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115-53-7 | Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9α,13α,14α)-
CAS No: 115-53-7 Catalog No: AG000FKR MDL No:MFCD00134303
Product Description
Catalog Number:
AG000FKR
Chemical Name:
Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9α,13α,14α)-
CAS Number:
115-53-7
Molecular Formula:
C19H23NO4
Molecular Weight:
329.3902
MDL Number:
MFCD00134303
IUPAC Name:
(1R,9S,10S)-3-hydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one
InChI:
InChI=1S/C19H23NO4/c1-20-7-6-19-10-14(21)16(24-3)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9,12-13,22H,6-8,10H2,1-3H3/t12-,13+,19-/m1/s1
InChI Key:
INYYVPJSBIVGPH-QHRIQVFBSA-N
SMILES:
COC1=C[C@@H]2[C@@H]3Cc4c([C@@]2(CC1=O)CCN3C)c(O)c(cc4)OC
EC Number:
204-094-6
UNII:
63LT81K70N
Properties
Complexity:
562
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
3
Defined Bond Stereocenter Count:
0
Exact Mass:
329.163g/mol
Formal Charge:
0
Heavy Atom Count:
24
Hydrogen Bond Acceptor Count:
5
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
329.396g/mol
Monoisotopic Mass:
329.163g/mol
Rotatable Bond Count:
2
Topological Polar Surface Area:
59A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.2
Literature
| Title | Journal |
|---|---|
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| Gastrodin inhibits cell proliferation in vascular smooth muscle cells and attenuates neointima formation in vivo. | International journal of molecular medicine 20121101 |
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| Effects of alkaloid sinomenine on levels of IFN-γ, IL-1β, TNF-α and IL-6 in a rat renal allograft model. | Immunotherapy 20120801 |
| Tissue-specific metabolite profiling of alkaloids in Sinomenii Caulis using laser microdissection and liquid chromatography-quadrupole/time of flight-mass spectrometry. | Journal of chromatography. A 20120727 |
| Sinomenine can prolong high-risk corneal graft survival in a rat model. | Immunotherapy 20120601 |
| Activation of PI3K/Akt and ERK signaling pathways antagonized sinomenine-induced lung cancer cell apoptosis. | Molecular medicine reports 20120501 |
| Synthesis and biological evaluation of novel sinomenine derivatives as anti-inflammatory agents. | European journal of medicinal chemistry 20120401 |
| Determination of sinomenine sustained-release capsules in healthy Chinese volunteers by liquid chromatography-tandem mass spectrometry. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120315 |
| Six alkaloids inhibit secretion of IL-1α, TXB(2), ET-1 and E-selectin in LPS-induced endothelial cells. | Immunological investigations 20120101 |
| Effect of the Japanese herbal medicine, Boiogito, on the osteoarthritis of the knee with joint effusion. | Sports medicine, arthroscopy, rehabilitation, therapy & technology : SMARTT 20120101 |
| Naloxone inhibits immune cell function by suppressing superoxide production through a direct interaction with gp91phox subunit of NADPH oxidase. | Journal of neuroinflammation 20120101 |
| Inhibitory Effect of Curcumol on Jak2-STAT Signal Pathway Molecules of Fibroblast-Like Synoviocytes in Patients with Rheumatoid Arthritis. | Evidence-based complementary and alternative medicine : eCAM 20120101 |
| A nonpolar blueberry fraction blunts NADPH oxidase activation in neuronal cells exposed to tumor necrosis factor-α. | Oxidative medicine and cellular longevity 20120101 |
| Oxidative stress and microglial cells in Parkinson's disease. | Mediators of inflammation 20120101 |
| Reactive oxygen species and inhibitors of inflammatory enzymes, NADPH oxidase, and iNOS in experimental models of Parkinson's disease. | Mediators of inflammation 20120101 |
| Protective effects of sinomenine against doxorubicin-induced nephrosis in rats. | Journal of Asian natural products research 20120101 |
| Preparation and in vitro evaluation of tacrolimus-loaded ethosomes. | TheScientificWorldJournal 20120101 |
| Sinomenine reduces invasion and migration ability in fibroblast-like synoviocytes cells co-cultured with activated human monocytic THP-1 cells by inhibiting the expression of MMP-2, MMP-9, CD147. | Rheumatology international 20111101 |
| Sinomenine protects against ischaemic brain injury: involvement of co-inhibition of acid-sensing ion channel 1a and L-type calcium channels. | British journal of pharmacology 20111101 |
| (7R,8S,9S,12S)-1-Benz-yloxy-13,14-didehydro-12-hy-droxy-2,13-dimeth-oxy-N-methyl-morphinane. | Acta crystallographica. Section E, Structure reports online 20111001 |
