The identification of an impurity product, 4,6-dimethyl-3,5-diphenylpyridin-2-one in an amphetamine importation seizure, a potential route specific by-product for amphetamine synthesized by the APAAN to P2P, Leuckart route

Power, John D.; O’Brien, John E.; Talbot, Brian; Barry, Michael; Kavanagh, Pierce V.

doi:10.1016/j.forsciint.2014.04.029

Cited by 12 publications

(29 citation statements)

References 18 publications

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“…This similar peak pattern was evidence, that the used SPE procedure was capable to extract the various organic compounds from the aqueous waste samples which were identified as following:Benzyl alcohol (A) is an impurity which was up to now only reported in methamphetamine samples 31,32. 4M5PP is one of the most commonly reported impurities of amphetamine12,33,35,40,41,[45][46][47] and considered route specific for the Leuckart reaction. This compound (F) was also found by others in methamphetamine31,32,[34][35][36] and in amphetamine 12,37 samples.…”

supporting

confidence: 62%

“…The result was a very similar peak pattern which can be seen in the supplemental material. Phenylacetic acid is reported by Power et al to be present in an amphetamine sample and it was proposed, that this compound could originate from the hydrolysis of APAAN 40. Of note is that Stojanovska et al33 reported that benzyl alcohol was found in methamphetamine samples that also contained 1-phenyl-2-propanol (F) which is, according to them, indicative of these samples being synthesised via the reductive amination route.…”

mentioning

confidence: 97%

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Characterisation of aqueous waste produced during the clandestine production of amphetamine following the Leuckart route utilising solid‐phase extraction gas chromatography–mass spectrometry and capillary electrophoresis with contactless conductivity detection

Hauser

Hulshof

Rößler

et al. 2018

Drug Testing and Analysis

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Chemical waste from the clandestine production of amphetamine is of forensic and environmental importance due to its illegal nature which often leads to dumping into the environment. In this study, 27 aqueous amphetamine waste samples from controlled Leuckart reactions performed in Germany, the Netherlands, and Poland were characterised to increase knowledge about the chemical composition and physicochemical characteristics of such waste. Aqueous waste samples from different reaction steps were analysed to determine characteristic patterns which could be used for classification. Conductivity, pH, density, ionic load, and organic compounds were determined using different analytical methods. Conductivity values ranged from 1 to over 200 mS/cm, pH values from 0 to 14, and densities from 1.0 to 1.3 g/cm . A capillary electrophoresis method with contactless conductivity detection (CE-C D) was developed and validated to quantify chloride, sulphate, formate, ammonium, and sodium ions which were the most abundant ions in the investigated waste samples. A solid-phase extraction sample preparation was used prior to gas chromatography-mass spectrometry analysis to determine the organic compounds. Using the characterisation data of the known samples, it was possible to assign 16 seized clandestine waste samples from an amphetamine production to the corresponding synthesis step. The data also allowed us to draw conclusions about the synthesis procedure and used chemicals. The presented data and methods could support forensic investigations by showing the probative value of synthesis waste when investigating the illegal production of amphetamine. It can also act as starting point to develop new approaches to tackle the problem of clandestine waste dumping.

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supporting

confidence: 62%

mentioning

confidence: 97%

Characterisation of aqueous waste produced during the clandestine production of amphetamine following the Leuckart route utilising solid‐phase extraction gas chromatography–mass spectrometry and capillary electrophoresis with contactless conductivity detection

Hauser

Hulshof

Rößler

et al. 2018

Drug Testing and Analysis

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“…[8] The present investigation extends our research efforts into the identification of impurities that might be formed during acidic hydrolysis of APAAN for amphetamine production. [8] The present investigation extends our research efforts into the identification of impurities that might be formed during acidic hydrolysis of APAAN for amphetamine production.…”

Section: Introductionmentioning

confidence: 62%

“…[8] The commercially supplied reagent APAAN utilized in the experiments was stated to be greater than 98% in purity although the synthesis method was not specified. Indeed, along with previously reported Leuckart synthesis byproducts (most notably naphthalenes, di-phenylisopropylamines and formyl-amphetamines) another by-product 4,6-dimethyl-3,5-diphenylpyridin-2-one was recently detected in the APAAN to P2P hydrolysis.…”

Section: X-ray Crystallographymentioning

confidence: 99%

Forensic analysis of P2P derived amphetamine synthesis impurities: identification and characterization of indene by‐products

