Pirenzepine

Base Information

• Chemical Name: Pirenzepine
• CAS No.: 28797-61-7
• Molecular Formula: C19H21 N5 O2
• Molecular Weight: 351.408
• European Community (EC) Number: 249-228-4
• UNII: 3G0285N20N
• DSSTox Substance ID: DTXSID7023487
• Nikkaji Number: J20.030A
• Wikipedia: Pirenzepine
• Wikidata: Q419550
• NCI Thesaurus Code: C76002
• Pharos Ligand ID: 9YCCSB38CVR4,9YXAA9YQM41S
• Metabolomics Workbench ID: 42985
• ChEMBL ID: CHEMBL9967
• Mol file: 28797-61-7.mol

Synonyms:Dihydrochloride, Pirenzepine;Gastrotsepin;Gastrozepin;L-S 519;LS 519;LS-519;LS519;Piren basan;Piren-basan;Pirenzepin;Pirenzepin ratiopharm;pirenzepin von ct;Pirenzepin-ratiopharm;Pirenzepine;Pirenzepine Dihydrochloride;Pyrenzepine;Ulcoprotect;Ulgescum;Von Ct, Pirenzepin

Chemical Property of Pirenzepine

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 8.44E-12mmHg at 25°C
• Melting Point: 226 - 230 C
• Boiling Point: 541.7°C at 760 mmHg
• Flash Point: 281.4°C
• PSA: 74.23000
• LogP: 2.80740
• Storage Temp.: Store at RT
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 351.16952493
• Heavy Atom Count: 26
• Complexity: 534

Purity/Quality:

99% ^*data from raw suppliers

Pirenzepine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCN(CC1)CC(=O)N2C3=CC=CC=C3C(=O)NC4=C2N=CC=C4
• Recent EU Clinical Trials: A double-blind placebo-controlled study of the safety, tolerability and efficacy of 12 months’ treatment with ACI-91 in patients with mild to moderate Alzheimer’s Disease
• Uses: Pirenzepine, is an M1 selective antagonist, that is used in the treatment of peptic ulcers, as it reduces gastric acid secretion and reduces muscle spasm. antifungal
• Therapeutic Function: Antiulcer, Antiemetic

Technology Process of Pirenzepine

There total 20 articles about Pirenzepine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-oxo-11,2'-(4''-methylpiperazin-1''-yl)acetyl-5,11-dihydro-6H-pyrido<2,3-b><1,4>benzodiazepin-6-one (84446-20-8) → pirenzepine (28797-61-7)

Guidance literature:

With hydrogen; nickel; In diethylene glycol dimethyl ether; at 50 ℃; for 16h;

Reference yield: 87.0%

1-methyl-piperazine (109-01-3) + 11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one (28797-48-0) → pirenzepine (28797-61-7)

Guidance literature:

In benzene; for 18h; Further byproducts given. Yields of byproduct given; Heating;

Reference yield:

[11C]methyl iodide (54245-42-0) + N-Demethyl-Pirenzepin (63257-31-8,122859-63-6) → pirenzepine (28797-61-7)

Guidance literature:

In dimethyl sulfoxide; at 20 ℃; for 0.0333333h; Temperature;

DOI:10.1016/j.ejmech.2020.112623

upstream raw materials:

1-methyl-piperazine

11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

chloroacetyl chloride

5H-benzo[e]pyrido[3,2-b][1,4]diazepin-6(11H)-one

Refernces

• 1、 Budesinsky, Milos,Symersky, Jindrich,Podlaha, Jaroslav,Podlahova, Jana,Polivka, Zdenek,Protiva, Miroslav. "Unexpected Formation of a 11H-Pyridoquinazolin-11-one Derivative from 5,11-Dihydro-6H-pyrido-1,4-benzodiazepin-6-one". . p. 1229 - 1235. Retrieved 2007/10/02.
• 2、 Kovac, T.,Oklobdzija, M.,Comisso, G.,Decorte, E.,Fajdiga, T.,et al.. "New Synthesis of 11-Acyl-5,11-dihydro-6H-pyridobenzodiazepin-6-ones and Related Studies". . p. 1339 - 1349. Retrieved 2007/10/02.