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

Molecular Formula	HI
Molecular Weight	127.9124
Charge	0
Count

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

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 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
Analysis of coptisine, berberine and palmatine in adulterated Chinese medicine by capillary electrophoresis-electrospray ion trap mass spectrometry.	2000 Jan 14	10670817
Inhibition of type A monoamine oxidase by coptisine in mouse brain.	2001 Dec 28	11833714
In vitro cytotoxicity of the protoberberine-type alkaloids.	2001 Jul	11473418
[Study on the quality standards for xianghe suppository].	2001 Sep	11799783
Molecular cloning of columbamine O-methyltransferase from cultured Coptis japonica cells.	2002 Nov	12423366
Rat lens aldose reductase inhibitory activities of Coptis japonica root-derived isoquinoline alkaloids.	2002 Nov 20	12428952
Positive cooperation of protoberberine type 2 alkaloids from Corydalis cava on the GABA(A) binding site.	2003 Apr	12709895
[Determination of four alkaloids in Berberis plants by HPLC].	2003 Dec	15617491
Separation of protoberberine quaternary alkaloids from a crude extract of Enantia chlorantha by centrifugal partition chromatography.	2004 Jul 2	15281263
A new glucosyl feruloyl quinic acid as a potential marker for roots and rhizomes of goldenseal, Hydrastis canadensis.	2004 Nov	15568768
[Quality assessment of Coptis chinensis in China].	2005 Apr	16011089
Protective role of Coptidis Rhizoma alkaloids against peroxynitrite-induced damage to renal tubular epithelial cells.	2005 Mar	15807993
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
Nonaqueous capillary electrophoresis coupled with laser-induced native fluorescence detection for the analysis of berberine, palmatine, and jatrorrhizine in Chinese herbal medicines.	2006 Jun	16833085
Studies of the interaction between palmatine hydrochloride and human serum albumin by fluorescence quenching method.	2006 Jun 7	16549318
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
RNA specific molecules: cytotoxic plant alkaloid palmatine binds strongly to poly(A).	2006 May 1	16497501
Molecular aspects on the specific interaction of cytotoxic plant alkaloid palmatine to poly(A).	2006 Nov 15	16678250
Protoberberine alkaloids and their reversal activity of P-gp expressed multidrug resistance (MDR) from the rhizome of Coptis japonica Makino.	2006 Sep	17024849
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
Simultaneous quantification of three alkaloids of Coptidis Rhizoma in rat urine by high-performance liquid chromatography: application to pharmacokinetic study.	2007 Dec	17891749
DNA-binding affinities and sequence specificities of protoberberine alkaloids and their demethylated derivatives: a comparative study.	2007 Feb	17311227
Molecular recognition of DNA by small molecules: AT base pair specific intercalative binding of cytotoxic plant alkaloid palmatine.	2007 Jul	17434677
Affinity chromatography with immobilized DNA stationary phase for biological fingerprinting analysis of traditional Chinese medicines.	2007 Jun 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 Jun 5	17512816
Pharmacological and therapeutic effects of Berberis vulgaris and its active constituent, berberine.	2008 Aug	18618524
Self-structure induction in single stranded poly(A) by small molecules: Studies on DNA intercalators, partial intercalators and groove binding molecules.	2008 Jun 1	18387354

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 `Sat Dec 16 18:33:52 GMT 2023` Edited by `admin` on `Sat Dec 16 18:33:52 GMT 2023`
Record UNII	REY4ILD57Z
Record Status	`Validated (UNII)`
Record Version

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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