678188-82-4

Basic information

• Product Name: Carbamic acid, [3-[(1-oxopropyl)[1-(2-phenylethyl)-4-piperidinyl]amino]propyl]-, 1,1-dimethylethyl ester
• CAS NO: 678188-82-4
• Molecular Formula: C24H39N3O3
• Molecular Weight: 417.592
• Mol File: 678188-82-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [3-[(1-oxopropyl)[1-(2-phenylethyl)-4-piperidinyl]amino]propyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [3-[(1-oxopropyl)[1-(2-phenylethyl)-4-piperidinyl]amino]propyl]-, 1,1-dimethylethyl ester(678188-82-4)
• EPA Substance Registry System: Carbamic acid, [3-[(1-oxopropyl)[1-(2-phenylethyl)-4-piperidinyl]amino]propyl]-, 1,1-dimethylethyl ester(678188-82-4)

Safety Data

• Hazardous Substances Data: 678188-82-4(Hazardous Substances Data)

Upstream product

• 75178-96-0 N-Boc-1,3-diaminopropane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 123-62-6 propionic acid anhydride 
• 678188-77-7 tert-butyl [3-(1-phenethylpiperidin-4-ylamino)propyl]carbamate 

Downstream Products

• 439099-20-4 C₃₀H₄₉N₅O₅ 
• 910544-23-9 N-[4-(N²,N³-bis(tert-butoxycarbonyl)guanidino)butyl]-N-(1-phenethylpiperidin-4-yl)propanamide 
• 439099-20-4 C₃₀H₄₉N₅O₅ 
• 439099-19-1 N-(3-amino-propyl)-N-(1-phenethyl-piperidin-4-yl)-propionamide 

Relevant articles and documents

Synthesis and pharmacological studies of new hybrid derivatives of fentanyl active at the μ-opioid receptor and I2-imidazoline binding sites

Two series of fentanyl-derived hybrid molecules bearing potent I2-imidazoline binding site (IBS) ligands (i.e., guanidine and BU224 moieties) linked with an aliphatic (m = 2, 3, 4, 6, 7, 8, 9 and 12 methylene units) or aromatic spacer were prepared. Their affinities for the μ-opioid receptors and for the I2-IBS were determined through competition binding studies on human postmortem brain membranes. Whereas the BU224 hybrid molecules bound to the μ-opioid receptor and the I2-IBS in the micromolar to low micromolar range, the alkaneguanidine series exhibited remarkable affinities in the nanomolar range for both receptors. [35S]GTPγS functional assays were performed on human postmortem brain membranes with selected ligands from each series (4f and 8g) showing the highest dual affinity for the μ-opioid receptor and I2-IBS affinities. Both compounds displayed agonist properties: at the μ-opioid receptor for the alkaneguanidine derivative 4f (spacer: six methylene units) and at a G-protein coupled receptor (GPCR) which remains to be determined for 8g. The lack of analgesic properties of 4f in vivo (i.e., hot plate and writhing tests in mice), discordant with the good in vitro binding data (Ki μ = 1.04 ± 0.28 nM, Ki I2 = 409 ± 238 nM), may possibly be due to the low intrinsic efficacy of the compound. Alternatively, a low access to the central nervous system for this kind of hybrid molecules cannot be ruled out. Two new compounds reported here (9f and 13), which were not dual acting, are worth mentioning for their outstanding binding affinities; 9f bound to the μ-opioid receptor with a picomolar affinity (Ki = 0.0098 ± 0.0033 nM), whereas 13 presented an I2-IBS affinity (Ki = 18 ± 11 nM) similar to the reference compound BU224.