Fluorescence derivatization of tertiary amines with 2-naphthyl chloroformate

Wintersteiger, Reinhold; Hartinger, A.

doi:10.1016/s0021-9673(00)82045-2

Cited by 35 publications

(9 citation statements)

References 12 publications

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“…2,3 Although these reagents allow the determination of primary and secondary amphetamines at mg mL 21 levels, no satisfactory reagents are known for tertiary amphetamines, and only a few procedures for the derivatization of these compounds have been reported so far. 4 Traditionally, the determination of tertiary amphetamines in biological samples by LC is based on the liquid-liquid extraction of the analytes from very large sample volumes and subsequent evaporation of the extraction solvent. These methods are time consuming and prone to errors, as there is a risk of losing the analytes during the evaporation step because of their volatility.…”

Section: Introductionmentioning

confidence: 99%

“…Another chloroformate, 2-naphthyl chloroformate, was used by Gübitz and co-workers to derivatize some tertiary amines. 4 According to the workers, tertiary amines undergo dealkylation when heated with 2-naphthyl chloroformate, forming the corresponding carbamates with the resulting secondary amines. The method was successfully applied to the determination of some tertiary antihistamines.…”

Section: Introductionmentioning

confidence: 99%

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Derivatization of tertiary amphetamines with 9-fluorenylmethyl chloroformate for liquid chromatography: determination of N-methylephedrine

Herráez‐Hernández

Campíns‐Falcó

2000

Analyst

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The fluorogenic reagent 9-fluorenylmethyl chloroformate (FMOC) was evaluated for the derivatization of tertiary amphetamines prior to liquid chromatographic analysis. Conditions for the derivatization were investigated, including the reaction time, the derivatization reagent concentration and the pH, using N-methylephedrine as a model compound. On the basis of these studies, a method for the quantification of N-methylephedrine is presented. The method involves derivatization with FMOC at ambient temperature and separation of the derivatives formed on a LiChrospher C18, 5 microns, 125 x 4 mm id column using acetonitrile-water gradient elution. The proposed procedure shows good linearity, accuracy and reproducibility in the 1.0-25.0 micrograms mL-1 concentration range. The limit of detection was 0.1 microgram mL-1 and the limit of quantification was 0.5 microgram mL-1. The utility of the assay was demonstrated by determining N-methylephedrine in water and urine samples.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Derivatization of tertiary amphetamines with 9-fluorenylmethyl chloroformate for liquid chromatography: determination of N-methylephedrine

Herráez‐Hernández

Campíns‐Falcó

2000

Analyst

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“…In such methods, derivatization typically entails dealkylation of the amine with 2-naphthyl chloroformate. 10,11 However, the conditions required to obtain satisfactory conversion yields (heating for 1 h at 100 °C) make this reaction very difficult to integrate into an on-line system. For these reasons, the determination of tertiary amphetamines by LC is usually based on the (off-line) extraction of the analytes from very large sample volumes and subsequent evaporation of the extraction solvent.…”

Section: Introductionmentioning

confidence: 99%

Automated trace enrichment for screening and/or determination of primary, secondary and tertiary amphetamines in biological samples by liquid chromatography

Herráez‐Hernández¹,

Campíns‐Falcó²

1999

Analyst

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A rapid and simple liquid chromatographic method for the automated determination of amphetamines in biological fluids was developed. The proposed procedure is based on the injection of 250 microL of sample into a 20 x 2.1 mm id precolumn (packed with a 30 microns Hypersil C18 stationary phase) for enrichment and purification of the analytes. Next, the analytes are transferred to a 5 microns LiChrospher 100 RP18, 125 x 4 mm id analytical column for their separation under reversed-phase conditions. Water was used to eliminate the matrix components from the precolumn and a 0.2 M phosphate buffer (pH 3) containing 2% triethylamine was the mobile phase for the resolution of the amphetamines. The UV detector was set at 210 nm. The method was applied to the determination of different primary, secondary and tertiary amphetamines in plasma and urine: beta-phenylethylamine, norephedrine, ephedrine, N-methylpseudoephedrine, pseudoephedrine, N-methylephedrine, amphetamine, 3-phenylpropylamine and methamphetamine. The method provides satisfactory linearity and reproducibility within the tested concentration range (1.0-10.0 micrograms mL-1) and limits of detection of 50-500 ng/mL-1.

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“…(147) Antihistamines, such as diphenhydramine, were converted through the tertiary amine group into fluorescent derivatives using 2-naphthyl chloroformate. (148) Aliphatic tertiary amines can be determined at the picomole level by postcolumn chemiluminescent detection, using tris(bipyridyl)ruthenium(III). (149) This topic of postcolumn electrochemiluminescence detection has been reviewed for both LC and CE.…”

Section: Aminesmentioning

confidence: 99%

Chemical Reagents and Derivatization Procedures in Drug Analysis

Danielson

Gallagher

Bao

2008

Encyclopedia of Analytical Chemistry

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This article describes both pre‐ and postcolumn derivatization chemistry used in conjunction with either chromatography or capillary electrophoresis (CE) to facilitate the determination of drugs. Generally, only prederivatization is used in gas chromatography (GC), principally to enhance the volatility, temperature stability, and/or detectability. The GC section considers derivatization of drugs by reagent class: alkylation, acylation, and silylation. The GC sample‐handling section describes an approach that combines the extraction and derivatization steps together. Both pre‐ and postcolumn derivatization are common approaches for high‐performance liquid chromatography (HPLC) and many of these methods have been adapted for CE. Derivatization for HPLC is often directed toward aliphatic amines, carboxylic acids, or alcohols that are difficult to detect at low levels by absorbance, luminescence, or electrochemical means. In addition, small hydrophilic molecules upon prederivatization are often converted into larger more hydrophobic compounds, making reversed‐phase HPLC easier or even feasible. The HPLC section considers derivatization of drugs based on the following types: alkaloids, amines, antibiotics, barbiturates, carbonyl compounds and carboxylic acids, catecholamines, hydroxy compounds, steroids, and sulfur compounds. For the GC and HPLC sections, tables are included, giving the structures of the more important derivatizing agents, the analytes, and the corresponding reaction products. A brief rationale for derivatization chemistry with CE concludes this article. For CE, derivatization is often done to improve detectability as the path length for absorbance detection is very short and fluorescence can be effective using laser‐based systems.

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Fluorescence derivatization of tertiary amines with 2-naphthyl chloroformate

Cited by 35 publications

References 12 publications

Derivatization of tertiary amphetamines with 9-fluorenylmethyl chloroformate for liquid chromatography: determination of N-methylephedrine

Derivatization of tertiary amphetamines with 9-fluorenylmethyl chloroformate for liquid chromatography: determination of N-methylephedrine

Automated trace enrichment for screening and/or determination of primary, secondary and tertiary amphetamines in biological samples by liquid chromatography

Chemical Reagents and Derivatization Procedures in Drug Analysis

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