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N-Methyl Hallucinogenic Amphetamine Analysis

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Rhodium:
LC and GC-MS Analysis of 4-Bromo-2,5-Dimethoxyphenethylamine (Nexus) and 2-Propanamine and 2-Butanamine Analogues
Jack DeRuiter, C. Randall Clark and F. Taylor Noggle
Journal of Chromatographic Science, Vol. 33, 583-590 (1995) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/2c-b.dob.4c-b.analysis.pdf)

Abstract
The street drug Nexus (4-bromo-2,5-dimethoxyphenethylamine) has appeared in clandestine samples in recent years. This hallucinogenic phenethylamine is prepared from the commercially available aldehyde, 2,5-dimethoxybenzaldehyde, and other readily available precursor chemicals and reagents. Nexus and some designer analogues are separated by liquid chromatography using a C18 stationary phase and an acidic (pH 3) mobile phase. Nexus, a brominated phenethylamine, shows enhanced reversed-phase retention relative to the unbrominated precursor phenethylamine. The mass spectra of these amines show fragment ions consistent with amine-dominated reactions common to phenethylamines and substituted phenethylamines. The gas chromatographic—mass spectrometric analysis of mixtures of the amines and the synthetic precursor nitroethenes show on-column reaction products that complicate the analytical results. These reaction products are identified as the imines that result from condensation of the amine with the substituted benzaldehyde, which is generated from the 2-nitroethene.
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Gas Chromatographic-Mass Spectrometric and High-Performance Liquid Chromatographic Analyses of the Bromination Products of the Regioisomeric Dimethoxyphenethylamines: Differentiation of Nexus from Five Positional Isomers
Jack DeRuiter, C. Randall Clark and F. Taylor Noggle
Journal of Chromatographic Science, Vol. 36, 23-28 (1998) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/2c-b.regioisomers.pdf)

Abstract
The brominated products from all six positional isomers of dimethoxyphenethylamine are prepared, and their analytical properties are evaluated. The major bromination product from 3,5-dimethoxyphenethylamine is the 2,6-dibromo isomer; all other regioisomers of dimethoxyphenethylamine yield a monobromo species as the major product. The mass spectra divide these compounds into two distinct groups: one group showing a strong m/z 180 ion via loss of bromine from the molecular ion (M-Br)+ and a second group showing no significant m/z 180 ion. The three compounds that do not show the m/z 180 ion in their electron-impact mass spectra are brominated 2,4-; 2,5-; and 2,6-dimethoxyphenethylamine. These compounds are well-resolved by reversed-phase liquid chromatographic methods using a Hypersil Elite C18 stationary phase and a mobile phase of phosphate buffer (pH 3) and methanol-acetonitrile.
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Liquid Chromatographic and Mass Spectral Methods of Identification for Regioisomeric Dimethoxyamphetamines and Brominated Dimethoxyamphetamines
Jack DeRuiter, Pamela Holston, C. Randall Clark and F. Taylor Noggle
Journal of Chromatographic Science, Vol. 36, 73-79 (1998) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/dma-dob.regioisomers.pdf)

Abstract
The six regioisomeric dimethoxyamphetamines are prepared from the commercially available dimethoxybenzaldehydes. The dimethoxyamphetamines show very similar mass spectra, and chromatographic methods must be used to differentiate the positional isomers. Bromination of the six isomeric dimethoxyamphetamines yields a monobromination product as the major component in all cases except for 3,5-dimethoxyamphetamine, which yields the 2,6-dibrominated species as the major product. Mass spectrometric analysis readily divides the regioisomeric bromodimethoxyamphetamines into two groups of three compounds each. Only those isomers having a bromine substituent "ortho-" to the alkylamine side-chain show a major fragment at m/z 194 from loss of bromine from the molecular ion. The major drug of abuse 4-bromo-2,5-dimethoxyamphetamine (DOB) is one of three compounds that do not yield the m/z 194 ion. Though the mass spectra for the three "non-m/z 194" isomers show some subtle differences, these compounds are best differentiated by a reversed-phase liquid chromatographic system.

Rhodium:
Gas Chromatographic and Mass Spectral Analysis of Amphetamine Products Synthesized from 1-Phenyl-2-Nitropropene
Jack DeRuiter, C. Randall Clark and F. Taylor Noggle
Journal of Chromatographic Science, Vol. 32, 511-519 (1994) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/amphetamine.phenylnitropropene.pdf)

Abstract
The conversion of 1-phenyl-2-nitropropene to amphetamine is investigated under a variety of reaction conditions using gas chromatography-mass spectrometry (GC-MS). This versatile intermediate is prepared by treating benzaldehyde with butylamine and nitroethane. GC—MS analysis revealed that amphetamine is produced as the major product upon catalytic reduction of 1-phenyl-2-nitropropene. However, a number of partial reduction products are also present in the mixture. Reduction of the nitropropene with a 5-molar excess of lithium aluminum hydride yields 1-phenyl-2-propanoxime as the major component. A variety of other partial reduction products and products of competing reactions are also present in this product mixture, as well as amphetamine. When this reduction is carried out with a large excess of lithium aluminum hydride, amphetamine is formed as the major product. 1-Phenyl-2-nitropropene is also converted to the ketone, 1-phenyl-2-propanone, by partial reduction and hydrolysis. Amination of this ketone under Leuckart and reductive amination conditions provide amphetamine as the principle product. GC—MS analysis reveals that these samples also contain several by-products characteristic of these routes of synthesis.
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Methods for the Differentiation of Methamphetamine from Regioisomeric Phenethylamines
F. Taylor Noggle, C. Randall Clark, Kamal H. Bouhadir and Jack DeRuiter
Journal of Chromatographic Science, Vol. 29, 31-36 (1991) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/meth-pea.differentiation.pdf)

