Oxidation-assisted structural elucidation of compounds containing a tertiary amine side chain using liquid chromatography mass spectrometry
A novel analytical technique for the structural elucidation of compounds bearing a tertiary amine side chain via “in vial” instantaneous oxidation and liquid chromatography mass spectrometry (LC-MS) was developed. A series of lidocaine homologs and benzimidazole derivatives with a major/single amine representative base peak in both their EI-MS and ESI-MS/MS spectra were subjected to oxidation by a 0.1% solution of hydrogen peroxide (including several 16O/18O exchange experiments), followed by LC-ESI-MS/MS analysis. The N-oxide counterparts promoted extensive fragmentation with complete coverage of all parts of the molecule, enabling detailed structural elucidation and unambiguous identification of the unoxidized analytes at low nanogram per milliliter levels.
Shamai Yamin, Tamar,Prihed, Hagit,Shifrovitch, Avital,Dagan, Shai,Weissberg, Avi
Electrochemical oxidation by square-wave potential pulses in the imitation of oxidative drug metabolism
Electrochemistry combined with mass spectrometry (EC-MS) is an emerging analytical technique in the imitation of oxidative drug metabolism at the early stages of new drug development. Here, we present the benefits of electrochemical oxidation by square-wa
Nouri-Nigjeh, Eslam,Permentier, Hjalmar P.,Bischoff, Rainer,Bruins, Andries P.
experimental part
p. 5519 - 5525
(2012/02/15)
FORMULATIONS OF N-OXIDE PRODRUGS OF LOCAL ANESTHETICS FOR THE TREATMENT OF PULMONARY INFLAMMATION ASSOCIATED WITH ASTHMA, BROCHITIS, AND COPD
A prodrug of lidocaine and related local anesthetic composition or formulation for delivery by aerosolization is described. The formulation containing an efficacious amount of lidocaine N-oxide prodrug or local anesthetic N-oxide prodrug able to inhibit i
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Page/Page column 7; 8; 18; 19
(2008/06/13)
Selectivities in the oxidation of tertiary amines and pyridine derivatives by perfluoro cis-2,3-dialkyloxaziridines
When tertiary amines 1 are reacted with perfluoro cis-2,3- dialkyloxaziridines 2 at -60 °C corresponding N-oxides 3 are formed in high yields. The process is chemoselective and diastereoselective. The chemoselectivity in the reaction of alkenyl substituted pyridines is solvent dependent, attack occurring exclusively at the carbon-carbon double bond or at the nitrogen atom under protic and aprotic conditions, respectively. Lower selectivities were obtained when standard reagents were used.
Arnone, Alberto,Metrangolo, Pierangelo,Novo, Barbara,Resnati, Giuseppe
p. 7831 - 7842
(2007/10/03)
In-vitro metabolism of lignocaine to its N-oxide
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Patterson,Hall,Nijjar,Khatra,Cowan
p. 326 - 326
(2007/10/02)
Quantification of lidocaine and several metabolites utilizing chemical ionization mass spectrometry and stable isotope labeling
Quantification of the suspected metabolites of lidocaine in humans was carried out using the direct insertion probe and chemical-ionization mass spectrometry. Deuterated analogs of the metabolites of lidocaine were added to serial human plasma and urine s
Nelson,Garland,Breck,Trager
p. 1180 - 1190
(2007/10/05)
Polarographic determination of tertiary amines through the assay of their amine oxides. I. Polarographic properties of simple aliphatic and aromatic amine oxides
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Hoffmann
p. 614 - 623
(2007/10/04)
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