PALMATINE IODIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H22NO4.I
Molecular Weight	479.3082
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=VUGARESHFWNHTD-UHFFFAOYSA-M

InChI=1S/C21H22NO4.HI/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;1H/q+1;/p-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
Inhibition of type A monoamine oxidase by coptisine in mouse brain.	2001 Dec 28	11833714
Monoamine oxidase inhibitors from rhizoma of Coptis chinensis.	2001 Feb	11270727
Rat lens aldose reductase inhibitory activities of Coptis japonica root-derived isoquinoline alkaloids.	2002 Nov 20	12428952
A simple method for fabrication of silver-coated sheathless electrospray emitters.	2003	12590392
Antifungal activity of Mahonia aquifolium extract and its major protoberberine alkaloids.	2003 Aug	12916091
[Determination of four alkaloids in Berberis plants by HPLC].	2003 Dec	15617491
High-performance capillary electrophoresis for determining the contents of berberine, jatrorrhizine and palmatine in Gegenqinlian decoction.	2003 Jul	12865220
Structural elucidation and identification of alkaloids in Rhizoma Coptidis by electrospray ionization tandem mass spectrometry.	2004 Nov	15532075
Simultaneous determinations of paeonol and palmatine hydrochloride in Shangshi Aerosols by HPLC method.	2005 Jul 1	15925262
Using oxidized carbon nanotubes as matrix for analysis of small molecules by MALDI-TOF MS.	2005 Jun	15907704
Spectrometric studies of cytotoxic protoberberine alkaloids binding to double-stranded DNA.	2005 Mar 1	15698803
[Studies on the alkaloids from herb of Corydalis adunca].	2005 Nov	16468373
A rapid and simple determination of protoberberine alkaloids in cortex phellodendri by 1H NMR and its application for quality control of commercial traditional Chinese medicine prescriptions.	2006 Jan 23	16061339
Evaluation of Cytotoxic Effects of Dichloromethane Extract of Guduchi (Tinospora cordifolia Miers ex Hook F & THOMS) on Cultured HeLa Cells.	2006 Jun	16786058
RNA specific molecules: cytotoxic plant alkaloid palmatine binds strongly to poly(A).	2006 May 1	16497501
[Quality analysis and evaluation of Rhizoma Coptidis under different cultivation conditions].	2006 Oct	17184122
Identification of palmatine and its metabolites in rat urine by liquid chromatography/tandem mass spectrometry.	2007	17534853
Thin-layer chromatography/desorption electrospray ionization mass spectrometry: investigation of goldenseal alkaloids.	2007 Apr 1	17338504
Free radical scavenging activity and lipoxygenase inhibition of Mahonia aquifolium extract and isoquinoline alkaloids.	2007 Jul 16	17634120
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 Apr 21	18395058
Antimicrobial properties of berberines alkaloids in Coptis chinensis Franch by microcalorimetry.	2008 Apr 24	17804078
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 Aug	18318017
Studies on alkaloids binding to GC-rich human survivin promoter DNA using positive and negative ion electrospray ionization mass spectrometry.	2008 Mar	17968851
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 Mar 1	18258496

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 IODIDE

Common Name

English

BERBINIUM, 7,8,13,13A-TETRADEHYDRO-2,3,9,10-TETRAMETHOXY-, IODIDE

Common Name

English

DIBENZO(A,G)QUINOLIZINIUM, 5,6-DIHYDRO-2,3,9,10-TETRAMETHOXY-, IODIDE (1:1)

Systematic Name

English

PALMATINE IODIDE [MI]

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID30964121