CAS 130-86-9|Protopine

Introduction：Basic information about CAS 130-86-9|Protopine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

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

Common Name	Protopine
CAS Number	130-86-9	Molecular Weight	353.369
Density	1.3±0.1 g/cm3	Boiling Point	547.5±49.0 °C at 760 mmHg
Molecular Formula	C₂₀H₁₉NO₅	Melting Point	211ºC
MSDS	ChineseUSA	Flash Point	284.9±29.8 °C
Symbol	GHS06	Signal Word	Danger

Names

Name	protopine
Synonym	More Synonyms

Protopine BiologicalActivity

Description	Protopine, an isoquinoline alkaloid contained in plants in northeast Asia.IC50 Value:Target:In vitro: Protopine was found to reduce nitric oxide (NO), cyclooxygenase-2 (COX-2), and prostaglandin E(2) (PGE(2)) production by LPS-stimulated Raw 264.7 cells, without a cytotoxic effect. Pre-treatment of Raw 264.7 cells with protopine reduced the production of pro-inflammatory cytokines [2]. Protopine is a novel microtubule stabilizer with anticancer activity in HRPC cells through apoptotic pathway by modulating Cdk1 activity and Bcl-2 family of proteins [3]. In HepG2 cells, protopine significantly increased CYP1A1 mRNA levels after 24h exposure at concentrations from 25 and 10 μM. Protopine also dose-dependently increased CYP1A1 and CYP1A2 mRNA levels in human hepatocytes [4].In vivo: Assays were performed on MDA-MB-231 human breast cancer cells, and the result showed that protopine exhibited anti-adhesive and anti-invasion effects in MDA-MB-231 cells; after treatment with protopine for 90 min, the expression of EGFR, ICAM-1, αv-integrin, β1-integrin and β5-integrin were remarkably reduced [1].
Related Catalog	Signaling Pathways >>Others >>OthersNatural Products >>AlkaloidResearch Areas >>Others
References	[1]. Bae DS, et al. Protopine reduces the inflammatory activity of lipopolysaccharide-stimulated murine macrophages. BMB Rep. 2012 Feb;45(2):108-13. [2]. Chen CH, et al. Protopine, a novel microtubule-stabilizing agent, causes mitotic arrest and apoptotic cell death in human hormone-refractory prostate cancer cell lines. Cancer Lett. 2012 Feb 1;315(1):1-11. [3]. Vrba J, et al. Protopine and allocryptopine increase mRNA levels of cytochromes P450 1A in human hepatocytes and HepG2 cells independently of AhR. Toxicol Lett. 2011 Jun 10;203(2):135-41. [4]. He K, et al. Protopine inhibits heterotypic cell adhesion in MDA-MB-231 cells through down-regulation of multi-adhesive factors. Afr J Tradit Complement Altern Med. 2014 Jan 28;11(2):415-24.

Description

Protopine, an isoquinoline alkaloid contained in plants in northeast Asia.IC50 Value:Target:In vitro: Protopine was found to reduce nitric oxide (NO), cyclooxygenase-2 (COX-2), and prostaglandin E(2) (PGE(2)) production by LPS-stimulated Raw 264.7 cells, without a cytotoxic effect. Pre-treatment of Raw 264.7 cells with protopine reduced the production of pro-inflammatory cytokines [2]. Protopine is a novel microtubule stabilizer with anticancer activity in HRPC cells through apoptotic pathway by modulating Cdk1 activity and Bcl-2 family of proteins [3]. In HepG2 cells, protopine significantly increased CYP1A1 mRNA levels after 24h exposure at concentrations from 25 and 10 μM. Protopine also dose-dependently increased CYP1A1 and CYP1A2 mRNA levels in human hepatocytes [4].In vivo: Assays were performed on MDA-MB-231 human breast cancer cells, and the result showed that protopine exhibited anti-adhesive and anti-invasion effects in MDA-MB-231 cells; after treatment with protopine for 90 min, the expression of EGFR, ICAM-1, αv-integrin, β1-integrin and β5-integrin were remarkably reduced [1].

Related Catalog

Signaling Pathways >>Others >>OthersNatural Products >>AlkaloidResearch Areas >>Others

References

[1]. Bae DS, et al. Protopine reduces the inflammatory activity of lipopolysaccharide-stimulated murine macrophages. BMB Rep. 2012 Feb;45(2):108-13.

[2]. Chen CH, et al. Protopine, a novel microtubule-stabilizing agent, causes mitotic arrest and apoptotic cell death in human hormone-refractory prostate cancer cell lines. Cancer Lett. 2012 Feb 1;315(1):1-11.

[3]. Vrba J, et al. Protopine and allocryptopine increase mRNA levels of cytochromes P450 1A in human hepatocytes and HepG2 cells independently of AhR. Toxicol Lett. 2011 Jun 10;203(2):135-41.

[4]. He K, et al. Protopine inhibits heterotypic cell adhesion in MDA-MB-231 cells through down-regulation of multi-adhesive factors. Afr J Tradit Complement Altern Med. 2014 Jan 28;11(2):415-24.

Chemical & Physical Properties

Density	1.3±0.1 g/cm3
Boiling Point	547.5±49.0 °C at 760 mmHg
Melting Point	211ºC
Molecular Formula	C₂₀H₁₉NO₅
Molecular Weight	353.369
Flash Point	284.9±29.8 °C
Exact Mass	353.126312
PSA	57.23000
LogP	3.76
Vapour Pressure	0.0±1.5 mmHg at 25°C
Index of Refraction	1.613
InChIKey	GPTFURBXHJWNHR-UHFFFAOYSA-N
SMILES	CN1CCc2cc3c(cc2C(=O)Cc2ccc4c(c2C1)OCO4)OCO3
Storage condition	Refrigerator

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VS2800000

CAS REGISTRY NUMBER :: 130-86-9

LAST UPDATED :: 199803

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C20-H19-N-O5

MOLECULAR WEIGHT :: 353.40

WISWESSER LINE NOTATION :: T I5 F6 C-10-65 DV JO LO PN VO A&O KH&&T&&J P1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 100 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: 5,24,1953

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 482 mg/kg

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

REFERENCE :: YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23, 1978-88. For publisher information, see ZYZAEU. Volume(issue)/page/year: 16(6),7,1981

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 31 mg/kg

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

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 11,640,1977

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 237 mg/kg

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

REFERENCE :: THERAP Therapie. (Doin, Editeurs, 8, Place de l'Odeon, F-75006 Paris, France) V.1- 1946- Volume(issue)/page/year: 28,767,1973

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 116 mg/kg

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

REFERENCE :: THERAP Therapie. (Doin, Editeurs, 8, Place de l'Odeon, F-75006 Paris, France) V.1- 1946- Volume(issue)/page/year: 28,767,1973

Safety Information

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H301
Precautionary Statements	P301 + P310 + P330
Safety Phrases	24/25
RIDADR	UN 1544
RTECS	VS2800000
Packaging Group	III
Hazard Class	6.1(b)

Synonyms

7-Methyl-6,8,9,16-tetrahydrobis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-one

Protopine

7-Methyl-6,8,9,16-tetrahydro[1,3]dioxolo[5,6]benzo[1,2-c][1,3]dioxolo[4,5]benzo[1,2-g]azecin-15(7H)-on

Biflorine

Protopin

Bis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-one, 6,8,9,16-tetrahydro-7-methyl-

EINECS 204-999-6

4,6,7,14-Tetrahydro-5-methyl-bis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-13(5H)-one

BIFLORIN

Hypercorine

4,6,7,14-Tetrahydro-5-Methyl

Tangeratin

Corydinine

Corydalis C

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