6098-20-0

Basic information

• Product Name: N-carbamoyl-2-propyl-pentanamide
• Synonyms: N-carbamoyl-2-propyl-pentanamide
• CAS NO: 6098-20-0
• Molecular Formula: C9H18N2O2
• Molecular Weight: 186.25
• Mol File: 6098-20-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.011g/cm³
• Refractive Index: 1.464
• CAS DataBase Reference: N-carbamoyl-2-propyl-pentanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-carbamoyl-2-propyl-pentanamide(6098-20-0)
• EPA Substance Registry System: N-carbamoyl-2-propyl-pentanamide(6098-20-0)

Safety Data

• Hazardous Substances Data: 6098-20-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H18N2O2/c1-3-5-7(6-4-2)8(12)11-9(10)13/h7H,3-6H2,1-2H3,(H3,10,11,12,13)

Upstream product

• 1636-27-7 di-n-propylmalonic acid 
• 57-13-6 urea 
• 2936-08-5 valproyl chloride 
• 2217-08-5 5,5-dipropylbarbituric acid 

Relevant articles and documents

Synthesis and evaluation of antiallodynic and anticonvulsant activity of novel amide and urea derivatives of valproic acid analogues

Valproic acid (VPA, 1) is a major broad spectrum antiepileptic and central nervous system drug widely used to treat epilepsy, bipolar disorder, and migraine. VPA's clinical use is limited by two severe and lifethreatening side effects, teratogenicity and hepatotoxicity. A number of VPA analogues and their amide, N-methylamide and urea derivatives, were synthesized and evaluated in animal models of neuropathic pain and epilepsy. Among these, two amide and two urea derivatives of 1 showed the highest potency as antineuropathic pain compounds, with ED50 values of 49 and 51 mg/kg for the amides (19 and 20) and 49 and 74 mg/kg for the urea derivatives (29 and 33), respectively. 19, 20, and 29 were equipotent to gabapentin, a leading drug for the treatment of neuropathic pain. These data indicate strong potential for the above-mentioned novel compounds as candidates for future drug development for the treatment of neuropathic pain. 2009 American Chemical Society.

Potent anticonvulsant urea derivatives of constitutional isomers of valproic acid

Valproic acid (VPA) is a major antiepileptic drug (AED); however, its use is limited by two life-threatening side effects: teratogenicity and hepatotoxicity. Several constitutional isomers of VPA and their amide and urea derivatives were synthesized and evaluated in three different anticonvulsant animal models and a mouse model for AED-induced teratogenicity. The urea derivatives of three VPA constitutional isomers propylisopropylacetylurea, diisopropylacetylurea, and 2-ethyl-3-methyl-pentanoylurea displayed a broad spectrum of anticonvulsant activity in rats with a clear superiority over their corresponding amides and acids. Enanatiomers of propylisopropylacetylurea and propylisopropylacetamide revealed enantioselective anticonvulsant activity, whereas only enantiomers of propylisopropylacetylurea displayed enantioselective teratogenicity. These potent urea derivatives caused neural tube defects, but only at doses markedly exceeding their effective dose, whereas VPA showed no separation between its anticonvulsant activity and teratogenicity. The broad spectrum of anticonvulsant activity of the urea derivatives coupled with their wide safety margin make them potential candidates to become new, potent AEDs.