Home Amines 518-17-2
518-17-2,MFCD06407824
Catalog No.:AA00I96I

518-17-2 | Evodiamine

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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA00I96I
Chemical Name:
Evodiamine
CAS Number:
518-17-2
Molecular Formula:
C19H17N3O
Molecular Weight:
303.3578
MDL Number:
MFCD06407824
SMILES:
O=C1c2ccccc2N(C2N1CCc1c2[nH]c2c1cccc2)C
Properties
Properties
 
BP:
575.1°C at 760 mmHg  
Form:
Solid  
MP:
278°  
Refractive Index:
1.5900 (estimate)  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
495  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
XLogP3:
3.1  

Literature

Title: Evodiamine, a plant alkaloid, induces calcium/JNK-mediated autophagy and calcium/mitochondria-mediated apoptosis in human glioblastoma cells.

Journal: Chemico-biological interactions 20130905

Title: Berberine and evodiamine influence serotonin transporter (5-HTT) expression via the 5-HTT-linked polymorphic region.

Journal: The pharmacogenomics journal 20121001

Title: New tricks for an old natural product: discovery of highly potent evodiamine derivatives as novel antitumor agents by systemic structure-activity relationship analysis and biological evaluations.

Journal: Journal of medicinal chemistry 20120913

Title: Transdermal behaviors comparisons among Evodia rutaecarpa extracts with different purity of evodiamine and rutaecarpine and the effect of topical formulation in vivo.

Journal: Fitoterapia 20120701

Title: Evodiamine, a dual catalytic inhibitor of type I and II topoisomerases, exhibits enhanced inhibition against camptothecin resistant cells.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20120515

Title: Cytotoxic effect of evodiamine in SGC-7901 human gastric adenocarcinoma cells via simultaneous induction of apoptosis and autophagy.

Journal: Oncology reports 20120501

Title: Pharmacokinetic comparisons of rutaecarpine and evodiamine after oral administration of Wu-Chu-Yu extracts with different purities to rats.

Journal: Journal of ethnopharmacology 20120131

Title: Six alkaloids inhibit secretion of IL-1α, TXB(2), ET-1 and E-selectin in LPS-induced endothelial cells.

Journal: Immunological investigations 20120101

Title: Enhanced antitumor efficacy of gemcitabine by evodiamine on pancreatic cancer via regulating PI3K/Akt pathway.

Journal: International journal of biological sciences 20120101

Title: Simultaneous determination and pharmacokinetic analysis of seven alkaloids and two flavonoids from rat plasma by HPLC-DAD after oral administration of Wuzhuyu decoction.

Journal: Journal of Asian natural products research 20120101

Title: In vitro cellular uptake of evodiamine and rutaecarpine using a microemulsion.

Journal: International journal of nanomedicine 20120101

Title: A drug screening method based on the autophagy pathway and studies of the mechanism of evodiamine against influenza A virus.

Journal: PloS one 20120101

Title: Binding mode pediction of evodiamine within vanilloid receptor TRPV1.

Journal: International journal of molecular sciences 20120101

Title: Induction of apoptosis by evodiamine involves both activation of mitotic arrest and mitotic slippage.

Journal: Oncology reports 20111201

Title: Simultaneous determination of evodiamine and rutecarpine in rabbit plasma by LC-ESI-MS and its application to pharmacokinetics.

Journal: Die Pharmazie 20111201

Title: [Studies on pharmacokinetics of evodiamine and rutaecarpine in rats plasma after oral administration extracts of euodiae fructus].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20111201

Title: Molecular mechanisms of activation of endothelial nitric oxide synthase mediated by transient receptor potential vanilloid type 1.

Journal: Cardiovascular research 20110801

Title: Evodiamine inhibits 12-O-tetradecanoylphorbol-13-acetate-induced activator protein 1 transactivation and cell transformation in human hepatocytes.

Journal: Phytotherapy research : PTR 20110701

Title: Acid sphingomyelinase contributes to evodiamine-induced apoptosis in human gastric cancer SGC-7901 cells.

Journal: DNA and cell biology 20110601

Title: Inhibitory effects of Zuo-Jin-Wan and its alkaloidal ingredients on activator protein 1, nuclear factor-κB, and cellular transformation in HepG2 cells.

