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

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H21NO3
Molecular Weight 287.3535
Optical Activity ( + )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GALANTAMINE, (+)-

SMILES

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

InChI

InChIKey=ASUTZQLVASHGKV-SUYBPPKGSA-N
InChI=1S/C17H21NO3/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/h3-6,12,14,19H,7-10H2,1-2H3/t12-,14-,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula C17H21NO3
Molecular Weight 287.3535
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.heterocycles.jp/newlibrary/libraries/abst/08228 | https://www.ncbi.nlm.nih.gov/pubmed/27505136

(+)-Galanthamine is an alkaloid benzazepine derived from norbelladine. In contrast to the (-)-Galanthamine, (+)-Galanthamine demonstrates substantially lower biological activity.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Chemoenzymatic Total Synthesis of (+)-Galanthamine and (+)-Narwedine from Phenethyl Acetate.
2016 Oct 4
Patents

Patents

Sample Use Guides

(+)-[11C]galanthamine (3.7 MBq) was administered to seven-week-old male ddY mice. Five animals were then sacrificed by exsanguination at time-points of 2, 5, 15, 30, and 60 min post-administration
Route of Administration: Oral
The inhibitory activities of (+)-galanthamine against AChE were measured using a modified version of the colorimetric method of Ellman. 2 mkL of a 10-mM solution of (+)-Galanthamine in 0.1 M phosphate buffer (pH 8) was mixed with 190 mkL of AChE solution (extracted from the brain tissue of a 9-week-old rat) in each well of a 96-well titer plate. After the incubation of the titer plate for 30 min at 37 C, 600 mkL of 10-mM 5,50-dithiobis-(2-nitrobenzoic acid) (DTNB), 100 mkL of 150 mM acetylthiocholine iodide and 100 mkL of buffer were successively added. Changes in UV absorbance of the reaction mixture were then measured at 2 min intervals in a 96-well plate reader at 415 nm, three times, consecutively.
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:41:44 GMT 2023
Edited
by admin
on Sat Dec 16 05:41:44 GMT 2023
Record UNII
8L3T05AQ82
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GALANTAMINE, (+)-
Common Name English
GALANTHAMINE, (+)-
Common Name English
ENT-GALANTHAMINE
Common Name English
6H-BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL, 4A,5,9,10,11,12-HEXAHYDRO-3-METHOXY-11-METHYL-, (4AR-(4A.ALPHA.,6.BETA.,8AR*))-
Common Name English
GALANTHAMINE, (3.ALPHA.,4A.BETA.,12A.BETA.)-
Common Name English
6H-BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL, 4A,5,9,10,11,12-HEXAHYDRO-3-METHOXY-11-METHYL-, (4AR,6S,8AR)-
Common Name English
(+)-GALANTHAMINE
Common Name English
GALANTAMINE HYDROBROMIDE IMPURITY F [EP IMPURITY]
Common Name English
Code System Code Type Description
CAS
60384-53-4
Created by admin on Sat Dec 16 05:41:44 GMT 2023 , Edited by admin on Sat Dec 16 05:41:44 GMT 2023
PRIMARY
PUBCHEM
906210
Created by admin on Sat Dec 16 05:41:44 GMT 2023 , Edited by admin on Sat Dec 16 05:41:44 GMT 2023
PRIMARY
FDA UNII
8L3T05AQ82
Created by admin on Sat Dec 16 05:41:44 GMT 2023 , Edited by admin on Sat Dec 16 05:41:44 GMT 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER
ENANTIOMER -> ENANTIOMER
Related Record Type Details
PARENT -> IMPURITY
Capillary electrophoresis
UNKNOWN
EP