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6080-33-7

6080-33-7 structure
6080-33-7 structure
  • Name: Sinomenine HCl
  • Chemical Name: Sinomenine Hydrochloride
  • CAS Number: 6080-33-7
  • Molecular Formula: C19H24ClNO4
  • Molecular Weight: 365.851
  • Catalog: Biochemical Plant extracts
  • Create Date: 2018-07-21 21:12:12
  • Modify Date: 2025-08-22 12:11:34
  • Sinomenine hydrochloride is a blocker of the NF-κB activation and also an activator of μ-opioid receptor.
Name Sinomenine Hydrochloride
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)
Description Sinomenine hydrochloride is a blocker of the NF-κB activation and also an activator of μ-opioid receptor.
Related Catalog
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.
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 white to beige
Storage condition 2-8°C
Water Solubility H2O: soluble20mg/mL, clear

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 DATA

ACUTE 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
Hazard Codes Xi
Safety Phrases 24/25
RIDADR NONH for all modes of transport
RTECS QD2163000
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