Study of the mechanism of the optical resolution of N-methylamphetamine via diastereoisomeric salt formation by the Pope-Peachey method

Kozma, Dávid; Madarász, Zoltán; Ács, Mária; Foggasy, Elemér

doi:10.1016/s0957-4166(00)86170-4

Cited by 8 publications

(5 citation statements)

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“…There, it is produced mainly from phenylacetone (P2P, BMK), which, analogous to amphetamine, leads to a racemic product 7,17,41 . Lately, it has been reported that the enantiomers of methamphetamine are separated by chiral resolution using tartaric acid, for example, via the so‐called “Pope–Peachey” method 16,17,47,48 . This results in products with different contents of the desired (S)‐enantiomer and the (R)‐enantiomer, which is considered as less potent by‐product 17,48 .…”

Section: Discussionmentioning

confidence: 99%

“…7,17,41 Lately, it has been reported that the enantiomers of methamphetamine are separated by chiral resolution using tartaric acid, for example, via the so-called "Pope-Peachey" method. 16,17,47,48 This results in products with different contents of the desired (S)enantiomer and the (R)-enantiomer, which is considered as less potent by-product. 17,48 However, it is possible to racemize the fraction with the undesired distomer and to subject it to chiral resolution again and again, to virtually yield (S)-methamphetamine only.…”

Section: Discussionmentioning

confidence: 99%

“…16,17,47,48 This results in products with different contents of the desired (S)enantiomer and the (R)-enantiomer, which is considered as less potent by-product. 17,48 However, it is possible to racemize the fraction with the undesired distomer and to subject it to chiral resolution again and again, to virtually yield (S)-methamphetamine only. A mild method for this purpose is the thiyl radical-mediated racemization, for example, with methyl thioglycolate.…”

Section: Discussionmentioning

confidence: 99%

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Determination of the enantiomeric composition of amphetamine, methamphetamine and 3,4‐methylendioxy‐N‐methylamphetamine (MDMA) in seized street drug samples from southern Germany

Losacker

Zörntlein

Schwarze

et al. 2021

Drug Testing and Analysis

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Amphetamine (speed), methamphetamine (crystal meth), and 3,4-methylenedioxy-Nmethylamphetamine (MDMA, ecstasy) represent the most frequently abused amphetamine-type stimulants (ATS). Differences in pharmacological potency and metabolism have been shown for the enantiomers of all three stimulants. Legal consequences in cases of drug possession may also differ according to the German law depending on the enantiomeric composition of the seized drug. Therefore, enantioselective monitoring of seized specimens is crucial for legal and forensic casework.Various kinds of samples of amphetamine (n = 143), MDMA (n = 94), and methamphetamine (n = 528) that were seized in southern Germany in 2019 and 2020 were analyzed for their chiral composition using different chromatographic methods.Whereas all samples of amphetamine and MDMA were racemic mixtures, the chiral composition of the methamphetamine specimens was diverse. Although the vast majority (n = 502) was present as (S)-methamphetamine, also specimens containing pure (R)-methamphetamine (n = 7) were found. Furthermore, few samples (n = 8) were of racemic nature or contained non-racemic mixtures of both enantiomers (n = 10).Because methamphetamine appears in varying enantiomeric compositions, any seizure should be analyzed using an enantioselective method. Amphetamine and MDMA, on the other hand, currently appear to be synthesized exclusively via racemic pathways and are not chirally purified. Nevertheless, regular monitoring of the chiral composition should be ensured.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Determination of the enantiomeric composition of amphetamine, methamphetamine and 3,4‐methylendioxy‐N‐methylamphetamine (MDMA) in seized street drug samples from southern Germany

Losacker

Zörntlein

Schwarze

et al. 2021

Drug Testing and Analysis

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“…The optical resolution of (±)‐methylamphetamine was conducted using the Pope‐Peachey method described by Kozma et al…”

Section: Methodsmentioning

confidence: 99%

Enantiomeric resolution of methylamphetamine and ephedrine: Does this affect the δ¹³C, δ¹⁵N, and δ²H stable isotope ratios of the product?

