Deoxypeganine

Base Information

• Chemical Name: Deoxypeganine
• CAS No.: 495-59-0
• Molecular Formula: C11H12N2
• Molecular Weight: 172.2264
• UNII: A3P6YTL6RH
• DSSTox Substance ID: DTXSID40197807
• Nikkaji Number: J275.526B
• Wikidata: Q27106379
• Metabolomics Workbench ID: 69497
• ChEMBL ID: CHEMBL355821
• Mol file: 495-59-0.mol

Synonyms:3-deoxy-peganine;3-deoxy-vasicine;3-deoxypeganine;3-deoxyvasicine;3-deoxyvasicine, fumarate;3-deoxyvasicine, hydrochloride;3-desoxypeganine;deoxyvasicine

Chemical Property of Deoxypeganine

Chemical Property:

• Boiling Point: 311.6°Cat760mmHg
• Flash Point: 142.3°C
• PSA: 15.60000
• Density: 1.23g/cm³
• LogP: 1.69950
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 172.100048391
• Heavy Atom Count: 13
• Complexity: 234

Purity/Quality:

99% ^*data from raw suppliers

1,2,3,9-tetrahydropyrrolo[2,1-b]quinazoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=NC3=CC=CC=C3CN2C1
• General Description: 3-Deoxyvasicine (also known as desoxypeganine) is an anticholinergic quinazoline alkaloid with therapeutic potential for conditions such as Alzheimer's disease, alcoholism, and nicotine dependence. Its biotransformation by liver microsomal enzymes leads to rapid oxidation into inactive metabolites like pegenone, which complicates its pharmacokinetics and dosage formulation. This metabolic instability highlights a key challenge in its development as a pharmaceutical agent.

Technology Process of Deoxypeganine

There total 29 articles about Deoxypeganine 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: 95.0%

C11H14N2 (1356132-39-2) → deoxypeganine (495-59-0)

Guidance literature:

With N-chloro-succinimide; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ol203313n

Reference yield: 90.0%

desoxypeganine tetrachlorozincate → deoxypeganine (495-59-0)

Guidance literature:

With sodium hydroxide; In water; at 90 - 100 ℃;

Reference yield: 86.0%

1,2,3,3a,4,9-hexahydropyrrolo<2,1-b>quinazoline (495-58-9) → deoxypeganine (495-59-0)

Guidance literature:

With oxygen; copper(II) acetate monohydrate; acetic acid; In methanol; for 7h; Solvent; Reagent/catalyst; Temperature; Time; Reflux;

DOI:10.3762/bjoc.9.135

upstream raw materials:

4-butanolide

2-amino-1-benzylamine

N-(2'-aminophenylmethyl)pyrrolidin-2-one

2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-b]quinazolinium; chloride

Downstream raw materials:

3-benzylidene-1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazoline

deoxyvasicinone

5-[1,2-Dihydro-9H-pyrrolo[2,1-b]quinazolin-(3E)-ylidenemethyl]-2-methoxy-phenol

3-[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazoline

Refernces

Biotransformation of desoxypeganine by microsomal enzymes of the rabbit liver

10.1002/ardp.200400921

The research details an in vitro study on the biotransformation of Desoxypeganine, an anticholinergic quinazoline alkaloid, by rabbit liver microsomal enzymes. The purpose of the study was to investigate the metabolic pathways and kinetics of Desoxypeganine, which has therapeutic potential for Alzheimer's disease, alcoholism, and nicotine dependence. The researchers used aerobic incubation with rabbit liver homogenates as the enzyme source, supplemented with NADPH, and identified metabolites through high-performance liquid chromatography and mass spectrometry. The main conclusion was that Desoxypeganine is readily oxidized to its inactive metabolite Pegenone, which poses a challenge for dosage in pharmaceutical formulations. Key chemicals used in the process included Desoxypeganine, Pegenone, Vasicinone, Isovasicinone, NADPH, and various buffer solutions for the incubation and extraction steps.

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