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	ClH
Molecular Weight	36.461
Charge	0
Count

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

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

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 156 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165459	Activator 1447
ERK1 and ERK2 cascade 8 Target ID: GO:0070371 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165459	Inhibitor 8504
Solute carrier family 22 member 1 18 Target ID: CHEMBL5685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26134304	Inhibitor 8504	0.9 µM [IC50]
Solute carrier family 22 member 2 8 Target ID: CHEMBL1743122 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26134304	Inhibitor 8504	2.3 µM [IC50]
Solute carrier family 22 member 3 6 Target ID: CHEMBL2073673 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26134304	Inhibitor 8504	2.3 µM [IC50]
Indoleamine 2,3-dioxygenase 20 Target ID: CHEMBL4685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25079795	Inhibitor 8504	6.3 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Colon cancer 66 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165459	Primary	Preclinical	Unknown Approved Use Unknown
Breast cancer 432 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25081696	Primary	Basic research	Unknown Approved Use Unknown
Non-small cell lung cancer 211 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 72 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14756686	Primary	Basic research	Unknown Approved Use Unknown
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25079795	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Bio-activity evaluation of Qinlian Siwu decoction on inhibiting mice uterine contraction in vitro and its components analysis].	2010-12	21438408
[Simultaneous determination of six alkaloids in Coptis chinensis of different regions by RP-HPLC].	2010-10	21174768
Simultaneous analysis of seven alkaloids in Coptis-Evodia herb couple and Zuojin pill by UPLC with accelerated solvent extraction.	2010-09	20715137
Extractions of isoquinoline alkaloids with butanol and octanol.	2010-09	20117181
[Metabolism, transformation and distribution of Coptis chinensis total alkaloids in rat].	2010-08	20931859
[Pharmacodyamic material basis of rhizoma coptidis on insulin resistance].	2010-07	20939284
Increased plasma exposures of five protoberberine alkaloids from Coptidis Rhizoma in streptozotocin-induced diabetic rats: is P-GP involved?	2010-06	20108175
[Simultaneous determination of the five alkaloids in Rhizoma Coptidis by nonaqueous capillary electrophoresis].	2010-04	20712125
Simultaneous determination of seven main alkaloids of Chelidonium majus L. by ultra-performance LC with photodiode-array detection.	2010-04	20183823
Supramolecular interaction of cucurbit[n]urils and coptisine by spectrofluorimetry and its analytical application.	2010-03-15	20152436
JinQi-Jiangtang tablet, a Chinese patent medicine, for pre-diabetes: a randomized controlled trial.	2010-03-10	20214831
Quality assurance for Chinese herbal formulae: standardization of IBS-20, a 20-herb preparation.	2010-02-22	20175906
Selective regulation of multidrug resistance protein in vascular smooth muscle cells by the isoquinoline alkaloid coptisine.	2010	20410605
Investigation of the anti-fungal activity of coptisine on Candida albicans growth by microcalorimetry combined with principal component analysis.	2009-10	19426275
Significant differences in alkaloid content of Coptis chinensis (Huanglian), from its related American species.	2009-08-24	19703289
Anti-Alzheimer and antioxidant activities of Coptidis Rhizoma alkaloids.	2009-08	19652386
A rapid and simple determination of protoberberine alkaloids in Rhizoma Coptidis by 1H NMR and its application for quality control of commercial prescriptions.	2009-07-12	19345543
Simple and reliable methods for the determination of sixteen marker components for quality control of Daochi pill by HPLC coupled with diode array detection.	2009-06-18	19533595
Development of a rapid resolution liquid chromatographic method for simultaneous analysis of four alkaloids in Rhizoma coptidis under different cultivation conditions.	2009-06-03	19485228
