Compounds based on benzene fused to oxole. They can be formed from methylated CATECHOLS such as EUGENOL.

Oral irritant properties of piperine and nicotine: psychophysical evidence for asymmetrical desensitization effects. (1/270)

Using a bipolar rating scale, human subjects rated the intensity of irritation sensation evoked by repeated application of piperine (75 p.p.m.) or nicotine (0.12%) to one side of the dorsal surface of the tongue. The intensity of irritation elicited by repeated application of piperine significantly increased, while irritation elicited by repeated nicotine significantly decreased. We additionally tested if nicotine or piperine desensitized the tongue. After either piperine or nicotine was repeatedly applied to one side of the tongue, a 5 or 10 min rest period ensued, followed by re-application of piperine or nicotine to both sides of the tongue. Subjects were asked to choose which side of the tongue gave rise to a stronger irritation in a two-alternative forced choice (2-AFC) paradigm. In addition, they gave separate ratings of the intensity of irritation on the two sides of the tongue. When piperine was applied bilaterally after unilateral pretreatment with piperine and a 10 min rest period, subjects consistently chose the non-pretreated side to yield stronger irritation and assigned significantly higher ratings to that side, indicative of piperine self-desensitization. A similar self-desensitization effect was found when bilateral application of nicotine followed unilateral treatment with nicotine and a 5 min rest period. Unilateral treatment with piperine also reduced nicotine-evoked irritation on the pretreated side (cross-desensitization), but treatment with nicotine did not affect piperine-evoked irritation. This asymmetrical cross-desensitization pattern is similar to that observed between capsaicin and nicotine and constitutes an additional similarity between piperine and capsaicin.  (+info)

Synthesis of optically active olivil type of lignan from L-arabinose using threo-selective aldol condensation as a key reaction. (2/270)

The threo-selective aldol condensation of (3R, 4S)-3-hydroxy-5-trityloxy-4-pentanolide, which was prepared from L-arabinose, with piperonal was applied to the stereoselective synthesis of the olivil type of lignan, (2R, 3R, 4R)-4-benzyl-4-hydroxy-3-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofura n.  (+info)

Effect of vanilloid drugs on gastrointestinal transit in mice. (3/270)

1. We have studied the effect of capsaicin, piperine and anandamide, drugs which activate vanilloid receptors and capsazepine, a vanilloid receptor antagonist, on upper gastrointestinal motility in mice. 2. Piperine (0.5 - 20 mg kg(-1) i.p.) and anandamide (0.5 - 20 mg kg(-1) i.p.), dose-dependently delayed gastrointestinal motility, while capsaicin (up to 3 mg kg(-1) i.p.) was without effect. Capsazepine (15 mg kg(-1) i.p.) neither per se affected gastrointestinal motility nor did it counteract the inhibitory effect of both piperine (10 mg kg(-1)) and anandamide (10 mg kg(-1)). 3. A per se non effective dose of SR141716A (0.3 mg kg(-1) i.p.), a cannabinoid CB(1) receptor antagonist, counteracted the inhibitory effect of anandamide (10 mg kg(-1)) but not of piperine (10 mg kg(-1)). By contrast, the inhibitory effect of piperine (10 mg kg(-1)) but not of anandamide (10 mg kg(-1)) was strongly attenuated in capsaicin (75 mg kg(-1) in total, s.c.)-treated mice. 4. Pretreatment of mice with N(G)-nitro-L-arginine methyl ester (25 mg kg(-1) i.p.), yohimbine (1 mg kg(-1), i.p.), naloxone (2 mg kg(-1) i.p.), or hexamethonium (1 mg kg(-1) i.p.) did not modify the inhibitory effect of both piperine (10 mg kg(-1)) and anandamide (10 mg kg(-1)). 5. The present study indicates that the vanilloid ligands anandamide and piperine, but not capsaicin, can reduce upper gastrointestinal motility. The effect of piperine involves capsaicin-sensitive neurones, but not vanilloid receptors, while the effect of anandamide involves cannabinoid CB(1), but not vanilloid receptors.  (+info)

Protective action of piperine against experimental gastric ulcer. (4/270)

AIM: To study the effects of piperine (Pip) on several experimental gastric ulcers in rats and mice. METHODS: The gastric mucosa damage was induced by stress, indometacin, HCl, and pyloric ligation in rats or mice. The number of gastric ulcers, the volume and acidity of gastric juices, and pepsin A activity were detected. RESULTS: Pip 25, 50, 100 mg/kg ig protected animals from gastric ulceration in a dose-dependent manner. The inhibitory rates were 16.9%, 36.0%, and 48.3% in stress ulcers; 4.4%, 51.1%, and 64.4% in indometacin ulcers; 19.2%, 41.5%, and 59.6% in HCl ulcers; 4.8%, 11.9%, and 26.2% in pyloric ligation ulcers, respectively; Pip inhibited the volume of gastric juice, gastric acidity, and pepsin A activity. CONCLUSION: Pip has the protective effects against gastric ulceration.  (+info)

