Sinomenine
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Hodoodo CAT#: H584348

CAS#: 115-53-7 (free base)

Description: Sinomenine is an alkaloid originally isolated from the root of the plant Sinomenium acutum. It is used in traditional medicine in China to treat rheumatic arthritis. Sinomenine has a wide spectrum analgesic effect in rodent models of nociceptive, inflammatory and neuropathic pain.


Chemical Structure

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Sinomenine
CAS# 115-53-7 (free base)

Theoretical Analysis

Hodoodo Cat#: H584348
Name: Sinomenine
CAS#: 115-53-7 (free base)
Chemical Formula: C19H23NO4
Exact Mass: 329.16
Molecular Weight: 329.400
Elemental Analysis: C, 69.28; H, 7.04; N, 4.25; O, 19.43

Price and Availability

Size Price Availability Quantity
20mg USD 330
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Related CAS #: 115-53-7 (free base)   6080-33-7 (HCl)  

Synonym: Sinomenine; Coculine; Cucoline; Kukoline

IUPAC/Chemical Name: (9alpha,13alpha,14alpha)-7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one

InChi Key: INYYVPJSBIVGPH-WTOJCKNJSA-N

InChi Code: 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+/m0/s1

SMILES Code: [H][C@]1([C@@]2(C3)C4=C(O)C(OC)=CC=C4C[C@]1([H])N(C)CC2)C=C(OC)C3=O

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:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO 0.0 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 329.40 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Zhao Z, Xiao J, Wang J, Dong W, Peng Z, An D. Anti-inflammatory effects of novel sinomenine derivatives. Int Immunopharmacol. 2015 Dec;29(2):354-360. doi: 10.1016/j.intimp.2015.10.030. Epub 2015 Oct 31. PubMed PMID: 26525983.

2: Gao T, Hao J, Wiesenfeld-Hallin Z, Wang DQ, Xu XJ. Analgesic effect of sinomenine in rodents after inflammation and nerve injury. Eur J Pharmacol. 2013 Dec 5;721(1-3):5-11. doi: 10.1016/j.ejphar.2013.09.062. Epub 2013 Oct 8. PubMed PMID: 24120369.

3: Tian S, Zhang R, Yang F, Wang T, Shen P, Tang J, Xu X, Xing L, Xu H, Su Z. [Synthesis of 4-palmitoyl-sinomenine and its anti-inflammation activity]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi. 2014 Mar;30(3):262-5. Chinese. PubMed PMID: 24606743.

4: Li D, Zhang T, Ji B. Influences of pH, urea and metal ions on the interaction of sinomenine with Lysozyme by steady state fluorescence spectroscopy. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Sep 15;130:440-6. doi: 10.1016/j.saa.2014.04.054. Epub 2014 Apr 19. PubMed PMID: 24813272.

5: Yi L, Luo JF, Xie BB, Liu JX, Wang JY, Liu L, Wang PX, Zhou H, Dong Y. α7 Nicotinic Acetylcholine Receptor is a Novel Mediator of Sinomenine Anti-Inflammation Effect in Macrophages Stimulated by Lipopolysaccharide. Shock. 2015 Aug;44(2):188-95. doi: 10.1097/SHK.0000000000000389. PubMed PMID: 25895149.

6: Oh YC, Kang OH, Kim SB, Mun SH, Park CB, Kim YG, Kim YI, Lee YS, Han SH, Keum JH, Shin DW, Ma JY, Kwon DY. Anti-inflammatory effect of sinomenine by inhibition of pro-inflammatory mediators in PMA plus A23187-stimulated HMC-1 Cells. Eur Rev Med Pharmacol Sci. 2012 Sep;16(9):1184-91. PubMed PMID: 23047501.

7: Zhang JX, Yang ZR, Wu DD, Song J, Guo XF, Wang J, Dong WG. Suppressive effect of sinomenine combined with 5-fluorouracil on colon carcinoma cell growth. Asian Pac J Cancer Prev. 2014;15(16):6737-43. PubMed PMID: 25169518.

8: Zhu L, Hao Y, Guan H, Cui C, Tian S, Yang D, Wang X, Zhang S, Wang L, Jiang H. Effect of sinomenine on vascular smooth muscle cell dedifferentiation and neointima formation after vascular injury in mice. Mol Cell Biochem. 2013 Jan;373(1-2):53-62. doi: 10.1007/s11010-012-1474-9. Epub 2012 Oct 13. PubMed PMID: 23065380.

