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
SMILES
CC[C@@]12CCCN3CCC4=C([C@H]13)N(C5=C4C=CC=C5)C(=O)C2
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
| Molecular Formula | C19H22N2O |
| Molecular Weight | 294.3908 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/2263666https://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.pdfCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/2287808
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2263666https://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.pdf
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/2287808
Vinburnine is a nutritional product, 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. (+/-)-Eburnamonine is the racemate of the alkaloid Vinburnine. Dextrorotatory, levorotatory, and racemic forms of eburnamonine exist in nature. The (-)-form, also known as vincamone (isolated from Vinca minor), is a drug that possesses a stimulating activity for muscle and is used as cerebrotonic, whereas both enantiomers have hypotensive effects.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P08172 Gene ID: 1129.0 Gene Symbol: CHRM2 Target Organism: Homo sapiens (Human) Sources: http://drugcentral.org/drugcard/2824 |
68.9 µM [Kd] | ||
Target ID: P11229 Gene ID: 1128.0 Gene Symbol: CHRM1 Target Organism: Homo sapiens (Human) |
7.54 µM [Kd] | ||
Target ID: P20309 Gene ID: 1131.0 Gene Symbol: CHRM3 Target Organism: Homo sapiens (Human) |
6.67 µM [Kd] | ||
Target ID: P08173 Gene ID: 1132.0 Gene Symbol: CHRM4 Target Organism: Homo sapiens (Human) |
23.7 µM [Kd] | ||
Target ID: acetylcholine neurotransmission |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | CERVOXAN Approved UseCerebrovascular diseases |
|||
PubMed
| Title | Date | PubMed |
|---|---|---|
| Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors. | 1997-07 |
|
| Metabolism of vincamine in the rat in vivo and in vitro. | 1980 |
|
| GENERAL METHODS OF SYNTHESIS OF INDOLE ALKALOIDS. IV. A SYNTHESIS OF DL-EBURNAMONINE. | 1965-04-05 |
Patents
Sample Use Guides
In Vitro Use Guide
Curator's Comment: Different concentrations of the drugs: vincamine, vinpocetine and eburnamonine (VINBURNINE) (4, 20 and 100 µM) induced minimal stimulation of the ATPase activity of the Bcrp and Pgp membrane transporters. The relative metabolic stability of eburnamonine compared to the other alkaloids suggests the use of eburnamonine or its derivatives as lead compounds for the development of antitumor and nootropic agents that need to cross the BBB and produce their pharmacological effects in the CNS.
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:21:46 GMT 2025
by
admin
on
Mon Mar 31 22:21:46 GMT 2025
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| Record UNII |
64UB2942IE
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| Record Status |
Validated (UNII)
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| Record Version |
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Eburnamonine
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64UB2942IE
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m4804
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2580-88-3
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