CAS 6451-73-6|Scoulerine

Introduction：Basic information about CAS 6451-73-6|Scoulerine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Scoulerine BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Synonyms

Common Name	Scoulerine
CAS Number	6451-73-6	Molecular Weight	327.374
Density	1.4±0.1 g/cm3	Boiling Point	503.3±50.0 °C at 760 mmHg
Molecular Formula	C₁₉H₂₁NO₄	Melting Point	192ºC
MSDS	/	Flash Point	258.2±30.1 °C

Names

Name	(S)-scoulerine
Synonym	More Synonyms

Scoulerine BiologicalActivity

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	Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>CancerSignaling Pathways >>Neuronal Signaling >>Beta-secretaseSignaling Pathways >>Cell Cycle/DNA Damage >>Microtubule/TubulinSignaling Pathways >>Cytoskeleton >>Microtubule/Tubulin
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.

Chemical & Physical Properties

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
InChIKey	KNWVMRVOBAFFMH-HNNXBMFYSA-N
SMILES	COc1cc2c(cc1O)C1Cc3ccc(OC)c(O)c3CN1CC2

Toxicological Information

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

Safety Information

Hazard Codes	Xi

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

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