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N-Methyl Hallucinogenic Amphetamine Analysis

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PolytheneSam:
Can you get Journal of Agricultural and Food Chemistry Vol. 22, No. 4, 1974 pages 658-664?  It has IR spectra and NMR, mass spec and UV data for apiole, dill apiole and myristicin in it.

Rhodium:
Insecticidal and synergistic components isolated from dill plants
E. Paul Lichtenstein, Tony T. Liang, Ken R. Schulz, Heinrich K. Schnoes, and Guy T. Carter
Journal of Agricultural and Food Chemistry 22(4), 658-664 (1964)




All JAOAC articles you requested in Post 494929 (Islamybad: "Did you see these? dimethoxyamphetamines ...", Serious Chemistry) has been retrieved, three of them has been posted above, and the last one in Post 487726 (Rhodium: "MDA - Precursors, Intermediates, and Impurities", Methods Discourse)

Rhodium:
Identification of Amphetamines and Related Sympathomimetic Amines
R. J. Warren, P. P. Begosh, And J. E. Zarembo
J. Ass. Off. Anal. Chem. 54(5), 1179-1191 (1971) (https://www.thevespiary.org/rhodium/Rhodium/pdf/amphetamine.identification.pdf)

Abstract
The IR, UV, and NMR spectral data as well as the pKa' values of a series of 18 phenylpropyl amines are presented and discussed. The series includes the amphetamines and many of the commercially available phenylpropyl amines being used in the field of medicine as sympathomimetic agents. These data provide a basis for rapid identification of samples from biological, forensic, and medical research.

Rhodium:
Spectroscopic and Chromatographic Identification of Dimethoxyamphetamines
Keith Bailey, Donald Legault, and Denise Verner
Journal of the AOAC, Vol. 57, No. 1, 70-78 (1974) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/jaoac.dma.identification.pdf)

Abstract
The qualitative analysis of the 6 isomeric dimethoxyamphetamines and their hydrochloride salts is described. Their ultraviolet spectra are insufficiently different for distinction, but mass, proton magnetic resonance, and infrared spectra allow a positive identification to be made, and reference spectra are provided. The application of gas-liquid and thin layer chromatographic systems for the analysis is discussed.
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The Mass Spectra of Dimethoxyamphetamine Hydrochlorides
K. Bailey
Anal. Chim. Acta 60, 287-292 (1972) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/dma-hcl.mass-spectra.pdf)

Summary
The six dimethoxyamphetamine hydrochlorides give weak but distinguishable mass spectra useful for analytical purposes. The principal fragmentation pathways are discussed in terms of the changing aromatic substitution pattern.
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Some chromatographic and electrophoretic data for amphetamine-like drugs
G. P. Cartoni, M. Lederer and F. Polidori
J. Chromatogr. 71, 370-375 (1972) (https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/amph.chromatographic.data.pdf)

Summary
Several amphetamine-like drugs has been differentiated using thin-layer chromatography on a range of supports, with several different solvent systems and two-dimensional development. Electrophoretic data is also supplied, as is TLC data on the dansyl derivatives of the substances. The following drugs were included in this study: Amphetamine, Methamphetamine, Dimethamphetamine, Ethylamphetamine, Methoxyphenamine, Phentermine, Methylphenidate, Phenmetrazine, Mephentermine, Prolintane, Ephedrine, Pseudoephedrine, Phencamphamine, Tranylcypromine and Diethylpropion.

