticum may have additive actions, (ii) that the two components Kawain and dihydromethysticin may enhance the effects of the anxiolytic serotonin-1A agonist ipsapirone and (iii) that activation of NMDA receptors and/or voltage dependent calcium channels may be involved in the elementary mechanism of action of some kava-pyrones.
Drug Metab Dispos. 2005 Oct;33(10):1555-63.
Pharmacokinetics and disposition of the kavalactone kawain: interaction with kava extract and kavalactones in vivo and in vitro.
METHODS AND RESULTS:
The oral pharmacokinetics of the kavalactone, Kawain (100 mg/kg), were determined in rats with and without coadministration of kava extract (256 mg/kg) to study the effect of the extract on drug disposition. Kawain was well absorbed, with >90% of the dose eliminated within 72 h, chiefly in urine. Compared with Kawain alone, coadministration with kava extract caused a tripling of KawainAUC(0-8 h) and a doubling of C(max). However, a 7-day pretreatment with kava extract (256 mg /kg/day) had no effect on the pharmacokinetics of Kawain administered on day 8.
CONCLUSIONS:
The 7-day pretreatment with kava extract only modestly induced hepatic P450 activities.
HPLC of Kavain
HNMR of Kawain
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
35.5300
2.9579
2.9579
.1747
4.0539
3.9670
High
86.8925
3.0810
Yes
Yes
Yes
No
No
No
0.0
No
Yes
Yes
Yes
Kavain (CAS number: 500-64-1) is a natural product of kavaic acid lactone isolated from the traditional medicinal plant Piper methysticum in the South Pacific region. Kava, as a traditional herb with a long history of use, has been widely studied for its remarkable anti-anxiety and calming effects. As one of the main active ingredients in kava, drunkyanin has been proven to have good anti-anxiety effects in animals and humans, and shows potential pharmacological activity in analgesic relief and neuroprotection. In recent years, with deeper analysis of its molecular mechanisms, research on drunlicin in the treatment of neuropsychiatric disorders has gradually attracted attention.
This paper aims to systematically review the chemical structure and physicochemical properties of drunken pepper, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, and to explore its clinical application prospects and future development directions, providing theoretical basis and research reference for natural product pharmacology and new drug development.
The chemical name of druniospicyl druniosciphyrin is 5,6-dihydro-6-methyl-2H-pyran-2-one type carboxylic acid lactone, with a molecular formula of C14H14O3 and a molecular weight of 230.2630. Its structure includes a typical carvalactone backbone, which has a relatively balanced hydrophobicity and hydrophilicity. The LogP value was 2.9579, indicating moderate lipid solubility, which helps penetrate cell membranes and the blood-brain barrier (BBB). The topological pole surface area (TPSA) is 35.53 Ų, and the relatively low pole surface area helps it absorb and distribute well in the body.
The low water solubility of druniophysicin (0.1747 mg/mL) suggests limited solubility in the aqueous phase but good lipid solubility, which is beneficial for its stable existence in lipid environments. It has high blood-brain barrier penetration ability, meeting the physicochemical characteristics of active drugs in the central nervous system. Additionally, the hERG channel inhibition test results were negative, indicating a low risk of cardiotoxicity; The Ames mutagenicity test result was 0.0, indicating a low genotoxicity risk and a solid safety foundation.
Drunken is mainly derived from kava (Piper methysticum Forst. f.) is a tropical shrub that grows in South Pacific island countries. The roots and rhizomes of kava have traditionally been used to prepare beverages, possessing pharmacological effects such as calming, anti-anxiety, and muscle relaxation. As one of the main active ingredients in Kava, the content and extraction purity of druniophorin directly affect the efficacy of Kava preparations.
Common extraction methods for drunken speciogen include solvent extraction, ultrasound-assisted extraction, and liquid-liquid distribution. Traditionally, ethanol or methanol is used as solvents to extract the rhizomes of Kava rhizomes, followed by liquid-liquid extraction and column chromatography for purification. In recent years, supercritical CO2 extraction technology has been widely used for the extraction of druniospicin due to its environmental friendliness, strong selectivity, and high extraction efficiency. This method can effectively avoid organic solvent residues and improve the purity and safety of the extract.
During extraction, temperature, solvent polarity, and extraction time are key factors affecting the yield and quality of drunctitol. Optimizing the extraction process not only helps increase the yield of drunk pepper extract but also provides technical support for its industrial production.
The pharmacological activity of drunk pepper mainly focuses on anti-anxiety, analgesia, and neuroprotection, with related research covering in vitro cell models, animal experiments, and some clinical observations.
Anti-anxiety effects
Drunken pepper hormone demonstrates significant anti-anxiety effects by regulating neurotransmitter balance in the central nervous system. Multiple animal behavioral experiments (such as the opening test and labyrinth test) have shown that duptophorin can significantly reduce anxiety levels in animals, with effects similar to benzodiazepines but with fewer side effects. Its mechanism of action mainly involves forward regulation of GABAA receptors, enhancing neuroinhibition signals mediated by γ-aminobutyric acid (GABA).
