Vincamine

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

MedKoo CAT#: 584378

CAS#: 1617-90-9

Description: Vincamine is a poorly soluble potent neuroprotector and cerebral vasodilator, used for the treatment for CNS disorders. In some cases, the bioavailability of pure compounds is strongly influenced by the co-administration of other constituents, and in some cases, the so called 'phytocomplex' may act as enhancer of absorption of selected phytochemicals.


Price and Availability

Size
Price

500mg
USD 200
Size
Price

1g
USD 340
Size
Price

5g
USD 770

Vincamine, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 584378
Name: Vincamine
CAS#: 1617-90-9
Chemical Formula: C21H26N2O3
Exact Mass: 354.1943
Molecular Weight: 354.45
Elemental Analysis: C, 71.16; H, 7.39; N, 7.90; O, 13.54


Synonym: Vincamine; Vinca Minor extract; periwinkle extract; Angiopac; Devincan; Equipur; Minorin; Novicet; Oxybral; Perval; Sostenil; Tripervan

IUPAC/Chemical Name: 14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester

InChi Key: RXPRRQLKFXBCSJ-GIVPXCGWSA-N

InChi Code: InChI=1S/C21H26N2O3/c1-3-20-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(17(15)18(20)22)21(25,13-20)19(24)26-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3/t18-,20+,21+/m1/s1

SMILES Code: O[C@@](C1)(C(OC)=O)N2C3=C(C=CC=C3)C4=C2[C@@]([C@@]1(CC)CCC5)([H])N5CC4


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:
>2 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:
293490


References

1: Hasa D, Perissutti B, Dall'Acqua S, Chierotti MR, Gobetto R, Grabnar I, Cepek C, Voinovich D. Rationale of using Vinca minor Linne dry extract phytocomplex as a vincamine's oral bioavailability enhancer. Eur J Pharm Biopharm. 2013 May;84(1):138-44. doi: 10.1016/j.ejpb.2012.11.025. Epub 2012 Dec 11. PubMed PMID: 23238273.

2: Mayo BC, Biggs SR, Hawkins DR, Chasseaud LF, Darragh A, Leaf FC. The metabolic fate of 11-bromo[15-3H]vincamine in man. Eur J Drug Metab Pharmacokinet. 1985 Jul-Sep;10(3):189-96. PubMed PMID: 4085521.

3: Verma P, Khan SA, Mathur AK, Shanker K, Lal RK. Regulation of vincamine biosynthesis and associated growth promoting effects through abiotic elicitation, cyclooxygenase inhibition, and precursor feeding of bioreactor grown Vinca minor hairy roots. Appl Biochem Biotechnol. 2014 Jun;173(3):663-72. doi: 10.1007/s12010-014-0883-5. Epub 2014 Apr 11. PubMed PMID: 24723203.

4: Hasa D, Perissutti B, Chierotti MR, Gobetto R, Grabnar I, Bonifacio A, Dall'Acqua S, Invernizzi S, Voinovich D. Mechanochemically induced disordered structures of vincamine: the different mediation of two cross-linked polymers. Int J Pharm. 2012 Oct 15;436(1-2):41-57. doi: 10.1016/j.ijpharm.2012.06.024. Epub 2012 Jun 19. PubMed PMID: 22721852.

5: Yin H, Sun YH. Vincamine-producing endophytic fungus isolated from Vinca minor. Phytomedicine. 2011 Jun 15;18(8-9):802-5. doi: 10.1016/j.phymed.2011.01.005. Epub 2011 Feb 18. PubMed PMID: 21315568.

6: Hasa D, Perissutti B, Grassi M, Chierotti MR, Gobetto R, Ferrario V, Lenaz D, Voinovich D. Mechanochemical activation of vincamine mediated by linear polymers: assessment of some "critical" steps. Eur J Pharm Sci. 2013 Sep 27;50(1):56-68. doi: 10.1016/j.ejps.2013.03.003. Epub 2013 Mar 21. PubMed PMID: 23524254.

