Introduction：Basic information about CAS 6080-33-7|Sinomenine HCl, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Sinomenine HCl |
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| CAS Number | 6080-33-7 | Molecular Weight | 365.851 |
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| Density | / | Boiling Point | 513.6ºC at 760 mmHg |
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| Molecular Formula | C19H24ClNO4 | Melting Point | 231.0 to 235.0 °C |
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| MSDS | ChineseUSA | Flash Point | 264.4ºC |
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Names
| Name | Sinomenine Hydrochloride |
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| Synonym | More Synonyms |
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Sinomenine HCl BiologicalActivity
| Description | Sinomenine hydrochloride is a blocker of the NF-κB activation and also an activator of μ-opioid receptor. |
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| Related Catalog | Signaling Pathways >>GPCR/G Protein >>Opioid ReceptorSignaling Pathways >>Neuronal Signaling >>Opioid ReceptorNatural Products >>AlkaloidResearch Areas >>Neurological DiseaseResearch Areas >>CancerResearch Areas >>Inflammation/Immunology |
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| Target | NF-κB μ-opioid receptor |
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| 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]. |
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| 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]. |
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| 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]. |
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| 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]. |
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| 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. |
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Chemical & Physical Properties
| Boiling Point | 513.6ºC at 760 mmHg |
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| Melting Point | 231.0 to 235.0 °C |
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| Molecular Formula | C19H24ClNO4 |
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| Molecular Weight | 365.851 |
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| Flash Point | 264.4ºC |
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| Exact Mass | 365.139374 |
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| PSA | 59.00000 |
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| LogP | 2.75800 |
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| Appearance of Characters | white to beige |
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| Storage condition | 2-8°C |
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| Water Solubility | H2O: soluble20mg/mL, clear |
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Toxicological Information
CHEMICAL IDENTIFICATION - RTECS NUMBER :
- QD2163000
- CHEMICAL NAME :
- 9-alpha,13-alpha,14-alpha-Morphinan-6-one, 7,8-didehydro-3,7-dimethoxy-4-hydroxy-17-methyl-, hydrochloride
- CAS REGISTRY NUMBER :
- 6080-33-7
- LAST UPDATED :
- 198803
- DATA ITEMS CITED :
- 1
- MOLECULAR FORMULA :
- C19-H23-N-O4.Cl-H
- MOLECULAR WEIGHT :
- 365.89
HEALTH HAZARD DATAACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 4830 ug/kg
- TOXIC EFFECTS :
- Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - cyanosis Lungs, Thorax, or Respiration - respiratory depression
- REFERENCE :
- NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 52,157,1956
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Safety Information
| Hazard Codes | Xi |
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| Safety Phrases | 24/25 |
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| RIDADR | NONH for all modes of transport |
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| RTECS | QD2163000 |
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Synonyms
| Morphinan-6-one, 7,8-didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-, (9α,13α,14α)-, hydrochloride (1:1) |
| 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) |