Analgesic effect
Drupiophorin demonstrated good analgesic effects across various pain models, involving multiple pain-related targets. Research shows that druniophorin can regulate TRPV1 and TRPA1 ion channels, inhibit the activity of prostaglandin synthases PTGS1 and PTGS2, and alleviate inflammatory pain. Additionally, its regulatory effects on opioid receptors (OPRD1, OPRM1, OPRK1) and dopamine D2 receptor (DRD2) suggest its potential application value in neuropathic pain and chronic pain management.
Neuroprotection and other effects
Drunken also demonstrates antioxidant and neuroprotective effects, helping to reduce nerve damage caused by oxidative stress. By regulating the 5-hydroxytryptamine transporter protein (SLC6A4) and other neurotransmitter systems, it may provide adjunctive therapeutic effects for depression and other neuropsychiatric disorders.
The pharmacological mechanism of druniospicin is relatively complex, involving coordinated regulation of multiple targets:
GABAA receptor: As a positive modulator of GABAA receptors, drunkarin enhances GABA-mediated chloride ion influx, promotes neuronal hyperpolarization, and exerts sedative and anti-anxiety effects. This mechanism is similar to benzodiazepines, but druniosamine has milder side effects and is less likely to cause dependence.
TRPV1 and TRPA1 ion channels: These two transient receptor potential channels play key roles in pain perception. Drunctial pepper extract reduces pain signal transmission by inhibiting the activity of TRPV1 and TRPA1, thereby exerting analgesic effects.
Prostaglandin synthase (PTGS1, PTGS2): Drupitol inhibits cyclooxygenase activity, reduces prostaglandin synthesis, and alleviates inflammation and related pain.
Opioid receptor system (OPRD1, OPRM1, OPRK1): Drupotol may enhance the analgesic effect of endogenous opioid peptides by modulating opioid receptor activity, thereby improving chronic pain conditions.
Dopamine D2 receptor (DRD2) and serotonin transporter (SLC6A4): Drupaminin regulates these neurotransmitter systems and may be involved in their anti-anxiety and antidepressant effects.
In summary, drunk speciogen achieves its complex neuroregulatory functions through multi-target and multi-pathway synergistic effects.
Drunken pepper has excellent druggable properties:
Molecular weight and lipid solubility: Molecular weight 230.2630 and LogP 2.9579 both comply with Lipinski's rules, which is beneficial for oral absorption and internal distribution.
Blood-brain barrier penetration: High BBB penetration allows duptophorin to effectively act on the central nervous system, exerting anti-anxiety and analgesic effects.
Safety: No hERG channel inhibition and no mutagenicity, indicating low risk of cardiotoxicity and genotoxicity, and good safety.
Pharmacokinetics: Current studies show that drunkyanin is rapidly absorbed orally, has a moderate plasma half-life, and can maintain effective blood concentrations. Its metabolism mainly occurs through hepatic enzyme systems, and the activity of these metabolites still requires further research.
Although druniophorin has low water solubility, limiting its bioavailability, formulation technologies (such as nanocarriers and liposomes) are expected to improve its solubility and absorption efficiency.
Drunken pepper, as a natural compound with multi-target effects, demonstrates good anti-anxiety and analgesic potential, with broad clinical application prospects:
Anti-anxiety drug development: Drupajicin's anti-anxiety effects are similar to traditional benzodiazepines, but with fewer side effects and a lower risk of dependence, making it promising to become a new generation of safe and effective anti-anxiety drugs.
Analgesia treatment: For inflammatory and neuropathic pain, druniophorin offers a new therapeutic approach through multi-target regulation, making it especially suitable for long-term management of chronic pain patients.
Adjunctive therapy for neuropsychiatric disorders: Drupaitchiin modulates dopamine and serotonin systems, suggesting its potential application value in depression, insomnia, and other neuropsychiatric disorders.
Future research should focus on the clinical pharmacokinetics, formulation optimization, and long-term safety evaluation of druniosacin. At the same time, based on their multi-target mechanisms of action and combined with modern drug design technologies, the development of structurally modified derivatives to enhance their activity and selectivity will greatly promote their clinical translation.
As an important active ingredient in the kava plant, drunk pepper shows broad application prospects in anti-anxiety and analgesia due to its unique chemical structure and multi-target pharmacological effects. Its excellent druggability and safety provide a solid foundation for new drug development. In the future, through in-depth mechanistic research, pharmacokinetic optimization, and clinical validation, drunkyanin is expected to become an important candidate molecule in the development of natural product drugs, providing new therapeutic options for neuropsychiatric disorders and pain management.
Shenshuai
Wenjing
Hedandan
