CAS Number6080-33-7
SynonymsCucoline, hydrochloride; (14α)-4-Hydroxy-3,7-dimethoxy-17-methyl-7,8-didehydromorphinan-6-one hydrochloride (1:1); (9α,13α,14α)-4-Hydroxy-3,7-dimethoxy-17-methyl-7,8-didehydromorphinan-6-one hydrochloride (1:1); Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (14α)-, hydrochloride (1:1)
Molecular FormulaC19H24ClNO4
Molecular Weight365.86
Purity98%
Boiling Point513.6ºC at 760 mmHg
Melting Point231.0 to 235.0 °C
Appearancewhite to beige
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 6080-33-7 |
| Catalog No. | 2A-9012457 |
| Chinese Name | 盐酸青藤碱 |
| Synonyms | Cucoline, hydrochloride; (14α)-4-Hydroxy-3,7-dimethoxy-17-methyl-7,8-didehydromorphinan-6-one hydrochloride (1:1); (9α,13α,14α)-4-Hydroxy-3,7-dimethoxy-17-methyl-7,8-didehydromorphinan-6-one hydrochloride (1:1); Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (14α)-, hydrochloride (1:1) |
| Molecular Formula | C19H24ClNO4 |
| Molecular Weight | 365.86 |
| Purity | 98 |
| Boiling Point | 513.6ºC at 760 mmHg |
| Melting Point | 231.0 to 235.0 °C |
| Appearance | white to beige |
| Water Solubility | H2O: soluble20mg/mL, clear |
| Storage Condition | 2-8°C |
| Application | Sinomenine hydrochloride is a blocker of NF-κB activation and an activator of μ-opioid receptors. |
| MDL Number | C19H24ClNO4 |
| SMILES | [Cl-].COc1ccc2C[C@H]3[C@H]4C=C(OC)C(=O)C[C@@]4(CCN3C)c2c1O.[H+] |
| InChI | InChI=1S/C19H23NO4.ClH/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;1H/t12-,13+,19-;/m1./s1 |
| InChI Key | InChIKey=YMEVIMJAUHZFMW-VUIDNZEBSA-N |
| Hazard Symbols | Transport |
| MSDS | msds/12457_1_6080_33_7.pdf |
| Bioactivity | Sinomenine hydrochloride is a blocker of the NF-κB activation and also an activator of μ-opioid receptor. Related Catalog Signaling Pathways >> GPCR/G Protein >> Opioid Receptor Signaling Pathways >> Neuronal Signaling >> Opioid Receptor Natural Products >> Alkaloid Research Areas >> Neurological Disease Research Areas >> Cancer Research Areas >> Inflammation/Immunology Target NF-κB μ-opioid receptor In Vitro Cell viability is gradually decreased with increasing Sinomenine hydrochloride concentration. The migration ability of MDA-MB-231 cells is significantly weakened by 0.25, 0.5, and 1 mM of Sinomenine hydrochloride treatment. The wound-healing assay reveals that 0.25 and 0.5 mM Sinomenine hydrochloride significantly suppress the healing of the wound. When the MDA-MB-231 cells are treated with 0.5 mM Sinomenine hydrochloride, the healing progress is about 50%, but in the group treated with 0.25 mM Sinomenine hydrochloride 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 hydrochloride treatment in a dose-dependent manne[1]. In Vivo I.p. Sinomenine hydrochloride 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 hydrochloride does not produce any observable side effect such as sedation, allergy or motor impairments. At 80 mg/kg, Sinomenine hydrochloride is mildly sedative in rats. Sinomenine hydrochloride at 80 mg/kg i.p. does not produce any observable side effects in mice. I.p or p.o. Sinomenine hydrochloride at 40 or 80 mg/kg dose-dependently reduces mechanical hypersensitivity in nerve injured mice. I.p. Sinomenine hydrochloride 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[2]. At doses of 10 to 40 mg/kg, Sinomenine hydrochloride dose-dependently increases the paw withdrawal threshold. In non-chronic constriction injury (CCI) healthy rats, Sinomenine hydrochloride at the dose range of 10 to 40 mg/kg does not change the immobility behavior in the forced swimming test[3]. 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 cells/well. Following incubation for 24 or 48 h in medium containing different concentrations of Sinomenine hydrochloride, 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 hydrochloride study, different doses of Sinomenine hydrochloride (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 hydrochloride treatment, mechanical hyperalgesia measure is performed 3 h after daily drug treatment. For antagonist studies, antagonists are given 10 min prior to 40 mg/kg Sinomenine hydrochloride 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]. 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. [3]. 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 Boiling Point 513.6ºC at 760 mmHg Melting Point 231.0 to 235.0 °C Molecular Formula C19H24ClNO4 Molecular Weight 365.851 Flash Point 264.4ºC Exact Mass 365.139374 PSA 59.00000 LogP 2.75800 Appearance of Characters white to beige Storage condition 2-8°C Water Solubility H2O: soluble20mg/mL, clear |
| Use of | Sinomenine hydrochloride is a blocker of the NF-κB activation and also an activator of μ-opioid receptor. Properties Name Sinomenine Hydrochloride Synonym More Synonyms Sinomenine HCl Biological Activity Description Sinomenine hydrochloride is a blocker of the NF-κB activation and also an activator of μ-opioid receptor. Related Catalog Signaling Pathways >> GPCR/G Protein >> Opioid Receptor Signaling Pathways >> Neuronal Signaling >> Opioid Receptor Natural Products >> Alkaloid Research Areas >> Neurological Disease Research Areas >> Cancer Research Areas >> Inflammation/Immunology μ-opioid receptor References [2]. 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. [3]. 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 Exact Mass 365.139374 PSA 59.00000 LogP 2.75800 Appearance of Characters white to beige |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available See reverse side of invoice or packing slip. |
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