Power

Kavanagh

McLaughlin

et al. 2016

Drug Testing and Analysis

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1-Phenyl-2-propanone (P2P) is an internationally monitored precursor that has become increasingly difficult for illicit amphetamine producers to source, which means that alternative routes to its preparation have become increasingly important. One such approach includes the hydrolysis of alpha-phenylacetoacetonitrile (APAAN) with sulfuric acid. Previously, we reported the identification of 4,6-dimethyl-3,5-diphenylpryid-2-one following implementation of hydrolysis conditions and it was proposed that this compound might serve as one route specific by-product in the APAAN to P2P conversion. This study continued to explore the presence of impurities formed during this conversion and expanded also into a second route of P2P synthesis starting from alpha-methylstyrene (AMS). All P2P products underwent the Leuckart procedure to probe the presence of P2P-related impurities that might have carried through to the final product. Two by-products associated with the APAAN hydrolysis route to P2P were identified as 2,3-diacetyl-2,3-diphenylsuccinonitrile (1) and 2-methyl-1-phenyl-1,3-dicarbonitrile-1H-indene (2), respectively. Two by-products associated with the AMS route to P2P and subsequent Leuckart reaction were 1,1,3-trimethyl-3-phenyl-2,3-dihydro-1H-indene (3) and 1-phenyl-N-(phenylethyl)propan-2-amine (4), respectively. The two indenes (2 and 3) identified in synthesized amphetamine originating from P2P suggested that it might be possible to differentiate between the two synthetic routes regarding the use of APAAN and AMS. Furthermore, the association of these compounds with amphetamine production appears to have been reported for the first time. The presence of compounds 1 - 4 in seized amphetamine samples and waste products could facilitate the suggestion whether APAAN or AMS were employed in the synthesis route to the P2P. Copyright © 2016 John Wiley & Sons, Ltd.

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“…Due to the minute abundance of these impurities, forensic drug profiling focuses on identification of impurities peaks rather than quantification of the compounds as detection and identification of target impurities are adequate to suggest possible route of synthesis. Chromatographic profiles of the organic impurities from amphetamine and methamphetamines drug seizures have been proven to offer valuable information that is useful for characterisation as well as comparing and identifying the similarities and/or differences among illicit drug seizures (Abdullah et al 2014;Power et al 2014;Stojanovska et al 2013; United Nations Office on Drugs and Crime (UNODC) 2014). In addition, extensive analysis of organic and inorganic compounds in drug profiling may establish the possible link or relationship between seizures; identify the origin or source of drug supply, drug trafficking route and distribution pattern as well as possible synthesis methods (Allan & Ely 2011).…”

Section: Introductionmentioning

confidence: 99%

Impurity Profiling of Amphetamine and Methamphetamine Using Gas Chromatography Mass Spectrometry (GCMS) Harmonised Methods

Desa¹,

Ismail²

2017

JSM

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Impurity profiling of drug seizures is a scientific approach employed to understand drug trafficking networks thus has becoming increasingly important in criminal investigation. This paper presents the feasibility of using the Collaborative Harmonisation of Methods for the Profiling of AmphetamineType Stimulants (CHAMP) established by the EuropeanCommission authority for impurity profiling of amphetamine and methamphetamine samples. Both drugs were analysed using similar extraction procedure and analytical conditions. The impurities were extracted from an alkaline buffer solution (pH8.1) using toluene prior to gas chromatography-mass spectrometry (GC-MS) analyses. The results showed that the reproducibility of the method for detecting amphetamine and methamphetamine ranged between 7. 4-8.9 and 6.2-8.4 4-methyl-5-phenylpyrimidine, bis-(1-phynelisopropyl) amine, N-formylamphetamine and N,N-di (b-phenylisopropyl) %RSD, respectively. Identification of impurities was performed by referencing against the available MS databases as well as to previous reported impurity profiling studies. Phenyl-2-propanone (P2P), also known as benzyl-methylketone (BMK), as well as other specific impurities such as

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The identification of an impurity product, 4,6-dimethyl-3,5-diphenylpyridin-2-one in an amphetamine importation seizure, a potential route specific by-product for amphetamine synthesized by the APAAN to P2P, Leuckart route

Cited by 12 publications

References 18 publications

Characterisation of aqueous waste produced during the clandestine production of amphetamine following the Leuckart route utilising solid‐phase extraction gas chromatography–mass spectrometry and capillary electrophoresis with contactless conductivity detection

Characterisation of aqueous waste produced during the clandestine production of amphetamine following the Leuckart route utilising solid‐phase extraction gas chromatography–mass spectrometry and capillary electrophoresis with contactless conductivity detection

Forensic analysis of P2P derived amphetamine synthesis impurities: identification and characterization of indene by‐products

Impurity Profiling of Amphetamine and Methamphetamine Using Gas Chromatography Mass Spectrometry (GCMS) Harmonised Methods

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