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V6383

Sigma-Aldrich

Vinpocetine

≥98%, solid

Synonym(s):

(3α,16α)-Eburnamenine-14-carboxylic acid ethyl ester, Eburnamenine-14-carboxylic acid ethyl ester

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About This Item

Empirical Formula (Hill Notation):
C22H26N2O2
CAS Number:
42971-09-5
Molecular Weight:
350.45
EC Number:
256-028-0
MDL number:
MFCD00211233
UNSPSC Code:
41106305
PubChem Substance ID:
24278182
NACRES:
NA.77

Quality Level

200

assay

≥98%

form

solid

color

white

solubility

DMSO: 5 mg/mL
H2O: insoluble

SMILES string

[H][C@]12N3CCC[C@@]1(CC)C=C(C(=O)OCC)n4c2c(CC3)c5ccccc45

InChI

1S/C22H26N2O2/c1-3-22-11-7-12-23-13-10-16-15-8-5-6-9-17(15)24(19(16)20(22)23)18(14-22)21(25)26-4-2/h5-6,8-9,14,20H,3-4,7,10-13H2,1-2H3/t20-,22+/m1/s1

InChI key

DDNCQMVWWZOMLN-IRLDBZIGSA-N

Gene Information

human ... PDE1A(5136) , PDE1B(5153) , PDE1C(5137)

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Biochem/physiol Actions

Ca2+-calmodulin-dependent phosphodiesterase I (PDE1) inhibitor.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Phosphodiesterases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Caution

Photosensitive

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
056H0188
118H46803
118H46801
097H0511
057H0279

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P Han et al.
The Journal of biological chemistry, 274(32), 22337-22344 (1999-07-31)
To understand the role cAMP phosphodiesterases (PDEs) play in the regulation of insulin secretion, we analyzed cyclic nucleotide PDEs of a pancreatic beta-cell line and used family and isozyme-specific PDE inhibitors to identify the PDEs that counteract glucose-stimulated insulin secretion.
M Cataldi et al.
Biochimica et biophysica acta, 1449(2), 186-193 (1999-03-20)
The present study investigates the potential role of the Ca2+-calmodulin-dependent type I phosphodiesterase (PDE)-cGMP-protein kinase G (PKG) pathway in spontaneous [Ca2+]i oscillations in GH3 cells using fura-2 single cell videoimaging. Vinpocetine (2.5-50 microM), a selective inhibitor of type I PDE
Yujun Cai et al.
The Journal of pharmacology and experimental therapeutics, 343(2), 479-488 (2012-08-24)
Abnormal vascular smooth muscle cell (SMC) activation is associated with various vascular disorders such as atherosclerosis, in-stent restenosis, vein graft disease, and transplantation-associated vasculopathy. Vinpocetine, a derivative of the alkaloid vincamine, has long been used as a cerebral blood flow
Balázs Gulyás et al.
Journal of the neurological sciences, 320(1-2), 110-117 (2012-07-31)
Although there is increasing evidence for microglial activation after an ischaemic stroke in the infarct core and the peri-infarct region, the "evolution" of the process in stroke patients is poorly known. Using PET and [((11))C]vinpocetine, we measured the regional changes
Sazal Patyar et al.
Pharmacological reports : PR, 63(3), 618-628 (2011-08-23)
A cerebrovascular accident, or stroke, is defined as the abrupt onset of a neurological deficit, which can be due to ischemia. Cerebral ischemia is caused by a reduction in blood flow that thereby decreases cerebral metabolism. Chronic cerebral hypoperfusion leads
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