CAS 5853-29-2|Cephaeline Dihydrochloride

Introduction：Basic information about CAS 5853-29-2|Cephaeline Dihydrochloride, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

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

Common Name	Cephaeline Dihydrochloride
CAS Number	5853-29-2	Molecular Weight	539.53
Density	/	Boiling Point	/
Molecular Formula	C₂₈H₄₀Cl₂N₂O₄	Melting Point	/
MSDS	/	Flash Point	/

Names

Name	(-)-cephaeline dihydrochloride
Synonym	More Synonyms

Cephaeline Dihydrochloride BiologicalActivity

Description	(-)-Cephaeline dihydrochloride is an enantiomer of Cephaeline dihydrochloride. Cephaeline dihydrochloride is a selective CYP2D6 inhibtor with IC50 of 121 μM.
Related Catalog	Signaling Pathways >>Metabolic Enzyme/Protease >>Cytochrome P450Research Areas >>Others
Target	IC50: 121 μM (CYP2D6)[1] Ki: 54 μM (CYP2D6)[1]
In Vitro	CYP2D6 reveals the highest metabolic activity for the generation of 9-O-demethylEmetine, whereas this enzyme also shows a significant metabolic activity for the generation of Cephaeline. IC50 of Cephaeline against CYP2C9, CYP2D6 and CYP3A4 is over 1000, 121 and 1000 μM, respectively. Further experiments are performed to determine inhibition constants (Ki) for Cephaeline on the CYP2D6 and CYP3A4 activities Graphic analysis of Dixon plots at various Cephaeline concentrations for each of the two CYP enzyme assays yield Kis of 54 and 355 μM for CYP2D6 and CYP3A4, respectively[1].
Kinase Assay	Cephaeline is dissolved in methanol to give concentrations of 0.1, 1, 10, 100 μM (only theophylline-O-demethylase activity with Cephaeline; 0.0985, June 2001 679 0.985, 9.85, 98.5 μM) [1]. Human liver microsomal protein is incubated with the selected marker substrates in the absence and presence of above concentrations of Cephaeline or Emetine (1-100 μM, only theophylline-O-demethylase activity with Cephaeline; 0.0985—98.5 μM, final concentration). Incubation conditions are chosen such that the product formation is linear with respect to both incubation times and protein concentrations, with substrate concentrations being at or below the Km for each enzyme. The effects of furafylline, sulphaphenazole, tranylcypromine, quinidine, and ketoconazole, selective inhibitors of CYP1A2, CYP2C9, CYP2C19, CYP2D6 and CYP3A4, respectively, are also determined in the same microsomal samples to provide comparisons with inhibitory potentials (IC50) of Cephaeline and Emetine towards the individual CYP form. The Ki s for Cephaeline and Emetine are determined by using the same pooled microsomal sample. This is achieved by varying the initial substrate concentrations (bufuralol 8, 16 and 32 μM; testosterone 45, 90 and 180u M) and using several inhibitor concentrations of 10, 50, and 100 μM. The Kis are estimated by graphic analysis of Dixon plots. These values are subsequently used as initial estimates for the nonlinear least-squares regression analysis[1].
References	[1]. Asano T, et al. Metabolism of ipecac alkaloids Cephaeline and Emetine by human hepatic microsomal cytochrome P450s, and their inhibitory effects on P450 enzyme activities. Biol Pharm Bull. 2001 Jun;24(6):678-82.

Chemical & Physical Properties

Molecular Formula	C₂₈H₄₀Cl₂N₂O₄
Molecular Weight	539.53
PSA	63.19000
LogP	5.70910
InChIKey	YAOHSWWVTZSRQM-JBKGYMEJSA-N
SMILES	CCC1CN2CCc3cc(OC)c(OC)cc3C2CC1CC1NCCc2cc(O)c(OC)cc21.Cl.Cl

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FJ9450000

CHEMICAL NAME :: Cephaeline hydrochloride

CAS REGISTRY NUMBER :: 5853-29-2

LAST UPDATED :: 199206

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C28-H38-N2-O4.2Cl-H

MOLECULAR WEIGHT :: 539.60

WISWESSER LINE NOTATION :: T B666 GNTT&J E2 LO1 MO1 D1- BT66 CMT&J HQ IO1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 10 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 104,421,1952

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 6500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 10,73,1917/1918

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 74970 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NCISP* National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. (Bethesda, MD 20205) Volume(issue)/page/year: JAN1986

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 20530 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NCISP* National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. (Bethesda, MD 20205) Volume(issue)/page/year: JAN1986

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 8 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 10,73,1917/1918

Safety Information

RIDADR	1544
Packaging Group	III
Hazard Class	6.1(b)

Synonyms

10,11,7'-Trimethoxy-emetan-6'-ol,Hydrochlorid

cephaeline dihydrochloride

10,11,7'-trimethoxy-emet-1'-ene-9,6'-diol

Alangicine

10,11,7'-trimethoxy-emetan-6'-ol,dihydrochloride

10,11,7'-Trimethoxy-emetan-6'-ol,Dihydrochlorid

EINECS 227-463-3

(-)-Cephaeline (dihydrochloride)

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