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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

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

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

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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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
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.
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
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
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
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