Date published: 2025-11-20

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(−)-Eburnamonine (CAS 4880-88-0)

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Alternate Names:
(3α,16α)-Eburnamenin-14(15H)-one, Vincamone]
Application:
(−)-Eburnamonine is a vasodilator that also acts as a cerebral metabolic stimulant
CAS Number:
4880-88-0
Purity:
≥99%
Molecular Weight:
294.4
Molecular Formula:
C19H22N2O
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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(−)-Eburnamonine is a natural compound of interest primarily in the field of organic and natural products chemistry. It is studied for its role as an indole alkaloid with a distinctive chemical structure that includes a complex polycyclic framework. Research on (−)-Eburnamonine often involves the exploration of its biosynthetic pathways in plants, which can illuminate the processes by which such alkaloids are constructed in nature. Additionally, it is used as a reference compound in synthetic chemistry to develop new synthetic methodologies that can construct the eburnamonine skeleton and related structures. The compound also serves as a starting point for the synthesis of analogs that can help elucidate structure-activity relationships.


(−)-Eburnamonine (CAS 4880-88-0) References

  1. Asymmetric synthesis of (-)-eburnamonine and (+)-epi-eburnamonine from (4S)-4-ethyl-4-[2-(hydroxycarbonyl)ethyl]-2-butyrolactone.  |  Wee, AG. and Yu, Q. 2001. J Org Chem. 66: 8935-43. PMID: 11749625
  2. Eburnamine derivatives and the brain.  |  Vas, A. and Gulyás, B. 2005. Med Res Rev. 25: 737-57. PMID: 16158388
  3. Synthesis of 15-methylene-eburnamonine from (+)-vincamine, evaluation of anticancer activity, and investigation of mechanism of action by quantitative NMR.  |  Woods, JR., et al. 2013. Bioorg Med Chem Lett. 23: 5865-9. PMID: 24055047
  4. Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction.  |  Huang, Y., et al. 2021. Nat Prod Bioprospect. 11: 99-103. PMID: 33155164
  5. Quaternary stereocentres via catalytic enantioconvergent nucleophilic substitution reactions of tertiary alkyl halides.  |  Wang, Z., et al. 2021. Nat Chem. 13: 236-242. PMID: 33432109
  6. 'Cerebroactive' drugs. Clinical pharmacology and therapeutic role in cerebrovascular disorders.  |  Spagnoli, A. and Tognoni, G. 1983. Drugs. 26: 44-69. PMID: 6349963
  7. Experimental approach of activity and mechanism(s) of action of drugs used in cerebral metabolic insufficiency. Application to 1-eburnamonine.  |  Linee, P., et al. 1981. Eur Neurol. 20: 253-7. PMID: 7262124
  8. Effect of (-)eburnamonine, papaverine and UDP-glucose on cerebral energy state during and after experimental hypoxia and ischaemia in beagle dog.  |  Villa, RF., et al. 1978. Eur Neurol. 17 Suppl 1: 97-112. PMID: 753643
  9. Microbial hydroxylation of (-)-eburnamonine by Mucor circinelloides and Streptomyces violens.  |  Adachi, T., et al. 1993. Chem Pharm Bull (Tokyo). 41: 611-3. PMID: 8477514
  10. Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors.  |  Jakubík, J., et al. 1997. Mol Pharmacol. 52: 172-9. PMID: 9224827

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

(−)-Eburnamonine, 100 mg

sc-202594
100 mg
$105.00

(−)-Eburnamonine, 5 g

sc-202594A
5 g
$1224.00