194719
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.
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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Dritan Hasa et al.
Molecular pharmaceutics, 10(1), 211-224 (2012-11-29)
In the present research a salt of vincamine, a poorly bioavailable indole alkaloid derived from the leaves of Vinca minor L., was synthesized in the solid state by means of a mechanochemical process employing citric acid as a reagent. The
Iron (III) Perchlorate-A Novel Reagent for the Conversion of Vincamine, Criocerine and 18-Iodocriocerine to Apovincamine: A New Method.
Lakshmi V and Bhaduri AP
ChemInform, 25(18) (1994)
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
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
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