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6080-33-7,MFCD19982816
Catalog No.:AA0039NL

6080-33-7 | 9α,13α,14α-Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, hydrochloride

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50mg
≥98%
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250mg
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1g
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5g
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25g
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100g
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250g
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0039NL
Chemical Name:
9α,13α,14α-Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, hydrochloride
CAS Number:
6080-33-7
Molecular Formula:
C19H24ClNO4
Molecular Weight:
365.8512
MDL Number:
MFCD19982816
SMILES:
COC1=C[C@@H]2[C@@H]3Cc4c([C@@]2(CC1=O)CCN3C)c(O)c(cc4)OC.Cl
NSC Number:
76021
Properties
Computed Properties
 
Complexity:
562  
Covalently-Bonded Unit Count:
2  
Defined Atom Stereocenter Count:
3  
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
2  

Literature

Title: Effects of sinomenine on the expression of microRNA-155 in 2,4,6-trinitrobenzenesulfonic acid-induced colitis in mice.

Journal: PloS one 20130101

Title: Design, synthesis and molecular docking studies of sinomenine derivatives.

Journal: Bioorganic & medicinal chemistry letters 20120915

Title: Anti-inflammatory effect of sinomenine by inhibition of pro-inflammatory mediators in PMA plus A23187-stimulated HMC-1 Cells.

Journal: European review for medical and pharmacological sciences 20120901

Title: Sinomenium acutum: a review of chemistry, pharmacology, pharmacokinetics, and clinical use.

Journal: Pharmaceutical biology 20120801

Title: Effects of alkaloid sinomenine on levels of IFN-γ, IL-1β, TNF-α and IL-6 in a rat renal allograft model.

Journal: Immunotherapy 20120801

Title: Sinomenine can prolong high-risk corneal graft survival in a rat model.

Journal: Immunotherapy 20120601

Title: Activation of PI3K/Akt and ERK signaling pathways antagonized sinomenine-induced lung cancer cell apoptosis.

Journal: Molecular medicine reports 20120501

Title: Synthesis and biological evaluation of novel sinomenine derivatives as anti-inflammatory agents.

Journal: European journal of medicinal chemistry 20120401

Title: Determination of sinomenine sustained-release capsules in healthy Chinese volunteers by liquid chromatography-tandem mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120315

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: Protective effects of sinomenine against doxorubicin-induced nephrosis in rats.

Journal: Journal of Asian natural products research 20120101

Title: 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.

Journal: Rheumatology international 20111101

Title: Sinomenine protects against ischaemic brain injury: involvement of co-inhibition of acid-sensing ion channel 1a and L-type calcium channels.

Journal: British journal of pharmacology 20111101

Title: 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: Journal of ethnopharmacology 20110901

Title: Anti-allergic effects of sinomenine by inhibition of prostaglandin D₂ and leukotriene C₄ in mouse bone marrow-derived mast cells.

Journal: Immunopharmacology and immunotoxicology 20110601

Title: Two new morphinane alkaloids from Sinomenium acutum.

Journal: Journal of Asian natural products research 20110601

Title: Synthesis and biological evaluation of unique stereodimers of sinomenine analogues as potential inhibitors of NO production.

Journal: Bioorganic & medicinal chemistry 20110515

Title: Immunosuppressive and anti-inflammatory activities of sinomenine.

Journal: International immunopharmacology 20110301

Title: Sinomenine inhibits microglial activation by Aβ and confers neuroprotection.

Journal: Journal of neuroinflammation 20110101

Title: HPLC and LC-MS analysis of sinomenine and its application in pharmacokinetic studies in rats.

Journal: Acta pharmacologica Sinica 20101101

Title: [Rat in vitro plasma-binding percentage determination of sinomenine hydrochloride by using microdialysis method and ultrafiltration].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20101001

Title: [Study on the alkaloids in the stems and leaves of Stephania cepharantha (II)].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20101001

Title: Protective effect of sinomenine on cartilage degradation and chondrocytes apoptosis.

Journal: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20100801

Title: [Effect of sinomenine on tumor necrosis factor-alpha and nuclear factor-kappaB in the heterotopic tissue in rats with endometriosis].