Journal: Fitoterapia 20110601

Title: [Determination of evodiamine and rutacarpine in zhuyu hewei zhitong capsules by HPLC].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20110401

Title: Evodiamine improves congnitive abilities in SAMP8 and APP(swe)/PS1(ΔE9) transgenic mouse models of Alzheimer's disease.

Journal: Acta pharmacologica Sinica 20110301

Title: [Optimization of a HPLC determination method for Evodia rutaecarpa].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20110201

Title: New strategies in the discovery of novel non-camptothecin topoisomerase I inhibitors.

Journal: Current medicinal chemistry 20110101

Title: Enhanced transdermal delivery of evodiamine and rutaecarpine using microemulsion.

Journal: International journal of nanomedicine 20110101

Title: [Synthesis, physicochemical and pharmacological properties of pentacyclic alkaloid-analogues].

Journal: Acta pharmaceutica Hungarica 20110101

Title: Optimization of extraction of evodiamine and rutaecarpine from fruit of Evodia rutaecarpa using modified supercritical CO(2).

Journal: Journal of chromatography. A 20101210

Title: Selection of evodiamine as a novel topoisomerase I inhibitor by structure-based virtual screening and hit optimization of evodiamine derivatives as antitumor agents.

Journal: Journal of medicinal chemistry 20101111

Title: Evodiamine as a novel antagonist of aryl hydrocarbon receptor.

Journal: Biochemical and biophysical research communications 20101105

Title: Evodiamine induces caspase-dependent apoptosis and S phase arrest in human colon lovo cells.

Journal: Anti-cancer drugs 20100901

Title: Anti-proliferative effects of evodiamine on human thyroid cancer cell line ARO.

Journal: Journal of cellular biochemistry 20100815

Title: Protein tyrosine kinase pathway-derived ROS/NO productions contribute to G2/M cell cycle arrest in evodiamine-treated human cervix carcinoma HeLa cells.

Journal: Free radical research 20100701

Title: A new quinolone and other constituents from the fruits of Tetradium ruticarpum: effects on neutrophil pro-inflammatory responses.

Journal: Chemistry & biodiversity 20100701

Title: Inhibitory effect and transcriptional impact of berberine and evodiamine on human white preadipocyte differentiation.

Journal: Fitoterapia 20100601

Title: Evodiamine-induced human melanoma A375-S2 cell death was mediated by PI3K/Akt/caspase and Fas-L/NF-kappaB signaling pathways and augmented by ubiquitin-proteasome inhibition.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20100401

Title: Inhibitory effect of evodiamine alone and in combination with rosiglitazone on in vitro adipocyte differentiation and in vivo obesity related to diabetes.

Journal: International journal of obesity (2005) 20100201

Title: Immobilizing topoisomerase I on a surface plasmon resonance biosensor chip to screen for inhibitors.

Journal: Journal of biomedical science 20100101

Title: Evodiamine inhibits adipogenesis via the EGFR-PKCalpha-ERK signaling pathway.

Journal: FEBS letters 20091119

Title: [Assay of evodin, evodiamine and rutaecarpine in Fructus Evodiae by QAMS].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20091101

Title: [Determination of evodiamine and rutaecarpine of compound Wuzhuyu cataplasm in plasma by SPE-HPLC: application to its pharmacokinetics].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20091101

Title: Effects of evodiamine and rutaecarpine on the secretion of corticosterone by zona fasciculata-reticularis cells in male rats.

Journal: Journal of cellular biochemistry 20091001

Title: Evodiamine represses hypoxia-induced inflammatory proteins expression and hypoxia-inducible factor 1alpha accumulation in RAW264.7.

Journal: Shock (Augusta, Ga.) 20090901

Title: Antiproliferation and apoptosis induced by evodiamine in human colorectal carcinoma cells (COLO-205).

Journal: Chemistry & biodiversity 20090601

Title: Evodiamine: a novel anti-cancer alkaloid from Evodia rutaecarpa.

Journal: Molecules (Basel, Switzerland) 20090518

Title: Evodiamine and rutaecarpine inhibit migration by LIGHT via suppression of NADPH oxidase activation.

Journal: Journal of cellular biochemistry 20090501

Title: [Study on vitro release and transdermal behaviors of Yulian cataplasm].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090401

Title: Evodiamine stabilizes topoisomerase I-DNA cleavable complex to inhibit topoisomerase I activity.

