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  • China
  • Product Name: Securinine
  • Price: ¥Inquiry/5mg
  • Purity: 98.0%
  • Stocking Period: 10 Day
  • Contact: Xueping-Zheng



5610-40-2

5610-40-2 structure
5610-40-2 structure

Name Securinine
Synonyms 1,2,3,4,10,10a-Hexahydro-10-hydroxy
securinine
securinin
Securinan-11-one (9CI)
(1S,2R,8S)-14-Oxa-7-azatetracyclo[6.6.1.0.0]pentadeca-9,11-dien-13-one
8H-6,11b-Methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one, 9,10,11,11a-tetrahydro-, (6S,11aR,11bS)-
Securan one
(6S,11aR,11bS)-9,10,11,11a-Tetrahydro-8H-6,11b-methanofuro(2,3-c)pyrido(1,2-a)azepin-2(6H)-one
(6S,11aR,11bS)-9,10,11,11a-Tetrahydro-8H-6,11b-methanofuro[2,3-c]-pyrido[1,2-a]azepin-2(6H)-one
SECURAN-11-ONE
Securinan-11-one
Securinan-11-on
(-)-Securinine
Description (-)-Securinine is plant-derived alkaloid and also a GABAA receptor antagonist.
Related Catalog
Target

GABAA receptor[1]

In Vitro (-)-Securinine is a major plant-derived alkaloid and also a GABAA receptor antagonist. (-)-Securinine is significantly potent on HeLa cells growth inhibition with IC50 values of 7.02±0.52 μg/mL (32.3 μM). (-)-Securinine induces apoptosis in a dose-dependent manner in the tested cells, increases the percentage of ROS positive cells and depolarized cells as well as stimulates the activity of ERK1/2, caspase-9 and -3/7. (-)-Securinine also induces cell cycle arrest in S phase. Real-time PCR analysis shows high expression of tumor necrosis factor receptor superfamily (TNFRSF) genes in the cells stimulated with (-)-Securinine[1].
In Vivo In this tumor model, tumor growth is significantly impaired with (-)-Securinine treatment indicating that (-)-Securinine has potential as an Acute Myeloid Leukemia (AML) therapeutic. (-)-Securinine treated mice (n=5 mice, bilateral tumors), exhibit an average of more than 75% smaller tumors than vehicle treated mice at the end of the study period[2].
Kinase Assay The cells are seeded in 12-well plates (1×105/well) and treated with (-)-Securinine at concentrations of 1.0 to 50.0 μg/mL. The control cells are exposed to DMSO at a concentration of 0.5% (v/v). After 6 h and 24 h of exposure, the activity of caspase-9 is measured by Caspase-Glo 9 Assay Kit and Glomax Multi+ Detection System, according to the manufacturer’s instruction. The activity of caspase-3/7 is assessed after 24 h of exposure the cells to (-)-Securinine. Then the cells are harvested and prepared using Muse Caspase-3/7 Assay Kit according with the manufacturer’s protocol. The stained cells are analyzed by Muse Cell Analyzer. The experiments are performed at least in three independent repeats[1].
Cell Assay The viability of the cells is determined by MTT assay. HeLa cells are seeded in 96-well plates at a density of 5×103 cells/well and treated for 24 h with (-)-Securinine in the concentration range of 1.0 to 20.0 μg/mL. The maximal concentrations of the solvents used in all the MTT experiments are 5.0% (v/v) and 1.0% (v/v) for methanol and DMSO, respectively. The absorption of the obtained formazan solution is measured with a plate reader. The viability results are presented as IC50 mean values of at least three independent experiments[1].
Animal Admin 6 week old female nude mice are used and injected bilaterally s.c. with 10×106 HL-60 cells. (-)-Securinine treatment is started 10 days after tumor cell injection. Palpable tumors are present for the established tumor model prior to initiating drug treatment. 15 mg/kg of (-)-Securinine or vehicle (30 µL of DMSO and 70 µL of water) are injected i.p. 2 or 3 times a day for 5 days followed by once a day for two days. This injection schedule is repeated for two additional weeks[2].
References

[1]. Stefanowicz-Hajduk J, et al. Securinine from Phyllanthus glaucus Induces Cell Cycle Arrest and Apoptosis in Human Cervical Cancer HeLa Cells. PLoS One. 2016 Oct 28;11(10):e0165372.

[2]. Kalpana Gupta, et al. Securinine, a Myeloid Differentiation Agent with Therapeutic Potential for AML. PLoS One. 2011; 6(6): e21203.

