Summary: Propiophenone (ethyl phenyl ketone, structural formula C6H5COCH2CH3) and its derivatives. They are commonly used in perfumes and pharmaceuticals.

Top Publications

  1. Matsunaga M, Uemura Y, Yonemoto Y, Kanai K, Etoh H, Tanaka S, et al. Long-lasting muscle relaxant activity of eperisone hydrochloride after percutaneous administration in rats. Jpn J Pharmacol. 1997;73:215-20 pubmed
    ..These results suggest that percutaneously administered eperisone is absorbed efficiently and shows potent and long-lasting muscle relaxant activity. ..
  2. Natarajan P, Katta S, Andrei I, Babu Rao Ambati V, Leonida M, Haas G. Positive antibacterial co-action between hop (Humulus lupulus) constituents and selected antibiotics. Phytomedicine. 2008;15:194-201 pubmed
    ..Ideas for other practical applications of this effect are put forth. The mechanism of the synergistic effect is briefly discussed but no attempt was made to prove it experimentally...
  3. Lee S, Kim H, Lee J, Lee I, Kang B. Inhibition of topoisomerase I activity and efflux drug transporters' expression by xanthohumol. from hops. Arch Pharm Res. 2007;30:1435-9 pubmed
  4. Ueno T, Kawana S. [A case of eperisone hydrochloride (myonal)--induced drug eruption leading to erythema and angioedema]. Arerugi. 2007;56:709-13 pubmed
    ..Some cases took several hours to exhibit symptoms even for urticaria/anaphylaxis types that were confirmed to induce an immediate allergic reaction. ..
  5. Yamaguchi N, Satoh Yamaguchi K, Ono M. In vitro evaluation of antibacterial, anticollagenase, and antioxidant activities of hop components (Humulus lupulus) addressing acne vulgaris. Phytomedicine. 2009;16:369-76 pubmed publisher
    ..Xanthohumol showed the highest activity in total oxygen radical absorbance capacity as well as singlet oxygen absorbance capacity. ..
  6. Gerhauser C. Broad spectrum anti-infective potential of xanthohumol from hop (Humulus lupulus L.) in comparison with activities of other hop constituents and xanthohumol metabolites. Mol Nutr Food Res. 2005;49:827-31 pubmed
    ..Overall, these activities further contribute to the broad spectrum of biological effects observed with XN. ..
  7. Belhadj Tahar H, Sadeg N. Methcathinone: a new postindustrial drug. Forensic Sci Int. 2005;153:99-101 pubmed
  8. Sakai K, Koyama N, Fukuda T, Mori Y, Onaka H, Tomoda H. Search method for inhibitors of Staphyloxanthin production by methicillin-resistant Staphylococcus aureus. Biol Pharm Bull. 2012;35:48-53 pubmed
    ..These results suggested that this screening method is useful and effective to find compounds targeting staphyloxanthin production, leading to a new type of chemotherapeutics against MRSA infection. ..
  9. Woodward J, Foster T, Salaoru A, Vink C. Direct observation of f-pair magnetic field effects and time-dependence of radical pair composition using rapidly switched magnetic fields and time-resolved infrared methods. Phys Chem Chem Phys. 2008;10:4020-6 pubmed publisher

More Information


  1. Cho Y, You S, Kim H, Cho C, Lee I, Kang B. Xanthohumol inhibits IL-12 production and reduces chronic allergic contact dermatitis. Int Immunopharmacol. 2010;10:556-61 pubmed publisher
    ..XN treatment reduced the degree of ear thickening induced by oxazolone. Taken together, XN might be effective as an anti-inflammatory agent to reduce skin inflammation by inhibiting IL-12 production. ..
  2. Stevens J, Page J. Xanthohumol and related prenylflavonoids from hops and beer: to your good health!. Phytochemistry. 2004;65:1317-30 pubmed
    ..The prenylflavonoid pathway is a possible target for breeding or biotechnological modification of hops with the aim of increasing xanthohumol levels for beer brewing and 8-prenylnaringenin levels for pharmaceutical production...
