240143-47-9

Basic information

• Product Name: 1-Piperazineacetonitrile,4-butyl-(9CI)
• Synonyms: 1-Piperazineacetonitrile,4-butyl-(9CI);(5-BUTYLPIPERAZIN-2-YL)ACETONITRILE
• CAS NO: 240143-47-9
• Molecular Formula: C10 H19 N3
• Molecular Weight: 181.28
• Product Categories: PIPERIDINE
• Mol File: 240143-47-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 283.2±25.0 °C(Predicted)
• Appearance: /
• Density: 0.953±0.06 g/cm3(Predicted)
• PKA: 7.44±0.10(Predicted)
• CAS DataBase Reference: 1-Piperazineacetonitrile,4-butyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperazineacetonitrile,4-butyl-(9CI)(240143-47-9)
• EPA Substance Registry System: 1-Piperazineacetonitrile,4-butyl-(9CI)(240143-47-9)

Safety Data

• Hazardous Substances Data: 240143-47-9(Hazardous Substances Data)

Upstream product

• 63981-41-9 4-butyl-piperazine-1-carboxylic acid ethyl ester 
• 107-14-2 chloroacetonitrile 
• 84473-66-5 1-butylpiperazine hydrobromide 

Downstream Products

• 4489-55-8 2-(4-butyl-piperazin-1-yl)-ethylamine 

Relevant articles and documents

2,3-dihydro-2-oxo-1H-benzimidazole-1-carboxamides with selective affinity for the 5-HT4 receptor: Synthesis and structure-affinity and structure-activity relationships of a new series of partial agonist and antagonist derivatives

A series of 2,3-dihydro-2-oxo-1H-benzimidazole-l-carboxamide derivatives bearing a piperazine moiety was synthesized. Their in vitro 5-HT4, 5-HT3, and D2 receptors affinities were evaluated by radioligand binding assay. For selected compounds functional studies at the 5-HT4 receptor were made by using precontracted (by carbachol) preparations of rat esophageal tunica muscularis mucosae (TMM). The influence of the 3-substituent of the benzimidazole ring, the 4-substituent of the piperazine moiety, and the alkylene spacer was studied. Compounds with an ethyl or a cyclopropyl substituent in the 3-position of the benzimidazole ring showed moderate to high affinity (K(i) = 6.7-75.4 nM) for the 5-HT4 receptor with selectivity over 5-HT3 and D2 receptors and moderate antagonist activity (pK(b) = 6.19- 7.73). Compounds with an isopropyl substituent in the 3-benzimidazole position exhibited moderate and selective 5-HT4 affinity (K(i) ≥ 38.9 nM) and a partial agonist activity (5a, i.a. = 0.94) higher than that of the reference compound BIMU 8 (i.a. = 0.70). This reversal of the pharmacological activity due only to a small structural difference might confirm the existence of two binding sites on the 5-HT4 receptor. In the alkylene spacer, a two-methylene chain is favorable to optimize the affinity and the antagonist or the partial agonist activity. In the ethyl and cyclopropyl series, 5-HT4 antagonist activity seems to be unrelated to the size of the 4-substituent of the piperazine moiety, whereas a methyl group is optimal for high partial agonist activity in the isopropyl series; however, the presence of a butyl substituent is a favorable pattern for 5-HT4 antagonism and even causes a reversal of the pharmacological profile in the isopropyl series (5h, pK(b) = 7.94). N-Butyl quaternization of 5a led to an improvement in affinity for the 5-HT4 receptor and maintained the high partial agonist activity (5r, K(i) = 66.3 nM, i.a. = 0.93).