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MedKoo Cat#: 413221 | Name: Cocculine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Chemical Structure

Cocculine
Cocculine
CAS#27675-39-4

Theoretical Analysis

MedKoo Cat#: 413221

Name: Cocculine

CAS#: 27675-39-4

Chemical Formula: C17H21NO2

Exact Mass: 271.1572

Molecular Weight: 271.36

Elemental Analysis: C, 75.25; H, 7.80; N, 5.16; O, 11.79

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Cocculine; Sinomenine; Coculine
IUPAC/Chemical Name
(2S,13bS)-2-methoxy-2,3,5,6,8,9-hexahydro-1H-indolo[7a,1-a]isoquinolin-12-ol
InChi Key
HJMBLPWMTXSDPK-RDJZCZTQSA-N
InChi Code
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
SMILES Code
CO[C@H]1CC=C2CCN3CCc4c([C@]23C1)cc(O)cc4
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 271.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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.