| Anti-inflammatory activities of Chinese herbal medicine sinomenine and Liang Miao San on tumor necrosis factor-α-activated human fibroblast-like synoviocytes in rheumatoid arthritis. | Journal of ethnopharmacology 20110901 |
| (7R,8S,9S,12S)-1-(4-Chloro-benz-yloxy)-13,14-didehydro-12-hy-droxy-2,13-dimeth-oxy-N-methyl-morphinane. | Acta crystallographica. Section E, Structure reports online 20110901 |
| (9S,13R,14S)-7,8-Didehydro-4-(4-fluoro-benz-yloxy)-3,7-dimeth-oxy-17-methyl-morphinan-6-one sesquihydrate. | Acta crystallographica. Section E, Structure reports online 20110801 |
| Anti-allergic effects of sinomenine by inhibition of prostaglandin D₂ and leukotriene C₄ in mouse bone marrow-derived mast cells. | Immunopharmacology and immunotoxicology 20110601 |
| Two new morphinane alkaloids from Sinomenium acutum. | Journal of Asian natural products research 20110601 |
| Synthesis and biological evaluation of unique stereodimers of sinomenine analogues as potential inhibitors of NO production. | Bioorganic & medicinal chemistry 20110515 |
| (8S,9S,10R)-4-(4-Chloro-benz-yloxy)-7,8-didehydro-3,7-dimeth-oxy-17-methyl-morphinan-6-one monohydrate. | Acta crystallographica. Section E, Structure reports online 20110501 |
| Immunosuppressive and anti-inflammatory activities of sinomenine. | International immunopharmacology 20110301 |
| Immunomodulation of Autoimmune Arthritis by Herbal CAM. | Evidence-based complementary and alternative medicine : eCAM 20110101 |
| Network target for screening synergistic drug combinations with application to traditional Chinese medicine. | BMC systems biology 20110101 |
| Sinomenine inhibits microglial activation by Aβ and confers neuroprotection. | Journal of neuroinflammation 20110101 |
| HPLC and LC-MS analysis of sinomenine and its application in pharmacokinetic studies in rats. | Acta pharmacologica Sinica 20101101 |
| (9S,13R,14S)-7,8-Didehydro-4-(4-iodo-benz-yloxy)-3,7-dimeth-oxy-17-methyl-morphinan-6-one monohydrate. | Acta crystallographica. Section E, Structure reports online 20101101 |
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| [Study on the alkaloids in the stems and leaves of Stephania cepharantha (II)]. | Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20101001 |
| Protective effect of sinomenine on cartilage degradation and chondrocytes apoptosis. | Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20100801 |
| [Effect of sinomenine on tumor necrosis factor-alpha and nuclear factor-kappaB in the heterotopic tissue in rats with endometriosis]. | Nan fang yi ke da xue xue bao = Journal of Southern Medical University 20100801 |
| Genetic and chemical comparison of Boi (Sinomeni Caulis et Rhizoma) and Seifuto (Caulis Sinomenii). | Journal of natural medicines 20100701 |
| Sinomenine pretreatment attenuates cold ischemia/reperfusion injury in rats: the role of heme oxygenase-1. | International immunopharmacology 20100601 |
| [The pharmacokinetics study on Sinomenine transdermal patch on anaesthetized Beagle dogs]. | Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20100601 |
| Development of patch and spray formulations for enhancing topical delivery of sinomenine hydrochloride. | Journal of pharmaceutical sciences 20100401 |
| Preparation and characterization of novel sinomenine microcapsules for oral controlled drug delivery. | Drug development and industrial pharmacy 20100401 |
| Sinomenine, theophylline, cysteine, and levamisole: Comparisons of their kinetic effects on mineral formation induced by matrix vesicles. | Journal of inorganic biochemistry 20100401 |
| [Preparation of sinomenine hydrochloride delayed-onset sustained-release tablets]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20100301 |
| Effect of sinomenine on the in vitro intestinal epithelial transport of selected compounds. | Phytotherapy research : PTR 20100201 |
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| Novel sinomenine derivative 1032 improves immune suppression in experimental autoimmune encephalomyelitis. | Biochemical and biophysical research communications 20100101 |
| The effective fraction isolated from Radix Astragali alleviates glucose intolerance, insulin resistance and hypertriglyceridemia in db/db diabetic mice through its anti-inflammatory activity. | Nutrition & metabolism 20100101 |
| Effects of sinomenine on proliferation and apoptosis in human lung cancer cell line NCI-H460 in vitro. | Molecular medicine reports 20100101 |
