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=C(OC)C=C2C(CC[N+]3=CC4=C(C=CC(OC)=C4OC)C=C23)=C1

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

Molecular Formula	C21H22NO4
Molecular Weight	352.4037
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/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 282 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 1076
Acetylcholinesterase 209 Target ID: CHEMBL3198 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23193393	Inhibitor 8504
Aryl hydrocarbon receptor 27 Target ID: CHEMBL3201 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24583342	Activator 1447
Cytochrome P450 2D6 62 Target ID: CHEMBL289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25285405	Substrate 661
Cytochrome P450 1A2 73 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25285405	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Cancer 609 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 74 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
Pharmacological and therapeutic effects of Berberis vulgaris and its active constituent, berberine.	2008-08	18618524
Identification of major alkaloids and steroidal saponins in rat serum by HPLC-diode array detection-MS/MS following oral administration of Huangbai-Zhimu herb-pair Extract.	2008-08	18318017
Self-structure induction in single stranded poly(A) by small molecules: Studies on DNA intercalators, partial intercalators and groove binding molecules.	2008-06-01	18387354
Simultaneous determination of eight bioactive alkaloids in Corydalis saxicola by high-performance liquid chromatography coupled with diode array detection.	2008-05-01	18446771
Analysis of major alkaloids in Rhizoma coptidis by capillary electrophoresis-electrospray-time of flight mass spectrometry with different background electrolytes.	2008-05	18425753
Antimicrobial properties of berberines alkaloids in Coptis chinensis Franch by microcalorimetry.	2008-04-24	17804078
Analysis of alkaloids in Coptis chinensis Franch by accelerated solvent extraction combined with ultra performance liquid chromatographic analysis with photodiode array and tandem mass spectrometry detections.	2008-04-21	18395058
Interaction of isoquinoline alkaloid palmatine with deoxyribonucleic acids: binding heterogeneity, and conformational and thermodynamic aspects.	2008-04	18421749
Simultaneous determination of berberine, palmatine and jatrorrhizine by liquid chromatography-tandem mass spectrometry in rat plasma and its application in a pharmacokinetic study after oral administration of coptis-evodia herb couple.	2008-03-01	18258496
Palmatine, a protoberberine alkaloid, inhibits both Ca(2+)- and cAMP-activated Cl(-) secretion in isolated rat distal colon.	2008-03	18204477
Studies on alkaloids binding to GC-rich human survivin promoter DNA using positive and negative ion electrospray ionization mass spectrometry.	2008-03	17968851
The microenvironment of DNA switches the activity of singlet oxygen generation photosensitized by berberine and palmatine.	2008-01-05	18173721
Fast fluorescent staining of protein in sodium dodecyl sulfate polyacrylamide gels by palmatine.	2008-01	18081205
Cytochrome P3A4 inhibitors and other constituents of Fibraurea tinctoria.	2007-12	17994701
Simultaneous quantification of three alkaloids of Coptidis Rhizoma in rat urine by high-performance liquid chromatography: application to pharmacokinetic study.	2007-12	17891749
Main antimicrobial components of Tinospora capillipes, and their mode of action against Staphylococcus aureus.	2007-09-04	17692848
Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.) 3: effect on human lens and retinal pigment epithelial cells.	2007-07-25	17645667
Free radical scavenging activity and lipoxygenase inhibition of Mahonia aquifolium extract and isoquinoline alkaloids.	2007-07-16	17634120
Determination of palmatine in canine plasma by liquid chromatography-tandem mass spectrometry with solid-phase extraction.	2007-07-01	17537686
Molecular recognition of DNA by small molecules: AT base pair specific intercalative binding of cytotoxic plant alkaloid palmatine.	2007-07	17434677
Affinity chromatography with immobilized DNA stationary phase for biological fingerprinting analysis of traditional Chinese medicines.	2007-06-22	17451725
Analysis of berberine and total alkaloid content in cortex phellodendri by near infrared spectroscopy (NIRS) compared with high-performance liquid chromatography coupled with ultra-visible spectrometric detection.	2007-06-05	17512816
Thin-layer chromatography/desorption electrospray ionization mass spectrometry: investigation of goldenseal alkaloids.	2007-04-01	17338504
High performance liquid chromatography-mass spectrometry analysis of protoberberine alkaloids in medicine herbs.	2007-04	17536728
Simultaneous determination of eight components in Radix Tinosporae by high-performance liquid chromatography coupled with diode array detector and electrospray tandem mass spectrometry.	2007-02-19	17084577
Amplification of DNA-binding affinities of protoberberine alkaloids by appended polyamines.	2007-02-15	17127054
DNA-binding affinities and sequence specificities of protoberberine alkaloids and their demethylated derivatives: a comparative study.	2007-02	17311227
RNA binding small molecules: studies on t-RNA binding by cytotoxic plant alkaloids berberine, palmatine and the comparison to ethidium.	2007-02	17156912
Identification of palmatine and its metabolites in rat urine by liquid chromatography/tandem mass spectrometry.	2007	17534853
Molecular aspects on the specific interaction of cytotoxic plant alkaloid palmatine to poly(A).	2006-11-15	16678250
[Determination of 3 kinds of components in huanglian jiedu decoction by HPLC under different UV wavelengths].	2006-10	17225535
[Quality analysis and evaluation of Rhizoma Coptidis under different cultivation conditions].	2006-10	17184122
Simultaneous analysis of nine active components in Gegen Qinlian preparations by high-performance liquid chromatography with diode array detection.	2006-09	17069251
Hypoglycemic and hypocholesterolemic effects of Coptis chinensis franch inflorescence.	2006-09	17031605
Protoberberine alkaloids and their reversal activity of P-gp expressed multidrug resistance (MDR) from the rhizome of Coptis japonica Makino.	2006-09	17024849
[Fingerprints of Rhizoma Coptidis from Shizhu by HPLC].	2006-07	17059001
Studies of the interaction between palmatine hydrochloride and human serum albumin by fluorescence quenching method.	2006-06-07	16549318
Nonaqueous capillary electrophoresis coupled with laser-induced native fluorescence detection for the analysis of berberine, palmatine, and jatrorrhizine in Chinese herbal medicines.	2006-06	16833085
Evaluation of Cytotoxic Effects of Dichloromethane Extract of Guduchi (Tinospora cordifolia Miers ex Hook F & THOMS) on Cultured HeLa Cells.	2006-06	16786058
Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.). 2. Palmatine, hydrastine, canadine, and hydrastinine.	2006-06	16780351
RNA specific molecules: cytotoxic plant alkaloid palmatine binds strongly to poly(A).	2006-05-01	16497501
Acetylcholinesterase inhibitors from Stephania venosa tuber.	2006-05	16640839
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
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.	2006-03-18	16293389
Disruption of nucleocytoplasmic trafficking of cyclin D1 and topoisomerase II by sanguinarine.	2006-03-02	16512916
[Studies on the alkaloids from herb of Corydalis adunca].	2005-11	16468373
The mechanism of guanine specific photooxidation in the presence of berberine and palmatine: activation of photosensitized singlet oxygen generation through DNA-binding interaction.	2005-10	16533018
[HPLC fingerprint for the Corydalis saxicola Bunting injection].	2005-09	16342690
Capillary electrochromatography with a neutral monolithic column for classification of analytes and determination of basic drugs in human serum.	2005-09	16167364

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:14:01 GMT 2025` Edited by `admin` on `Mon Mar 31 19:14:01 GMT 2025`
Record UNII	G50C034217
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BERBERICININE

Preferred Name

English

PALMATINE

Official 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 [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