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Molly M. Sherard ; Jamie S. Kaplan ; Jeffrey H. Simpson , et al. Nanomaterials,2024,14(11):917. DOI: 10.3390/nano14110917
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Abstract: Fentanyl (FTN) and synthetic analogs of FTN continue to ravage populations across the globe, including in the United States where opioids are increasingly being used and abused and are causing a staggering and growing number of overdose deaths each year. This growing pandemic is worsened by the ease with which FTN can be derivatized into numerous derivatives. Understanding the chemical properties/behaviors of the FTN class of compounds is critical for developing effective chemical detection schemes using nanoparticles (NPs) to optimize important chemical interactions. Halogen bonding (XB) is an intermolecular interaction between a polarized halogen atom on a molecule and e−-rich sites on another molecule, the latter of which is present at two or more sites on most fentanyl-type structures. Density functional theory (DFT) is used to identify these XB acceptor sites on different FTN derivatives. The high toxicity of these compounds necessitated a “fragmentation” strategy where smaller, non-toxic molecules resembling parts of the opioids acted as mimics of XB acceptor sites present on intact FTN and its derivatives. DFT of the fragments’ interactions informed solution measurements of XB using 19F NMR titrations as well as electrochemical measurements of XB at self-assembled monolayer (SAM)-modified electrodes featuring XB donor ligands. Gold NPs, known as monolayer-protected clusters (MPCs), were also functionalized with strong XB donor ligands and assembled into films, and their interactions with FTN “fragments” were studied using voltammetry. Ultimately, spectroscopy and TEM analysis were combined to study whole-molecule FTN interactions with the functionalized MPCs in solution. The results suggested that the strongest XB interaction site on FTN, while common to most of the drug’s derivatives, is not strong enough to induce NP-aggregation detection but may be better exploited in sensing schemes involving films.
Keywords: opioid ; fentanyl ; halogen bonding ; gold nanoparticle ; monolayer-protected cluster ; cyclic voltammetry
CAS No. : | 2905-56-8 | MDL No. : | MFCD00224901 |
Formula : | C12H17N | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | NZVZVGPYTICZBZ-UHFFFAOYSA-N |
M.W : | 175.27 | Pubchem ID : | 76190 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With tetrabutylammomium bromide; sodium hydroxide; In water; at 100℃; for 1h; | General procedure: SiO2-CuI (0.1 g,5 mol% Cu) was added to a mixture of amine (0.5 mmol), benzyl chloride, allyl bromide, or n-butyl chloride (0.5 mmol for N-substitution and 1 mmol for N,N-disubstitution), NaOH (2 mmol), and TBAB (0.25 mmol) in a round-bottom flask(25 mL) in water (4mL). The reaction mixture was stirred at 15C (in the case of N-benzylation, allylation, or alkylation of primary amines,Table 2) or 70-100C (in the case of N,N-dibenzylation, allylation, or alkylation of primary amines, Table 3), and 100C(N-benzylation, allylation, and alkylation of secondary amines, Table 4) for an appropriate time. After completion of the reaction (monitored by thin-layer chromatography, TLC), the reaction mixture was triturated with EtOAc (20 mL) and the SiO2-CuI was filtered off. The product was obtained after removal of the solvent under reduced pressure followed by column chromatography or crystallization from EtOAc-petroleum ether. |
90% | With silica copper(I) oxide; tetrabutylammomium bromide; potassium carbonate; In water; at 100℃; for 0.5h;Green chemistry; | General procedure: A mixture of secondary amine (0.5 mmol), benzyl chloride (0.127 g, 1 mmol), K2CO3 (0.139 g, 1 mmol), TBAB (0.082 g,0.25 mmol), and SiO2-Cu2O (0.2 g, 5 mol% Cu) in water (5 mL) in a round-bottom flask (50 mL) was stirred at 100 C. On completionof the reaction (monitored by TLC), the flask was cooledto room temperature and the mixture filtered. The residue was washed with water followed by ethyl acetate (3 × 10 mL). The combined organic extracts were washed with water (3 × 100mL) and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure, and the product was obtainedby crystallization from petroleum ether or ethyl acetate/ petroleumether, or by eluting the crude product through a columnof silica gel with ethyl acetate/petroleum ether. |
76% | With trimethylamine; In dichloromethane; at 20℃; for 6h;Inert atmosphere; | General procedure: Typical procedure: A solution of piperidine (0.84 g, 10.0 mmol), trimethylamine (1.01 g, 10.0 mmol) in dry CH2Cl2 (2 mL) under nitrogen atmosphere was cooled with an ice-water bath, then a solution of generation 1 bromide (3.83 g, 10.0 mmol) in dry CH2Cl2 (5mL) was slowly added. The mixture was stirred for 6 h at room temperature (TLC monitoring). After completion of the reaction, the crude product was puried by ash column chromatography on silica gel (petroleum ether: ethyl acetate 6:1,v/v) to afford 1-G1 as lightly yellow oil liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | General procedure: In a nitrogen-filled glovebox, to a 15 mL reaction tube equipped with a magnetic stirrer, were added Cp2ZrH2 (0.01mmol, 2.2 mg) as the catalyst, and the appropriate amide (0.2mmol); solvent was added when necessary. HBpin (3 equiv. peramide functional group) was then added, and the reaction tube was taken out from the glovebox and stirred at room temperature for 12-48 h. The resultant crude amines were either isolated using silica gel flash chromatography, or acidified by stirring with HCl in Et2O (2 mL, 1N) for 2 h, after which time precipitation was observed. Then, the reaction solution was transferred to a centrifuge tube and centrifuged three times. The supernatant was removed and the resulting solid was dried inan oven at 80 C for several hours to obtain the HCl salt of the amine. |
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