U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of ALLOCRYPTOPINE

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

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 TargetPharmacologyConditionPotency
250.0 µM [IC50]
530.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Curative
Unknown

PubMed

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.