Piperine, a major constituent of black pepper, inhibits human P-glycoprotein and CYP3A4. (5/270)

Dietary constituents (e.g., in grapefruit juice; NaCl) and phytochemicals (e.g., St. John's wort) are important agents modifying drug metabolism and transport and thereby contribute to interindividual variability in drug disposition. Most of these drug-food interactions are due to induction or inhibition of P-glycoprotein and/or CYP3A4. Preliminary data indicate that piperine, a major component of black pepper, inhibits drug-metabolizing enzymes in rodents and increases plasma concentrations of several drugs, including P-glycoprotein substrates (phenytoin and rifampin) in humans. However, there are no direct data whether piperine is an inhibitor of human P-glycoprotein and/or CYP3A4. We therefore investigated the influence of piperine on P-glycoprotein-mediated, polarized transport of digoxin and cyclosporine in monolayers of Caco-2 cells. Moreover, by using human liver microsomes we determined the effect of piperine on CYP3A4-mediated formation of the verapamil metabolites D-617 and norverapamil. Piperine inhibited digoxin and cyclosporine A transport in Caco-2 cells with IC(50) values of 15.5 and 74.1 microM, respectively. CYP3A4-catalyzed formation of D-617 and norverapamil was inhibited in a mixed fashion, with K(i) values of 36 +/- 8 (liver 1)/49 +/- 6 (liver 2) and 44 +/- 10 (liver 1)/77 +/- 10 microM (liver 2), respectively. In summary, we showed that piperine inhibits both the drug transporter P-glycoprotein and the major drug-metabolizing enzyme CYP3A4. Because both proteins are expressed in enterocytes and hepatocytes and contribute to a major extent to first-pass elimination of many drugs, our data indicate that dietary piperine could affect plasma concentrations of P-glycoprotein and CYP3A4 substrates in humans, in particular if these drugs are administered orally.  (+info)

Arylnaphthalide lignans from Cleistanthus collinus. (6/270)

Chemical examination of the aerial parts of Cleistanthus collinus afforded the arylanphthalide lignans, cleistanone (1), diphyllin (2), cleistanthins A (3), C (4) and D (5), and 4-O-(3"-O-methyl-beta-D-glucopyranosyl)-diphyllin (6). The first compound is a new member of the rare group of arylnaphthalide lignans containing an alkoxy group on the lactone ring. The structure of the compound was determined from its spectral data, chemical transformations and partial synthesis from diphyllin (2). The new lignan, 1 and its acetyl derivative, 7 were found to exhibit cytotoxicity against MT(2) cell lines.  (+info)

Individual differences in perception of bitterness from capsaicin, piperine and zingerone. (7/270)

It was recently shown that in some subjects capsaicin can evoke bitterness as well as burning and stinging, particularly in the circumvallate (CV) region of the tongue. Because perception of bitterness from capsaicin is characterized by large individual differences, the main goal of the present study was to learn whether people who taste capsaicin as bitter also report bitterness from structurally similar sensory irritants that are known to stimulate capsaicin-sensitive neurons. The irritancy and taste of capsaicin and two of its most commonly studied congeners, piperine and zingerone, were measured in individuals who had been screened for visibility of, and reliable access to, the CV papillae. Approximately half of these individuals reported tasting bitterness from all three irritants when the stimuli were swabbed directly onto the CV papillae. Concentrations that produced similar levels of burning sensation across subjects also produced similar (though lower) levels of bitter taste. These results are consistent with the hypothesis that capsaicin and its congeners stimulate bitterness via a common sensory receptor that is distributed differentially among individuals. Additionally, bitter tasters rated gustatory qualities (but not burning and stinging) slightly but significantly higher than did bitter non-tasters, which suggests that perception of capsaicin bitterness is associated with a higher overall taste responsiveness (but not chemesthetic responsiveness) in the CV region.  (+info)

Piperine enhances the bioavailability of the tea polyphenol (-)-epigallocatechin-3-gallate in mice. (8/270)

