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MedKoo Cat#: 125909 | Name: Vinburnine phosphate

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 phosphate
Vinburnine phosphate
CAS#94134-60-8 (phosphate)

Theoretical Analysis

MedKoo Cat#: 125909

Name: Vinburnine phosphate

CAS#: 94134-60-8 (phosphate)

Chemical Formula: C19H25N2O5P

Exact Mass: 392.1501

Molecular Weight: 392.39

Elemental Analysis: C, 58.16; H, 6.42; N, 7.14; O, 20.39; P, 7.89

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
4880-88-0 (free base) 94134-60-8 (phosphate)
Synonym
Eburnamonine (-)-form phosphate; vinburnine phosphate; CH846; CH-846; CH 846; Vinburnine; Eburnal; 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 phosphate
InChi Key
RVHMKJRPCKDXCS-VOMIJIAVSA-N
InChi Code
InChI=1S/C19H22N2O.H3O4P/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;1-5(2,3)4/h3-4,6-7,18H,2,5,8-12H2,1H3;(H3,1,2,3,4)/t18-,19+;/m1./s1
SMILES Code
OP(O)(O)=O.[H][C@]12N3CCC[C@@]1(CC)CC(=O)N4C5=CC=CC=C5C(CC3)=C24
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 392.39 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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