  3. Golden R, De Vane C, Laizure S, Rudorfer M, Sherer M, Potter W. Bupropion in depression. II. The role of metabolites in clinical outcome. Arch Gen Psychiatry. 1988;45:145-9 pubmed
    ..Alternatively, a curvilinear dose-response relationship may exist for bupropion metabolites. Future studies should explore the clinical utility of plasma metabolite measurements in enhancing the efficacy of treatment with bupropion. ..
  4. Wang Y, Chen Y, Wang J, Chen J, Aggarwal B, Pang X, et al. Xanthohumol, a prenylated chalcone derived from hops, suppresses cancer cell invasion through inhibiting the expression of CXCR4 chemokine receptor. Curr Mol Med. 2012;12:153-62 pubmed
    ..Together, our results suggested that XN, as a novel inhibitor of CXCR4, could be a promising therapeutic agent contributed to cancer treatment. ..
  5. Wolff H, Motyl M, Hellerbrand C, Heilmann J, Kraus B. Xanthohumol uptake and intracellular kinetics in hepatocytes, hepatic stellate cells, and intestinal cells. J Agric Food Chem. 2011;59:12893-901 pubmed publisher
    ..Fluorescence recovery after photobleaching experiments revealed that most XN molecules are bound to cellular proteins, which may alter properties of cellular factors. ..
  6. Boulanger Gobeil C, St Onge M, Laliberté M, Auger P. Seizures and hyponatremia related to ethcathinone and methylone poisoning. J Med Toxicol. 2012;8:59-61 pubmed publisher
    ..Clinicians must report future cases of toxicity related to the use of cathinone synthetic derivatives in order to increase our knowledge of these substances. ..
  7. Chang Y, Lin T, Lu C, Huang S, Wang Y, Wang S. Xanthohumol-induced presynaptic reduction of glutamate release in the rat hippocampus. Food Funct. 2016;7:212-26 pubmed publisher
  8. Wunderlich S, Zürcher A, Back W. Enrichment of xanthohumol in the brewing process. Mol Nutr Food Res. 2005;49:874-81 pubmed
    ..Results obtained led to a brewing technology that produced on an industrial scale pale wheat beer with more than 1 mg XN/L. ..
  9. Dietz B, Kang Y, Liu G, Eggler A, Yao P, Chadwick L, et al. Xanthohumol isolated from Humulus lupulus Inhibits menadione-induced DNA damage through induction of quinone reductase. Chem Res Toxicol. 2005;18:1296-305 pubmed
    ..This suggests that XH induces QR by covalently modifying the Keap1 protein. Therefore, XH and hops dietary supplements might function as chemopreventive agents, through induction of detoxification enzymes such as QR...
  10. Tronina T, Bartmańska A, Popłoński J, Huszcza E. Transformation of xanthohumol by Aspergillus ochraceus. J Basic Microbiol. 2014;54:66-71 pubmed publisher
    ..The major biotransformation product, was 8.6-fold stronger antioxidant than xanthohumol and 2.3-fold than ascorbic acid. ..
  11. Beyer J, Peters F, Kraemer T, Maurer H. Detection and validated quantification of nine herbal phenalkylamines and methcathinone in human blood plasma by LC-MS/MS with electrospray ionization. J Mass Spectrom. 2007;42:150-60 pubmed
    ..The presented LC-MS/MS assay was found applicable for sensitive detection and accurate and precise quantification of all studied analytes in plasma. ..
  12. Stevens J, Taylor A, Deinzer M. Quantitative analysis of xanthohumol and related prenylflavonoids in hops and beer by liquid chromatography-tandem mass spectrometry. J Chromatogr A. 1999;832:97-107 pubmed
    ..Thirteen commercial beers were analysed with the method. Isoxanthohumol, formed by isomerization of xanthohumol during the brewing process, was the most abundant flavonoid in hopped beers, ranging from 0.04 to 3.44 mg/l. ..
  13. Zmora P, Cieslak A, Jędrejek D, Stochmal A, Pers Kamczyc E, Oleszek W, et al. Preliminary in vitro study on the effect of xanthohumol on rumen methanogenesis. Arch Anim Nutr. 2012;66:66-71 pubmed
    ..However, the practical utility of this supplement needs further investigation under long-term in vivo conditions. ..
