6159-56-4

Basic information

• Product Name: Peganine
• Synonyms: Vasicine (20 mg);l-peganine
• CAS NO: 6159-56-4
• Molecular Formula: C₁₁H₁₂N₂O
• Molecular Weight: 188.22578
• Mol File: 6159-56-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 211 °C
• Boiling Point: 373.8±52.0 °C(Predicted)
• Appearance: /
• Density: 1.37±0.1 g/cm3(Predicted)
• PKA: 13.08±0.20(Predicted)
• CAS DataBase Reference: Peganine(CAS DataBase Reference)
• NIST Chemistry Reference: Peganine(6159-56-4)
• EPA Substance Registry System: Peganine(6159-56-4)

Safety Data

• Hazardous Substances Data: 6159-56-4(Hazardous Substances Data)

Usage

Uses

(±)-Vasicine (peganine) is a quinazoline alkaloid isolated from nature. It can be used for the preparation of Vicinal Tricarbonyls and cyano analogs as electrophilic participants in forming pharmacophoric templates for drug discovery.

Upstream product

• 4403-69-4 2-amino-1-benzylamine 
• 19444-84-9 3-hydroxyoxolan-2-one 
• 1904-78-5 2-nitrobenzylamine 
• 139080-85-6 3-Oxo-2,3,4,9-tetrahydro-1H-pyrrolo[2,1-b]quinazoline-3a-carboxylic acid tert-butyl ester 
• 7647-01-0 hydrogenchloride 
• 100061-16-3 3-hydroxy-1-(2-nitro-benzyl)-pyrrolidin-2-one 
• 64-19-7 acetic acid 
• 139080-84-5 3-Hydroxy-2,3,4,9-tetrahydro-1H-pyrrolo[2,1-b]quinazoline-3a-carboxylic acid tert-butyl ester 

Downstream Products

• 118-92-3 anthranilic acid 
• 64-19-7 acetic acid 
• 18549-38-7 vasicine 
• 6159-55-3 (+)-vasicinol 
• 7174-27-8 peganine hydrochloride 
• 491-36-1 4-Hydroxyquinazoline 

Relevant articles and documents

Process for the production of vasicine

The present invention relates to an improved process for the production of vasicine of formula (1) from the Adhatoda vasica, said process comprising the steps of: extracting the dried and pulverized leaves with an alcoholic extract at an ambient temperature, concentrating the alcoholic extract to obtain a concentrated extract, treating and stirring extract with an aqueous organic acid for 2-24 hours, extracting the acid solution of with an organic solvent, separating the organic layer and aqueous acidic layer, basifying the aqueous acidic solution with a base, extracting the basified solution with an organic solvent, separating the organic layer, drying and filtering, evaporating the organic layer to obtain an amorphous residue, and treating the amorphous residue with an organic solvent or mixture of organic solvents to obtain vasicine.

The chemistry of vicinal tricarbonyls. an efficient synthesis of (±)-vasicine

Addition of 2-aminobenzylamine to the vinyl vicinal tricarbonyl reagent leads to a short synthesis of (±)-vasicine. In this reaction, the VTC reagent acts as a trielectrophile.