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| [Research advances of mechanism of sinomenine in treating rheumatoid arthritis]. | Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine 20090801 |
| Immunoregulatory effects of sinomenine on the T-bet/GATA-3 ratio and Th1/Th2 cytokine balance in the treatment of mesangial proliferative nephritis. | International immunopharmacology 20090701 |
| [Effects of sinomenine on the cultured smooth muscle cell MAPK PKC activities and intracellular free Ca2+]. | Zhongguo ying yong sheng li xue za zhi = Zhongguo yingyong shenglixue zazhi = Chinese journal of applied physiology 20090501 |
| Sinomenine influences capacity for invasion and migration in activated human monocytic THP-1 cells by inhibiting the expression of MMP-2, MMP-9, and CD147. | Acta pharmacologica Sinica 20090401 |
| [Effect of sinomenine on the expression of chemokines and chemokine receptors in dendritic cells from patients with rheumatoid arthritis]. | Nan fang yi ke da xue xue bao = Journal of Southern Medical University 20090401 |
| (9S,13R,14R)-7,8-Didehydro-3,4,7-trimeth-oxy-17-methyl-morphinan-6-one. | Acta crystallographica. Section E, Structure reports online 20090401 |
| Screening of bioactive compounds from moutan cortex and their anti-inflammatory activities in rat synoviocytes. | Evidence-based complementary and alternative medicine : eCAM 20090301 |
| [Preparation of gastric retenting and chronopharmacologic drug delivery tablets of sinomenine hydrochloride]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090301 |
| Fast screening and structural elucidation of G-quadruplex ligands from a mixture via G-quadruplex recognition and NMR methods. | Biochimie 20090201 |
| Separation and detection of isoquinoline alkaloids using MEEKC coupled with field-amplified sample injection induced by ACN. | Electrophoresis 20090201 |
| [Study on optimization of formulation and preparation process of sinomenine liposomes]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090201 |
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| Anti-angiogenic effects of pterogynidine alkaloid isolated from Alchornea glandulosa. | BMC complementary and alternative medicine 20090101 |
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| Sinomenine suppresses TNF-alpha-induced VCAM-1 expression in human umbilical vein endothelial cells. | Journal of ethnopharmacology 20071101 |
| Effect of sinomenine on collagen-induced arthritis in mice. | Autoimmunity 20071101 |
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| Voltammetric determination of sinomenine in biological fluid using a glassy carbon electrode modified by a composite film of polycysteic acid and carbon nanotubes. | Combinatorial chemistry & high throughput screening 20070801 |
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| Retraction: Pharmacokinetic interaction of paeoniflorin and sinomenine: pharmacokinetic parameters and tissue distribution characteristics in rats and protein binding ability in vitro. | Journal of pharmacological sciences 20070701 |
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| In vivo analysis and spatial profiling of phytochemicals in herbal tissue by matrix-assisted laser desorption/ionization mass spectrometry. | Analytical chemistry 20070401 |
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| Sinomenine, a natural dextrorotatory morphinan analog, is anti-inflammatory and neuroprotective through inhibition of microglial NADPH oxidase. | Journal of neuroinflammation 20070101 |
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| Suppression of Th1 and Th2 immune responses in mice by Sinomenine, an alkaloid extracted from the chinese medicinal plant Sinomenium acutum. | Planta medica 20061201 |
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| The effects of sinomenine on intestinal absorption of paeoniflorin by the everted rat gut sac model. | Journal of ethnopharmacology 20060220 |
| Behavioral effects of sinomenine in murine models of anxiety. | Life sciences 20051205 |
| Pharmacokinetic interaction of paeoniflorin and sinomenine: pharmacokinetic parameters and tissue distribution characteristics in rats and protein binding ability in vitro. | Journal of pharmacological sciences 20051201 |
| [Study of the relative recovery of sinomenine microdialysis system and it's influential factor]. | Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20051201 |
| The pharmacokinetics and tissue distribution of sinomenine in rats and its protein binding ability in vitro. | Life sciences 20051104 |
