VINBURNINE, (±)-

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H22N2O
Molecular Weight	294.3908
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12N3CCC[C@@]1(CC)CC(=O)N4C5=CC=CC=C5C(CC3)=C24

InChI

InChIKey=WYJAPUKIYAZSEM-MOPGFXCFSA-N

InChI=1S/C19H22N2O/c1-2-19-9-5-10-20-11-8-14-13-6-3-4-7-15(13)21(16(22)12-19)17(14)18(19)20/h3-4,6-7,18H,2,5,8-12H2,1H3/t18-,19+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2263666 | https://www.exercise.com/supplements/vinburnine | http://www.drugfuture.com/chemdata/eburnamonine.html | https://www.ncbi.nlm.nih.gov/pubmed/14306194 | https://ir.nctu.edu.tw/bitstream/11536/25464/1/000233154200020.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/2263666
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2287808

Vinburnine is a nutritional product, which is semi-synthesized from vincamine. It is a peripheral vasodilator with cerebral activities that also act as a cerebral metabolic stimulant and appears to be able to relax the smooth muscle cells within the walls of blood vessels. Some evidence also suggests that vinburnine stimulates acetylcholine neurotransmission. Acetylcholine is a very important neurotransmitter responsible for a number of cognitive functions, such as memory and learning.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Muscarinic acetylcholine receptor M2 121 Target ID: P08172 Gene ID: 1129.0 Gene Symbol: CHRM2 Target Organism: Homo sapiens (Human) Sources: http://drugcentral.org/drugcard/2824	Modulator 828	68.9 µM [Kd]
Muscarinic acetylcholine receptor M1 169 Target ID: P11229 Gene ID: 1128.0 Gene Symbol: CHRM1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827	Modulator 828	7.54 µM [Kd]
Muscarinic acetylcholine receptor M3 159 Target ID: P20309 Gene ID: 1131.0 Gene Symbol: CHRM3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827	Modulator 828	6.67 µM [Kd]
Muscarinic acetylcholine receptor M4 86 Target ID: P08173 Gene ID: 1132.0 Gene Symbol: CHRM4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827	Positive Allosteric Modulator 179	23.7 µM [Kd]
acetylcholine neurotransmission 2 Target ID: acetylcholine neurotransmission Sources: https://www.ncbi.nlm.nih.gov/pubmed/2263666	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cerebrovascular diseases 9 Sources: http://en.pharmacodia.com/web/drug/1_11912.html http://www.mims.com/india/drug/info/vinburnine?mtype=generic	Primary		Approved 8429	CERVOXAN Approved Use Cerebrovascular diseases
Unknown 2578

PubMed

Title	Date	PubMed
GENERAL METHODS OF SYNTHESIS OF INDOLE ALKALOIDS. IV. A SYNTHESIS OF DL-EBURNAMONINE.	1965 Apr 5	14306194
Metabolism of vincamine in the rat in vivo and in vitro.	1980	7192994
Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.	1997 Jul	9224827

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dosage is 60 mg taken twice a day.

Route of Administration: Oral

In Vitro Use Guide

Different concentrations of the three drugs, vincamine, vinpocetine, and eburnamonine, (4, 20 and 100 uM) induced minimal stimulation of the ATPase activity of the Bcrp and Pgp membrane transporters.

Name

Type

Language

VINBURNINE, (±)-

Common Name

English

EBURNAMENIN-14(15H)-ONE, (±)-

Systematic Name

English

DL-EBURNAMONINE

Common Name

English

VINCANORINE

Common Name

English

(±)-VINCAMONE

Common Name

English

(±)-EBURNAMONINE

Common Name

English

EBURNAMONINE (±)-FORM [MI]

Common Name

English

Code System Code Type Description

WIKIPEDIA

Eburnamonine