1474-02-8

Basic information

• Product Name: N-(1-benzylpiperidin-4-yl)-N-phenylpropionamide
• Synonyms: N-(1-benzylpiperidin-4-yl)-N-phenylpropionamide;1-Benzyl-4-(N-phenylpropionamido)piperidine;Benzyl Fentanyl;N-(1-Benzyl-4-piperidyl)- propionanilide;N-Phenyl-N-[1-(phenylmethyl)-4-piperidinyl]-propanamide;NSC 73402;R 4129;N-[1-(1-Benzyl-2-phenylethyl)-4-piperidinyl]-N-phenylpropanamide
• CAS NO: 1474-02-8
• Molecular Formula: C₂₁H₂₆N₂O
• Molecular Weight: 322.44394
• EINECS: 216-014-7
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 1474-02-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 74-76 °C
• Boiling Point: 502.2°Cat760mmHg
• Flash Point: 257.5°C
• Appearance: /
• Density: 1.113g/cm³
• Vapor Pressure: 3.36E-08mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: Controlled Substance, -20°C Freezer
• PKA: 7.84±0.20(Predicted)
• CAS DataBase Reference: N-(1-benzylpiperidin-4-yl)-N-phenylpropionamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(1-benzylpiperidin-4-yl)-N-phenylpropionamide(1474-02-8)
• EPA Substance Registry System: N-(1-benzylpiperidin-4-yl)-N-phenylpropionamide(1474-02-8)

Safety Data

• Hazardous Substances Data: 1474-02-8(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Oil

Uses

A Fentanyl analog. An opiate receptor. Controlled Substance

InChI:InChI=1/C21H26N2O/c1-2-21(24)23(19-11-7-4-8-12-19)20-13-15-22(16-14-20)17-18-9-5-3-6-10-18/h3-12,20H,2,13-17H2,1H3

Upstream product

• 1155-56-2 1-benzyl-N-phenylpiperidin-4-amine 
• 123-62-6 propionic acid anhydride 
• 79-03-8 propionyl chloride 
• 3612-20-2 1-phenylmethyl-4-piperidone 
• 793-19-1 bis(2-methoxycarbonylethyl)benzylamine 
• 100-39-0 benzyl bromide 
• 1609-66-1 Norfentanyl 
• 62-53-3 aniline 
• 1155-57-3 N-(1-benzylpiperidin-4-ylidene)aniline 
• 100-46-9 benzylamine 
• 5156-58-1 N-(1-Benzyl-4-piperidyl)-N-phenylpropanamide Hydrochloride 

Downstream Products

• 85893-42-1 trans-(+/-)-N-(1-Benzyl-2-cyano-4-piperidyl)-N-phenylpropanamide 
• 1609-66-1 Norfentanyl 
• 937738-85-7 C₂₃H₂₉N₃O₂ 

Relevant articles and documents

TMSCF2Br-Enabled Fluorination–Aminocarbonylation of Aldehydes: Modular Access to α-Fluoroamides

A protocol for the modular assembly of the α-fluoroamide motif has been developed, which provides a practical method for the efficient synthesis of structurally diverse α-fluoroamides from easily available aldehydes and tertiary amines through a three-component fluorination–aminocarbonylation process. The key to the success of this process is taking advantage of the multiple roles of the unique difluorocarbene reagent TMSCF2Br (TMS=trimethylsilyl). The mechanism of the process involves the 1,2-fluorine and oxygen migrations of the in situ formed TMS-protected α-aminodifluoromethyl carbinol intermediates, which represents a new type of deoxyfluorination reaction.

Metabolism of fentanyl and acetylfentanyl in human-induced pluripotent stem cell-derived hepatocytes

To evaluate the capability of human-induced pluripotent stem cell-derived hepatocytes (h-iPS-HEP) in drug metabolism, the profiles of the metabolites of fentanyl, a powerful synthetic opioid, and acetylfentanyl, an N-acetyl analog of fentanyl, in the cells were determined and analyzed. Commercially available h-iPSHEP were incubated with fentanyl or acetylfentanyl for 24 or 48 h. After enzymatic hydrolysis, the medium was deproteinized with acetonitrile, then analyzed by LC/MS. Desphenethylated metabolites and some hydroxylated metabolites, including 4′-hydroxy-fentanyl and β-hydroxy-fentanyl, were detected as metabolites of fentanyl and acetylfentanyl in the medium. The main metabolite of fentanyl with h-iPS-HEP was the desphenethylated metabolite, which was in agreement with in vivo results. These results suggest that h-iPSHEP may be useful as a tool for investigating drug metabolism.

A photochromic agonist for μ-opioid receptors

Opioid receptors (ORs) are widely distributed in the brain, the spinal cord, and the digestive tract and play an important role in nociception. All known ORs are G-protein-coupled receptors (GPCRs) of family A. Another well-known member of this family, rhodopsin, is activated by light through the cis/trans isomerization of a covalently bound chromophore, retinal. We now show how an OR can be combined with a synthetic azobenzene photoswitch to gain light sensitivity. Our work extends the reach of photopharmacology and outlines a general strategy for converting Family A GPCRs, which account for the majority of drug targets, into photoreceptors. Lighting up the opioid receptor: Photofentanyl-2 is a photochromic version of the well-known analgesic fentanyl. It is a potent agonist in the dark (or when illuminated with blue light) and loses activity when irradiated with UV light. It can be used to optically control the μ-opioid receptor, converting a G-protein-coupled receptor (GPCR) into a photoreceptor.