Publications by authors named "Paul E Pigou"

The Akabori-Momotani reaction can be used to synthesise pseudoephedrine in 50% yield from N-methylalanine and benzaldehyde. This paper investigates electronic effects of substituted benzaldehydes on the reaction to synthesise amphetamine type stimulants and identifies several new Akabori-Momotani by-products, 1-[(4-methoxybenzyl)(methyl)amino]ethanol (11c), 2-(4-methoxyphenyl)-3,4-dimethyl-1,3-oxazolidine (12c), 1,2,3,4-tetramethyl-5,6-di-(4-methoxyphenyl)piperazine (13c) and 1,2,4,5-tetramethyl-3,6-di-(4-methoxyphenyl)piperazine (14c). This paper also investigates pseudoephedrine and methamphetamine isomeric distribution from the Akabori-Momotani reaction with the aid of molecular modelling to understand why more pseudoephedrine than ephedrine is produced.

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The synthesis of impurities detected in clandestinely manufactured Amphetamine Type Stimulants (ATS) has emerged as more desirable than simple "fingerprint" profiling. We have been investigating the impurities formed when phenyl-2-propanone (P2P) 5, a key ATS precursor, is synthesised in three steps; an aldol condensation of benzaldehyde and methyl ethyl ketone (MEK); a Baeyer-Villiger reaction; and ester hydrolysis. We have identified and selectively synthesised several impurities that may be used as route specific markers for this series of synthetic steps.

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Matrix-assisted laser desorption ionization (MALDI) mass spectrometry (MS) is an excellent analytical technique for the rapid and sensitive analysis of macromolecules (>700 Da), such as peptides, proteins, nucleic acids, and synthetic polymers. However, the detection of smaller organic molecules with masses below 700 Da using MALDI-MS is challenging due to the appearance of matrix adducts and matrix fragment peaks in the same spectral range. Recently, nanostructured substrates have been developed that facilitate matrix-free laser desorption ionization (LDI), contributing to an emerging analytical paradigm referred to as surface-assisted laser desorption ionization (SALDI) MS.

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The emphasis in the literature regarding illicit drugs has been overwhelmingly on the subject of harm caused by their ingestion. Little has been reported on the potential and real harm associated with the illicit manufacture of drugs. This paper describes the increasing prevalence of clandestine drug laboratories in Australia, overwhelmingly devoted to the manufacture of methamphetamine.

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Solid-phase microextraction (SPME) followed by gas chromatography-mass spectrometry (GC-MS) is a simple, reliable technique for the recovery and analysis of many organic explosives. However, this technique is impractical for the analysis of ammonium nitrate-type explosives due to the extreme polarity, low molecular weight, and high volatility of the amine moiety. This article describes an initial investigation of a derivatization process utilizing alkylchloroformates that converts ammonium nitrate and methylammonium nitrate into a form suitable for recovery by SPME and analysis by GC-MS.

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Due to their high polarity and low vapor pressure, most amine salts of amphetamine-type drugs are not directly amenable to headspace recovery using solid-phase microextraction (SPME). Described in this article is a simple vapor-phase procedure for the conversion of solid drug salt samples into their free bases by the use of triethylamine. This process can be conducted simultaneously with headspace SPME, the outcome being that solid drug salts can be sampled directly for GC-MS without the need for dissolution and chemical processing.

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Six ninhydrin analogues containing oxygen, sulfur, and selenium substituents at the C-5 position, 5-(4-nitrophenyl)ninhydrin, and benzo[f]furoninhydrin were evaluated as fingerprint development reagents. The analogues all showed good fingerprint color development but were not superior to ninhydrin in this respect. The benzo[f]furoninhydrin complex was strongly luminescent at room temperature following zinc complexation, while the remaining analogues required cooling to -196 degrees C to produce optimum luminescence.

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