ChemicalBook > CAS DataBase List > PROTOPINE HYDROCHLORIDE

PROTOPINE HYDROCHLORIDE

Product Name: PROTOPINE HYDROCHLORIDE
CAS No.: 6164-47-2
Chemical Name: PROTOPINE HYDROCHLORIDE
Synonyms: Nsc11440;FUMARINE;MACLEYINE;PROTOPINE HCL;PROTOHYPERICIN(RG);Argemonine (protopine;FUMARINE HYDROCHLORIDE;PROTOPINE HYDROCHLORIDE;13a-secoberbin-13a-one,7-methyl-2,3:9,10-bis(methylenedioxy)-hydrochloride;7,13A-Secoberbin-13A-one, 7-methyl-2,3:9,10-bis(methylenedioxy)-, hydrochloride
CBNumber: CB8276092
Molecular Formula: C20H20ClNO5
Formula Weight: 389.83
MOL File: 6164-47-2.mol

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PROTOPINE HYDROCHLORIDE Property

storage temp.: 2-8°C
solubility: Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form: solid

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Safety

Hazard Codes: T
Risk Statements: 25
Safety Statements: 36/37/39-45
RIDADR: 1544
WGK Germany: 3
RTECS: UL2000000
HazardClass: 6.1(b)
PackingGroup: III
Hazardous Substances Data: 6164-47-2(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: P8489
Product name: Protopine hydrochloride
Purity: ≥98%, solid
Packaging: 5mg
Price: $233.5
Updated: 2025/07/31

Cayman Chemical

Product number: 23366
Product name: Protopine (hydrochloride)
Purity: ≥98%
Packaging: 500μg
Price: $93
Updated: 2024/03/01

Cayman Chemical

Product number: 23366
Product name: Protopine (hydrochloride)
Purity: ≥98%
Packaging: 1mg
Price: $166
Updated: 2024/03/01

AK Scientific

Product number: 8223AH
Product name: Protopine hydrochloride
Packaging: 1mg
Price: $282
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: HBL0000189
Product name: PROTOPINE HYDROCHLORIDE
Purity: 95.00%
Packaging: 5MG
Price: $910.32
Updated: 2021/12/16

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PROTOPINE HYDROCHLORIDE Chemical Properties,Usage,Production

Description

Protopine is an alkaloid found in Berberidaceae, Ranunculaceae, Rutaceae, Fumariaceae, and Papaveraceae with diverse biological activities. It inhibits platelet aggregation induced by ADP, arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607), platelet-activating factor (PAF), and collagen in rabbit platelet-rich plasma at a concentration of 100 μM. Protopine inhibits contraction of isolated rat thoracic aorta induced by norepinephrine and is a non-selective inhibitor of I_Ca, I_K, I_K1, and I_Na in guinea pig ventricular myocytes. Protopine inhibits the growth of H. pylori with an MIC₅₀ value of 100 μg/ml. It reduces growth of PC3 and DU145 prostate cancer cells in a dose-dependent manner via induction of mitotic cell cycle arrest. Protopine (0.005 mg/kg) increases latency to first seizure in a mouse model induced by pentylenetetrazole .

Uses

Protopine hydrochloride may be used in the calibration curve preparation for the quantification of alkaloids from Fumaria capreolata using liquid chromatography coupled to diode array detection and electrospray ionization tandem mass spectrometry (LC-DAD-MS) and tandem mass spectrometry(MS/MS). It may also be used as an alkaloid in cytotoxicity and permeability studies carcinogenic cell lines.

General Description

Protopine is a celandine alkaloid and a bioactive compound associated with the plant families including fumariaceae, berberidaceae?and papaveraceae. It is metabolized by demethylenation in the presence of the cytochrome enzymes cytochrome P450 family 2 subfamily d polypeptide 1 (CYP2D1) and cytochrome P450 family 2 subfamily c polypeptide 11 (CYP2C11).

Biochem/physiol Actions

Protopine possesses anti-parasitic, antimicrobial and anti-inflammatory property. It mediates mitotic arrest by favoring tubulin polymerization. Protopine elicits anti-invasive effects in breast cancer tumor progression.. It also provides protection against oxidative stress-induced cell death.

in vivo

Protopine (0.1 and 1 mg/kg, i.p.) hydrochloride alleviates Scopolamine (HY-N0296) (1 mg/kg)-induced memory impairment in mice^[1].
Protopine (5-20 mg/kg, i.v.) hydrochloride inhibits tumor growth and inhibits PI3K/Akt, and induces cleavage of caspase-3 in xenograft BALB/c mice (s.c. with HepG2 or Huh-7 cells)^[2].
Protopine (5-20 mg/kg, i.p.) hydrochloride shows antidepressant-like effect in mice HTR and TST tests^[3].
Protopine (1-4 mg/kg, i.p., once daily for 3 days) hydrochloride shows protective effect on the focal cerebral ischaemic induced injury in rats^[4].

