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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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Dritan Hasa et al.
International journal of pharmaceutics, 436(1-2), 41-57 (2012-06-23)
The aims of this research were to prepare highly bioavailable binary cogrounds (vincamine-AcDiSol(®) or PVP-Cl) by means of a mechanochemical process and to study the mediation of each polymer in the induction of physical transformations of the drug. From a
Synthesis of Vinca Alkaloids and Related Compounds. PART LVIII. A Novel Formal Synthesis of (-)-Criocerine from (+)-Vincamine
Moldvai I, et al.
Synthetic Communications, 21(8-9), 965-967 (1991)
Dylan B England et al.
Organic letters, 9(17), 3249-3252 (2007-07-31)
A synthesis of (+/-)-3H-epivincamine is reported. Important steps include (1) a Rh(II)-catalyzed intramolecular [3+2]-cycloaddition of an alpha-diazo indolo amide, (2) a reductive ring opening of the cycloadduct, (3) a decarboethoxylation reaction, and (4) a base-induced keto-amide ring contraction.
Mostafa A M Shehata et al.
Journal of pharmaceutical and biomedical analysis, 38(1), 72-78 (2005-05-24)
Three different stability indicating assay methods are developed and validated for determination of vincamine in the presence of its degradation product (vincaminic acid). The first method is based on the derivative ratio zero crossing spectrophotometric technique using 0.1 N hydrochloric
Paul E Polak et al.
Journal of neurochemistry, 121(2), 206-216 (2012-02-01)
The endogenous neurotransmitter noradrenaline (NA) plays several roles in maintaining brain homeostasis, including exerting anti-inflammatory and neuroprotective effects. The primary source of NA in the CNS are tyrosine hydroxylase (TH)-positive neurons located in the Locus coeruleus (LC) which send projections
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