Journal: Nan fang yi ke da xue xue bao = Journal of Southern Medical University 20100801

Title: Genetic and chemical comparison of Boi (Sinomeni Caulis et Rhizoma) and Seifuto (Caulis Sinomenii).

Journal: Journal of natural medicines 20100701

Title: Sinomenine pretreatment attenuates cold ischemia/reperfusion injury in rats: the role of heme oxygenase-1.

Journal: International immunopharmacology 20100601

Title: [The pharmacokinetics study on Sinomenine transdermal patch on anaesthetized Beagle dogs].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20100601

Title: Development of patch and spray formulations for enhancing topical delivery of sinomenine hydrochloride.

Journal: Journal of pharmaceutical sciences 20100401

Title: Preparation and characterization of novel sinomenine microcapsules for oral controlled drug delivery.

Journal: Drug development and industrial pharmacy 20100401

Title: Sinomenine, theophylline, cysteine, and levamisole: Comparisons of their kinetic effects on mineral formation induced by matrix vesicles.

Journal: Journal of inorganic biochemistry 20100401

Title: [Preparation of sinomenine hydrochloride delayed-onset sustained-release tablets].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20100301

Title: Effect of sinomenine on the in vitro intestinal epithelial transport of selected compounds.

Journal: Phytotherapy research : PTR 20100201

Title: [Research progress on immunosuppressive activity of monomers extracted from Chinese medicine].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20100201

Title: Novel sinomenine derivative 1032 improves immune suppression in experimental autoimmune encephalomyelitis.

Journal: Biochemical and biophysical research communications 20100101

Title: [Study on the detoxification of alcohol extracts from orientvine and its effective component on withdrawal syndromes of morphine].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20090901

Title: [Research advances of mechanism of sinomenine in treating rheumatoid arthritis].

Journal: Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine 20090801

Title: Immunoregulatory effects of sinomenine on the T-bet/GATA-3 ratio and Th1/Th2 cytokine balance in the treatment of mesangial proliferative nephritis.

Journal: International immunopharmacology 20090701

Title: [Effects of sinomenine on the cultured smooth muscle cell MAPK PKC activities and intracellular free Ca2+].

Journal: Zhongguo ying yong sheng li xue za zhi = Zhongguo yingyong shenglixue zazhi = Chinese journal of applied physiology 20090501

Title: 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.

Journal: Acta pharmacologica Sinica 20090401

Title: [Effect of sinomenine on the expression of chemokines and chemokine receptors in dendritic cells from patients with rheumatoid arthritis].

Journal: Nan fang yi ke da xue xue bao = Journal of Southern Medical University 20090401

Title: [Preparation of gastric retenting and chronopharmacologic drug delivery tablets of sinomenine hydrochloride].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090301

Title: Fast screening and structural elucidation of G-quadruplex ligands from a mixture via G-quadruplex recognition and NMR methods.

Journal: Biochimie 20090201

Title: Separation and detection of isoquinoline alkaloids using MEEKC coupled with field-amplified sample injection induced by ACN.

Journal: Electrophoresis 20090201

Title: [Study on optimization of formulation and preparation process of sinomenine liposomes].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090201

Title: [Study on pharmacokinetics and absolute bioavailability of sinomenine in beagle dogs].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090201

Title: [Effects of sinomenine on synovial fluid and serum content of interleukin-1beta in rabbits with osteoarthritis].

Journal: Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine 20081201

Title: Sinomenine ameliorates arthritis via MMPs, TIMPs, and cytokines in rats.

Journal: Biochemical and biophysical research communications 20081114

Title: [Bioequivalence study of sinomenine patch by microdialysis].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20081101

Title: Activation of opioid mu-receptor by sinomenine in cell and mice.

Journal: Neuroscience letters 20081010

Title: Sinomenine versus NSAIDs for the treatment of rheumatoid arthritis: a systematic review and meta-analysis.

Journal: Planta medica 20081001

Title: Development and evaluation of the Sinomenine transdermal patch.