Abstract
The analytical profiles are described for five amines, methamphetamine, and four isomeric phenethylamines of MW = 149. These five amines all contain an unsubstituted benzyl moiety, thus the regioisomerism is within the carbon-carbon bond located - to the amine moiety. Therefore these phenethylamines are regioisomeric within the imine fragment (m/z = 58), which is the base peak in the electron impact (EI) mass spectrum of methamphetamine. The ultraviolet absorption spectra for these compounds show the characteristic phenethylamine absorption bands in the (250-260 nm) range. These amines are best differentiated by chromatographic separation and are well resolved by liquid chromatographic techniques. The five regioisomeric amines are separated using an isocratic reversed-phase system consisting of a C18 stationary phase and a mobile phase of pH 3 phosphate buffer and methanol. The elution order under these conditions appears to parallel the length of the carbon chain attached to the aromatic ring.
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-Benzyl-N-Methylphenethylamine (BNMPA), an Impurity of Illicit Methamphetamine Synthesis: III. Detection of BNMPA and Metabolites in Urine of Methamphetamine Users
Karla A. Moore, Abd Ismaiel and Alphonse Poklis
Journal of Analytical Toxicology, Vol. 20, 89-92 (1996) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/bnmpa-3.detection.pdf)

Abstract
Eighty urine specimens collected from drug rehabilitation programs, which had been screened by immunoassay and confirmed positive by gas chromatography–mass spectrometry (GC–MS) for methamphetamine, were further analyzed for a-benzyl-N-methylphenethylamine (BNMPA) and its urinary metabolites, N-demethyl-BNMPA, diphenyl-2-propanone (DP2P), diphenyl-2-propanol, p-OH-N-demethyl-BNMPA, and p-OH-BNMPA. BNMPA is an impurity of illicit methamphetamine synthesis. Analysis of BNMPA and its metabolites was performed by quantitative GC–MS following -glucuronidase hydrolysis, liquid–liquid extraction, and derivatization with heptafluorobutyric anhydride. Two urine specimens contained detectable amounts of BNMPA and/or its metabolites. One contained trace amounts (greater than the limit of detection but less than the limit of quantitation) of N-demethyl-BNMPA and DP2P, as well as 0.04 mg/L p-OH-N-demethyl-BNMPA. The other contained trace amounts of BNMPA, p-OH-BNMPA, and p-OH-N-demethyl-BNMPA, as well as 0.03 mg/L N-demethyl-BNMPA. Prior to analyzing these urine specimens, pure reference material of p-OH-BNMPA was made available, and analysis confirmed our previous tentative identification of p-OH-BNMPA as a major metabolite of BNMPA. Detection of BNMPA or its metabolites in biological samples may serve as a marker of illicit methamphetamine administration.
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Identification of -Phenylethylamine in judicial Samples
E. Meyer, J. F. Van Bocxlaer, W. E. Lambert, L. Thienpont and A. P. De Leenheer
Journal of Analytical Toxicology, Vol. 20, 116-120 (1996) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/alpha-pea.identification.pdf)

Abstract
-Phenylethylamine was recently identified in samples from several judicial cases using chromatographic (high-performance liquid chromatography–diode-array detection, gas chromatography–mass spectrometry, and gas chromatography–Fourier transform infrared detection) and spectrometric (nuclear magnetic resonance) techniques. In the first case, 1 kg of a white powder was found in a basement laboratory. It contained caffeine and more than 15% -phenylethylamine. In the second case, two white powders were seized from a female. One powder consisted of pure amphetamine, and the other was a mixture of caffeine, amphetamine, and -phenylethylamine. Four months later, a couple, who were known drug users, were found dead in their apartment. Urine samples of both victims contained large amounts of amphetamine together with -phenylethylamine. Recently, 0.13 kg of a white powder and 0.30 kg of an orange powder were seized during a law enforcement operation. Both powders were mixtures of caffeine, amphetamine, and -phenylethylamine. The data presented demonstrate the recent and unrelated repetitive occurrence of -phenylethylamine in the circuit of illicit drugs.
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Analysis of Impurities in Illicit Methamphetamine
K. Tanaka, T. Ohmori And T. Inoue
Forensic Science International 56, 157-165 (1992) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/meth.impurities.japan.pdf)

