CAS 115-53-7|Sinomenine

Introduction：Basic information about CAS 115-53-7|Sinomenine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Sinomenine BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles5
7. Synonyms

Common Name	Sinomenine
CAS Number	115-53-7	Molecular Weight	329.390
Density	1.3±0.1 g/cm3	Boiling Point	513.6±50.0 °C at 760 mmHg
Molecular Formula	C₁₉H₂₃NO₄	Melting Point	180ºC
MSDS	/	Flash Point	264.4±30.1 °C
Symbol	GHS07	Signal Word	Warning

Names

Name	Sinomenine
Synonym	More Synonyms

Sinomenine BiologicalActivity

Description	Sinomenine, an alkaloid extracted from Sinomenium acutum, is a blocker of the NF-κB activation[1]. Sinomenine also is an activator of μ-opioid receptor[2].
Related Catalog	Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>CancerSignaling Pathways >>GPCR/G Protein >>Opioid ReceptorSignaling Pathways >>Autophagy >>AutophagyResearch Areas >>Inflammation/ImmunologySignaling Pathways >>Neuronal Signaling >>Opioid ReceptorResearch Areas >>Neurological Disease
Target	NF-κB[1], μ-opioid receptor[2]
In Vitro	Cell viability gradually decreased with increasing Sinomenine concentration. The migration ability of MDA-MB-231 cells is significantly weakened by 0.25, 0.5, and 1 mM of Sinomenine treatment. The wound-healing assay reveals that 0.25 and 0.5 mM Sinomenine significantly suppress the healing of the wound. When the MDA-MB-231 cells are treated with 0.5 mM Sinomenine, the healing progress is about 50%, but in the group treated with 0.25 mM Sinomenine and the untreated control, the healing is about 80% and nearly 95%, respectively. The IB assay following inhibitor of NF-κB (IκB) antibody IP shows that the binding of NF-κB to IκB is inhibited by Sinomenine treatment in a dose-dependent manne[1].
In Vivo	Sinomenine (i.p.) produces antinociception in the hot plate and tail flick tests in male rats at 40 mg/kg, but not at lower doses (10 or 20 mg/kg). At 10 to 40 mg/kg Sinomenine does not produce any observable side effect such as sedation, allergy or motor impairments. At 80 mg/kg, Sinomenine is mildly sedative in rats. Antinociception is also seen mice at 60 min following 80 mg/kg i.p. Sinomenine, but not at lower doses (20 or 40 mg/kg), in the tail flick test. Sinomenine at 80 mg/kg i.p. does not produce any observable side effects in mice. I.p or p.o. Sinomenine at 40 or 80 mg/kg dose-dependently reduces mechanical hypersensitivity in nerve injured mice. I.p. Sinomenine at 40 mg/kg, but not lower doses or vehicle, significantly decreases mechanical and cold allodynia for up to 240 min without producing motor deficits or sedation[3]. At doses of 10 to 40 mg/kg, Sinomenine dose-dependently increases the paw withdrawal threshold. In non-chronic constriction injury (CCI) healthy rats, Sinomenine at the dose range of 10 to 40 mg/kg does not change the immobility behavior in the forced swimming test[4].
Cell Assay	The MDA-MB-231 human triple negative and 4T1 mouse breast cancer cell lines are used in this study. For the experiments, the cells are grown in 24-well plates at 3.5×104/well. Following incubation for 24 or 48 h in medium containing different concentrations of Sinomenine, proliferation of the cells are detected with Cell Counting Kit-8 solution according to the manufacturer's instructions[1].
Animal Admin	Male Sprague-Dawley rats weighing of 250 to 300 g are used in this experiment. For the duration of action of acute Sinomenine study, different doses of Sinomenine (10 to 40 mg/kg) are administered 1 day after surgery and then paw withdrawal threshold is measured every 30 min for 4 hours. For the study involving daily Sinomenine treatment, mechanical hyperalgesia measure is performed 3 h after daily drug treatment. For antagonist studies, antagonists were given 10 min prior to 40 mg/kg Sinomenine administration[3].
References	[1]. 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. [2]. Wang MH, et al. Activation of opioid mu-receptor by sinomenine in cell and mice.Neurosci Lett. 2008 Oct 10;443(3):209-12. [3]. 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. [4]. Zhu Q, et al. Antinociceptive effects of sinomenine in a rat model of neuropathic pain. Sci Rep. 2014 Dec 1;4:7270.

Chemical & Physical Properties

Density	1.3±0.1 g/cm3
Boiling Point	513.6±50.0 °C at 760 mmHg
Melting Point	180ºC
Molecular Formula	C₁₉H₂₃NO₄
Molecular Weight	329.390
Flash Point	264.4±30.1 °C
Exact Mass	329.162720
PSA	59.00000
LogP	1.25
Vapour Pressure	0.0±1.4 mmHg at 25°C
Index of Refraction	1.625
InChIKey	INYYVPJSBIVGPH-QHRIQVFBSA-N
SMILES	COC1=CC2C3Cc4ccc(OC)c(O)c4C2(CCN3C)CC1=O
Storage condition	2~8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QD2170000

CHEMICAL NAME :: 9-alpha,13-alpha,14-alpha-Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-

CAS REGISTRY NUMBER :: 115-53-7

BEILSTEIN REFERENCE NO. :: 0095280

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C19-H23-N-O4

MOLECULAR WEIGHT :: 329.43

WISWESSER LINE NOTATION :: T6 G666/FQ 2AF Q DV FX ON BUT&TTJ CO1 HQ IO1 O1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 580 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold

REFERENCE :: YHHPAL Yaoxue Xuebao. Acta Pharmaceutica Sinica. Pharmaceutical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1953- Suspended 1966-78. Volume(issue)/page/year: 10,673,1963

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 285 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: YHHPAL Yaoxue Xuebao. Acta Pharmaceutica Sinica. Pharmaceutical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1953- Suspended 1966-78. Volume(issue)/page/year: 8,177,1960

Safety Information

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302-H315-H319-H335
Precautionary Statements	P301 + P312 + P330-P305 + P351 + P338
Hazard Codes	T: Toxic;
Risk Phrases	R45
Safety Phrases	53-22-26-36/37/39-45
RIDADR	UN 1544
WGK Germany	3
RTECS	QD2170000
Packaging Group	III
Hazard Class	6.1(b)

Articles5

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

Zhong Xi Yi Jie He Xue Bao 7(8) , 775-8, (2009)

[New study progress of sinomenine].

Zhongguo Zhong Yao Za Zhi 30(20) , 1573-6, (2005)

To further understand sinomenine, this paper has introduced the abstract technology, assaying, pharmaceutical chemistry, pharmacological action, pharmacotoxicology, pharmacokinetics and clinical appli...

Immunosuppressive and anti-inflammatory activities of sinomenine.

Int. Immunopharmacol. 11(3) , 373-6, (2011)

Sinomenine (SN), a pure compound extracted from the Sinomenium acutum plant, has been found to inhibit T- and B-lymphocyte activation, proliferation and function and to interfere with the differentiat...

Synonyms

EINECS 204-094-6

MFCD00134303

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