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P7412

Sigma-Aldrich

Pirenzepine dihydrochloride

≥98% (TLC), 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:
Molecular Weight:
424.32
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Assay

≥98% (TLC)

form

powder

color

white

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)

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.

Caution

Hygroscopic; store desiccated at room temperature.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

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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Corinne G Jolivalt et al.
The Journal of pharmacology and experimental therapeutics, 374(1), 44-51 (2020-04-25)
Muscarinic antagonists promote sensory neurite outgrowth in vitro and prevent and/or reverse multiple indices of peripheral neuropathy in rodent models of diabetes, chemotherapy-induced peripheral neuropathy, and HIV protein-induced neuropathy when delivered systemically. We measured plasma concentrations of the M1 receptor-selective
Pirenzepine Dihydrochloride
El-Obeild HA, et al.
Anal. Profiles Drug Subst., 16, 445-506 (1987)
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)
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)
Pirenzepine promotes the dimerization of muscarinic M1 receptors through a three-step binding process
Ilien B, et al.
The Journal of Biological Chemistry, 13(6), jbc-M109 (2009)

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