Simultaneous determination of 11 active components in two well-known traditional Chinese medicines by HPLC coupled with diode array detection for quality control.	2009-05-01	19264437
Purification of alkaloids from Corydalis yanhusuo W. T. Wang using preparative 2-D HPLC.	2009-05	19347864
Hydroxyl radical scavenging activities of isoquinoline alkaloids isolated from Coptis chinensis.	2009-03	19387576
Inhibitory Effects of Coptidis rhizoma and Berberine on Cocaine-induced Sensitization.	2009-03	18955248
[Effect of additives on absorption of Coptis chinensis total alkaloids and pharmacokinetics in mice].	2009-02	19445164
Bear bile: dilemma of traditional medicinal use and animal protection.	2009-01-12	19138420
Covalent bonding of azoles to quaternary protoberberine alkaloids.	2008-12	18781707
[Studies on chemical constituents in the anti-myocardial ischemia effective fraction of Corydalis yanhusuo].	2008-11	19260272
Inhibitory activities of the alkaloids from Coptidis Rhizoma against aldose reductase.	2008-11	19023536
Alkaloids from Corydalis saxicola and their anti-hepatitis B virus activity.	2008-05	18493964
Antimicrobial properties of berberines alkaloids in Coptis chinensis Franch by microcalorimetry.	2008-04-24	17804078
[Analysis of the main components of coptis-evodia herb couple by HPLC-DAD-MS].	2008-03	18630268
[Absorption of coptisine chloride and berberrubine across human intestinal epithelial by using human Caco-2 cell monolayers].	2007-12	18330249
Simultaneous quantification of three alkaloids of Coptidis Rhizoma in rat urine by high-performance liquid chromatography: application to pharmacokinetic study.	2007-12	17891749
Analysis of Central European Corydalis species by nonaqueous capillary electrophoresis-electrospray ion trap mass spectrometry.	2007-08-03	17395190
Comparative analysis of the chemical profile of wild and cultivated populations of Corydalis saxicola by high-performance liquid chromatography.	2007-07-13	17624901
High performance liquid chromatography-mass spectrometry analysis of protoberberine alkaloids in medicine herbs.	2007-04	17536728
[Effect of alkaloids from celandine on calcium accumulation and oxidative phosphorylation in mitochondria depending on their DNA intercalating properties].	2006-11-15	17100287
Simultaneous analysis of alkaloids from Zanthoxylum nitidum by high performance liquid chromatography-diode array detector-electrospray tandem mass spectrometry.	2006-09-18	16730156
Simultaneous analysis of nine active components in Gegen Qinlian preparations by high-performance liquid chromatography with diode array detection.	2006-09	17069251
[Fingerprints of Rhizoma Coptidis from Shizhu by HPLC].	2006-07	17059001
Bioavailabilty and pharmacokinetics of four active alkaloids of traditional Chinese medicine Yanhuanglian in rats following intravenous and oral administration.	2006-06-16	16644173
Selective inhibition of vascular smooth muscle cell proliferation by coptisine isolated from Coptis rhizoma, one of the crude drugs composing Kampo medicines Unsei-in.	2006-05	16635741
[Qualitative and quantitative determination of the main components of huanglianjiedu decoction by HPLC-UV/MS].	2006-04	16856488
Disruption of nucleocytoplasmic trafficking of cyclin D1 and topoisomerase II by sanguinarine.	2006-03-02	16512916
Simultaneous determination of four active alkaloids from a traditional Chinese medicine Corydalis saxicola Bunting. (Yanhuanglian) in plasma and urine samples by LC-MS-MS.	2006-02-02	16356790
Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway.	2006-01-17	16417634
[Studies on the alkaloids from herb of Corydalis adunca].	2005-11	16468373
Double blockade of cell cycle progression by coptisine in vascular smooth muscle cells.	2005-10-15	16140275
Development of monoclonal antibody against isoquinoline alkaloid coptisine and its application for the screening of medicinal plants.	2004-03	19003234
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991-01-01	1710653

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 `Tue Apr 01 19:47:45 GMT 2025` Edited by `admin` on `Tue Apr 01 19:47:45 GMT 2025`
Record UNII	4RSB8UY88E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-119754

Preferred Name

English

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

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

Systematic Name

English

Code System Code Type Description

FDA UNII

4RSB8UY88E