Manufacturing by-products from, and stereochemical outcomes of the biotransformation of benzaldehyde used in the synthesis of methamphetamine

Cox, Matthew; Klass, Gunter; Koo, Christina

doi:10.1016/j.forsciint.2009.04.010

Cited by 13 publications

(9 citation statements)

References 15 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%

“…As illustrated in Figure , methamphetamine can be synthesized via a number of routes from either (1 R ,2 S )‐(−)‐ephedrine ( 4, EPH) / (1 S ,2 S )‐(+)‐pseudoephedrine ( 5, PSE), or 1‐phenyl‐2‐propanone (P2P) . Compound 4/5 can be extracted either from cold medications or from the ephedra plant along with 4 other ephedrine‐type alkaloids ( 1, 3, 7, and 8) prepared semi‐synthetically by reductive amination (RA) of L ‐phenylacetylcarbinol (L‐PAC), which is obtained from the fermentation of benzaldehyde; or manufactured synthetically from propiophenone . Compound 4/5 is then reduced to d‐methamphetamine by a variety of methods, including Emde, Hypo, Mosco, Red Phosphorus, and Birch routes .…”

Section: Introductionmentioning

confidence: 99%

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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%

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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“…A pre-precursor of methamphetamine, phenylpropan-1,2-diol (PAC-diol) was obtained from the Lphenylacetylcarbinol process by using glucose and bread yeast. Subsequently, a precursor of methamphetamine, phenylpropan-2-one (Phenylacetone, P2P) was obtained by a pinacol-pinacolon rearrangement reaction on PAC-diol 40,41 .…”

Section: Methodsmentioning

confidence: 99%

Amine-rich carbon nanodots as a fluorescence probe for methamphetamine precursors

Brown

Cresswell

et al. 2015

Anal. Methods

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Amine-functionalized carbon dots (A-CDs) were synthesized by one-step hydrothermal reaction of urea and citric acid. The purified CD sample exhibits a surface states dominated fluorescence emission with a quantum yield of 30%. The A-CDs demonstrate excellent sensitivity toward methamphetamine pre-precursor and precursor, and a remarkable selectivity against common drug cutting agents (diluents) such as Aspirin, Paracetamol, etc. The specific selectivity of CDs towards such type of drug precursor molecules is first time reported, which appears to be related to the spatial distribution of the surface functional groups. The fluorescence-based sensing mechanism is revealed by a detailed analysis on the static and dynamic fluorescence behaviour. We further demonstrated an immobilization strategy for fabricating solid-state sensors, and the retained sensitivity of the A-CDs after immobilization. The study reveals the potential of the use of a CDs as an effective sensing probe for illicit drugs, which is in demand.

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“…Alternatively, the traditional approach is to convert enantiomers to diastereoisomers using commercial chiral derivatizing reagents that can then be separated by conventional GC using achiral columns. Recently, we have used this method to successfully determine the stereochemical composition of methamphetamine obtained by the biotransformation of benzaldehyde (12). …”

mentioning

confidence: 99%

Stereochemical Analysis of Methorphan Using (−)‐Menthyl Chloroformate

Koo

Cox

Klass

et al. 2012

Journal of Forensic Sciences

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Forensic laboratories around the world have seen an increase in the number of drug seizures containing methorphan. Levomethorphan is a narcotic and a controlled substance, and its enantiomer dextromethorphan is an antitussive agent used in over-the-counter medications. For the forensic analysis of seized drugs containing methorphan, it is important to report the stereochemical composition of the drug. Ideally, a method based on common forensic laboratory instrumentation is desirable. The use of the chiral derivatizing agent (-)-menthyl chloroformate followed by routine gas chromatography-mass spectrometry analysis of the derivative was shown to successfully determine the stereochemical composition of methorphan. This approach was applied to a street seizure containing methorphan proving that it was pure dextromethorphan. The derivatives of dextro- and levomethorphan were subjected to mass spectroscopic and nuclear magnetic resonance analysis, which confirmed that the structure of the derivatives remained unchanged as a result of the derivatization process.

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Manufacturing by-products from, and stereochemical outcomes of the biotransformation of benzaldehyde used in the synthesis of methamphetamine

Cited by 13 publications

References 15 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

Amine-rich carbon nanodots as a fluorescence probe for methamphetamine precursors

Stereochemical Analysis of Methorphan Using (−)‐Menthyl Chloroformate

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