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Merck
CN

194719

Vincamine

98%

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About This Item

Empirical Formula (Hill Notation):
C21H26N2O3
CAS Number:
1617-90-9
Molecular Weight:
354.44
NACRES:
NA.22
PubChem Substance ID:
24851332
UNSPSC Code:
12352005
EC Number:
216-576-3
MDL number:
MFCD00078054
Assay:
98%

Key Documents

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InChI key

RXPRRQLKFXBCSJ-GIVPXCGWSA-N

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 string

CC[C@@]12CCCN3CCc4c(C13)n(c5ccccc45)[C@](O)(C2)C(=O)OC

assay

98%

optical activity

[α]23/D +42.8°, c = 1 in pyridine

mp

232 °C (dec.) (lit.)

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Application

Vincamine can be used as a starting material to synthesize:
  • Vincamine acid, which is employed as a precursor in the synthesis of vinpocetine by dehydration and esterification using sulfuric acid.
  • Apovincamine using iron(III) perchlorate.
  • (-)-Criocerine via one-step iodination reaction.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBR8117V
BCBJ6068V
BCBP5884V
BCBG9758V
1448214V

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Adám Vas et al.
Medicinal research reviews, 25(6), 737-757 (2005-09-15)
The Apocynaceae plant family contains a great number of so called eburnamine-vincamine alkaloids. Quite a few of these alkaloids exert varied pharmacological activities on the cell multiplication, cardiovascular system, and brain functions. Many derivatives were also synthesized to find pharmacologically
S Caccamese et al.
Journal of chromatography. A, 893(1), 47-54 (2000-10-24)
The four enantiomeric pairs of vincamine group alkaloids were separated by HPLC using Chiralpak AD as chiral stationary phase (CSP) and various n-hexane-2-propanol and n-hexane-ethanol mobile phases. (+)-cis-Vincamine, which is used in pharmaceutical preparations, is eluted much faster than its
K Cambon et al.
Neuroscience, 171(3), 840-851 (2010-10-07)
The Balb/c strain and the C57BL/6 strain show constitutive differences for tyrosine hydroxylase expression, and noradrenaline (NA) prefrontal transmission. Male mice of these strains also show striking differences in social interaction behaviors, with an increased aggressiveness for the Balb/c strain.
Hong Yin et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 18(8-9), 802-805 (2011-02-15)
Vinca minor is a plant containing the alkaloid vincamine, which is used in the pharmaceutical industry as a cerebral stimulant and vasodilator. The objective of this study was to determine whether endophytic fungi isolated from V. minor produce vincamine. Primary
Mazák Károly et al.
Journal of chromatography. A, 996(1-2), 195-203 (2003-07-02)
A reversed-phase thin-layer chromatographic method was developed and applied to quantitate the lipophilicity of sparingly water-soluble eburnane alkaloids of therapeutic interest. Our method development included calibration, optimization and validation procedures, using also sets of auxiliary compounds. The log P(TLC) values
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