Summary
Impurity profiles of methamphetamine samples seized in Japan have been investigated. The samples are extracted with small amounts of hexane under alkaline conditions and the extracts are analyzed by gas chromatography (GC). Several impurity peaks are found in each chromatogram and the comparison of impurity profiles permits the establishment of common or different origins of methamphetamine seizures. The presence of ephedrine, which is a starting material for illegal methamphetamine preparations, is confirmed in all samples. In addition, methamphetamine dimer is newly found as an impurity and its structure is elucidated by the comparison of its retention time on GC and its mass spectrum with that of the authentic compound synthesized by condensation of cis-1,2-dimethyl-3-phenyl aziridine and (+)-methamphetamine.
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Gas Chromatographic and Mass Spectral Analysis of Methamphetamine Synthesized From Allylbenzene
F. Taylor Noggle, C. Randall Clark and Jack DeRuiter
Journal of Chromatographic Science, Vol 33, 153-161 (1995) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/meth.allylbenzene.pdf)

Abstract
The synthesis of methamphetamine from allylbenzene is investigated using gas chromatography–mass spectrometry. Treatment of allylbenzene with HBr yields 1-phenyl-2-bromopropane as a major product. Smaller amounts of 1-phenyl-3-bromopropane, as well as 2,3-, 1,2-, and 1,3-dibromopropane, are also formed during the course of this reaction; both diastereomeric forms of 1,2-dibromopropane are detected in the product mixture. Amination of the crude bromination product with methylamine yields primarily methamphetamine and other amines characteristic of this synthetic method, including the methamphetamine isomer, N-methyl-1-phenyl-1-propanamine.

Rhodium:
Investigation and Identification of the Bromination Products of Dimethoxyamphetamines
Keith Bailey, Denise R. Gagné, and Richard K. Pike
Journal of the AOAC, Vol. 59, No. 5, pp. 1162-1169 (1976) (https://www.thevespiary.org/rhodium/Rhodium/pdf/jaoac.dob-analogs.pdf)

Abstract
The qualitative analysis of the aromatic bromination products of the 6 isomeric dimethoxyamphetamines and their hydrochloride or hydrobromide salts is described. Their ultraviolet, mass, and proton magnetic resonance spectra are not sufficiently different for distinction but infrared spectra allow a positive identification to be made and reference spectra are provided for the bromination products of 2,4-, 2,5-, 2,6-, 4,5-, and 3,5-dimethoxyamphetamines. The application of gas-liquid and thin layer chromatography for the analysis of these products is discussed. The bromination of 2,3-dimethoxyamphetamine consistently gave mixtures which could not be separated satisfactorily; spectra are included for completeness of the comparison of products.

Rhodium:
Identification of 2-, 3-, and 4-Methoxyamphetamines and 2-, 3-, and 4-Methylamphetamines
Keith Bailey Harry D. Beckstead, Donald Legault, and Denise Verner
Journal of the AOAC 57(5), 1134-1143  (1974) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/metyl.methoxy.amph.pdf)

Abstract
The identity of samples of 2-, 3-, and 4-Methoxyamphetamines and 2-, 3-, and 4-Methylamphetamines is conclusively established by comparison of their spectra. Ultraviolet, proton magnetic resonance, and mass spectra distinguish and identify the two series and infrared spectra differentiate isomers; reference spectra and data are provided. Thin layer and gas-liquid chromatographic systems suitable for distinguishing these compounds are described.
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Identification of Impurities in Illicit Methamphetamine Samples
Robert P. Barron, Alice V. Kruegel, James. M. Moore and Theodore C. Kram
Journal of the AOAC 57(5), 1147-1158  (1974) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/jaoac.meth.impurities.pdf)

Abstract
Three impurities have been identified in illicit methamphetamine samples. One of these, N-formyl-methamphetamine, is an intermediate in the synthesis of methamphetamine by the Leuckart reaction. The remaining two, N,?,?-trimethyldiphenethylamine and ?-benzyl-N-methylphenethylamine are by-products of methamphetamine synthesis. Ultraviolet, infrared, nuclear magnetic resonance, and gas chromatographic-mass spectral techniques were used to identify these compounds. The data obtained are discussed and synthetic pathways are postulated to explain the presence of each compound in samples of methamphetamine.

Rhodium:
The Identification of Methoxy-N-Methylamphetamines
Charles C. Clark
Journal of Forensic Sciences 29(4), 1056-1071 (1984) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/methoxy-n-methyl-amphetamines.pdf)

Abstract
Thirteen mono, di, and trimethoxy-N-methylamphetamines have been synthesized and characterized. Gas-liquid chromatographic data and ultraviolet, infrared, proton magnetic resonance and mass spectra are presented. The specificity of each technique for the identification of methoxy-N-methylamphetamines is discussed.
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Differentiation of 2,3-Methylenedioxyamphetamine from 3,4-Methylenedioxyamphetamine
William H. Soine, Robert E. Shark and Delbert T. Agee
Journal of Forensic Sciences 28(2), 386-390 (1983) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/23-mda.34-mda.differentiation.pdf)

Abstract
The 2,3- and 3,4-methylenedioxyamphetamine isomers can be distinguished using the sulfuric acid color test, gas chromatography, infrared spectroscopy, mass spectrometry, and 13C nuclear magnetic resonance.

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