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Sigma-Aldrich

Vincamine

98%

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About This Item

Empirical Formula (Hill Notation):
C21H26N2O3
CAS Number:
1617-90-9
Molecular Weight:
354.44
EC Number:
216-576-3
MDL number:
MFCD00078054
UNSPSC Code:
12352005
PubChem Substance ID:
24851332
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
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Reserpine crystallized, ≥99.0% (HPLC)

Sigma-Aldrich

83580

Reserpine

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
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.
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
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
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)
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