1616609-90-5

Basic information

• Product Name: 3-(benzo[d][1,3]dioxol-5-yl)-N,N-diisopropylbenzamide
• Synonyms: 3-(benzo[d][1,3]dioxol-5-yl)-N,N-diisopropylbenzamide
• CAS NO: 1616609-90-5
• Molecular Weight: 325.408
• Mol File: 1616609-90-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-(benzo[d][1,3]dioxol-5-yl)-N,N-diisopropylbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(benzo[d][1,3]dioxol-5-yl)-N,N-diisopropylbenzamide(1616609-90-5)
• EPA Substance Registry System: 3-(benzo[d][1,3]dioxol-5-yl)-N,N-diisopropylbenzamide(1616609-90-5)

Safety Data

• Hazardous Substances Data: 1616609-90-5(Hazardous Substances Data)

Upstream product

• 24351-56-2 3-(benzo[d][1,3]dioxol-5-yl)benzoic acid 
• 108-18-9 diisopropylamine 
• 585-76-2 m-bromobenzoic acid 
• 94839-07-3 3,4-(methylenedioxy)-benzeneboronic acid 

Relevant articles and documents

Efficient modulation of γ-aminobutyric acid type a receptors by piperine derivatives

Piperine activates TRPV1 (transient receptor potential vanilloid type 1 receptor) receptors and modulates γ-aminobutyric acid type A receptors (GABAAR). We have synthesized a library of 76 piperine analogues and analyzed their effects on GABAAR by means of a two-microelectrode voltage-clamp technique. GABAAR were expressed in Xenopus laevis oocytes. Structure-activity relationships (SARs) were established to identify structural elements essential for efficiency and potency. Efficiency of piperine derivatives was significantly increased by exchanging the piperidine moiety with either N,N-dipropyl, N,N-diisopropyl, N,N-dibutyl, p-methylpiperidine, or N,N-bis(trifluoroethyl) groups. Potency was enhanced by replacing the piperidine moiety by N,N-dibutyl, N,N-diisobutyl, or N,N-bistrifluoroethyl groups. Linker modifications did not substantially enhance the effect on GABAAR. Compound 23 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dipropyl-2,4-pentadienamide] induced the strongest modulation of GABAA (maximal GABA-induced chloride current modulation (IGABA-max = 1673% ± 146%, EC 50 = 51.7 ± 9.5 μM), while 25 [(2E,4E)-5-(1,3-benzodioxol- 5-yl)-N,N-dibutyl-2,4-pentadienamide] displayed the highest potency (EC 50 = 13.8 ± 1.8 μM, IGABA-max = 760% ± 47%). Compound 23 induced significantly stronger anxiolysis in mice than piperine and thus may serve as a starting point for developing novel GABA AR modulators.