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

MedKoo Cat#: 584348 | Name: Sinomenine

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Description:

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

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

Sinomenine

CAS#115-53-7 (free base)

Theoretical Analysis

MedKoo Cat#: 584348

Name: Sinomenine

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

Chemical Formula: C19H23NO4

Exact Mass: 329.1627

Molecular Weight: 329.40

Elemental Analysis: C, 69.28; H, 7.04; N, 4.25; O, 19.43

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 250.00	2 weeks

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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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Sinomenine is a nicotinic acetylcholine receptor agonist. It has been shown to inhibit the oxidation of proteins and rate constant, and to have an anti-inflammatory effect. Sinomenine also has an apoptosis pathway that leads to cell death by inhibiting the Bcl-2 protein.

In vitro activity:

Sinomenine played an antitumor role in gastric cancer cells via circTRPM7/miR-145-5p/PBX3 axis. circTRPM7 expression was reduced in sinomenine-treated gastric cancer cells, and overexpression of circTRPM7 upregulated the growth and metastasis of Sinomenine-treated gastric cancer cells. Reference: Chem Biol Drug Des. 2023 Oct;102(4):870-881. https://pubmed.ncbi.nlm.nih.gov/37495546/

In vivo activity:

Sinomenine had a therapeutic effect on orthotopic liver carcinoma in a rat model. Sinomenine reduced tumor volume, improved tissue lesions, and promoted cancer cell apoptosis. Sinomenine decreased levels of inflammatory cytokines and decreased the numbers of erythrocytes, leukocytes and platelets. Sinomenine decreased Ki-67, CD44, VEGF and CD31 expressions. Sinomenine decreased Bcl-2, Cyclin D1, CDK4, CDK6 and Survivin levels, but increased Bax, Cleaved-caspase3/pro-caspase3, P21 and P27 levels. Reference: Histol Histopathol. 2023 Nov 30:18683. https://pubmed.ncbi.nlm.nih.gov/38084512/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	50.0	151.80

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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:

1. Yan J, Yang J, Shen H, Gao R, Lv S. Sinomenine regulates circTRPM7-related pathway to inhibit gastric cancer cell growth and metastasis. Chem Biol Drug Des. 2023 Oct;102(4):870-881. doi: 10.1111/cbdd.14297. Epub 2023 Jul 26. PMID: 37495546. 2. Zhu Z, Zhou H, Chen F, Deng J, Yin L, He B, Hu Q, Wang T. Sinomenine Derivatives: Synthesis, Antitumor Activity, and Apoptotic Induction in MCF-7 Cells via IL-6/PI3K/Akt/NF-κB Signaling Pathway. ChemMedChem. 2022 Jul 19;17(14):e202200234. doi: 10.1002/cmdc.202200234. Epub 2022 Jun 9. PMID: 35612514. 3. Zhang Y, Ran H, Hui S, Qian L. Effects of sinomenine on a rat orthotopic liver carcinoma model. Histol Histopathol. 2023 Nov 30:18683. doi: 10.14670/HH-18-683. Epub ahead of print. PMID: 38084512. 4. Jiang H, Lu Q, Xu J, Huo G, Cai Y, Geng S, Xu H, Zhang J, Li H, Yuan K, Huang G. Sinomenine ameliorates adjuvant-induced arthritis by inhibiting the autophagy/NETosis/inflammation axis. Sci Rep. 2023 Mar 9;13(1):3933. doi: 10.1038/s41598-023-30922-3. PMID: 36894604; PMCID: PMC9998614.

In vitro protocol:

In vivo protocol:

1. Zhang Y, Ran H, Hui S, Qian L. Effects of sinomenine on a rat orthotopic liver carcinoma model. Histol Histopathol. 2023 Nov 30:18683. doi: 10.14670/HH-18-683. Epub ahead of print. PMID: 38084512. 2. Jiang H, Lu Q, Xu J, Huo G, Cai Y, Geng S, Xu H, Zhang J, Li H, Yuan K, Huang G. Sinomenine ameliorates adjuvant-induced arthritis by inhibiting the autophagy/NETosis/inflammation axis. Sci Rep. 2023 Mar 9;13(1):3933. doi: 10.1038/s41598-023-30922-3. PMID: 36894604; PMCID: PMC9998614.

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.