132373-81-0

Basic information

• Product Name: VAMICAMIDE
• Synonyms: Vamicamide [INN]; Vamicamide (+-)-; (+-)-(2R*,4R*)-4-Dimethylamino-2-phenyl-2-(2-pyridyl)valeramide; (+-)-(R*)-alpha-((R*)-2-(Dimethylamino)propyl)-alpha-phenyl-2-pyridineacetamide; (R*,R*)-(+-)-alpha-(2-(Dimethylamino)propyl)-alpha-phenyl-2-pyridineacetmide; UNII-RU10K34QRU; 2-Pyridineacetamide, alpha-(2-(dimethylamino)propyl)-alpha-phenyl-, (R*,R*)-(+-)-; (2R,4R)-4-(dimethylamino)-2-phenyl-2-(pyridin-2-yl)pentanamide
• CAS NO: 132373-81-0
• Molecular Formula: C₁₈H₂₃N₃O
• Molecular Weight: 297.4
• Mol File: 132373-81-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 156-157°
• Boiling Point: 477.6°C at 760 mmHg
• Flash Point: 242.7°C
• Appearance: /
• Density: 1.099g/cm³
• Vapor Pressure: 2.76E-09mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: VAMICAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: VAMICAMIDE(132373-81-0)
• EPA Substance Registry System: VAMICAMIDE(132373-81-0)

Safety Data

• Hazardous Substances Data: 132373-81-0(Hazardous Substances Data)

Usage

Originator

Vamicamide,Fujisawa Pharmaceutical

Uses

Antiepileptic; anticonvulsant.

Manufacturing Process

Conc. sulfuric acid (11 ml) was added to 4-(N,N-dimethylamino)-2-phenyl-2- (2-pyridyl)-valeronitrile (6.3 g) at 0°C. Then water (1 ml) was added thereto. After being heated at 90°C for 3 hours, the mixture was poured into ice-water, adjusted to pH 10 with 10% aqueous sodium hydroxide and extracted with ethyl acetate (3x50ml). The extracts were combined, and washed with water, dried over magnesium sulfate and evaporated under reduced pressure. The obtained crude crystal was recrystallized from diethyl ether to give 4-(N,N_x0002_dimethylamino)-2-phenyl-2-(2-pyridyl)-valeramide (1.89 g). MP: 132-134°C. Recrystallization from 40% water ethanol gave MP: 156-157°C. The structure of the product was confirmed by UR, NMR (CDCl3) spectra and elemental analysis.

Therapeutic Function

Anticholinergic, Spasmolytic

InChI:InChI=1/C18H23N3O/c1-14(21(2)3)13-18(17(19)22,15-9-5-4-6-10-15)16-11-7-8-12-20-16/h4-12,14H,13H2,1-3H3,(H2,19,22)/t14-,18-/m1/s1

Upstream product

• 99132-31-7 4-(dimethylamino)-2-phenyl-2-(2-pyridyl)pentanenitrile 
• 101509-01-7 4-oxo-2-phenyl-2-(2-pyridyl)pentanenitrile 
• 5005-36-7 phenyl-pyridin-2-yl-acetonitrile 
• 97987-88-7 (2R*,4R*)-4-dimethylamino-2-phenyl-2-(pyridin-2-yl)-valeramide 

Related news

Determination of the R,R- and S,S-enantiomers of VAMICAMIDE (cas 132373-81-0) in human serum and urine by high-performance liquid chromatography on a Chiral-AGP column08/10/2019

An enantioselective liquid chromatographic assay for the determinations of the R,R- and S,S-enantiomers of vamicamide, a potent anticholinergic drug, in human serum and urine is described. Racemic vamicamide and internal standard were purified from biological fluids using a two-step extraction p...detailed

Effects of VAMICAMIDE (cas 132373-81-0) on Urinary Bladder Functions in Conscious Dog and Rat Models of Urinary Frequency08/09/2019

PurposeTo investigate the usefulness of vamicamide, (plus/minus)-(2R*, 4R*)-4-dimethylamino-2-phenyl-2-(2-pyridyl)valeramide, as a novel drug for the treatment of urinary frequency and incontinence.detailed

Relevant articles and documents

Synthesis and Anticholinergic Activity of the Four Stereoisomers of 4-(Dimethylamino)-2-phenyl-2-(2-pyridyl)pentanamide

The four stereoisomers of 4-(dimethylamino)-2-phenyl-2-(2-pyridyl)pentanamide were synthesized, and the absolute configuration were determined by X-ray crystallography.Pharmacological testing for anticholinergic activity revealed great differences in pote