Journal: Molecules (Basel, Switzerland) 20090327

Title: Intragastric administration of evodiamine suppresses NPY and AgRP gene expression in the hypothalamus and decreases food intake in rats.

Journal: Brain research 20090109

Title: The permeability and the efflux of alkaloids of the Evodiae fructus in the Caco-2 model.

Journal: Phytotherapy research : PTR 20090101

Title: Enhancement of apoptosis of human hepatocellular carcinoma SMMC-7721 cells through synergy of berberine and evodiamine.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20081201

Title: Immunoregulatory effect of evodiamine in mice of various germlines.

Journal: Zhongguo shi yan xue ye xue za zhi 20080801

Title: Reactive oxygen species and nitric oxide regulate mitochondria-dependent apoptosis and autophagy in evodiamine-treated human cervix carcinoma HeLa cells.

Journal: Free radical research 20080501

Title: Evodiamine improves diet-induced obesity in a uncoupling protein-1-independent manner: involvement of antiadipogenic mechanism and extracellularly regulated kinase/mitogen-activated protein kinase signaling.

Journal: Endocrinology 20080101

Title: Nitric oxide activated by p38 and NF-kappaB facilitates apoptosis and cell cycle arrest under oxidative stress in evodiamine-treated human melanoma A375-S2 cells.

Journal: Free radical research 20080101

Title: Critical roles of reactive oxygen species in mitochondrial permeability transition in mediating evodiamine-induced human melanoma A375-S2 cell apoptosis.

Journal: Free radical research 20071001

Title: [Methodological studies on equivalent relationship between granule for clinical prescription and clinical decoction of fructus evodiae].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20070601

Title: Anti-proliferative effects of evodiamine on human prostate cancer cell lines DU145 and PC3.

Journal: Journal of cellular biochemistry 20070501

Title: Anti-inflammatory effects and mechanisms of the ethanol extract of Evodia rutaecarpa and its bioactive components on neutrophils and microglial cells.

Journal: European journal of pharmacology 20070126

Title: In vitro and in vivo antiallergic effect of the fructus of Evodia rutaecarpa and its constituents.

Journal: Biological & pharmaceutical bulletin 20070101

Title: Chemical and biological comparisons on Evodia with two related species of different locations and conditions.

Journal: Journal of ethnopharmacology 20061124

Title: Caspase-dependent and caspase-independent apoptosis induced by evodiamine in human leukemic U937 cells.

Journal: Molecular cancer therapeutics 20060901

Title: Determination of evodiamine and rutecarpine in human serum by liquid chromatography-tandem mass spectrometry.

Journal: Analytical and bioanalytical chemistry 20060701

Title: Evodiamine inhibits in vitro angiogenesis: Implication for antitumorgenicity.

Journal: Life sciences 20060404

Title: Anti-inflammatory principles from the fruits of Evodia rutaecarpa and their cellular action mechanisms.

Journal: Archives of pharmacal research 20060401

Title: Development and validation of HPLC methods for the analysis of phenethylamine and indoloquinazoline alkaloids in Evodia species.

Journal: Journal of separation science 20060301

Title: [Effect of protein kinase C on human melanoma A375-S2 cell death induced by evodiamine].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20051101

Title: Evodiamine induced human melanoma A375-S2 cell death partially through interleukin 1 mediated pathway.

Journal: Biological & pharmaceutical bulletin 20050601

Title: Antitumor mechanism of evodiamine, a constituent from Chinese herb Evodiae fructus, in human multiple-drug resistant breast cancer NCI/ADR-RES cells in vitro and in vivo.

Journal: Carcinogenesis 20050501

Title: Evodiamine abolishes constitutive and inducible NF-kappaB activation by inhibiting IkappaBalpha kinase activation, thereby suppressing NF-kappaB-regulated antiapoptotic and metastatic gene expression, up-regulating apoptosis, and inhibiting invasion.

Journal: The Journal of biological chemistry 20050429

Title: Roles of SIRT1 and phosphoinositide 3-OH kinase/protein kinase C pathways in evodiamine-induced human melanoma A375-S2 cell death.

Journal: Journal of pharmacological sciences 20050401

Title: Induction of mitotic arrest and apoptosis in human prostate cancer pc-3 cells by evodiamine.