(-)-Epigallocatechin-3-gallate (EGCG), from green tea (Camellia sinensis), has demonstrated chemopreventive activity in animal models of carcinogenesis. Previously, we reported the bioavailability of EGCG in rats (1.6%) and mice (26.5%). Here, we report that cotreatment with a second dietary component, piperine (from black pepper), enhanced the bioavailability of EGCG in mice. Intragastric coadministration of 163.8 micromol/kg EGCG and 70.2 micromol/kg piperine to male CF-1 mice increased the plasma C(max) and area under the curve (AUC) by 1.3-fold compared to mice treated with EGCG only. Piperine appeared to increase EGCG bioavailability by inhibiting glucuronidation and gastrointestinal transit. Piperine (100 micromol/L) inhibited EGCG glucuronidation in mouse small intestine (by 40%) but not in hepatic microsomes. Piperine (20 micromol/L) also inhibited production of EGCG-3"-glucuronide in human HT-29 colon adenocarcinoma cells. Small intestinal EGCG levels in CF-1 mice following treatment with EGCG alone had a C(max) = 37.50 +/- 22.50 nmol/g at 60 min that then decreased to 5.14 +/- 1.65 nmol/g at 90 min; however, cotreatment with piperine resulted in a C(max) = 31.60 +/- 15.08 nmol/g at 90 min, and levels were maintained above 20 nmol/g until 180 min. This resulted in a significant increase in the small intestine EGCG AUC (4621.80 +/- 1958.72 vs. 1686.50 +/- 757.07 (nmol/g.min)). EGCG appearance in the colon and the feces of piperine-cotreated mice was slower than in mice treated with EGCG alone. The present study demonstrates the modulation of the EGCG bioavailablity by a second dietary component and illustrates a mechanism for interactions between dietary chemicals.  (+info)

Benzodioxoles are chemical compounds that consist of a benzene ring (a six-carbon cyclic structure with alternating double bonds) linked to two oxide groups through methane bridges. They can be found naturally in some plants, such as nutmeg and tea, but they are also synthesized for use in various pharmaceuticals and illicit drugs.

In the medical field, benzodioxoles are used in the synthesis of certain drugs, including some antimicrobials, antihelmintics (drugs that treat parasitic worm infections), and muscle relaxants. However, they are perhaps best known for their use as a structural component in certain illicit drugs, such as ecstasy (MDMA) and related substances.

It's important to note that while benzodioxoles themselves may have some medical uses, many of the drugs that contain this structure can be dangerous when used improperly or without medical supervision.