  14. Liau A, Liu J, Lin L, Chiu Y, Shu Y, Tsai C, et al. Optimization of a simple method for the chiral separation of methamphetamine and related compounds in clandestine tablets and urine samples by beta-cyclodextrine modified capillary electrophoresis: a complementary method to GC-MS. Forensic Sci Int. 2003;134:17-24 pubmed
    ..The method, as described herein, represents a good complementary method to GC-MS for use in forensic and clinical analysis. ..
  15. Drenzek J, Seiler N, Jaskula Sztul R, Rausch M, Rose S. Xanthohumol decreases Notch1 expression and cell growth by cell cycle arrest and induction of apoptosis in epithelial ovarian cancer cell lines. Gynecol Oncol. 2011;122:396-401 pubmed publisher
    ..These findings suggest that xanthohumol could be useful as a therapeutic agent in ovarian cancer. ..
  16. Possemiers S, Heyerick A, Robbens V, De Keukeleire D, Verstraete W. Activation of proestrogens from hops (Humulus lupulus L.) by intestinal microbiota; conversion of isoxanthohumol into 8-prenylnaringenin. J Agric Food Chem. 2005;53:6281-8 pubmed
  17. Suyama J, Sakloth F, Kolanos R, Glennon R, Lazenka M, Negus S, et al. Abuse-Related Neurochemical Effects of Para-Substituted Methcathinone Analogs in Rats: Microdialysis Studies of Nucleus Accumbens Dopamine and Serotonin. J Pharmacol Exp Ther. 2016;356:182-90 pubmed publisher
    ..03). These results support a relationship between these molecular, neurochemical, and behavioral measures and support a role for molecular structure as a determinant of abuse-related neurochemical and behavioral effects of MCAT analogs. ..
  18. Choi J, Kim H, Lee K, Choi H, Lee I, Kang B. Increased IL-2 production in T cells by xanthohumol through enhanced NF-AT and AP-1 activity. Int Immunopharmacol. 2009;9:103-7 pubmed publisher
    ..These results suggest that XN increased IL-2 production at the transcriptional levels via the up-regulation of NF-AT and AP-1 in PMA/Io-activated EL-4 T cells. ..
  19. Plazar J, Filipic M, Groothuis G. Antigenotoxic effect of Xanthohumol in rat liver slices. Toxicol In Vitro. 2008;22:318-27 pubmed
    ..Although the mechanism of the protective effect of XN is unclear, our results indicate that XN exhibits antigenotoxic effects in fresh liver tissue and provide additional evidence for the cancer preventive potential of XN. ..
  20. Legette L, Ma L, Reed R, Miranda C, Christensen J, Rodriguez Proteau R, et al. Pharmacokinetics of xanthohumol and metabolites in rats after oral and intravenous administration. Mol Nutr Food Res. 2012;56:466-74 pubmed publisher
    ..15±0.01?mg/L and 2.49±0.10?h* ?mg/L in the oral high group. The bioavailability of XN is dose-dependent and approximately 0.33, 0.13, and 0.11 in rats, for the low-, medium-, and high-dose groups, respectively. ..
  21. Soares R, Azevedo I. Inhibition of S1P by polyphenols prevents inflammation and angiogenesis: NFkappaB, a downstream effector?. Free Radic Biol Med. 2007;42:311 pubmed
  22. Kang J, Jung J, Kim H, Lim H, Jang S, Oh S. Neuroprotective effect of benzylideneacetophenone derivative on the MPTP model of neurodegeneration in mice. Arch Pharm Res. 2008;31:1098-107 pubmed publisher
    ..These results suggest that JC3 can be a neuroprotective agent in an MPTP-induced model of PD. ..
  23. Wikström M, Thelander G, Nyström I, Kronstrand R. Two fatal intoxications with the new designer drug methedrone (4-methoxymethcathinone). J Anal Toxicol. 2010;34:594-8 pubmed
    ..This suggests a rather narrow "therapeutic" window and emphasizes the danger in taking this kind of drug for recreational purposes. ..