Density 1.3±0.1 g/cm3
Boiling Point 459.0±45.0 °C at 760 mmHg
Melting Point 140-142ºC
Molecular Formula C13H15NO2
Molecular Weight 217.264
Flash Point 197.0±19.6 °C
Exact Mass 217.110275
PSA 29.54000
LogP 0.60
Vapour Pressure 0.0±1.1 mmHg at 25°C
Index of Refraction 1.633
Storage condition 2-8C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VS4115000
CHEMICAL NAME :
Securinine, (-)-
CAS REGISTRY NUMBER :
5610-40-2
LAST UPDATED :
199201
DATA ITEMS CITED :
18
MOLECULAR FORMULA :
C13-H15-N-O2
MOLECULAR WEIGHT :
217.29

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>800 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CHHTAT Zhonghua Yixue Zazhi. Chinese Medical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1915- Suspended 1967-72. Volume(issue)/page/year: 54,234,1974
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
41 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
REFERENCE :
CHHTAT Zhonghua Yixue Zazhi. Chinese Medical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1915- Suspended 1967-72. Volume(issue)/page/year: 54,234,1974
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
15100 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
REFERENCE :
CHHTAT Zhonghua Yixue Zazhi. Chinese Medical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1915- Suspended 1967-72. Volume(issue)/page/year: 54,234,1974
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
17400 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
REFERENCE :
CHHTAT Zhonghua Yixue Zazhi. Chinese Medical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1915- Suspended 1967-72. Volume(issue)/page/year: 54,234,1974
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4300 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 83,800,1963
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
270 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
REFERENCE :
CHHTAT Zhonghua Yixue Zazhi. Chinese Medical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1915- Suspended 1967-72. Volume(issue)/page/year: 54,234,1974
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
31800 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
REFERENCE :
CHHTAT Zhonghua Yixue Zazhi. Chinese Medical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1915- Suspended 1967-72. Volume(issue)/page/year: 54,234,1974
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
20420 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
REFERENCE :
CHHTAT Zhonghua Yixue Zazhi. Chinese Medical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1915- Suspended 1967-72. Volume(issue)/page/year: 54,234,1974
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
6230 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
REFERENCE :
CHHTAT Zhonghua Yixue Zazhi. Chinese Medical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1915- Suspended 1967-72. Volume(issue)/page/year: 54,234,1974
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
19320 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
REFERENCE :
CHHTAT Zhonghua Yixue Zazhi. Chinese Medical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1915- Suspended 1967-72. Volume(issue)/page/year: 54,234,1974
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>10 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
REFERENCE :
CHHTAT Zhonghua Yixue Zazhi. Chinese Medical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1915- Suspended 1967-72. Volume(issue)/page/year: 54,234,1974
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
>54 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CHHTAT Zhonghua Yixue Zazhi. Chinese Medical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1915- Suspended 1967-72. Volume(issue)/page/year: 54,234,1974
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
8 mg/kg
TOXIC EFFECTS :
Cardiac - pulse rate increase, without fall in BP Behavioral - convulsions or effect on seizure threshold Gastrointestinal - changes in structure or function of salivary glands
REFERENCE :
CHHTAT Zhonghua Yixue Zazhi. Chinese Medical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1915- Suspended 1967-72. Volume(issue)/page/year: 54,234,1974
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
500 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
REFERENCE :
CHHTAT Zhonghua Yixue Zazhi. Chinese Medical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1915- Suspended 1967-72. Volume(issue)/page/year: 54,234,1974
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
10 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Gastrointestinal - changes in structure or function of salivary glands
REFERENCE :
CHHTAT Zhonghua Yixue Zazhi. Chinese Medical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1915- Suspended 1967-72. Volume(issue)/page/year: 54,234,1974
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
10 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - miosis (pupillary constriction) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
CHHTAT Zhonghua Yixue Zazhi. Chinese Medical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1915- Suspended 1967-72. Volume(issue)/page/year: 54,234,1974
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Amphibian - frog
DOSE/DURATION :
>100 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Ear) - change in acuity Behavioral - somnolence (general depressed activity) Kidney, Ureter, Bladder - other changes
REFERENCE :
CHHTAT Zhonghua Yixue Zazhi. Chinese Medical Journal. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1915- Suspended 1967-72. Volume(issue)/page/year: 54,234,1974 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
50 mg/kg
SEX/DURATION :
male 5 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
REFERENCE :
NATWAY Naturwissenschaften. (Springer-Verlag, Heidelberger Platz 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.1- 1913- Volume(issue)/page/year: 52,483,1965
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Hazard Codes T: Toxic;
Risk Phrases R23/24/25
Safety Phrases 36/37/39-45
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS VS4115000