Journal: Pakistan journal of pharmaceutical sciences 20081001

Title: pH-dependent, stereoselective dimerization of sinomenine.

Journal: Organic letters 20080904

Title: [Dynamic determination of sinomenine in skin by microdialysis].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20080701

Title: [Inhibitory effect of sinomenine on H2O2-induced apoptosis in neonatal rat cardiomyocytes].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080401

Title: Biocatalyzed cross-coupling of sinomenine and guaiacol by Antrodiella semisupina.

Journal: Organic letters 20080320

Title: Inhibition of the antigen-induced activation of RBL-2H3 cells by sinomenine.

Journal: International immunopharmacology 20080301

Title: [Role of alkaloid sinomenine in chronic rejection in the rat heart transplantation model].

Journal: Zhonghua xin xue guan bing za zhi 20080201

Title: Morphinane alkaloid dimers from Sinomenium acutum.

Journal: Journal of natural products 20080101

Title: Sinomenine inhibits activation of rat retinal microglia induced by advanced glycation end products.

Journal: International immunopharmacology 20071205

Title: Sinomenine suppresses TNF-alpha-induced VCAM-1 expression in human umbilical vein endothelial cells.

Journal: Journal of ethnopharmacology 20071101

Title: Effect of sinomenine on collagen-induced arthritis in mice.

Journal: Autoimmunity 20071101

Title: Vasodilatation induced by sinomenine lowers blood pressure in spontaneously hypertensive rats.

Journal: Clinical and experimental pharmacology & physiology 20071001

Title: [Preparation of sinomenine microemulsion and its transdermal absorption].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20071001

Title: [Studies on preparation of sinomenine hydrochloride-loaded bovine serum albumin microspheres].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20071001

Title: Sinomenine inhibits primary CD4+ T-cell proliferation via apoptosis.

Journal: Cell biology international 20070801

Title: Sinomenine promotes differentiation but impedes maturation and co-stimulatory molecule expression of human monocyte-derived dendritic cells.

Journal: International immunopharmacology 20070801

Title: Assessment of in vitro and in vivo recovery of sinomenine using microdialysis.

Journal: Skin research and technology : official journal of International Society for Bioengineering and the Skin (ISBS) [and] International Society for Digital Imaging of Skin (ISDIS) [and] International Society for Skin Imaging (ISSI) 20070801

Title: Preparative isolation and purification of sinomenine from Sinomenium acutum by centrifugal partition chromatography.

Journal: Journal of separation science 20070801

Title: Sinomenine, an antirheumatic alkaloid, ameliorates clinical signs of disease in the Lewis rat model of acute experimental autoimmune encephalolmyelitis.

Journal: Biological & pharmaceutical bulletin 20070801

Title: Voltammetric determination of sinomenine in biological fluid using a glassy carbon electrode modified by a composite film of polycysteic acid and carbon nanotubes.

Journal: Combinatorial chemistry & high throughput screening 20070801

Title: [The effect of sinomenine on nNOS activity of brain tissues in morphine dependent and withdrawal mice].

Journal: Zhongguo ying yong sheng li xue za zhi = Zhongguo yingyong shenglixue zazhi = Chinese journal of applied physiology 20070801

Title: [Effects of sinomenine on NO/nNOS system in cerebellum and spinal cord of morphine-dependent and withdrawal mice].

Journal: Sheng li xue bao : [Acta physiologica Sinica] 20070625

Title: Sinomenine attenuates 2, 4, 6-trinitrobenzene sulfonic acid-induced colitis in mice.

Journal: International immunopharmacology 20070501

Title: Sinomenine inhibits maturation of monocyte-derived dendritic cells through blocking activation of NF-kappa B.

Journal: International immunopharmacology 20070501

Title: [Effects of sinomenine on intracellular free calcium concentration and the activity of protein kinase in cultured rabbit aortic smooth muscle cells].

Journal: Zhongguo ying yong sheng li xue za zhi = Zhongguo yingyong shenglixue zazhi = Chinese journal of applied physiology 20070501

Title: Effect of sinomenine on human cytochrome P450 activity.