1960: Benzodioxoles-1,3 substitués, Bull. Soc. chim. Fr., 5e série, vol.27, Nr. 4, 1960, S. 638-642, mit B. Millet. 1961: ...
Yellow-green couplers include resorcinol, 4-chlororesorcinol, and benzodioxoles. These compounds produce broad-band absorption ...
v t e (Webarchive template wayback links, All stub articles, Botany stubs, Plant toxins, Benzodioxoles). ...
The 1,1-diaryl group is also present in derivatives such as the benzodioxoles and hydantoins. Acyclic analogs have also been ...
Benzodioxoles, Benzylisoquinoline alkaloids). ...
Benzodioxoles, Carboxamides). ...
Benzodioxoles, Entactogens and empathogens, Monitored short pages). ...
Benzodioxoles, Heterocyclic compounds with 6 rings). ...
Benzodioxoles, Carboxamides, Monoamine oxidase inhibitors, Cannabinoids, Endocannabinoid reuptake inhibitors). ...
Benzodioxoles, All stub articles, Psychoactive drug stubs). ...
Benzodioxoles, All stub articles, Psychoactive drug stubs). ...
Benzodioxoles, All stub articles, Psychoactive drug stubs). ...
Benzodioxoles, Entactogens and empathogens, Euphoriants, Psychedelic drugs, Serotonin-norepinephrine-dopamine releasing agents ...
Benzodioxoles, Carbamates, Furofurans, HIV protease inhibitors, Thiazoles, All stub articles, Antiinfective agent stubs). ...
Benzodioxoles, Phenol ethers, Lignans). ...
Benzodioxoles, All stub articles, Respiratory system drug stubs). ...
Benzodioxoles, 4-Morpholinyl compounds, All stub articles, Analgesic stubs). ...
Benzodioxoles, Allyl compounds, Pyrogallol ethers, Hydroxyquinol ethers, All stub articles, Aromatic compound stubs). ...
Benzodioxoles, All stub articles, Organic compound stubs). ...
Benzodioxoles, Serotonin receptor agonists). ...
Benzodioxoles, Entactogens and empathogens, Serotonin-norepinephrine releasing agents, Substances discovered in the 1990s). ...
Benzodioxoles, Serotonin-norepinephrine-dopamine releasing agents, Entactogens and empathogens). ...
Benzodioxoles, Cathinones, Norepinephrine-dopamine reuptake inhibitors, Pyrrolidinophenones, Euphoriants, Stimulants, Designer ...
Benzodioxoles, Serotonin releasing agents). ...
Benzodioxoles, Alkaloids). ...
Benzodioxoles, Cyclopropanes, All stub articles, Psychoactive drug stubs). ...
Benzodioxoles, Oxygen heterocycles, All stub articles, Alkaloid stubs). ...
Benzodioxoles: Phenethylamine: { Lophophine }. *Amphetamines: { 2-Methyl-MDA. *2,3-MDA. *3,4-MDA (tenamfetamine) ...
1960: Benzodioxoles-1,3 substitués, Bull. Soc. chim. Fr., 5e série, vol.27, Nr. 4, 1960, S. 638-642, mit B. Millet. 1961: ...
Benzodioxoles, Carboxamides, Monoamine oxidase inhibitors, Cannabinoids, Endocannabinoid reuptake inhibitors). ...
Benzodioxoles D3.438.115 D3.633.100.115 Benzoflavones D3.438.150.266.450.175 D3.633.100.150.266.450.175 Benzofurans D3.438.127 ...
Benzodioxoles: novel cannabinoid-1 receptor inverse agonists for the treatment of obesity. ... allowed the identification of benzodioxoles as a novel CB1R inverse agonist series. Extensive multidimensional optimization was ...
Benzodioxoles D3.438.115 D3.633.100.115 Benzoflavones D3.438.150.266.450.175 D3.633.100.150.266.450.175 Benzofurans D3.438.127 ...
Benzodioxoles / administration & dosage* Actions. * Search in PubMed * Search in MeSH * Add to Search ...
MeSH Terms: Aminophenols/pharmacokinetics*; Aminopyridines/pharmacokinetics; Benzodioxoles/pharmacokinetics; Bronchi/metabolism ...
Benzodioxoles / therapeutic use Actions. * Search in PubMed * Search in MeSH * Add to Search ...
Benzodioxoles D3.438.115 D3.633.100.115 Benzoflavones D3.438.150.266.450.175 D3.633.100.150.266.450.175 Benzofurans D3.438.127 ...
Benzodioxoles Preferred Term Term UI T636482. Date04/13/2005. LexicalTag NON. ThesaurusID NLM (2006). ... Benzodioxoles Preferred Concept UI. M0483258. Registry Number. 0. Scope Note. Compounds based on benzene fused to oxole. They ... Benzodioxoles. Tree Number(s). D03.383.246.118. D03.633.100.115. Unique ID. D052117. RDF Unique Identifier. http://id.nlm.nih. ...
Benzodioxoles Preferred Term Term UI T636482. Date04/13/2005. LexicalTag NON. ThesaurusID NLM (2006). ... Benzodioxoles Preferred Concept UI. M0483258. Registry Number. 0. Scope Note. Compounds based on benzene fused to oxole. They ... Benzodioxoles. Tree Number(s). D03.383.246.118. D03.633.100.115. Unique ID. D052117. RDF Unique Identifier. http://id.nlm.nih. ...
Benzodioxoles - Preferred Concept UI. M0483258. Scope note. Compounds based on benzene fused to oxole. They can be formed from ...
Benzocaine N0000008139 Benzocycloheptenes N0000007542 Benzodiazepines N0000007547 Benzodiazepinones N0000167113 Benzodioxoles ...
HN - 2006(1980); use BENZOATES 1977-1979 MH - Benzodioxoles UI - D052117 MN - D3.383.246.118 MN - D3.438.115 MS - Compounds ...
Mitra I, Roy K and Saha A (2009) QSAR of antilipid peroxidative activity of substituted benzodioxoles using chemometric tools, ...
Saracatinib as a metastasis inhibitor in metastatic castration-resistant prostate cancer: A University of Chicago Phase 2 Consortium and DOD/PCF Prostate Cancer Clinical Trials Consortium Study. Prostate. 2016 Feb 15; 76(3):286-93 ...
Background: Plaque rupture and acute atherothrombosis, resulting from continued progression of atherosclerotic plaques (APs), are major contributors to acute clinical events such as stroke or myocardial infarction. This article aimed to explore the gene signatures and potential molecular mechanisms in the progression and instability of APs and to identify novel biomarkers and interventional targets for AP rupture. Methods: The microarray data were downloaded from the Gene Expression Omnibus (GEO) database and grouped into discovery and validation cohorts. In the discovery cohort, Weighted Gene Co-Expression Network Analysis was performed for finding co-expression modules, and the Metascape database was used to perform functional enrichment analysis. Differential Expression Genes analysis subsequently was performed in the validation cohort for verification of the obtained results. Common genes were introduced into Metascape database for protein-protein interaction and functional enrichment ...
Benzodioxoles Benzoflavones Benzofurans Benzoic Acid Benzoin Benzolamide Benzomorphans Benzophenanthridines Benzophenoneidum ...

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