  24. Cho Y, Kim H, Kim Y, Lee K, Choi H, Lee I, et al. Differential anti-inflammatory pathway by xanthohumol in IFN-gamma and LPS-activated macrophages. Int Immunopharmacol. 2008;8:567-73 pubmed publisher
    ..7 cells, the binding activity of STAT-1alpha and IRF-1 was inhibited by XN. This suggests that differential signaling pathways are used by XN for the inhibition of excess inflammatory mediators depending on the stimuli in macrophages. ..
  25. Nagel J, Culley L, Lu Y, Liu E, Matthews P, Stevens J, et al. EST analysis of hop glandular trichomes identifies an O-methyltransferase that catalyzes the biosynthesis of xanthohumol. Plant Cell. 2008;20:186-200 pubmed publisher
    ..OMT3 was inactive with all substrates tested. The lupulin gland-specific EST data set expands the genomic resources for H. lupulus and provides further insight into the metabolic specialization of glandular trichomes...
  26. Yang Z, Jiang M, Li F, Xu K, Tan G. [Studies on the chemical constituents from Asarum Chinese Franch. f. fargesii (Franch.) C. Y. Cheng (II)]. Zhong Yao Cai. 2006;29:130-2 pubmed
    ..The compound II and III were isolated from the genus of Asarum for the first time. ..
  27. Colgate E, Miranda C, Stevens J, Bray T, Ho E. Xanthohumol, a prenylflavonoid derived from hops induces apoptosis and inhibits NF-kappaB activation in prostate epithelial cells. Cancer Lett. 2007;246:201-9 pubmed
  28. Blanquer Rosselló M, Oliver J, Valle A, Roca P. Effect of xanthohumol and 8-prenylnaringenin on MCF-7 breast cancer cells oxidative stress and mitochondrial complexes expression. J Cell Biochem. 2013;114:2785-94 pubmed publisher
    ..These results suggest that XN in low dose (0.01 µM) and 8PN at all assayed doses (0.001-20 µM) presumably improve mitochondrial function, whereas a high dose of XN (5 µM) worsens the functionality of this organelle. ..
  29. Huszcza E, Bartmańska A, Tronina T. Glycosylation of xanthohumol by fungi. Z Naturforsch C. 2008;63:557-60 pubmed
    ..One of them, Beauveria bassiana AM278, converted xanthohumol into a glucosylated derivative. This product was identified as xanthohumol 4'-O-beta-D-4'''-methoxyglucopyranoside. ..
  30. Taur J, Rodriguez Proteau R. Effects of dietary flavonoids on the transport of cimetidine via P-glycoprotein and cationic transporters in Caco-2 and LLC-PK1 cell models. Xenobiotica. 2008;38:1536-50 pubmed publisher
    ..These results suggest that flavonoids may have potential to alter the disposition profile of cimetidine and possibly other therapeutics that are mediated by P-gp and/or cation transport systems. ..
  31. Sikk K, Taba P, Haldre S, Bergquist J, Nyholm D, Zjablov G, et al. Irreversible motor impairment in young addicts--ephedrone, manganism or both?. Acta Neurol Scand. 2007;115:385-9 pubmed
    ..Parkinsonian syndrome related to intravenous use of a "designer" psychostimulant, derived from pseudoephedrine using potassium permanganate as the oxidant, has been observed in drug addicts in Estonia...
  32. Mendes V, Monteiro R, Pestana D, Teixeira D, Calhau C, Azevedo I. Xanthohumol influences preadipocyte differentiation: implication of antiproliferative and apoptotic effects. J Agric Food Chem. 2008;56:11631-7 pubmed publisher
    ..Results suggest that XN may reduce adipocyte number, contributing to adipocyte hypertrophy. Taking into consideration the consequences of adipocyte hypertrophy, XN does not seem to improve the metabolic profile associated with obesity. ..
