Vindeburnol

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 461534

CAS#: 68779-67-9

Description: Vindeburnol is a structural analog of the cerebral vasodilator vincamine that bears neuroprotective properties.


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Vindeburnol is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 461534
Name: Vindeburnol
CAS#: 68779-67-9
Chemical Formula: C17H20N2O
Exact Mass: 268.1576
Molecular Weight: 268.36
Elemental Analysis: C, 76.09; H, 7.51; N, 10.44; O, 5.96


Synonym: Vindeburnol; RU 24722; RU-24722; RU24722;

IUPAC/Chemical Name: (41S,12R,13aR)-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridin-12-ol

InChi Key: KOIGYXJOGRVNIS-LYRGGWFBSA-N

InChi Code: InChI=1S/C17H20N2O/c20-15-10-11-4-3-8-18-9-7-13-12-5-1-2-6-14(12)19(15)17(13)16(11)18/h1-2,5-6,11,15-16,20H,3-4,7-10H2/t11-,15-,16+/m1/s1

SMILES Code: O[C@H]1N2C3=C(C4=C2C=CC=C4)CCN5[C@@]3([H])[C@@](CCC5)([H])C1


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
2934.99.03.00


References

1: Polak PE, Kalinin S, Braun D, Sharp A, Lin SX, Feinstein DL. The vincamine derivative vindeburnol provides benefit in a mouse model of multiple sclerosis: effects on the Locus coeruleus. J Neurochem. 2012 Apr;121(2):206-16. doi: 10.1111/j.1471-4159.2012.07673.x. Epub 2012 Feb 17. PubMed PMID: 22288774.

2: Mondal P, Argade NP. Stereoselective synthesis of (-)-desethyleburnamonine, (-)-vindeburnol and (-)-3-epitacamonine: observation of a substrate dependent diastereoselectivity reversal of an aldol reaction. Org Biomol Chem. 2016 Nov 8;14(44):10394-10406. PubMed PMID: 27734054.

3: Mondal P, Argade NP. Correction: Stereoselective synthesis of (-)-desethyleburnamonine, (-)-vindeburnol and (-)-3-epitacamonine: observation of a substrate dependent diastereoselectivity reversal of an aldol reaction. Org Biomol Chem. 2016 Nov 8;14(44):10534. PubMed PMID: 27775144.

4: Patat A, Le Go A, Foulhoux P. Dose-response relationship of vindeburnol based on spectral analysis of posturographic recordings. Eur J Clin Pharmacol. 1985;29(4):455-9. PubMed PMID: 3912189.

5: Barzaghi F, Dragonetti M, Formento ML, Gueniau C, Nencioni A, Mantegazza P. A comparison of some of the pharmacological properties of the new eburnamenine derivative vindeburnol with those of vincamine, vinburnine, dihydroergotoxine mesilate and nicergoline. Arzneimittelforschung. 1986 Oct;36(10):1442-8. PubMed PMID: 3814205.

6: Patat A, Foulhoux P, Venet R, Memin Y. [Application of spectrum analysis of equilibration recordings (posturography) in clinical pharmacology of vindeburnol]. Therapie. 1984 Nov-Dec;39(6):639-45. French. PubMed PMID: 6531737.

7: Vas A, Gulyás B. Eburnamine derivatives and the brain. Med Res Rev. 2005 Nov;25(6):737-57. Review. PubMed PMID: 16158388.

8: Caccamese S, Principato G, Jokela R, Tolvanen A, Din Belle D. Chiral HPLC separation and CD spectra of the enantiomers of the alkaloid tacamonine and related compounds. Chirality. 2001;13(10):691-3. PubMed PMID: 11746802.

9: Patat A, Klein MJ. [Evaluation of the activity of vindeburnol by spectral analysis of human EEG]. Therapie. 1986 Jul-Aug;41(4):305-10. French. PubMed PMID: 3554597.

10: Braun D, Feinstein DL. The locus coeruleus neuroprotective drug vindeburnol normalizes behavior in the 5xFAD transgenic mouse model of Alzheimer's disease. Brain Res. 2017 Dec 21. pii: S0006-8993(17)30563-2. doi: 10.1016/j.brainres.2017.12.028. [Epub ahead of print] PubMed PMID: 29274883.

11: Porquet D, Appel M, Fournier T, Bertaux O, Biou D, Féger J. Evaluation of the hepatotoxicological effects of a drug in an in vivo/in vitro model. Experientia. 1992 Mar 15;48(3):257-61. PubMed PMID: 1372265.

12: Salacz L, Charpentier C, Suffert J, Girard N. Desymmetrizing Hydroformylation of Dihydromuconic Acid Diesters: Application to the Synthesis of (±)-Vindeburnol. J Org Chem. 2017 Feb 17;82(4):2257-2262. doi: 10.1021/acs.joc.6b02939. Epub 2017 Feb 8. PubMed PMID: 28124911.

13: Cambon K, Dos-Santos Coura R, Groc L, Carbon A, Weissmann D, Changeux JP, Pujol JF, Granon S. Aggressive behavior during social interaction in mice is controlled by the modulation of tyrosine hydroxylase expression in the prefrontal cortex. Neuroscience. 2010 Dec 15;171(3):840-51. doi: 10.1016/j.neuroscience.2010.09.015. Epub 2010 Oct 20. PubMed PMID: 20923695.

14: Weissmann D, Labatut R, Gillon J, Richard F, Pujol J. [Measurement of brain tyrosine hydroxylase concentrations by quantitative autoradiography after transfer of soluble proteins to nitro-cellulose]. C R Acad Sci III. 1988;306(14):457-60. French. PubMed PMID: 2457416.

15: Schmitt P, Reny-Palasse V, Bourde O, Garcia C, Pujol JF. Further characterization of the long-term effect of RU24722 on tyrosine hydroxylase in the rat locus coeruleus. J Neurochem. 1993 Oct;61(4):1423-9. PubMed PMID: 8104233.

16: Debure LI, Bezin L, Ginovart N, Rousset C, Pujol JF, Weissmann D. RU24722 induces spatially organized phenotypic plasticity in the locus coeruleus. Neuroreport. 1994 Sep 8;5(14):1793-6. PubMed PMID: 7827334.

17: Bezin L, Ortemann C, Ogier M, Astier B, Pujol JF, Renaud B, Lambas-Señas L. Enhanced tail pinch-induced activation of catecholamine metabolism in the pericerulean area of RU 24722-treated rats. Brain Res. 2004 Dec 24;1030(1):1-10. PubMed PMID: 15567332.

18: Marcel D, Raison S, Bezin L, Pujol JF, Weissmann D. Plasticity of tyrosine hydroxylase gene expression within BALB/C and C57Black/6 mouse locus coeruleus. Neurosci Lett. 1998 Feb 13;242(2):77-80. PubMed PMID: 9533398.

19: Bezin L, Marcel D, Garcia C, Blum D, Lafargue P, Lellouche JP, Pujol JF, Weissmann D. In situ examination of tyrosine hydroxylase activity in the rat locus coeruleus using (3',5')-[(3)H(2)]-alpha-fluoromethyl-tyrosine as substrate of the enzyme. Synapse. 2000 Mar 1;35(3):201-11. PubMed PMID: 10657027.

20: Garcia C, Denoroy L, Le Cavorsin M, Pujol JF, Weissmann D. Pharmacological modulations of adrenergic phenotype in medullary C2 and C3 cell groups of adult rat. J Chem Neuroanat. 1996 Aug;11(2):131-42. PubMed PMID: 8877600.