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MedKoo Cat#: 526559 | Name: Vinburnine
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Description:

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

Vinburnine, also known as Eburnamonine, is a vasodilator. Vinburnine is a synthetic derivative of vincamine and functions primarily as a vasodilator, particularly targeting cerebral circulation. It exhibits selective inhibition of phosphodiesterase (PDE) enzymes, leading to increased intracellular cyclic AMP (cAMP) levels and enhanced cerebral blood flow. In vitro assays indicate moderate binding affinity to PDE1 with IC₅₀ values in the micromolar range (~3–10 µM).

Chemical Structure

Vinburnine
Vinburnine
CAS#4880-88-0 (free base)

Theoretical Analysis

MedKoo Cat#: 526559

Name: Vinburnine

CAS#: 4880-88-0 (free base)

Chemical Formula: C19H22N2O

Exact Mass: 294.1732

Molecular Weight: 294.40

Elemental Analysis: C, 77.52; H, 7.53; N, 9.52; O, 5.43

Price and Availability

Size Price Availability Quantity
5mg USD 150.00 Ready to ship
10mg USD 250.00 Ready to ship
25mg USD 350.00 Ready to ship
50mg USD 550.00 Ready to ship
100mg USD 950.00 Ready to ship
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Related CAS #
4880-88-0 (free base) 94134-60-8 (phosphate)
Synonym
CH846; CH-846; CH 846; Vinburnine; Eburnal; Eburnamonine; (-)-Vincamone; (-)-Eburnamonine
IUPAC/Chemical Name
(41S,13aS)-13a-ethyl-2,3,5,6,13,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridin-12(41H)-one
InChi Key
WYJAPUKIYAZSEM-MOPGFXCFSA-N
InChi Code
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
SMILES Code
C(C)[C@]12[C@]3(C=4N(C=5C(C4CCN3CCC1)=CC=CC5)C(=O)C2)[H]
Appearance
White to off-white 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, not in water
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).
HS Tariff Code
2934.99.9001
More Info
Certificate of Analysis
View CoA: current batch, Lot#A25M05B15
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 294.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Louajri A, Harraga S, Toubin G, Kantelip JP. Red blood cell metabolism and hemoglobin oxygen affinity. Effect of vinburnine on normobaric hypoxic rats. Biol Pharm Bull. 1999 Aug;22(8):773-4. PubMed PMID: 10480311. 2: Schena D, Menegazzi S, Barba A. Bullous fixed drug eruption induced by vinburnine. Contact Dermatitis. 1992 Sep;27(3):187. PubMed PMID: 1451466. 3: Acciavatti A, Domini L, Galigani C, Saletti M, Guideri F, Auteri A, Di Perri T. [The effects of vinburnine on the blood rheology parameters and on the oxyhemoglobin dissociation curve and 2,3-diphosphoglycerate. In vitro research]. Recenti Prog Med. 1990 Nov;81(11):710-5. Italian. PubMed PMID: 2287807. 4: Drago F, Grassi M, Valerio C, Spadaro F, D'Agata V, Lauria N. Effects of vinburnine on experimental models of learning and memory impairments. Pharmacol Biochem Behav. 1990 Sep;37(1):53-7. PubMed PMID: 2263666. 5: Sado PA, Gibassier D, Leverge R. [The effect of modification of excipients for the bioavailability of vinburnine]. J Pharm Belg. 1989 May-Jun;44(3):221-9. French. PubMed PMID: 2795425. 6: Sado PA, Gibassier D, Leverge R. [The oral liquid form of vinburnine: biopharmaceutics]. J Pharm Belg. 1989 Jan-Feb;44(1):50-9. French. PubMed PMID: 2724048. 7: 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. 8: Maksay G, Bíró T, Kiss B. Vinburnine decelerates [3H]N-methylscopolamine binding to recombinant human muscarinic M1-M4 acetylcholine receptors. Eur J Pharmacol. 2004 Jan 12;483(2-3):229-32. PubMed PMID: 14729111. 9: Chauveau E, Prignet JM, Carloz E, Duval JL, Gilles B. [Lymphocytic colitis likely attributable to use of vinburnine (Cervoxan)]. Gastroenterol Clin Biol. 1998 Mar;22(3):362. French. PubMed PMID: 9762227. 10: Domini L, Acciavatti A, Galigani C, Saletti M, De Franco V, Pecchi S, Auteri A, Di Perri T. [The effects of the acute administration of vinburnine on blood rheology, oxygen transport and regional circulation under normal conditions and in hypoxemia. In vivo research]. Recenti Prog Med. 1990 Nov;81(11):716-23. Italian. PubMed PMID: 2287808. 11: Bentue-Ferrer D, Philouze V, Pape D, Reymann JM, Allain H, Van den Driessche J. Comparative evaluation of scavenger properties of exifone, piracetam and vinburnine. Fundam Clin Pharmacol. 1989;3(4):323-8. PubMed PMID: 2807130. 12: Sado PA, Gibassier D, Leverge R. [Simultaneous determination of vinburnine and 6-hydroxyvinburnine in human plasma by high-performance liquid chromatography]. J Chromatogr. 1988 Dec 29;434(1):157-67. French. PubMed PMID: 3243809. 13: Giordano F, Pavan M, La Manna A, Bettinetti GP, Pavesi L, Bovis G. Complexation behavior of vinburnine with beta and gamma cyclodextrins in aqueous solution and in the solid state. Farmaco Prat. 1988 Nov;43(11):345-55. PubMed PMID: 3243350. 14: Sado PA, Gibassier D, Leverge R. [Bioavailability of vinburnine in man: importance of combination with ascorbic acid]. J Pharm Belg. 1986 Jan-Feb;41(1):17-28. French. PubMed PMID: 3701564. 15: Sado PA, Gibassier D, Le Verge R, Acerbi D, Schiantarelli P. [Relative bioavailability of vinburnine in man (microgranules/gels)]. J Pharm Belg. 1985 Sep-Oct;40(5):308-22. French. PubMed PMID: 4087124.

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