| [New study progress of sinomenine]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20051001 |
| [Changes in cAMP and cGMP levels in neonatal rat histaminergic neurons of tuberomammillary nucleus following 48-hour morphine exposure and effects of sinomenine intervention]. | Di 1 jun yi da xue xue bao = Academic journal of the first medical college of PLA 20050901 |
| [Effect of sinomenine on adjuvant arthritis and its mechanisms]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20050901 |
| Impact of release characteristics of sinomenine hydrochloride dosage forms on its pharmacokinetics in beagle dogs. | World journal of gastroenterology 20050807 |
| Sinomenine inhibits B7-H1 and B7-DC expression on human renal tubular epithelial cells. | International immunopharmacology 20050801 |
| Morphinane alkaloids with cell protective effects from Sinomenium acutum. | Journal of natural products 20050701 |
| [Effect of penetration enhancers on the transdermal penetration of sinomenine liposome patch]. | Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20050701 |
| Determination of sinomenine in human plasma by HPLC/ESI/ion trap mass spectrum. | Clinica chimica acta; international journal of clinical chemistry 20050601 |
| [Research on extracting process for Fengshitongbi capsules]. | Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20050601 |
| Supercritical fluid extraction of sinomenine from Sinomenium acutum (Thumb) Rehd et Wils. | Journal of chromatography. A 20050520 |
| Influence of co-administrated sinomenine on pharmacokinetic fate of paeoniflorin in unrestrained conscious rats. | Journal of ethnopharmacology 20050513 |
| Requirement for ERK activation in sinomenine-induced apoptosis of macrophages. | Immunology letters 20050415 |
| Effect of sinomenine on cytokine expression of macrophages and synoviocytes in adjuvant arthritis rats. | Journal of ethnopharmacology 20050408 |
| [Immunopharmacological action of sinomenine, an alkaloid isolated from Sinomenium acutum, and its mechanism of action in treating rheumatoid arthritis]. | Yao xue xue bao = Acta pharmaceutica Sinica 20050201 |
| Quantification of sinomenine in caulis sinomenii collected from different growing regions and wholesale herbal markets by a modified HPLC method. | Biological & pharmaceutical bulletin 20050101 |
| The anti-angiogenic effect of sinomenine. | Angiogenesis 20050101 |
| Electropharmacological actions of the constituents of Sinomeni Caulis et Rhizome and Mokuboi-to in guinea pig heart. | The American journal of Chinese medicine 20050101 |
| N-inversion-associated conformational dynamics is unusually rapid in morphine alkaloids. | Journal of natural products 20041101 |
| [Inhibitory effect of sinomenine on expression of cyclooxygenase-2 in lipopolysaccharide-induced PC-12 cells]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20040901 |
| Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones. | Journal of ethnopharmacology 20040401 |
| [Synthesis and anti-inflammatory analgesic activities of sinomenine derivatives]. | Yao xue xue bao = Acta pharmaceutica Sinica 20040301 |
| Sinomenine blocks tissue remodeling in a rat model of chronic cardiac allograft rejection. | Transplantation 20030415 |
| Regulation of hepatobiliary excretion of sinomenine by P-glycoprotein in Sprague-Dawley rats. | Life sciences 20030411 |
| Effect of sinomenine on morphine dependence in isolated guinea pig ileum. | Di 1 jun yi da xue xue bao = Academic journal of the first medical college of PLA 20030401 |
| [The effect of sinomenine on cyclooxygenase activity and the expression of COX-1 and COX-2 mRNA in human peripheral monocytes]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20030401 |
| [Study on the permeability of 125I-sinomenine via the transdermal delivery way in rats]. | Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20020601 |
| [Effect of sinamine on withdrawal symptom and neurotransmitter of morphine-dependent rats]. | Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20020501 |
| [Study progress in Sinomenium acutum (Thunb.) Rehd. et Wils]. | Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20020301 |
| [Advances in the study on transdermal permeation of active elements of natural drugs in vitro]. | Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20020101 |
| The alkaloid sinomenine in rat transplant models: and yet it does move. | Transplant international : official journal of the European Society for Organ Transplantation 20010101 |
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