GALANTAMINE, (+)-

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

SMILES

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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

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

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acetylcholinesterase 209	Inhibitor 8,504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2,596

PubMed

Show entries

Title	Date	PubMed
Chemoenzymatic Total Synthesis of (+)-Galanthamine and (+)-Narwedine from Phenethyl Acetate.	2016 Oct 4	27505136

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Patents

Sample Use Guides

In Vivo Use Guide

(+)-[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

In Vitro Use Guide

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.