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

Molecular Formula	C21H23NO5
Molecular Weight	369.411
Charge	0
Count

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

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
Alkaloids from Mongolian species Hypecoum lactiflorum Kar. et Kir. Pazij.	2009	19521913
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
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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 20:11:20 GMT 2023` Edited by `admin` on `Fri Dec 15 20:11:20 GMT 2023`
Record UNII	EK27J8ROYB
Record Status	`Validated (UNII)`
Record Version

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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