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27675-39-4-Cocculine Cocculine

Cocculine

For research use only. Not for therapeutic Use.

  • CAT Number: I025055
  • CAS Number: 27675-39-4
  • Molecular Formula: C17H21NO2
  • Molecular Weight: 271.36
  • Purity: 98%
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Related Small Molecules: Cephaeline dihydrochloride     Amoxicillin sodium     Diprotin A TFA    

Cocculine is isolated from root of Sinomenium acutum and is used as an antirheumatic and an antineuralgic.


Catalog Number I025055
CAS Number 27675-39-4
Synonyms

Cocculine; Sinomenine; Coculine

Molecular Formula C17H21NO2
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name (2S,13bS)-2-methoxy-2,3,5,6,8,9-hexahydro-1H-indolo[7a,1-a]isoquinolin-12-ol
InChI InChI=1S/C17H21NO2/c1-20-15-5-3-13-7-9-18-8-6-12-2-4-14(19)10-16(12)17(13,18)11-15/h2-4,10,15,19H,5-9,11H2,1H3/t15-,17-/m0/s1
InChIKey HJMBLPWMTXSDPK-RDJZCZTQSA-N
SMILES CO[C@H]1CC=C2CCN3CCc4c([C@]23C1)cc(O)cc4
Reference

1: Retraction. Basic Clin Pharmacol Toxicol. 2020 Jun;126(6):498. doi: 10.1111/bcpt.13412. Epub 2020 Apr 23. PMID: 32410349.
2: Liu W, Zhang Y, Zhu W, Ma C, Ruan J, Long H, Wang Y. Sinomenine Inhibits the Progression of Rheumatoid Arthritis by Regulating the Secretion of Inflammatory Cytokines and Monocyte/Macrophage Subsets. Front Immunol. 2018 Sep 26;9:2228. doi: 10.3389/fimmu.2018.02228. PMID: 30319663; PMCID: PMC6168735.
3: Retraction statement: Lipopolysaccharides-mediated injury to chondrogenic ATDC5 cells can be relieved by Sinomenine via downregulating microRNA-192. Phytother Res. 2020 Sep;34(9):2420. doi: 10.1002/ptr.6838. Epub 2020 Aug 7. PMID: 32959945.
4: Liu Z, Duan ZJ, Chang JY, Zhang ZF, Chu R, Li YL, Dai KH, Mo GQ, Chang QY; and the PLOS ONE Editors. Retraction: Sinomenine Sensitizes Multidrug-Resistant Colon Cancer Cells (Caco-2) to Doxorubicin by Downregulation of MDR-1 Expression. PLoS One. 2019 Apr 9;14(4):e0215388. doi: 10.1371/journal.pone.0215388. PMID: 30964927; PMCID: PMC6456210.
5: Zhu W, Zhang Y, Huang Y, Lu L. Chinese Herbal Medicine for the Treatment of Drug Addiction. Int Rev Neurobiol. 2017;135:279-295. doi: 10.1016/bs.irn.2017.02.013. Epub 2017 Mar 25. PMID: 28807162.
6: Liu S, Xu S, Wang Z, Guo Y, Pan W, Shen Z. Anti-Depressant-Like Effect of Sinomenine on Chronic Unpredictable Mild Stress-Induced Depression in a Mouse Model. Med Sci Monit. 2018 Oct 26;24:7646-7653. doi: 10.12659/MSM.908422. PMID: 30362468; PMCID: PMC6215386.
7: Pérol D, Provençal J, Hardy-Bessard AC, Coeffic D, Jacquin JP, Agostini C, Bachelot T, Guastalla JP, Pivot X, Martin JP, Bajard A, Ray-Coquard I. Can treatment with Cocculine improve the control of chemotherapy-induced emesis in early breast cancer patients? A randomized, multi-centered, double-blind, placebo-controlled Phase III trial. BMC Cancer. 2012 Dec 17;12:603. doi: 10.1186/1471-2407-12-603. PMID: 23244208; PMCID: PMC3582626.
8: Xu F, Li Q, Wang Z, Cao X. Sinomenine inhibits proliferation, migration, invasion and promotes apoptosis of prostate cancer cells by regulation of miR-23a. Biomed Pharmacother. 2019 Apr;112:108592. doi: 10.1016/j.biopha.2019.01.053. Epub 2019 Feb 18. PMID: 30784907.
9: Zheng XL, Jiang NF, Luo D, Gao HS, Ding AS. (7R,8S,9S,12S)-1-Benz- yloxy-13,14-didehydro-12-hy-droxy-2,13-dimeth-oxy-N-methyl-morphinane. Acta Crystallogr Sect E Struct Rep Online. 2011 Oct 1;67(Pt 10):o2662-3. doi: 10.1107/S1600536811037226. Epub 2011 Sep 17. PMID: 22058779; PMCID: PMC3201304.
10: Zheng XL, Jiang NF, Gao HS, Luo D, Ding AS. (7R,8S,9S,12S)-1-(4-Chloro-benz- yloxy)-13,14-didehydro-12-hy-droxy-2,13-dimeth-oxy-N-methyl-morphinane. Acta Crystallogr Sect E Struct Rep Online. 2011 Sep 1;67(Pt 9):o2480. doi: 10.1107/S160053681103443X. Epub 2011 Aug 27. PMID: 22059035; PMCID: PMC3200812.

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