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Details

Stereochemistry RACEMIC
Molecular Formula C17H19NO3
Molecular Weight 285.3377
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NARWEDINE, (±)-

SMILES

[H][C@]12CC(=O)C=C[C@]13CCN(C)CC4=CC=C(OC)C(O2)=C34

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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://link.springer.com/referenceworkentry/10.1007/978-1-4614-0560-3_2

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

Sources: Chemische Berichte (1957), 90, 2197-202.Journal of the Chemical Society (1964), (Nov.), 4655-7.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
[On the pharmacology of the Amaryllidaceae alkaloids galanthamine, narwedine, hemanthamine and tazettine].
1961
An efficient synthesis of (±)-narwedine and (±)-galanthamine by an improved phenolic oxidative coupling.
2001
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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
Created
by admin
on Sat Dec 16 05:41:43 GMT 2023
Edited
by admin
on Sat Dec 16 05:41:43 GMT 2023
Record UNII
ATP706417H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NARWEDINE, (±)-
Common Name English
(±)-NARWEDINE
Common Name English
DL-NARWEDINE
Common Name English
GALANTHAMINE, 3-DEOXY-3-OXO-, (±)-
Common Name English
6H-BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-ONE, 4A,5,9,10,11,12-HEXAHYDRO-3-METHOXY-11-METHYL-, (4AR,8AR)-REL-
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID60168190
Created by admin on Sat Dec 16 05:41:43 GMT 2023 , Edited by admin on Sat Dec 16 05:41:43 GMT 2023
PRIMARY
CAS
1668-86-6
Created by admin on Sat Dec 16 05:41:43 GMT 2023 , Edited by admin on Sat Dec 16 05:41:43 GMT 2023
PRIMARY
FDA UNII
ATP706417H
Created by admin on Sat Dec 16 05:41:43 GMT 2023 , Edited by admin on Sat Dec 16 05:41:43 GMT 2023
PRIMARY
PUBCHEM
10356588
Created by admin on Sat Dec 16 05:41:43 GMT 2023 , Edited by admin on Sat Dec 16 05:41:43 GMT 2023
PRIMARY