7: 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.

8: Jucker M, Bättig K, Meier-Ruge W. Effects of aging and vincamine derivatives on pericapillary microenvironment: stereological characterization of the cerebral capillary network. Neurobiol Aging. 1990 Jan-Feb;11(1):39-46. Erratum in: Neurobiol Aging 1990 Nov-Dec;11(6):675. PubMed PMID: 2325815.

9: Hasa D, Perissutti B, Cepek C, Bhardwaj S, Carlino E, Grassi M, Invernizzi S, Voinovich D. Drug salt formation via mechanochemistry: the case study of vincamine. Mol Pharm. 2013 Jan 7;10(1):211-24. doi: 10.1021/mp300371f. Epub 2012 Dec 6. PubMed PMID: 23186380.

10: Fayed AH. Brain trace element concentration of rats treated with the plant alkaloid, vincamine. Biol Trace Elem Res. 2010 Sep;136(3):314-9. doi: 10.1007/s12011-009-8550-3. Epub 2009 Nov 10. PubMed PMID: 19902161.

11: Pu H, Jiang H, Chen R, Wang H. Studies on the interaction between vincamine and human serum albumin: a spectroscopic approach. Luminescence. 2014 Aug;29(5):471-9. doi: 10.1002/bio.2572. Epub 2013 Aug 24. PubMed PMID: 24039032.

12: Beltagi AM. Development and validation of an adsorptive stripping voltammetric method for the quantification of vincamine in its formulations and human serum using a Nujol-based carbon paste electrode. Chem Pharm Bull (Tokyo). 2008 Dec;56(12):1651-7. PubMed PMID: 19043234.

13: Fischhof PK, Möslinger-Gehmayr R, Herrmann WM, Friedmann A, Russmann DL. Therapeutic efficacy of vincamine in dementia. Neuropsychobiology. 1996;34(1):29-35. PubMed PMID: 8884757.

14: Hou E, Wang Y, Li D, Li N, Chen H, Bu H. [Tissue culture of Vinca minor and determination of vincamine]. Zhongguo Zhong Yao Za Zhi. 2011 Apr;36(7):823-7. Chinese. PubMed PMID: 21761716.

15: Federico A, D'Amore I. Vincamine TPS activity on glycoconjugate metabolism of the brain: effect on lysosomal enzymes. Int J Clin Pharmacol Res. 1984;4(4):277-9. PubMed PMID: 6500774.

16: Dal Bo L, Ceriani G, Broccali G. Determination of vincamine in human plasma by high-performance liquid chromatography with ultraviolet detection. J Chromatogr. 1992 Jan 3;573(1):158-62. PubMed PMID: 1564097.

17: Vereczkey L. Pharmacokinetics and metabolism of vincamine and related compounds. Eur J Drug Metab Pharmacokinet. 1985 Apr-Jun;10(2):89-103. Review. PubMed PMID: 3899662.

18: Woods JR, Riofski MV, Zheng MM, O'Banion MA, Mo H, Kirshner J, Colby DA. Synthesis of 15-methylene-eburnamonine from (+)-vincamine, evaluation of anticancer activity, and investigation of mechanism of action by quantitative NMR. Bioorg Med Chem Lett. 2013 Nov 1;23(21):5865-9. doi: 10.1016/j.bmcl.2013.08.095. Epub 2013 Sep 6. PubMed PMID: 24055047; PubMed Central PMCID: PMC3867447.

19: Martucci N, Manna V, Agnoli A. Pharmaco-EEG study on vincamine and on teproside in patients with chronic cerebrovascular disease. Int J Clin Pharmacol Res. 1984;4(4):291-302. PubMed PMID: 6500776.

20: Machová J, Bauer V, Bilcíková L. Trachealis responses induced by vincamine and vinpocetine; inhibition by indomethacin and Ca2+ dependence. Eur J Pharmacol. 1989 Mar 29;162(3):387-95. PubMed PMID: 2744076.