Journal: Clinica chimica acta; international journal of clinical chemistry 20070401

Title: Determination of sinomenine in Sinomenium acutum by capillary electrophoresis with electrochemiluminescence detection.

Journal: Analytica chimica acta 20070321

Title: A spectroscopic and molecular modeling study of sinomenine binding to transferrin.

Journal: Bioorganic & medicinal chemistry letters 20070315

Title: [The effects of sinomenine on the expresssion of ICAM-1 and IL-2 during the rejection of rat cardiac allograft].

Journal: Xi bao yu fen zi mian yi xue za zhi = Chinese journal of cellular and molecular immunology 20070301

Title: Pharmacokinetic study of free-form sinomenine in rat skin by microdialysis coupled with liquid chromatography-electrospray mass spectrometry.

Journal: Biomedical chromatography : BMC 20070101

Title: Three major urinary metabolites of sinomenine in rats.

Journal: Journal of Asian natural products research 20070101

Title: Sinomenine, a natural dextrorotatory morphinan analog, is anti-inflammatory and neuroprotective through inhibition of microglial NADPH oxidase.

Journal: Journal of neuroinflammation 20070101

Title: Mechanisms responsible for poor oral bioavailability of paeoniflorin: Role of intestinal disposition and interactions with sinomenine.

Journal: Pharmaceutical research 20061201

Title: Suppression of Th1 and Th2 immune responses in mice by Sinomenine, an alkaloid extracted from the chinese medicinal plant Sinomenium acutum.

Journal: Planta medica 20061201

Title: [Effects of Caulis Sinomenii and sinomenine on morphine-induced place preference and brain histamine level in mice].

Journal: Nan fang yi ke da xue xue bao = Journal of Southern Medical University 20061201

Title: Synthesis and anti-inflammatory activities investigation of sinomenine derivatives on ring C.

Journal: Natural product research 20060901

Title: [Determination in vitro of rat plasma protein binding rate of sinomenine by using microdialysis method].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20060901

Title: In vitro pharmacological actions of sinomenine on the smooth muscle and the endothelial cell activity in rat aorta.

Journal: Life sciences 20060815

Title: Effect of sinomenine on gene expression of the IL-1 beta-activated human synovial sarcoma.

Journal: Life sciences 20060710

Title: [Study on determination of entrapment efficiency of sinomenine liposomes].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20060501

Title: [Effects of the alkaloid sinomenine on COX-2 activity and acute rejection in heart allografts: an experiment with rats].

Journal: Zhonghua yi xue za zhi 20060404

Title: The effects of sinomenine on intestinal absorption of paeoniflorin by the everted rat gut sac model.

Journal: Journal of ethnopharmacology 20060220

Title: Behavioral effects of sinomenine in murine models of anxiety.

Journal: Life sciences 20051205

Title: Pharmacokinetic interaction of paeoniflorin and sinomenine: pharmacokinetic parameters and tissue distribution characteristics in rats and protein binding ability in vitro.

Journal: Journal of pharmacological sciences 20051201

Title: [Study of the relative recovery of sinomenine microdialysis system and it's influential factor].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20051201

Title: The pharmacokinetics and tissue distribution of sinomenine in rats and its protein binding ability in vitro.

Journal: Life sciences 20051104

Title: [New study progress of sinomenine].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20051001

Title: [Changes in cAMP and cGMP levels in neonatal rat histaminergic neurons of tuberomammillary nucleus following 48-hour morphine exposure and effects of sinomenine intervention].

Journal: Di 1 jun yi da xue xue bao = Academic journal of the first medical college of PLA 20050901

Title: [Effect of sinomenine on adjuvant arthritis and its mechanisms].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20050901

Title: Impact of release characteristics of sinomenine hydrochloride dosage forms on its pharmacokinetics in beagle dogs.

Journal: World journal of gastroenterology 20050807

Title: Sinomenine inhibits B7-H1 and B7-DC expression on human renal tubular epithelial cells.