9: Hong Y, Yang J, Shen X, Zhu H, Sun X, Wen X, Bian J, Hu H, Yuan L, Tao J, Lei P, Shen G. Sinomenine hydrochloride enhancement of the inhibitory effects of anti-transferrin receptor antibody-dependent on the COX-2 pathway in human hepatoma cells. Cancer Immunol Immunother. 2013 Mar;62(3):447-54. doi: 10.1007/s00262-012-1337-y. Epub 2012 Sep 2. PubMed PMID: 22941037.

10: Lu Z, Chen W, Viljoen A, Hamman JH. Effect of sinomenine on the in vitro intestinal epithelial transport of selected compounds. Phytother Res. 2010 Feb;24(2):211-8. doi: 10.1002/ptr.2914. PubMed PMID: 19585475.

11: Liu WG, Ling PX, Lin XK, Chen JY, Wang SJ, Li P, Wu XJ, Zhao DM, Liu SH. Therapeutic effect of an injectable sustained-release sinomenine hydrochloride and sodium hyaluronate compound in a rabbit model of osteoarthritis. Chin Med J (Engl). 2012 Jul;125(14):2543-7. PubMed PMID: 22882937.

12: Liu X, Chen T, Liu X, Chen Y, Wang L. Penetration effect of ostrich oil as a promising vehicle on transdermal delivery of sinomenine. J Oleo Sci. 2013;62(9):657-64. PubMed PMID: 24005010.

13: Shukla SM, Sharma SK. Sinomenine inhibits microglial activation by Aβ and confers neuroprotection. J Neuroinflammation. 2011 Sep 14;8:117. doi: 10.1186/1742-2094-8-117. PubMed PMID: 21917137; PubMed Central PMCID: PMC3182919.

14: Chen Z, Tao Z, Zhang N, Ren J, Deng Y, Xiao B. [The role of sinomenine in treatment of allergic rhinitis mice model and its mechanism]. Lin Chung Er Bi Yan Hou Tou Jing Wai Ke Za Zhi. 2013 Jan;27(2):81-4. Chinese. PubMed PMID: 23650707.

15: Li D, Hong D, Guo H, Chen J, Ji B. Probing the influences of urea on the interaction of sinomenine with human serum albumin by steady-state fluorescence. J Photochem Photobiol B. 2012 Dec 5;117:126-31. doi: 10.1016/j.jphotobiol.2012.09.007. Epub 2012 Oct 8. PubMed PMID: 23110856.

16: Yang Z, Liu Y, Yuan F, Li Z, Huang S, Shen H, Yuan B. Sinomenine inhibits microglia activation and attenuates brain injury in intracerebral hemorrhage. Mol Immunol. 2014 Aug;60(2):109-14. doi: 10.1016/j.molimm.2014.03.005. Epub 2014 May 8. PubMed PMID: 24815539.

17: Cheng Y, Li F, Wang D, Zhang Y, Yuan F, Zhang J. Sinomenine inhibits the expression of PD L1 in the peripheral blood mononuclear cells of mesangial proliferative nephritis patients. Mol Med Rep. 2013 Apr;7(4):1223-8. doi: 10.3892/mmr.2013.1302. Epub 2013 Feb 1. PubMed PMID: 23381841.

18: Zhu Q, Sun Y, Zhu J, Fang T, Zhang W, Li JX. Antinociceptive effects of sinomenine in a rat model of neuropathic pain. Sci Rep. 2014 Dec 1;4:7270. doi: 10.1038/srep07270. PubMed PMID: 25434829; PubMed Central PMCID: PMC4248268.

19: Yan H, Yan M, Li HD, Jiang P, Deng Y, Cai HL. Pharmacokinetics and penetration into synovial fluid of systemical and electroporation administered sinomenine to rabbits. Biomed Chromatogr. 2015 Jun;29(6):883-9. doi: 10.1002/bmc.3369. Epub 2014 Nov 7. PubMed PMID: 25376167.

20: Chen Y, Zhang L, Lu X, Wu K, Zeng J, Gao Y, Shi Q, Wang X, Chang LS, He D. Sinomenine reverses multidrug resistance in bladder cancer cells via P-glycoprotein-dependent and independent manners. Pharmazie. 2014 Jan;69(1):48-54. PubMed PMID: 24601223.