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

Abstract

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.

1-Deoxynojirimycin: Occurrence, Extraction, Chemistry, Oral Pharmacokinetics, Biological Activities and In Silico Target Fishing

“…Another study has reported the derivatization of mulberry sample by using 9-fluorenylmethyl chloroformate, which reacts with primary and secondary amines under mild conditions producing DNJ derivatives. However, the reaction of 9-fluorenylmethyl chloroformate with tertiary amines requires dealkylation [68,69].…”

Determination of methylamine, dimethylamine, and trimethylamine in air by high-performance liquid chromatography with derivatization using 9-fluorenylmethylchloroformate

“…1, the dealkylation of the initially formed TMA-FMOC derivative (Rxn 1) can yield an identical FMOC derivative product (Rxn 2) as DMA (Rxn 3). 24,30 However, the dealkylation of the TMA-FMOC acylammonium salt is slow at room temperature and hence the DMA-FMOC carbamate product is insignicant. As a result TMA is detected as an acyl ammonium salt and eluted before the carbamates of MA and DMA.…”

“…Short chained aliphatic amines (e.g., methylamine (MA), dimethylamine (DMA), and trimethylamine (TMA)) are well known for their potential in the formation of secondary organic aerosols. 1,2 Moreover, they are widely publicized malodorants (pungent, rotten-sh like smell) with low odor threshold values (in the range of [21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][33][34][35][36][37][38][39][40][41][42][43][44][45][46][47], and 0.032-0.21 ppb (v/v), respectively for MA, DMA, and TMA). 3 Amines in the presence of nitrogen oxides or other nitrosating agents can easily form N-nitrosamines which can pose potential health hazards as mutagens and carcinogens.…”

“…22 For the sampling of airborne amines, the commonly used methods include sorbent tubes (STs), cartridges (e.g., C 18 cartridges), annular-denuders, and midget impingers. 9,20,[23][24][25] In this study, a number of experiments were conducted to analyze gaseous amines through the combination of chemical derivatization and HPLC-UV analysis. MA, DMA, and TMA were selected as the target compounds considering their wide environmental distribution and similar odor properties.…”

High-Performance Liquid Chromatographic Analysis of Drugs of Abuse in Biologic Samples

“…The limit of detection and quantification were 0.1 and 0.5 µg/ml, respectively. 10) Simple and rapid determination of APs and ephedrines with diode array detection was performed using solid-phase extraction. The recovery rates were at least 85%.…”