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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19NO3
Molecular Weight 285.3377
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NARWEDINE

SMILES

COC1=CC=C2CN(C)CC[C@@]34C=CC(=O)C[C@@H]3OC1=C24

InChI

InChIKey=QENVUHCAYXAROT-YOEHRIQHSA-N
InChI=1S/C17H19NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,14H,7-10H2,1-2H3/t14-,17-/m0/s1

HIDE SMILES / InChI

Molecular Formula C17H19NO3
Molecular Weight 285.3377
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Narwedine, (±)- is an immediate precursor to the therapeutically valuable alkaloid (-)-galanthamine. Galantamine is a competitive and reversible cholinesterase inhibitor used for the treatment of mild to moderate Alzheimer's disease and various other memory impairments. Narwedine pronounced antinarcotic action, facilitates the transmission of nervous excitation in n- and mcholinergic synapses. Stimulates respiration and possessed a brief hypotensive effect.

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Test cell lines (T-lymphoblastic leukemia CEM, chronic myelogenous leukemia K562, breast carcinoma MCF7, cervical carcinoma HeLa, malignant melanoma G-361, and human fibroblasts BJ) were obtained from the American Type Culture Collection. Cell line suspensions (ca. 1.0  10^5 cells/mL) were placed in 96-well microtiter plates and after 24 h stabilization (time zero), test compounds which were serially diluted in DMSO were added (4 x 20 µL aliquots). Control cultures were treated with DMSO alone, such that final DMSO concentration in the incubation mixtures never exceeded 0.6%. Narwedine was evaluated at six 3-fold dilutions and the highest final concentration was generally 50 µM. After 72 h incubation, 100 µl Calcein AM solution (Molecular Probes, Invitrogen, CA, USA) was added, and incubation was continued for a further hour. The fluorescence of viable cells was then quantified using a Fluoroskan Ascent instrument (Labsystems, Finland). The percentage of surviving cells in each well was calculated by dividing the intensity of the fluorescence signals from the exposed wells by the intensity of signals from control wells and multiplying by 100.
Substance Class Chemical
Record UNII
38CR9WB857
Record Status Validated (UNII)
Record Version