PALMATINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H22NO4
Molecular Weight	352.4037
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(C=C1OC)C3=CC4=C(C=[N+]3CC2)C(OC)=C(OC)C=C4

InChI

InChIKey=QUCQEUCGKKTEBI-UHFFFAOYSA-N

InChI=1S/C21H22NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,9-12H,7-8H2,1-4H3/q+1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25526561 | http://www.alliedacademies.org/articles/pharmacological-activities-palmatine-alkaloid-compound-isolated-from-guatteria-friesiana-prospects-for-new-drug-development.pdf

Palmatine is a protoberberine alkaloid. Palmatine is major component of herbal preparations mainly used in traditional medicine Chinese, Korean and Indian. Palmatine can be found in various medicinal plants such as Coptis chinensis, Rhizoma coptidis, Corydalis yanhusuo, Radix tinosporae, among others. It exerts diverse pharmacological and biological properties. Palmatine has been proposed as a promising DNA phototherapy drug, notably due to its ability to produce in situ singlet oxygen only when interacting with DNA.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 278 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25526561 \| https://www.ncbi.nlm.nih.gov/pubmed/25829078 \| https://www.ncbi.nlm.nih.gov/pubmed/18421749	Binding Agent 1064
Acetylcholinesterase 207 Target ID: CHEMBL3198 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23193393	Inhibitor 8297
Aryl hydrocarbon receptor 26 Target ID: CHEMBL3201 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24583342	Activator 1430
Cytochrome P450 2D6 61 Target ID: CHEMBL289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25285405	Substrate 661
Cytochrome P450 1A2 72 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25285405	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25043857 https://www.ncbi.nlm.nih.gov/pubmed/27175745 https://www.ncbi.nlm.nih.gov/pubmed/27181460 https://www.ncbi.nlm.nih.gov/pubmed/27444887	Primary	Preclinical	Unknown Approved Use Unknown
Gastric ulcer 67 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27858308	Primary	Preclinical	Unknown Approved Use Unknown
Amnesia 11 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23193393	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Differential inhibitory effects of protoberberines on sterol and chitin biosyntheses in Candida albicans.	1999 May	10382888
Analysis of coptisine, berberine and palmatine in adulterated Chinese medicine by capillary electrophoresis-electrospray ion trap mass spectrometry.	2000 Jan 14	10670817
Human topoisomerase I poisoning by protoberberines: potential roles for both drug-DNA and drug-enzyme interactions.	2000 Jun 20	10852708
Inhibition of type A monoamine oxidase by coptisine in mouse brain.	2001 Dec 28	11833714
Potentiation of nerve growth factor-induced neurite outgrowth in PC12 cells by a Coptidis Rhizoma extract and protoberberine alkaloids.	2002 Nov	12506995
Photostabilization of an entomopathogenic fungus using composite clay matrices.	2003 Feb	12785057
[Study on the solubility changes of Rhizoma Coptidis' main chemical constituents influenced by the proportion of Rhizoma Coptidis and Fructus Evodiae].	2003 Jul	15139107
Coptidis Rhizoma: protective effects against peroxynitrite-induced oxidative damage and elucidation of its active components.	2004 Apr	15099450
Quaternary isoquinoline alkaloids from Xylopia parviflora.	2004 Apr	15081299
Electrophoretic ion migration directly to probe can concentrate charged analyte species for matrix-assisted laser desorption/ionization mass spectrometry.	2005	15645506
Using oxidized carbon nanotubes as matrix for analysis of small molecules by MALDI-TOF MS.	2005 Jun	15907704
Protective role of Coptidis Rhizoma alkaloids against peroxynitrite-induced damage to renal tubular epithelial cells.	2005 Mar	15807993
[Studies on the alkaloids from herb of Corydalis adunca].	2005 Nov	16468373
[HPLC fingerprint for the Corydalis saxicola Bunting injection].	2005 Sep	16342690
Evaluation of Cytotoxic Effects of Dichloromethane Extract of Guduchi (Tinospora cordifolia Miers ex Hook F & THOMS) on Cultured HeLa Cells.	2006 Jun	16786058
Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.). 2. Palmatine, hydrastine, canadine, and hydrastinine.	2006 Jun	16780351
Simultaneous determination of berberine and palmatine in rat plasma by HPLC-ESI-MS after oral administration of traditional Chinese medicinal preparation Huang-Lian-Jie-Du decoction and the pharmacokinetic application of the method.	2006 Mar 18	16293389
Disruption of nucleocytoplasmic trafficking of cyclin D1 and topoisomerase II by sanguinarine.	2006 Mar 2	16512916
RNA specific molecules: cytotoxic plant alkaloid palmatine binds strongly to poly(A).	2006 May 1	16497501
Hypoglycemic and hypocholesterolemic effects of Coptis chinensis franch inflorescence.	2006 Sep	17031605
Cytochrome P3A4 inhibitors and other constituents of Fibraurea tinctoria.	2007 Dec	17994701
DNA-binding affinities and sequence specificities of protoberberine alkaloids and their demethylated derivatives: a comparative study.	2007 Feb	17311227
Interaction of isoquinoline alkaloid palmatine with deoxyribonucleic acids: binding heterogeneity, and conformational and thermodynamic aspects.	2008 Apr	18421749
Antimicrobial properties of berberines alkaloids in Coptis chinensis Franch by microcalorimetry.	2008 Apr 24	17804078
The microenvironment of DNA switches the activity of singlet oxygen generation photosensitized by berberine and palmatine.	2008 Jan-Feb	18173721
Simultaneous determination of eight bioactive alkaloids in Corydalis saxicola by high-performance liquid chromatography coupled with diode array detection.	2008 Sep-Oct	18446771

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 0.5 or 1 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

Mouse preosteoclastic cell line (RAW 264.7) has a higher sensitivity to palmatine than mouse osteoblastic cell line (MC3T3-E1); the cell survival rates significantly decreased at 40 μM palmatine.

Name

Type

Language

PALMATINE

Official Name

English

BERBERICININE

Common Name

English

5,6-DIHYDRO-2,3,9,10-TETRAMETHOXYDIBENZO(A,G)QUINOLIZINIUM

Systematic Name

English

PALMATINE (NEGATIVE MARKER) (CONSTITUENT OF GOLDENSEAL) [DSC]

Common Name

English

O,O-DIMETHYLDEMETHYLENEBERBERINE

Common Name

English

PALMATINE [INCI]

Common Name

English

PALMATINE [MI]

Common Name

English

PALMATINE CATION

Common Name

English

PALMATINE ION

Common Name

English

Palmatine [WHO-DD]

Common Name

English

Code System Code Type Description

PUBCHEM

19009