Journal: The Journal of urology 20050101

Title: Protective effects of evodiamine on myocardial ischemia-reperfusion injury in rats.

Journal: Planta medica 20041201

Title: Evodiamine functions as an agonist for the vanilloid receptor TRPV1.

Journal: Organic & biomolecular chemistry 20040821

Title: [Studies on the chemical constituents of Evodia rutaecarpa (Juss.) Benth].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20040801

Title: Inhibitory effects of evodiamine on the growth of human prostate cancer cell line LNCaP.

Journal: International journal of cancer 20040710

Title: Induction of mitotic arrest and apoptosis by evodiamine in human leukemic T-lymphocytes.

Journal: Life sciences 20040521

Title: Inhibition by evodiamine of hepatocyte growth factor-induced invasion and migration of tumor cells.

Journal: Biological & pharmaceutical bulletin 20040401

Title: Atypical apoptosis in L929 cells induced by evodiamine isolated from Evodia rutaecarpa.

Journal: Journal of Asian natural products research 20040301

Title: Evodiamine induces tumor cell death through different pathways: apoptosis and necrosis.

Journal: Acta pharmacologica Sinica 20040101

Title: Intracellular regulation of evodiamine-induced A375-S2 cell death.

Journal: Biological & pharmaceutical bulletin 20031101

Title: [Evodiamine induces A375-S2 cell death through two different pathways].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20030901

Title: The nociceptive and anti-nociceptive effects of evodiamine from fruits of Evodia rutaecarpa in mice.

Journal: Planta medica 20030501

Title: [Advances in pharmacological study of Evodia rutaecarpa and its effective constituents].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20030401

Title: Protective effects of calcitonin gene-related peptide-mediated evodiamine on guinea-pig cardiac anaphylaxis.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20030301

Title: Evodiamine, a constituent of Evodiae Fructus, induces anti-proliferating effects in tumor cells.

Journal: Cancer science 20030101

Title: Effects of evodiamine on gastrointestinal motility in male rats.

Journal: European journal of pharmacology 20021220

Title: Anti-invasive and metastatic activities of evodiamine.

Journal: Biological & pharmaceutical bulletin 20021101

Title: [Studies on evodiamine induced HeLa cell apoptosis].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20020901

Title: Modulation of drug-metabolizing enzymes by extracts of a herbal medicine Evodia rutaecarpa in C57BL/6J mice.

Journal: Life sciences 20020802

Title: Pharmacological profile of evodiamine in isolated rabbit corpus cavernosum.

Journal: European journal of pharmacology 20020620

Title: The alkaloid rutaecarpine is a selective inhibitor of cytochrome P450 1A in mouse and human liver microsomes.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20020301

Title: [Determination of evodiamine and rutaecarpine in Evodia rutaecarpa (Juss.) Benth after compatibility with Coptis chinensis Franch].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20011201

Title: Capsaicin-like anti-obese activities of evodiamine from fruits of Evodia rutaecarpa, a vanilloid receptor agonist.

Journal: Planta medica 20011001

Title: Inhibitory effects of evodiamine on in vitro invasion and experimental lung metastasis of murine colon cancer cells.

Journal: Biological & pharmaceutical bulletin 20010801

Title: Inhibitory effect of evodiamine on aldosterone release by Zona glomerulosa cells in male rats.

Journal: The Chinese journal of physiology 20010630

Title: The positive inotropic and chronotropic effects of evodiamine and rutaecarpine, indoloquinazoline alkaloids isolated from the fruits of Evodia rutaecarpa, on the guinea-pig isolated right atria: possible involvement of vanilloid receptors.

Journal: Planta medica 20010401

Title: Wang S, et al. Scaffold Diversity Inspired by the Natural Product Evodiamine: Discovery of Highly Potent and Multitargeting Antitumor Agents. J Med Chem. 2015 Aug 27;58(16):6678-96.

Title: Li RF,et al. Effects of Evodiamine on the Pharmacokinetics of Dapoxetine and Its Metabolite Desmethyl Dapoxetine inRats. Pharmacology. 2016;97(1-2):43-7.

Title: Shi L, et al. Evodiamine exerts anti-tumor effects against hepatocellular carcinoma through inhibiting β-catenin-mediated angiogenesis. Tumour Biol. 2016 Sep;37(9):12791-12803.

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