  33. Dorn C, Massinger S, Wuzik A, Heilmann J, Hellerbrand C. Xanthohumol suppresses inflammatory response to warm ischemia-reperfusion induced liver injury. Exp Mol Pathol. 2013;94:10-6 pubmed publisher
    ..In conclusion, these data indicate the potential of xanthohumol application to prevent adverse inflammatory responses to I/R-induced liver damage such as after surgical liver resection or transplantation. ..
  34. Cheng W, Zhu C, Xu W, Fan X, Yang Y, Li Y, et al. Phenylpropene diglycosides from the bark of Machilus wangchiana. J Asian Nat Prod Res. 2012;14:1046-53 pubmed publisher
    ..Their structures were determined by spectroscopic and chemical methods. In the preliminary assay, compounds 2 and 5-8 reduced dl-galactosamine (GalN)-induced hepatocyte (WB-F344 cells) damage with 37-41% inhibitions at 10 ?M...
  35. Paul B, Cole K. Cathinone (Khat) and methcathinone (CAT) in urine specimens: a gas chromatographic-mass spectrometric detection procedure. J Anal Toxicol. 2001;25:525-30 pubmed
  36. Formaker B, Mott A, Frank M. The effects of topical anesthesia on oral burning in burning mouth syndrome. Ann N Y Acad Sci. 1998;855:776-80 pubmed
    ..001) after anesthesia, suggesting BMS dysgeusia is related to the activation of peripheral taste mechanisms. The results also suggest that BMS oral burning may be a disorder of peripheral pain pathways in some patients. ..
  37. Wainwright C, Parratt J. Alifedrine, a positive inotropic agent that moderately reduces the severity of ischaemia and reperfusion-induced ventricular arrhythmias. Eur J Pharmacol. 1988;147:373-80 pubmed
    ..These results suggest that alifedrine has an unusual and useful spectrum of pharmacological activity in that it combines antiarrhythmic activity with an ability to improve cardiac function...
  38. Metzenauer P, Dedecke R, Gobel H, Martorana P, Stroman F, Szelenyi I. Effects of the novel beta-adrenergic partial agonist alifedrine on cardiac performance in dogs with acute ischemic left ventricular failure. J Cardiovasc Pharmacol. 1989;14:103-8 pubmed
    ..Thus, alifedrine in this model markedly improved left ventricular function by balanced stimulation of the myocardium and reduction of pre- and afterload...
  39. Wang C, Bavcon Kralj M, Kosmrlj B, Yao J, Košenina S, Polyakova O, et al. Stability and removal of selected avobenzone's chlorination products. Chemosphere. 2017;182:238-244 pubmed publisher
    ..On the basis of the formation of various stable degradation products, including substituted acetophenones, benzoic acids and phenols, identified by GC-MS, the degradation pathway has been proposed. ..
  40. Viegas O, Zegura B, Pezdric M, Novak M, Ferreira I, Pinho O, et al. Protective effects of xanthohumol against the genotoxicity of heterocyclic aromatic amines MeIQx and PhIP in bacteria and in human hepatoma (HepG2) cells. Food Chem Toxicol. 2012;50:949-55 pubmed publisher
    ..Our findings confirm the evidence that XN displays strong chemopreventive effects against genotoxicity of HAAs, and provides additional mechanistic information to assess its potential chemopreventive efficiency in humans. ..
  41. Gatica Arias A, Farag M, Stanke M, Matousek J, Wessjohann L, Weber G. Flavonoid production in transgenic hop (Humulus lupulus L.) altered by PAP1/MYB75 from Arabidopsis thaliana L. Plant Cell Rep. 2012;31:111-9 pubmed publisher
    ..Chemical analysis revealed higher levels of anthocyanins, rutin, isoquercitin, kaempferol-glucoside, kaempferol-glucoside-malonate, desmethylxanthohumol, xanthohumol, ?-acids and ?-acids in transgenic plants compared to wild-type plants...
  42. Araujo J, Goncalves P, Martel F. Chemopreventive effect of dietary polyphenols in colorectal cancer cell lines. Nutr Res. 2011;31:77-87 pubmed publisher
    ..Thus, caution is mandatory when attempting to extrapolate the observations obtained in CRC cell line studies to humans. ..
