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P3510

Sigma-Aldrich

Papaverine hydrochloride

powder

Synonym(s):

6,7-Dimethoxy-1-veratrylisoquinoline hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C20H21NO4 · HCl
CAS Number:
61-25-6
Molecular Weight:
375.85
Beilstein/REAXYS Number:
3921435
EC Number:
200-502-1
MDL number:
MFCD00012745
UNSPSC Code:
41106305
PubChem Substance ID:
24278152
NACRES:
NA.77

assay

≥98%

Quality Level

100

form

powder

color

white

solubility

H2O: 25 mg/mL

SMILES string

COC1=C(OC)C=C(C(CC2=CC(OC)=C(OC)C=C2)=NC=C3)C3=C1.Cl

InChI

1S/C20H21NO4.ClH/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16;/h5-8,10-12H,9H2,1-4H3;1H

InChI key

UOTMYNBWXDUBNX-UHFFFAOYSA-N

Gene Information

human ... PDE4B(5142)

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General description

Papaverine hydrochloride belongs to the group of benzylisoquinoline alkaloid. It is obtained from opium poppy.

Application

Papaverine hydrochloride has been used:
  • in oxygenated Krebs solution for tissue mechanics analysis
  • as a vasodilator in heparinized horse serum in tissue uptake technique
  • as an inhibitor of H-MPP+ uptake into stably transfected 293 cells expressing either extraneuronal monoamine transporter (EMT) human or EMT rat

Biochem/physiol Actions

Papaverine is originally used to resolve male impotence.
Smooth muscle relaxant and cerebral vasodilator; phosphodiesterase 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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, 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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Activation of the extraneuronal monoamine transporter (EMT) from rat expressed in 293 cells
Grundemann D, et al.
British Journal of Pharmacology, 137(6), 910-918 (2002)
Intra-arterial papaverine infusions for the treatment of cerebral vasospasm induced by aneurysmal subarachnoid hemorrhage
Liu James K and Couldwell William T
Neurocritical Care, 2(2), 124-132 (2005)
Increased glomerular albumin permeability in old spontaneously hypertensive rats
Bakoush O, et al.
Nephrology, Dialysis, and Transplantation, 19(7), 1724-1731 (2004)
Effects of antiallergic agents, compound 48/80, and some reference inhibitors on the activity of partially purified human lung tissue adenosine cyclic 3',5'-monophosphate and guanosine cyclic 3',5'-monophosphate phosphodiesterases.
H Bergstrand et al.
Molecular pharmacology, 13(1), 38-43 (1977-01-01)
Differential roles of endothelin-1 in angiotensin II-induced atherosclerosis and aortic aneurysms in apolipoprotein E-null mice
Suen RS, et al.
The American Journal of Pathology, 179(3), 1549-1559 (2011)
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