Journal: International immunopharmacology 20050801

Title: [Effect of penetration enhancers on the transdermal penetration of sinomenine liposome patch].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20050701

Title: Determination of sinomenine in human plasma by HPLC/ESI/ion trap mass spectrum.

Journal: Clinica chimica acta; international journal of clinical chemistry 20050601

Title: [Research on extracting process for Fengshitongbi capsules].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20050601

Title: Supercritical fluid extraction of sinomenine from Sinomenium acutum (Thumb) Rehd et Wils.

Journal: Journal of chromatography. A 20050520

Title: Influence of co-administrated sinomenine on pharmacokinetic fate of paeoniflorin in unrestrained conscious rats.

Journal: Journal of ethnopharmacology 20050513

Title: Requirement for ERK activation in sinomenine-induced apoptosis of macrophages.

Journal: Immunology letters 20050415

Title: Effect of sinomenine on cytokine expression of macrophages and synoviocytes in adjuvant arthritis rats.

Journal: Journal of ethnopharmacology 20050408

Title: [Immunopharmacological action of sinomenine, an alkaloid isolated from Sinomenium acutum, and its mechanism of action in treating rheumatoid arthritis].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20050201

Title: Quantification of sinomenine in caulis sinomenii collected from different growing regions and wholesale herbal markets by a modified HPLC method.

Journal: Biological & pharmaceutical bulletin 20050101

Title: The anti-angiogenic effect of sinomenine.

Journal: Angiogenesis 20050101

Title: Electropharmacological actions of the constituents of Sinomeni Caulis et Rhizome and Mokuboi-to in guinea pig heart.

Journal: The American journal of Chinese medicine 20050101

Title: N-inversion-associated conformational dynamics is unusually rapid in morphine alkaloids.

Journal: Journal of natural products 20041101

Title: [Inhibitory effect of sinomenine on expression of cyclooxygenase-2 in lipopolysaccharide-induced PC-12 cells].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20040901

Title: [Synthesis and anti-inflammatory analgesic activities of sinomenine derivatives].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20040301

Title: Sinomenine blocks tissue remodeling in a rat model of chronic cardiac allograft rejection.

Journal: Transplantation 20030415

Title: Regulation of hepatobiliary excretion of sinomenine by P-glycoprotein in Sprague-Dawley rats.

Journal: Life sciences 20030411

Title: Effect of sinomenine on morphine dependence in isolated guinea pig ileum.

Journal: Di 1 jun yi da xue xue bao = Academic journal of the first medical college of PLA 20030401

Title: [The effect of sinomenine on cyclooxygenase activity and the expression of COX-1 and COX-2 mRNA in human peripheral monocytes].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20030401

Title: [Study on the permeability of 125I-sinomenine via the transdermal delivery way in rats].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20020601

Title: [Effect of sinamine on withdrawal symptom and neurotransmitter of morphine-dependent rats].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20020501

Title: [Study progress in Sinomenium acutum (Thunb.) Rehd. et Wils].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20020301

Title: [Advances in the study on transdermal permeation of active elements of natural drugs in vitro].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20020101

Title: The alkaloid sinomenine in rat transplant models: and yet it does move.

Journal: Transplant international : official journal of the European Society for Organ Transplantation 20010101

Title: Song L, et al. Sinomenine inhibits breast cancer cell invasion and migration by suppressing NF-κB activation mediated by IL-4/miR-324-5p/CUEDC2 axis. Biochem Biophys Res Commun. 2015 Aug 28;464(3):705-10.

Title: Wang MH, et al. Activation of opioid mu-receptor by sinomenine in cell and mice.Neurosci Lett. 2008 Oct 10;443(3):209-12.

Title: Gao T, et al. Analgesic effect of sinomenine in rodents after inflammation and nerve injury. Eur J Pharmacol. 2013 Dec 5;721(1-3):5-11.

Title: Zhu Q, et al. Antinociceptive effects of sinomenine in a rat model of neuropathic pain. Sci Rep. 2014 Dec 1;4:7270.

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Tags:6080-33-7 Molecular Formula|6080-33-7 MDL|6080-33-7 SMILES|6080-33-7 9α,13α,14α-Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, hydrochloride