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Key Documents

Safety Information

194719

Sigma-Aldrich

Vincamine

98%

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About This Item

Empirical Formula (Hill Notation):
C21H26N2O3
CAS Number:
Molecular Weight:
354.44
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

optical activity

[α]23/D +42.8°, c = 1 in pyridine

mp

232 °C (dec.) (lit.)

SMILES string

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

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

InChI key

RXPRRQLKFXBCSJ-GIVPXCGWSA-N

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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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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
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
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
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.

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