Rhodium:
Isolation and Characterisation of Simple Psychotropic Substances as 2C-I and 2C-T-2, Hard to Get Standard Compounds: How to Save a Million!
Mogens Johannsen
Forensic Science International 136 (Suppl. 1), p 97-98 (2003)

The use of simple psychotropic compounds as standards in the analysis of forensic samples demands a reliable source for providing the necessary references. Even though there is a wide spread use of these reference substances the commercialisation has been hampered by several factors. First of all the time, paperwork and money, which have to be spend on written applications for import and export certificates. These are usually time limited, issued on a case-to-case basis and relatively costly. Secondly, more companies only offers the desired compounds in small 1 ml ampoules containing e.g. 1 mg of the active compounds at prizes exceeding 50 EUR a piece. Thirdly, companies as e.g. Sigma-Aldrich import many controlled substances from the USA. Due to the stringent rules of exportation from the USA and the decision that controlled substances may not be re-exported within Europe they can not be distributed via the usual routes i.e. through Germany for Scandinavian deliveries, but has to be send directly from the USA to the recipient country. This does not improve on the practicability and time of delivery, which can exceed several months if possible at all, if the compounds have to be imported from e.g. the USA. However, even for pan-European deliveries one usually has to be armed with patience. Finally, novel designer drugs will usually not be commercially available for a long period of time. All these facts contrast the often-enormous amounts of police seizures that contains the wanted compounds and at no cost, for the forensic laboratory, what so ever. The sole problem is to be able to isolate or synthesise, purify and of course thoroughly characterise the compounds in order to meet the requirements of a chemical reference substance.

A simple and general extraction methodology has been used to isolate and purify MDMA (pKa 8.5), methamphetamine (pKa 9.9), 2C-I (pKa ~9) and 2C-T-2 (pKa ~9) in amounts ranging from 1-15000 mg from different seizures. The procedure, which is quite straight forward, involves a liquid-liquid extraction of a neutralised aqueous phase containing the street sample with ether. Adjustment of pH with HCl delivers the insoluble hydrochloride salt of the active alkaloid, which can be re-crystallised from IPA and ether to give the desired compound. The procedure is tolerant to many of the usual additives and adulterants present in street samples such as caffeine (pKa 3.6), phenazone (pKa 1.5), salicylic acid (pKa 3.0) and salicylic acid amide (pKa 8.2). These impurities can either be removed by careful adjustment of pH during the acidification of the mother liquor or by re-crystallisation of the crude hydrochloride salts. It can, however be noted that most of the alkaloidic impurities are less basic than the psychotropic compound itself making the selective protonation of the designer drug relatively easy. The obtained compounds all give satisfactorily chemical analysis (i.e. GC-MS, 1H and 13C NMR, HPLC, IR and micro elemental analysis) and therefore meet the requirements for reference substances. Moreover, it can be mentioned that quantification of e.g. the purified MDMA hydrochloride gave a concentration of exactly 100%. In the case of 2C-I and 2C-T-2 no reference compounds or spectra were available and since standard 1H and 13C NMR does not give conclusive evidence to establish the position of the substituents on the aromatic ring, a series of 2D-NOESY NMR experiments were conducted. Based on these results it was possible to verify the structure of these relatively new designer drugs.
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The Synthetic Route Specific Impurities in 3,4-Methylenedioxyphenylpropanone and 3,4-Methylenedioxymethamphetamine Prepared from Isosafrole and Piperonal
Malgorzata Swist, Dariusz Zuba, Roman Stanaszek, Jaroslaw Wilamowski, and Andrzej Parczewski
Forensic Science International 136 (Suppl. 1), p 102-103 (2003)

