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P7412

Sigma-Aldrich

Pirenzepine dihydrochloride

≥98% (TLC), powder

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

Quality Level

200

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.

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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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)
Ion-paired pirenzepine-loaded micelles as an ophthalmic delivery system for the treatment of myopia
Li Y, et al.
Nanomedicine: Nanotechnology, Biology, and Medicine, 13(6), 2079-2089 (2017)
Mariko Iwase et al.
Biological & pharmaceutical bulletin, 40(10), 1654-1660 (2017-10-03)
OTC drugs have an important role in self-medication. However, the pharmacokinetic properties of some OTC drugs have not been fully investigated and reports concerning their drug interactions are insufficient. Several gastrointestinal drugs are available as OTC drugs. Because of their
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
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)
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