Grzechnik

George

Mitchell

et al. 2018

Drug Testing and Analysis

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The use of stable isotope ratio mass spectrometry (IRMS) as a profiling tool for methylamphetamine has evolved over the last decade. Stable isotope ratios of carbon (δ C), nitrogen (δ N), and hydrogen (δ H) of methylamphetamine are useful in determining the precursor used to manufacture methylamphetamine, and in many cases the synthetic origin of the methylamphetamine precursor. More recently, samples of seized methylamphetamine show that a resolution step is being employed in the manufacturing process. We sought to determine whether the δ C, δ N, and δ H values were affected by either a resolution performed on racemic methylamphetamine or a resolution on racemic ephedrine, a commonly used precursor to methylamphetamine. We found that for the types of resolution studied, IRMS is still able to provide useful information on the provenance of a methylamphetamine sample.

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“…[8][9][10][11] In some cases, diastereomeric salt formation using a modified version of the PopePeachy method showed high dependence on changes in pressure and temperature, thus affecting the enantiomeric excess (ee) of the products. [12][13][14] α-Methoxyphenylacetic acid (MPAA) is widely used as a resolving agent and building block in various organic syntheses. 15 Phenylacetic acids and their derivatives are very versatile platform molecules.…”

Section: Introductionmentioning

confidence: 99%

Gas Antisolvent Approach for the Precipitation of α-Methoxyphenylacetic Acid – (R)-1-Cyclohexylethylamine Diateromeric Salt

Zodge

Kőrösi

Tárkányi

et al. 2017

Chem.Biochem.Eng.Q.

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One of the major drawbacks of diastereomeric salt precipitation based enantioseparation is the time and solvent requirement of crystallization. In the gas antisolvent (GAS) approach, supercritical carbon dioxide is applied as an antisolvent, and the precipitation takes place in a couple of minutes. By setting the process parameters diastereomeric excess, yields, and selectivity can be controlled. Applicability of the process is demonstrated on the resolution of racemic 2-methoxyphenylacetic acid with enantiopure (R)-(−)-1-cyclohexylethylamine. Diastereomeric excess values over 55 % along with 80 % yields were achieved at optimal conditions in a single step.

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Study of the mechanism of the optical resolution of N-methylamphetamine via diastereoisomeric salt formation by the Pope-Peachey method

Cited by 8 publications

References 1 publication

Determination of the enantiomeric composition of amphetamine, methamphetamine and 3,4‐methylendioxy‐N‐methylamphetamine (MDMA) in seized street drug samples from southern Germany

Determination of the enantiomeric composition of amphetamine, methamphetamine and 3,4‐methylendioxy‐N‐methylamphetamine (MDMA) in seized street drug samples from southern Germany

Enantiomeric resolution of methylamphetamine and ephedrine: Does this affect the δ¹³C, δ¹⁵N, and δ²H stable isotope ratios of the product?

Gas Antisolvent Approach for the Precipitation of α-Methoxyphenylacetic Acid – (R)-1-Cyclohexylethylamine Diateromeric Salt

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Study of the mechanism of the optical resolution of N-methylamphetamine via diastereoisomeric salt formation by the Pope-Peachey method

Cited by 8 publications

References 1 publication

Determination of the enantiomeric composition of amphetamine, methamphetamine and 3,4‐methylendioxy‐N‐methylamphetamine (MDMA) in seized street drug samples from southern Germany

Determination of the enantiomeric composition of amphetamine, methamphetamine and 3,4‐methylendioxy‐N‐methylamphetamine (MDMA) in seized street drug samples from southern Germany

Enantiomeric resolution of methylamphetamine and ephedrine: Does this affect the δ13C, δ15N, and δ2H stable isotope ratios of the product?

Gas Antisolvent Approach for the Precipitation of α-Methoxyphenylacetic Acid – (R)-1-Cyclohexylethylamine Diateromeric Salt

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Enantiomeric resolution of methylamphetamine and ephedrine: Does this affect the δ¹³C, δ¹⁵N, and δ²H stable isotope ratios of the product?