65655-59-6

Basic information

• Product Name: Pacrinolol
• Synonyms: Pacrinolol;(-)-3-[4-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]amino]-2-hydroxypropoxy]phenyl]-2-butenenitrile;HOE-224
• CAS NO: 65655-59-6
• Molecular Formula: C23H28N2O4
• Molecular Weight: 396.4794
• Mol File: 65655-59-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 606.7°Cat760mmHg
• Flash Point: 320.7°C
• Appearance: /
• Density: 1.135g/cm³
• Vapor Pressure: 1.42E-15mmHg at 25°C
• Refractive Index: 1.563
• CAS DataBase Reference: Pacrinolol(CAS DataBase Reference)
• NIST Chemistry Reference: Pacrinolol(65655-59-6)
• EPA Substance Registry System: Pacrinolol(65655-59-6)

Safety Data

• Hazardous Substances Data: 65655-59-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C23H28N2O4/c1-17(10-12-24)19-5-7-21(8-6-19)29-16-20(26)15-25-13-11-18-4-9-22(27-2)23(14-18)28-3/h4-10,14,20,25-26H,11,13,15-16H2,1-3H3/b17-10+

Upstream product

• 99-93-4 4-Hydroxyacetophenone 
• 19152-55-7 1-[4-(2-oxiranylmethoxy)phenyl]-1-ethanone 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 115795-51-2 (+/-)-3-<4-(2,3-oxidopropoxy)phenyl>-cis-crotonsaurenitril 

Relevant articles and documents

Synthesis of the highly cardioselective β-sympathicolytic pacrinolol

The synthesis is described of the enantiomerically pure (-)-3-(3,4-dimethoxyphenylethylamino-2-hydroxypropoxy] phenyl]-cis-crotonic acid nitrile (13b) (free base) and its hydrochloride (13c) (pacrinolol, Hoe 224 A) starting from p-hydroxyacetophenone (1) and racemic epichlorohydrin (2). The p-(2,3-oxidopropoxy)acetophenone (2) resulting from this reaction is C-homologisized to (8); reactions of this with homoveratrylamine (9) leads to (10a), the racemic structural analog of (13b). Resolution of the racemate is achieved by fractional crystallisation of the diastereoisomeric mandelates (13a) and (14a) to afford the enantiomerically pure title compound (13c) and its dextrarotatory optical antipode (14c). Structural confirmation of (13b) and (13c) was achieved through physicochemical and spectroscopic data especially from the 1H-NMR- and MS-spectra. Pacrinolol (13c) is a highly cardioselective β-sympathicolytic with significant and long acting blood pressure lowering properties (intravenous and oral in the dog).