Animal Model:	5-hydroxy-DL-tryptophan (5-HTP)-induced mice model^[3]
Dosage:	5, 10, 20 mg/kg
Administration:	i.p.
Result:	Increased the number of 5-HTP-induced head twitch response (HTR). Decreased the immobility time tested in the Tail suspension test (TST).

References

[1] LEVENT üSTüNES. In Vitro Study of the Anticholinergic and Antihistaminic Activities of Protopine and Some Derivatives[J]. Journal of Natural Products , 1988, 51 5: 1021-1022. DOI: 10.1021/np50059a043
[2] FENG-NIEN KO . Antiplatelet effects of protopine isolated from Corydalis tubers[J]. Thrombosis research, 1989, 56 2: Pages 289-298. DOI: 10.1016/0049-3848(89)90170-9
[3] FENG-NIEN KO . Ca2+-Channel Blockade in Rat Thoracic Aorta by Protopine Isolated from Corydalis Tubers[J]. Japanese journal of pharmacology, 1992, 58 1: Pages 1-9. DOI: 10.1016/s0021-5198(19)39771-9
[4] LONG-SHENG SONG. Electrophysiological effects of protopine in cardiac myocytes: inhibition of multiple cation channel currents[J]. British Journal of Pharmacology, 2009, 129 5: 893-900. DOI: 10.1038/sj.bjp.0703132
[5] GAIL B MAHADY. In vitro susceptibility of Helicobacter pylori to isoquinoline alkaloids from Sanguinaria canadensis and Hydrastis canadensis.[J]. Phytotherapy Research, 2003, 17 3: 217-221. DOI: 10.1002/ptr.1108
[6] CHUN-HAN CHEN . Protopine, a novel microtubule-stabilizing agent, causes mitotic arrest and apoptotic cell death in human hormone-refractory prostate cancer cell lines[J]. Cancer letters, 2012, 315 1: Pages 1-11. DOI: 10.1016/j.canlet.2011.09.042
[7] Y. PROKOPENKO. In Vivo Anticonvulsant Activity of Extracts and Protopine from the Fumaria schleicheri Herb[J]. Scientia Pharmaceutica, 2015, 13 1: 547-554. DOI: 10.3390/scipharm84030547

PROTOPINE HYDROCHLORIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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PROTOPINE HYDROCHLORIDE Suppliers

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6164-47-2, PROTOPINE HYDROCHLORIDERelated Search:

Berberine hydrochloride OPIUM HUNNEMANINE 2-(2-METHYLPHENYL)ACETOPHENONE 6-METHYL-BENZO[1,3]DIOXOLE-5-CARBALDEHYDE CHEMBRDG-BB 5553033 CHEMBRDG-BB 5532546 2-(1,3-BENZODIOXOL-5-YL)-1-PHENYL-1-ETHANONE, 95%+ CHEMBRDG-BB 5545019 3,4-Methylenedioxyacetophenone PIPERONYL METHYL KETONE 3′,4′-(Methylenedioxy)propiophenone PROTOPINE HYDROCHLORIDE Protopine

13a-secoberbin-13a-one,7-methyl-2,3:9,10-bis(methylenedioxy)-hydrochloride

PROTOPINE HCL

PROTOPINE HYDROCHLORIDE

MACLEYINE

FUMARINE

FUMARINE HYDROCHLORIDE

7,13A-Secoberbin-13A-one, 7-methyl-2,3:9,10-bis(methylenedioxy)-, hydrochloride

Argemonine (protopine

Bis[1,3]benzodioxolo[4,5-C:5',6'-G]azecin-13(5H)-one, 4,6,7,14-tetrahydro-5-methyl-, hydrochloride

Nsc11440

PROTOHYPERICIN(RG)

6164-47-2

C20H19NO5HCl

Calcium Channel Modulators

Cell Signaling and Neuroscience

Cell Biology

BioChemical

Inhibitors and Activators

Ion Channels

Voltage-gated Ion Channels

Nutrition Research

Alkaloids

AlkaloidVoltage-gated Ion Channels

Biochemicals Found in Plants

Calcium Channel Modulators

Inhibitors and Activators