A. Benderly

Synthesis of side-chain monofluorinated amphetamines

Abstract R- and S-2-Amino-3-fluoro-1-phenylprupane were prepared in approximately 50% yields by the action of HF-pyridine on R- and S-2-benzylaziridine. (±)-2-Amino-3-fluoro-1-(4-chlorophenyl)propane was similarly prepared from (±)-2-(4-chlorobenzyl)aziridine. Structures of products were confirmed by n.m.r. and mass spectroscopy. In contrast, when 2-benzyl-N-tosylaziridine was reacted with HF in pyridine, the C 2 atom of the aziridine ring was the site of fluorination and the N-tosylated derivative of 3-amino-2-fluoro-1-phenylpropane was obtained in excellent yield.

Analysis of a monofluorinated analogue of amphetamine in brain tissue using gas chromatography with electron-capture detection

1. Difficulties encountered in the analysis of the monofluorinated amphetamine, 2-amino-3-fluoro-1-phenylpropane (AFP), are discussed. 2. A novel assay procedure and its application to the analysis of AFP in the rat brain are described. The procedure involves pentafluorobenzoylation of AFP under aqueous conditions and quantitation by a gas chromatography equipped with a capillary column and an electron-capture detector.

Determination of 5-hydroxytryptamine in rat brain regions by gas-liquid chromatography with electron-capture detection

An assay method for measurement of 5-hydroxytryptamine in rat brain areas is described. The procedure involves extraction with a liquid ion exchanger followed by acetylation and reaction with pentafluoropropionic anhydride. The resultant beta-carboline is separated and quantitated using gas-liquid chromatography with electron-capture detection. The procedure also works well with 5-methoxytryptamine standards, and the tissue samples were checked simultaneously for the presence of this amine. The results indicate that concentrations of 5-methoxytryptamine in all areas studied (brain stem, hypothalamus, frontal cortex, and striatum) are less than 10 ng/g.

Comparison of the effects of amphetamine and a fluorinated analogue on locomotion and exploratory activity in the mouse

(+)-Amphetamine (AM) and its fluorinated analogue (+)-2-amino-3-fluoro-1-phenylpropane (fluoroamphetamine, FAM) were compared with regard to their effects on locomotor and exploratory activity in mice. Both drugs caused a reduction in spontaneous exploration, but this effect was more marked with FAM than with AM at 1 h after injection. Both compounds increased locomotor activity 10 min after injection, but FAM had sedative effects after 1 h, while AM continued to be stimulatory.

Para-chlorophenylethylamine in brains of rats treated with a monoamine oxidase inhibitor and p-chlorophenylalanine

1. The accumulation of p-chlorophenylethylamine (pCPE) in rat brain after administration of pargyline plus p-chlorophenylalanine (pCPA) is demonstrated. 2. Measurements of pCPE in brain were performed at 0.25 h, 1 h and 4 h after administration of pCPA to pargyline-pretreated rats, and amounts of pCPE were shown to increase with time.