Voachalotine

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MedKoo CAT#: 461826

CAS#: 664-25-5

Description: Voachalotine is a monoterpenic indole alkaloid from Tabernaemontana catharinensis.


Price and Availability

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Pricing updated 2020-08-15. Prices are subject to change without notice.

Voachalotine 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#: 461826
Name: Voachalotine
CAS#: 664-25-5
Chemical Formula: C22H26N2O3
Exact Mass: 66.1943
Molecular Weight: 366.46
Elemental Analysis: C, 72.11; H, 7.15; N, 7.64; O, 13.10


Synonym: Voachalotine;

IUPAC/Chemical Name: methyl (E)-9-ethylidene-11-(hydroxymethyl)-5-methyl-5,6,8,9,10,11,11a,12-octahydro-6,10-methanoindolo[3,2-b]quinolizine-11-carboxylate

InChi Key: IWEYXWIPVZEVPT-PQMHYQBVSA-N

InChi Code: InChI=1S/C22H26N2O3/c1-4-13-11-24-18-10-16(13)22(12-25,21(26)27-3)19(24)9-15-14-7-5-6-8-17(14)23(2)20(15)18/h4-8,16,18-19,25H,9-12H2,1-3H3/b13-4-

SMILES Code: O=C(C1(CO)C2/C(CN3C(C2)C(N(C)C4=C5C=CC=C4)=C5CC13)=C\C)OC


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).

HS Tariff Code:
2934.99.03.00


References

1: Nicola C, Salvador M, Gower AE, Moura S, Echeverrigaray S. Chemical constituents antioxidant and anticholinesterasic activity of Tabernaemontana catharinensis. ScientificWorldJournal. 2013 Jul 28;2013:519858. doi: 10.1155/2013/519858. eCollection 2013. PubMed PMID: 23983637; PubMed Central PMCID: PMC3745974.

2: Gonçalves MS, Vieira IJ, Oliveira RR, Braz-Filho R. Application of preparative high-speed counter-current chromatography for the separation of two alkaloids from the roots of Tabernaemontana catharinensis (Apocynaceae). Molecules. 2011 Sep 2;16(9):7480-7. doi: 10.3390/molecules16097480. PubMed PMID: 21892126.

3: Andrade MT, Lima JA, Pinto AC, Rezende CM, Carvalho MP, Epifanio RA. Indole alkaloids from Tabernaemontana australis (Muell. Arg) Miers that inhibit acetylcholinesterase enzyme. Bioorg Med Chem. 2005 Jun 2;13(12):4092-5. PubMed PMID: 15911323.

4: Vieira IJ, Medeiros WL, Monnerat CS, Souza JJ, Mathias L, Braz-Filho R, Pinto AC, Sousa PM, Rezende CM, Epifanio Rde A. Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures. An Acad Bras Cienc. 2008 Sep;80(3):419-26. PubMed PMID: 18797794.

5: Zhou H, Liao X, Yin W, Ma J, Cook JM. General approach for the synthesis of 12-methoxy-substituted sarpagine indole alkaloids including (-)-12-methoxy-N(b)-methylvoachalotine, (+)-12-methoxy-N(a)-methylvellosimine, (+)-12-methoxyaffinisine, and (-)-fuchsiaefoline. J Org Chem. 2006 Jan 6;71(1):251-9. PubMed PMID: 16388644.