Profiling of drugs appears a useful method in criminal investigation aimed at searching for illicit drug production and distribution. It is based on physical and chemical characterisation of seized samples of drugs. Profiling serves as a tool to relate different street drug seizures to a common source, to determine the origin of drug manufactured from natural sources or synthetic routes for synthetic drugs and to identify addictives or impurities found in illicit drugs which may cause public health risks because of their inherent chemical or biological hazards. Concerning 3,4-methylenedioxymethamphetamine (MDMA), the main synthesis routes used for its production has been already well known, though only a few articles deal with profiling of MDMA seizures. One of the most popular synthesis method of MDMA is the low pressure reductive amination of 3,4-methylenedioxyphenyl-2-propanone (MDP2P or PMK) which can be prepared by two different routes, i.e. by oxidising isosafrole in an acid medium or from piperonal via 1-(3,4-methylenedioxyphenyl)-2-nitro-1-propene. The main aim of our study was to establish which impurities found in the prepared PMK are also present in the final product (MDMA) as well as to establish which of the impurities found in PMK are parent compounds for other impurities found in MDMA final product. PMK was obtained by oxidising isosafrole and from piperonal. Each synthesis was repeated three times in order to establish variety in composition of impurities between different batches of PMK. Fourier transform infrared spectroscopy (FTIR) was used for identification of the final products. Thin layer chromatography (TLC) and gas chromatography coupled to mass spectrometry (GC-MS) were applied to identify precursors, intermediates, and by-products. The impurity profile of 1-(3,4-methylenedioxyphenyl)- 2-nitro-1-propene, which is an intermediate in the 'nitropropene route', and the profiles of PMK prepared by different routes, were obtained, and ’route specific’ impurities were found. The impurities in commercially available precursors, isosafrole and piperonal, were also analysed by means of TLC and GC-MS. MDMA was prepared by low pressure reductive amination from PMK. Each synthesis route was repeated in triplicate in order to establish variety in composition of impurities between different batches of MDMA. MDMA hydrochloride was obtained from both - crude and distilled MDMA in its basic form.

Impurities of MDMA were extracted as follow: 200 mg of the final product of MDMA hydrochloride synthesis was dissolved in 2 ml of buffer (extraction was performed in two different buffers: phosphate buffer of pH 7 and carbonate buffer of pH 10), the suspension was vigorously shaken for 25 min at 1800 rpm, then a volume of 200 µl of n-heptane, containing 35 mg/l diphenylamine as an internal standard, was added and again vigorously shaken for 30 min. The organic phase was subjected to TLC and GC-MS analysis. TLC impurity profiles of both PMK and MDMA were obtained on Merck aluminium plates (Kieselgel 60 F-254) and spots were visualised with UV and/or ninhydrine. The mobile phase was a mixture of chloroform: methanol (9:1, v/v). GC-MS analysis was carried out on Hewlett-Packard 6890 series gas chromatograph coupled to 5984B mass spectrometer. Chromatographic separation was achieved on HP5-MS fused silica capillary column (30 m x 0.25 mm x 0.25 µm) and helium 6.0 was used as a carrier gas (1.0 ml/min). The injection (2 µl) was made splitless by the autosampler. The following temperature program was applied: 50°C maintained for 1 min, then ramped at 10°C/min up to 150°C, maintained 5.5 min, and again increased to 280°C at 10°C /min ramp, and then maintained for the final 10 min. Mass spectrometer was operated in positive electron ionisation mode (EI). A full-scan mass spectra 40-500 amu were obtained. The repeatability of the procedure was tested by triplicate extractions of MDMA impurities and triplicate injections of each extract. The analysis of the distilled reaction mixture after PMK synthesis from isosafrole showed the presence of different oxygenated products of isosafrole, including acetonide, carbanate and diformate.

The results of the study show that the extraction of impurities from MDMA at pH 10 was significantly more efficient compared to pH 7. Therefore the impurity profiles (pH 10) were richer and chromatographic peak areas were bigger. Extraction at pH 7 revealed only one possible 'MDMA route specific' marker, 3,4-methylenedioxy-N-methylbenzylamine, whilst extraction at pH 10 enabled also to detect other markers, e.g. N,N-dimethyl-[1,2-(methylenedioxy)-4-(2-aminopropyl)]benzene and N-ethyl,N-methyl-[1,2-(methylenedioxy)-4-(2-aminopropyl)]benzene. The proposed analytical procedures enable identification of the precursors (isosafrole, safrole, piperonal), intermediates (e.g. 1-(3,4-methylenedioxyphenyl)-2-nitro-1-propene) and some reaction by-products (N,N-dimethyl-[1,2-(methylenedioxy)-4-(2-aminopropyl)]benzene and N-ethyl,N-methyl-[1,2-(methylenedioxy)-4-(2-aminopropyl)]benzene), and determination the 'route specific' impurities.

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