The synthesis and investigation of impurities found in Clandestine Laboratories: Baeyer–Villiger Route Part I; Synthesis of P2P from benzaldehyde and methyl ethyl ketone

Doughty, David G.; Painter, Benjamin; Pigou, Paul E.; Johnston, Martin R.

doi:10.1016/j.forsciint.2016.03.034

Cited by 10 publications

(4 citation statements)

References 12 publications

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“…The precursors/pre‐precursors are identified as the following: P2P derived from PAA or nitrostyrene, P2P mixed, P2P unknown, EPH/PSE. The details of chemistry and impurities in methamphetamine production have been discussed extensively by the existing publications …”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Simultaneous detection and quantitation of organic impurities in methamphetamine by ultra‐high‐performance liquid chromatography–tandem mass spectrometry, a complementary technique for methamphetamine profiling

Brown

Toske

2018

Drug Testing and Analysis

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The analysis of organic impurities plays an important role in the impurity profiling of methamphetamine, which in turn provides valuable information about methamphetamine manufacturing, in particular its synthetic route, chemicals, and precursors used. Ultra-high-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) is ideally suited for this purpose due to its excellent sensitivity, selectivity, and wide linear range in multiple reaction monitoring (MRM) mode. In this study, a dilute-and-shoot UHPLC-MS/MS method was developed for the simultaneous identification and quantitation of 23 organic manufacturing impurities in illicit methamphetamine. The developed method was validated in terms of stability, limit of detection (LOD), lower limit of quantification (LLOQ), accuracy, and precision. More than 100 illicitly prepared methamphetamine samples were analyzed. Due to its ability to detect ephedrine/pseudoephedrine and its high sensitivity for critical target markers (eg, chloro-pseudoephedrine, N-cyclohexylamphetamine, and compounds B and P), more impurities and precursor/pre-precursors were identified and quantified versus the current procedure by gas chromatography-mass spectrometry (GC-MS). Consequently, more samples could be classified by their synthetic routes. However, the UHPLC-MS/MS method has difficulty in detecting neutral and untargeted emerging manufacturing impurities and can therefore only serve as a complement to the current method. Despite this deficiency, the quantitative information acquired by the presented UHPLC-MS/MS methodology increased the sample discrimination power, thereby enhancing the capacity of methamphetamine profiling program (MPP) to conduct sample-sample comparisons.

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Section: Resultsmentioning

confidence: 99%

“…P2P, on the other hand, can be produced in a number of ways, including synthesized from α‐phenylacetoacetonitrile (APAAN), phenylacetic acid (PAA), or nitrostyrene. . P2P is then converted to d,l‐methamphetamine via a variety of reductive animation reactions (RAs), typically the mercury amalgam (Hg/Al) or a Leuckart type process .…”

Section: Introductionmentioning

confidence: 99%

Simultaneous detection and quantitation of organic impurities in methamphetamine by ultra‐high‐performance liquid chromatography–tandem mass spectrometry, a complementary technique for methamphetamine profiling

Brown

Toske

2018

Drug Testing and Analysis

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“…To circumvent legal control, P2P is clandestinely synthesized from various precursors, such as phenylacetic acid, α‐phenylacetoacetonitrile (APAAN), α‐phenylacetoacetamide (APAA), methyl 3‐oxo‐2‐phenylbutyrate (methyl α‐phenylacetoacetate, MAPA), and methyl ester of P2P glycidic acid 1 . Moreover, P2P is also synthesized from benzaldehyde via phenyl‐2‐nitropropene 2 and by Baeyer–Villiger reaction 3 …”

Section: Introductionmentioning

confidence: 99%

“…1 Moreover, P2P is also synthesized from benzaldehyde via phenyl-2-nitropropene 2 and by Baeyer-Villiger reaction. 3 MAPA was newly added to Table I of the United Nations Convention and the list of the stimulants' raw materials of Japan in 2020.…”

Section: Introductionmentioning

confidence: 99%

Analysis of potential phenylacetone precursors (ethyl 3‐oxo‐2‐phenylbutyrate, methyl 3‐oxo‐4‐phenylbutyrate, and ethyl 3‐oxo‐4‐phenylbutyrate) by gas chromatography/mass spectrometry and their conversion to phenylacetone

Tsujikawa

Okada

Segawa

et al. 2021

Drug Testing and Analysis

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Methyl 3-oxo-2-phenylbutyrate (MAPA) is a recently circulating precursor of phenylacetone (P2P), a precursor of amphetamine and methamphetamine. MAPA has a hybrid chemical structure of acetoacetic acid ester and P2P. Acetoacetic acid ester is de-esterified and decarboxylated to give the ketone by heating under acidic conditions; therefore, MAPA is presumed to be converted to P2P by such treatment. Considering that ethyl 3-oxo-2-phenylbutyrate (EAPA), methyl 3-oxo-4-phenylbutyrate (MGPA), and ethyl 3-oxo-4-phenylbutyrate (EGPA) have the same chemical features as MAPA, these three compounds are potential P2P precursors. The authors examined the analysis of these compounds by gas chromatography-mass spectrometry (GC-MS) and their conversion to P2P by heating under acidic and basic conditions. These compounds were remarkably decomposed into P2P during GC-MS analysis regardless of the injection method and injector temperature. EAPA and EGPA also caused ester exchange to methyl ester by injection of methanol solution. P2P production and transesterification were almost prevented by methoxime derivatization. These compounds were converted to P2P by heating under acidic conditions. The reaction of MGPA and EGPA proceeded quicker than that of EAPA. The important by-product associated with the reaction was phenylacetylcarbinol (formed from EAPA and MGPA), which will be converted to (pseudo)ephedrine, important methamphetamine impurities. By heating under basic conditions, MGPA and EGPA were converted to P2P but EAPA was mainly converted to phenylacetic acid. In the future, when these compounds are in circulation, our study will be useful for identifying and elucidating the synthetic method of P2P.

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Chemical Forensics

Vanninen

Lignell

Heikkinen

et al. 2020

21st Century Prometheus

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The synthesis and investigation of impurities found in Clandestine Laboratories: Baeyer–Villiger Route Part I; Synthesis of P2P from benzaldehyde and methyl ethyl ketone

Cited by 10 publications

References 12 publications

Simultaneous detection and quantitation of organic impurities in methamphetamine by ultra‐high‐performance liquid chromatography–tandem mass spectrometry, a complementary technique for methamphetamine profiling

Simultaneous detection and quantitation of organic impurities in methamphetamine by ultra‐high‐performance liquid chromatography–tandem mass spectrometry, a complementary technique for methamphetamine profiling

Analysis of potential phenylacetone precursors (ethyl 3‐oxo‐2‐phenylbutyrate, methyl 3‐oxo‐4‐phenylbutyrate, and ethyl 3‐oxo‐4‐phenylbutyrate) by gas chromatography/mass spectrometry and their conversion to phenylacetone

Chemical Forensics

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