Coptisine chloride

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H14NO4.Cl
Molecular Weight	355.772
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Cl-].C1OC2=C(O1)C=C3C(CC[N+]4=C3C=C5C=CC6=C(OCO6)C5=C4)=C2

InChI

InChIKey=LUXPUVKJHVUJAV-UHFFFAOYSA-M

InChI=1S/C19H14NO4.ClH/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14;/h1-2,5-8H,3-4,9-10H2;1H/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula	C19H14NO4
Molecular Weight	320.3188
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25079795 | https://www.ncbi.nlm.nih.gov/pubmed/26228628 | https://www.ncbi.nlm.nih.gov/pubmed/26134304

Coptisine (COP), a protoberberine alkaloid, is widely found in Chinese medicinal plants (family Berberidaceae, Ranunculaceae and Papaveraceae). It is reported that COP has a wide range of pharmacological and biological activities, including antibacterial, hypoglycemic, anti-tumorigenic, and gastric-mucous membrane protection. Considerable attention has been focused on its activity against central nervous system disorders, such as improving the symptoms of Alzheimer’s disease and even preventing its onset, by exerting antidepressant effects as a potent type A monoamine oxidase inhibitor. Coptisine was found to be an efficient uncompetitive Indoleamine 2,3-dioxygenase inhibitor. Coptisine is a potent inhibitor of human organic cation transporters.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165459	Activator 1430
ERK1 and ERK2 cascade 8 Target ID: GO:0070371 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165459	Inhibitor 8297
Solute carrier family 22 member 1 18 Target ID: CHEMBL5685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26134304	Inhibitor 8297	0.9 µM [IC50]
Solute carrier family 22 member 2 8 Target ID: CHEMBL1743122 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26134304	Inhibitor 8297	2.3 µM [IC50]
Solute carrier family 22 member 3 6 Target ID: CHEMBL2073673 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26134304	Inhibitor 8297	2.3 µM [IC50]
Indoleamine 2,3-dioxygenase 19 Target ID: CHEMBL4685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25079795	Inhibitor 8297	6.3 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Colon cancer 62 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165459	Primary	Preclinical	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25081696	Primary	Basic research	Unknown Approved Use Unknown
Non-small cell lung cancer 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28351307	Primary	Basic research	Unknown Approved Use Unknown
Osteosarcoma 22 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24607417	Primary	Preclinical	Unknown Approved Use Unknown
Hepatoma 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14756686	Primary	Basic research	Unknown Approved Use Unknown
Leukemia 87 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14756686	Primary	Basic research	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25079795	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991 Jan-Feb	1710653
Potentiation of nerve growth factor-induced neurite outgrowth in PC12 cells by a Coptidis Rhizoma extract and protoberberine alkaloids.	2002 Nov	12506995
Positive cooperation of protoberberine type 2 alkaloids from Corydalis cava on the GABA(A) binding site.	2003 Apr	12709895
Chemical comparison of goldenseal (Hydrastis canadensis L.) root powder from three commercial suppliers.	2003 Dec 3	14640583
Cytotoxic effects of Coptis chinensis and Epimedium sagittatum extracts and their major constituents (berberine, coptisine and icariin) on hepatoma and leukaemia cell growth.	2004 Jan-Feb	14756686
Development of monoclonal antibody against isoquinoline alkaloid coptisine and its application for the screening of medicinal plants.	2004 Mar	19003234
Sensitivity improvement on detection of Coptidis alkaloids by sweeping in capillary electrophoresis.	2005 Feb 7	15664741
Spectrometric studies of cytotoxic protoberberine alkaloids binding to double-stranded DNA.	2005 Mar 1	15698803
[Qualitative and quantitative determination of the main components of huanglianjiedu decoction by HPLC-UV/MS].	2006 Apr	16856488
[Fingerprints of Rhizoma Coptidis from Shizhu by HPLC].	2006 Jul	17059001
[Effect of alkaloids from celandine on calcium accumulation and oxidative phosphorylation in mitochondria depending on their DNA intercalating properties].	2006 Mar-Apr	17100287
Selective inhibition of vascular smooth muscle cell proliferation by coptisine isolated from Coptis rhizoma, one of the crude drugs composing Kampo medicines Unsei-in.	2006 May	16635741
Simultaneous analysis of nine active components in Gegen Qinlian preparations by high-performance liquid chromatography with diode array detection.	2006 Sep	17069251
Simultaneous analysis of alkaloids from Zanthoxylum nitidum by high performance liquid chromatography-diode array detector-electrospray tandem mass spectrometry.	2006 Sep 18	16730156
High performance liquid chromatography-mass spectrometry analysis of protoberberine alkaloids in medicine herbs.	2007 Apr	17536728
Analysis of Central European Corydalis species by nonaqueous capillary electrophoresis-electrospray ion trap mass spectrometry.	2007 Aug 3	17395190
Simultaneous quantification of three alkaloids of Coptidis Rhizoma in rat urine by high-performance liquid chromatography: application to pharmacokinetic study.	2007 Dec	17891749
Comparative analysis of the chemical profile of wild and cultivated populations of Corydalis saxicola by high-performance liquid chromatography.	2007 Sep-Oct	17624901
Antimicrobial properties of berberines alkaloids in Coptis chinensis Franch by microcalorimetry.	2008 Apr 24	17804078
Selective regulation of multidrug resistance protein in vascular smooth muscle cells by the isoquinoline alkaloid coptisine.	2010	20410605
[Simultaneous determination of the five alkaloids in Rhizoma Coptidis by nonaqueous capillary electrophoresis].	2010 Apr	20712125
JinQi-Jiangtang tablet, a Chinese patent medicine, for pre-diabetes: a randomized controlled trial.	2010 Mar 10	20214831
Simultaneous analysis of seven alkaloids in Coptis-Evodia herb couple and Zuojin pill by UPLC with accelerated solvent extraction.	2010 Sep	20715137

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 50,100 or 150mg/kg body weight daily

Route of Administration: Oral

In Vitro Use Guide

In HCT-116 cells, Coptisine exhibited cell cytotoxicity at a high rate (IC50 was 27.13 μg/mL vs 282.2 μg/mL in human colorectal epithelial cells FHC). Besides, Coptisine (2.5 μg/mL) decreased the survival rate of cells time-dependently .

Substance Class	Chemical Created by `admin` on `Sat Dec 16 12:47:48 GMT 2023` Edited by `admin` on `Sat Dec 16 12:47:48 GMT 2023`
Record UNII	4RSB8UY88E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Coptisine chloride

Common Name

English

Coptisine hydrochloride

Common Name

English

Bis[1,3]benzodioxolo[5,6-a:4′,5′-g]quinolizinium, 6,7-dihydro-, chloride (1:1)

Systematic Name

English

NSC-119754

Code

English

Berbinium, 7,8,13,13a-tetradehydro-2,3:9,10-bis(methylenedioxy)-, chloride

Systematic Name

English

Code System Code Type Description

FDA UNII

4RSB8UY88E