ALLOCRYPTOPINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H23NO5
Molecular Weight	369.411
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C2CC(=O)C3=CC4=C(OCO4)C=C3CCN(C)CC2=C1OC

InChI

InChIKey=HYBRYAPKQCZIAE-UHFFFAOYSA-N

InChI=1S/C21H23NO5/c1-22-7-6-14-9-19-20(27-12-26-19)10-15(14)17(23)8-13-4-5-18(24-2)21(25-3)16(13)11-22/h4-5,9-10H,6-8,11-12H2,1-3H3

HIDE SMILES / InChI

Description
Sources: DOI: 10.3987/REV-10-673 | https://www.ncbi.nlm.nih.gov/pubmed/28708094 | https://www.ncbi.nlm.nih.gov/pubmed/23524574 | https://www.ncbi.nlm.nih.gov/pubmed/25261036

Allocryptopine is isoquinoline alkaloid found primarily in the plant families Fumariaceae, Papaveraceae, Berberidaceae, Ranunculaceae, Rutaceae, and Sapindaceae. It have been reported to possess strong antibacterial, anti-inflammatoty, antiparasitic, antineoplastic and anti-addictive activities. Allocryptopine inhibits human acetylcholinesterase and butyrylcholinesterase. It blocks hERG current in HEK293 cells. Allocryptopine strongly enhanced the I(peak) of the T353I channel by enhancing the plasma membrane (PM) expression of Nav1.5 and rescued defective trafficking after co-incubation with HEK293 cells that carry mutation channel 24 h. A possible preparation for the treatment of HIV-1 and HIV-2 viruses containing pharmaceutically effective amounts of allocryptopine has been patented.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Acetylcholinesterase 207 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28708094	Inhibitor 8297	250.0 µM [IC50]
Butyrylcholinesterase 46 Target ID: CHEMBL1914 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28708094	Inhibitor 8297	530.0 µM [IC50]
Outward potassium current 1 Target ID: Outward potassium current Sources: https://www.ncbi.nlm.nih.gov/pubmed/27403141	Inhibitor 8297
Slow delayed rectifier potassium current 1 Target ID: Slow delayed rectifier potassium current Sources: https://www.ncbi.nlm.nih.gov/pubmed/27403141	Inhibitor 8297
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27054913	Inhibitor 8297
Cytochrome P450 2C9 50 Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27054913	Inhibitor 8297
Cytochrome P450 2C19 51 Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27054913	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Arrhythmia 38 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27403141	Primary	Basic research	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28708094	Primary	Basic research	Unknown Approved Use Unknown
Plasmodium falciparum malaria 63 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25516845	Curative	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibitory effect of isoquinoline alkaloids on movement of second-stage larvae of Toxocara canis.	2002 Dec	12499659
Assay of nematocidal activity of isoquinoline alkaloids using third-stage larvae of Strongyloides ratti and S. venezuelensis.	2002 Mar 1	11809332
Inhibition of mouse liver respiration by Chelidonium majus isoquinoline alkaloids.	2003 Dec 15	14615066
Two new protopines argemexicaines A and B and the anti-HIV alkaloid 6-acetonyldihydrochelerythrine from formosan Argemone mexicana.	2003 Feb	12624820
Antifungal activity of the methanolic extract and alkaloids of Glaucium oxylobum.	2003 Jul	12837370
Iodination and radiolabeling of alpha-allocryptopine with iodine-125.	2005 Jan	15498685
Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway.	2006 Jan 17	16417634
Rapid determination of protopine, allocryptopine, sanguinarine and chelerythrine in fruits of Macleaya cordata by microwave-assisted solvent extraction and HPLC-ESI/MS.	2006 Nov-Dec	17144252
Analysis of Central European Corydalis species by nonaqueous capillary electrophoresis-electrospray ion trap mass spectrometry.	2007 Aug 3	17395190
Conventional sample enrichment strategies combined with high-performance liquid chromatography-solid phase extraction-nuclear magnetic resonance analysis allows analyte identification from a single minuscule Corydalis solida plant tuber.	2007 Sep 7	17628575
Effect of alpha-allocryptopine on transient outward potassium current in rabbit ventricular myocytes.	2008	18434730
Alkaloids from Papaver nudicaule L.	2008 May 10	18569698
Alkaloids from Mongolian species Hypecoum lactiflorum Kar. et Kir. Pazij.	2009	19521913
[Alkaloids from Macleaya cordata].	2009 Jul	19873781
Analysis of alkaloids in Macleaya cordata (Willd.) R. Br. using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry.	2009 Mar 13	18774138
Electron ionisation mass spectral study of 2-(2-carboxy-4, 5-dimethoxyphenyl)-6,7-dimethoxyisoquinolinium inner salt.	2009 Nov	20099515
Isoquinoline alkaloids from Macleaya cordata active against plant microbial pathogens.	2009 Nov	19967990
Phytochemical and antimicrobial characterization of Macleaya cordata herb.	2010 Dec	20600683
Optimization of microwave-assisted extraction of protopine and allocryptopine from stems of Macleaya cordata (Willd) R. Br. using response surface methodology.	2010 Jul	20533346
A study on separation and extraction of four main alkaloids in Macleaya cordata (Willd) R. Br. with strip dispersion hybrid liquid membrane.	2010 Jul	20512809
Metabolic diversification of benzylisoquinoline alkaloid biosynthesis through the introduction of a branch pathway in Eschscholzia californica.	2010 Jun	20427510
Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Chelidonium majus (Papaveraceae).	2010 Nov	21213973
Extractions of isoquinoline alkaloids with butanol and octanol.	2010 Sep	20117181
Protopine and allocryptopine increase mRNA levels of cytochromes P450 1A in human hepatocytes and HepG2 cells independently of AhR.	2011 Jun 10	21419197

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 0.15 ml of [125I] iodo-a-allocryptopine

Route of Administration: Intravenous

In Vitro Use Guide

The antiplasmodial assay on chloroquine-resistant strains of Plasmodium falciparum (PfK1) was conducted. The alkaloid allocryptopine presented IC50 value against P. falciparum of 1.46 ug/mL.

Name

Type

Language

ALLOCRYPTOPINE

Common Name

English

.BETA.-HOMOCHELIDONINE

Common Name

English

THALICTRIMINE

Common Name

English

5,7,8,15-TETRAHYDRO-3,4-DIMETHOXY-6-METHYLBENZO(E)(1,3)DIOXOLO(4,5-K)(3)BENZAZECIN-14(6H)-ONE

Systematic Name

English

NSC-404531

Code

English

.ALPHA.-FAGARINE

Common Name

English

ALLOCRYPTOPINE [MI]

Common Name

English

5,7,8,15-TETRAHYDRO-3,4-DIMETHOXY-6-METHYL(1,3)BENZODIOXOLO(5,6-E)(2)BENZAZECIN-14(6H)-ONE

Systematic Name

English

BENZO(E)(1,3)DIOXOLO(4,5-K)(3)BENZAZECIN-14(6H)-ONE, 5,7,8,15-TETRAHYDRO-3,4-DIMETHOXY-6-METHYL- (VAN)

Common Name

English

Code System Code Type Description

MERCK INDEX

m1527