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6451-73-6

6451-73-6 structure
6451-73-6 structure
  • Name: Scoulerine
  • Chemical Name: (S)-scoulerine
  • CAS Number: 6451-73-6
  • Molecular Formula: C19H21NO4
  • Molecular Weight: 327.374
  • Catalog: Natural product Alkaloid
  • Create Date: 2018-08-20 15:31:46
  • Modify Date: 2025-08-21 13:10:37
  • Scoulerine ((-)-Scoulerine), an isoquinoline alkaloid, is a potent antimitotic compound. Scoulerine is also an inhibitor of BACE1 (ß-site amyloid precursor protein cleaving enzyme 1). Scoulerine inhibits proliferation, arrests cell cycle, and induces apoptosis in cancer cells[1].
Name (S)-scoulerine
Synonyms 2,9-DIOXY-3,10-DIMETHOXYBERBINE
(±)-Scoulerine
3,10-Dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-2,9-diol
6H-Dibenzo(a,g)quinolizine-2,9-diol, 5,8,13,13a-tetrahydro-3,10-dimethoxy-
6H-Dibenzo[a,g]quinolizine-2,9-diol, 5,8,13,13a-tetrahydro-3,10-dimethoxy-
Scoulerin
Aequaline
Alkaloid HF-1
l-scoulerine
(RS)-Scoulerine
scoulerine
l-skoulerine
Description Scoulerine ((-)-Scoulerine), an isoquinoline alkaloid, is a potent antimitotic compound. Scoulerine is also an inhibitor of BACE1 (ß-site amyloid precursor protein cleaving enzyme 1). Scoulerine inhibits proliferation, arrests cell cycle, and induces apoptosis in cancer cells[1].
Related Catalog
In Vitro Scoulerine ((-)-Scoulerine) inhibits mini-panel of human leukemic cells, MOLT-4 (WT), Jurkat (TP53 mutated), Raji (TP53 mutated), HL-60 (TP53 null), U-937 (TP53 mutated), and HEL 92.1.7 (wild-type), with IC50s ranging from 2.7 µM to 6.5 µM[1]. Scoulerine (2.5-20 µM; 24 hours) decreases proliferation of Jurkat and MOLT-4 cells[1]. Scoulerine (2.5-20 µM; 24 hours) induces MOLT-4 and Jurkat cells apoptosis[1]. Scoulerine induces G2 or M cell cycle arrest[1]. Scoulerine (2.5-5 µM; 24 hours) shows an upregulation of p53 protein in p53 wild-type MOLT-4 cells[1]. Scoulerine (2.5-5 µM; 24-48 hours) activates caspase-3/7, -8 and -9 in a dose-dependent manner[1]. Scoulerine (5-10 µM; 24 hours) disrupts microtubule structure of A549 lung carcinoma cells[1] Cell Proliferation Assay[1] Cell Line: Jurkat and MOLT-4 cells Concentration: 2.5, 5, 10, 15 and 20 µM Incubation Time: 24 hours Result: Significantly reduced the viability and proliferation of Jurkat and MOLT-4 cells in a dose dependent manner. Apoptosis Analysis[1] Cell Line: MOLT-4 and Jurkat cells Concentration: 2.5, 5, 10, 15 and 20 µM Incubation Time: 24 hours Result: Induced MOLT-4 and Jurkat cells apoptosis. Cell Cycle Analysis[1] Cell Line: Jurkat and MOLT-4 leukemic cells Concentration: 2.5-20 µM Incubation Time: 16 hours Result: Induced cell cycle arrest at the G2/M transition. Western Blot Analysis[1] Cell Line: MOLT-4 cells Concentration: 2.5, 5 µM Incubation Time: 24 hours Result: Showed an upregulation of p53 protein in p53 wild-type MOLT-4 cells.
References

[1]. Habartova K, et al. Scoulerine affects microtubule structure, inhibits proliferation, arrests cell cycle and thus culminates in the apoptotic death of cancer cells. Sci Rep. 2018;8(1):4829. Published 2018 Mar 19.
Density 1.4±0.1 g/cm3
Boiling Point 503.3±50.0 °C at 760 mmHg
Melting Point 192ºC
Molecular Formula C19H21NO4
Molecular Weight 327.374
Flash Point 258.2±30.1 °C
Exact Mass 327.147064
PSA 62.16000
LogP 2.16
Vapour Pressure 0.0±1.3 mmHg at 25°C
Index of Refraction 1.680

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DR9808600
CHEMICAL NAME :
13a-alpha-Berbine-2,9-diol, 3,10-dimethoxy-
CAS REGISTRY NUMBER :
6451-73-6
LAST UPDATED :
199012
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C19-H21-N-O4
MOLECULAR WEIGHT :
327.41
WISWESSER LINE NOTATION :
T D6 B666 KN&TT&J GO1 HQ PO1 QQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NCNSA6 National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. (Washington, DC) Volume(issue)/page/year: 5,26,1953
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
275 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
REFERENCE :
MZUZA8 Meditsinskii Zhurnal Uzbekistana. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) No.1- 1957- Volume(issue)/page/year: (6),39,1977
Hazard Codes Xi
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