  43. Buckwold V, Wilson R, Nalca A, Beer B, Voss T, Turpin J, et al. Antiviral activity of hop constituents against a series of DNA and RNA viruses. Antiviral Res. 2004;61:57-62 pubmed
    ..These hop constituents might serve as interesting lead compounds from which more active anti-HCV, anti-Rhino and anti-herpesvirus antiviral agents could be synthesized. ..
  44. Hughes T, Marton M, Jones A, Roberts C, Stoughton R, Armour C, et al. Functional discovery via a compendium of expression profiles. Cell. 2000;102:109-26 pubmed
    ..We also show that the compendium can be used to characterize pharmacological perturbations by identifying a novel target of the commonly used drug dyclonine. ..
  45. Brandt S, Daley P, Cozzi N. Analytical characterization of three trifluoromethyl-substituted methcathinone isomers. Drug Test Anal. 2012;4:525-9 pubmed publisher
  46. Dhooghe L, Naessens T, Heyerick A, De Keukeleire D, Vlietinck A, Pieters L, et al. Quantification of xanthohumol, isoxanthohumol, 8-prenylnaringenin, and 6-prenylnaringenin in hop extracts and derived capsules using secondary standards. Talanta. 2010;83:448-56 pubmed publisher
  47. Wei X, Ding L, Gao J, Li J, Zhang S, Shen J, et al. [Pharmacokinetics and bioequivalence of eperisone hydrochloride tablet in healthy subjects]. Yao Xue Xue Bao. 2004;39:309-11 pubmed
    ..The relative bioavalability of the test tablet was (101 +/- 13)%. The assay was proved to be sensitive, accurate and convenient. The two formulations were bioequivalent. ..
  48. Hanson K, Clegg R. Bioconvertible vitamin antioxidants improve sunscreen photoprotection against UV-induced reactive oxygen species. J Cosmet Sci. 2003;54:589-98 pubmed
    ..The bioconversion forms an antioxidant reservoir that deactivates the ROS generated (within the strata granulosum, spinosum, and basale) by the UV photons that the sunscreens do not block in the stratum corneum. ..
  49. Eshleman A, Wolfrum K, Hatfield M, Johnson R, Murphy K, Janowsky A. Substituted methcathinones differ in transporter and receptor interactions. Biochem Pharmacol. 2013;85:1803-15 pubmed publisher
    ..Thus, direct interactions with hVMAT2 and serotonin, dopamine, and hSigma1 receptors may not explain psychoactive effects. The primary mechanisms of action may be as inhibitors or substrates of DAT, SERT and NET. ..
  50. Binder R, Machata G, Stead H. [Analysis of potassium permanganate as addictive drug "precursor"]. Arch Kriminol. 2003;211:160-5 pubmed
    ..Nevertheless it seems necessary to analyze all seized samples for impurities and to establish a table of "impurity profiling" in the future in order to receive more information and to find correlations in selected cases. ..
  51. Zsila F, Hollosi M, Gergely A. Stereochemical study of tolperisone, a muscle relaxant agent, by circular dichroism and ultraviolet spectroscopy. Chirality. 2000;12:720-6 pubmed
    ..The chirality rule proposed by Snatzke for nonplanar benzoyl chromophores predicts the absolute configuration of (-)-tolperisone hydrochloride to be R, in agreement with other alpha-methyl-beta-amino-ketones. ..
  52. Pokrajac M, Miljkovic B, Misailović B. Mass spectrometric investigation of 2-aminopropiophenones and some of their metabolites. Rapid Commun Mass Spectrom. 1991;5:59-61 pubmed
  53. Cermak P, Olsovska J, Mikyška A, Dušek M, Kadleckova Z, Vanicek J, et al. Strong antimicrobial activity of xanthohumol and other derivatives from hops (Humulus lupulus L.) on gut anaerobic bacteria. APMIS. 2017;125:1033-1038 pubmed publisher
    ..Our study, thus, shows a potential of purified hop compounds, especially xanthohumol, as alternatives for treatment of infections caused by select anaerobic bacteria, namely nosocomial diarrhoea caused by resistant strains. ..