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P7412

Sigma-Aldrich

Pirenzepine dihydrochloride

≥98% (TLC), muscarinic acetylcholine receptor antagonist, powder

Synonym(s):

5,11-Dihydro-11-[(4-methyl-1-piperazinyl)acetyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C19H21N5O2 · 2HCl
CAS Number:
29868-97-1
Molecular Weight:
424.32
EC Number:
249-907-5
MDL number:
MFCD00055214
UNSPSC Code:
12352200
PubChem Substance ID:
24277863
NACRES:
NA.77

Key Documents

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Product Name

Pirenzepine dihydrochloride, ≥98% (TLC), powder

Quality Level

200

assay

≥98% (TLC)

form

powder

color

white to light yellow

solubility

H2O: 50 mg/mL

SMILES string

Cl[H].Cl[H].CN1CCN(CC1)CC(=O)N2c3ccccc3C(=O)Nc4cccnc24

InChI

1S/C19H21N5O2.2ClH/c1-22-9-11-23(12-10-22)13-17(25)24-16-7-3-2-5-14(16)19(26)21-15-6-4-8-20-18(15)24;;/h2-8H,9-13H2,1H3,(H,21,26);2*1H

InChI key

FFNMBRCFFADNAO-UHFFFAOYSA-N

Gene Information

human ... CHRM1(1128)

Related Categories

General description

Pirenzepine dihydrochloride is an anticholinergic agent. It is also considered as an antiulcer drug. It is used to treat myopia, gastric and duodenal ulcers. Pirenzepine dihydrochloride induces the dimerization of muscarinic M1 receptors.

Application

Pirenzepine dihydrochloride has been used
  • in transactivation of fibroblast growth factor receptor (FGFR).
  • as a supplement in cell culture.
  • for the stimulation of human fibroblasts

Biochem/physiol Actions

Selective M1 muscarinic acetylcholine receptor antagonist.

Features and Benefits

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

Disclaimer

Hygroscopic; store desiccated at room temperature.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLCG9791
079K1733V
079K1733
127K1102
016K1498

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Pirenzepine Dihydrochloride
El-Obeild HA, et al.
Anal. Profiles Drug Subst., 16, 445-506 (1987)
Pirenzepine
Carmine AA and Brogden RN
Drugs, 30(2), 85-126 (1985)
Muscarinic acetylcholine type 1 receptor activity constrains neurite outgrowth by inhibiting microtubule polymerization and mitochondrial trafficking in adult sensory neurons
Sabbir MG, et al.
Frontiers in Neuroscience, 12(3), 229-237 (2018)
A Elhusseiny et al.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism, 19(7), 794-802 (1999-07-21)
Acetylcholine is an important regulator of local cerebral blood flow. There is, however, limited information available on the possible sites of action of this neurotransmitter on brain intraparenchymal microvessels. In this study, a combination of molecular and functional approaches was
Effect of the antimuscarinic agent pirenzepine on the in vivo biliary secretion of dogs in response to various stimuli.
Madrid JA, et al.
Physiologia Bohemoslovaca, 37(1), 67-77 (1988)
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