E is for Ecstasy by Nicholas Saunders

Appendix 4: Bibliography

Anon: Analytical Profiles of Substituted 3,4-Methylenedioxyamphetamines: Designer Drugs Related to MDA. Published by CND Analytical, Auburn, Alabama. 109 p. (1988).

An atlas of spectra, chromatographic behaviour, outlines of chemical preparations, and a brief history of MDA, and over a score of its homologues, is presented. Spectra of the usual synthetic precursors are also given. MDMA is represented with its UV, IR (both salt and base), MS, and HPLC characteristics.

Andrey, R.E. and Moffat, A.C. Gas-Liquid Chromatographic Retention Indices of 1318 Substances of Toxicological Interest on SE-30 or OV-1 Stationary Phase. J. Chromatog. 220 195-252 (1981).

The GC characteristics of many abuse drugs are presented in a review format. MDMA is included without experimental detail.

Bailey, K., By, A.W., Legault, D. and Verner, D. Identification of the N-Methylated Analogs of the Hallucinogenic Amphetamines and Some Isomers. J.A.O.A.C. 58 62-69 (1975).

MDMA and four analogous methamphetamine derivatives (corresponding to 2-, 3-, and 4-methoxyamphetamine (MA) and 3-methoxy-4,5-methylenedioxyamphetamine (MMDA)) were synthesized and spectroscopically characterized. The synthesis was from the corresponding phenylacetone through the Leuckart reaction with N-methylformamide. The reported m.p. (of the hydrochloride salt) is 147-8 degrees C. The U.V., NMR, IR and mass spectral data are presented. Rf values (five systems) and GC retention times (four systems) are also given.

Churchill, K.T. Identification of 3,4-Methylenedioxymethamphetamine. Microgram 18 123-132 (1985).

An analytical profile, through spectrographic tools such as UV, TLC, GC, NMR, MS, is presented for a sample of MDMA seized in Georgia. Comparisons with MDA are presented.

Clark, C.R., Noggle, F.T. and De Ruiter, J. Liquid Chromatographic and Mass Spectal Analysis of N,N-disubstituted 3,4-Methylenedioxyamphetamines. J. Liq. Chrom. 13 263- 274 (1990).

The preparation of the N-methyl-N-ethyl, the N-methyl-N-propyl, and the N-methyl-N-isopropyl homologues of MDMA is described, but no physical properties are given. The route involves the reductive methylation of the appropriate preformed N-alkyl MDA homologues. Chromatographic properties, and some mass spectroscopic data, are presented.

Clark, C.R., DeRuiter, J. and Noggle, F.T. GC-MS Identification of Amine-Solvent Condensation Products Formed During Analysis of Drugs of Abuse. J. Chrom. Sci. 30 399-404 (1992).

It is reported that during the GC-MS analysis of methanol solutions of primary amines such as MDA, amphetamine and phenethylamine, there is the formation of a small amount of the Schiff base product between the amine and formaldehyde. This product co-elutes, and is not the tetrahydroisoquinoline. Methanol solutions of MDMA result in detectable methylation, with the formation of N,N-dimethyl-MDA.

Clark, C.R., Valaer, A.K., DeRuiter, J. and Noggle, F.T. Synthesis, Stability and Analytical Profiles of 3,4-Methylenedioxyamphetamines: Derivatives of "Ecstasy"(MDMA). J. Alabama Acad. Sci. 64 34-48 (1993).

A number of the known homologues of MDMA were prepared to study their properties for eventual analytical purposes. The tools used were GCMS and HPLC using a reversed phase system.

Cody, J.T and Schwartzhoff, R. Fluorescence Polarizatrion Immunoassay Detection of Amphetamine, Methamphetamine, and Illicit Amphetamine Analogues. J. Anal. Toxicol. 17 26-30 (1993).

The Abbott Diagnostic Amphetamine/Methamphetamine II and Amphetamine Class Reagents were evaluated on the Abbott TDx for cross-reactivity to amphetamine and methamphetamine sterioisomers, several of their metabolites, and various illicit drugs. MDA, MDMA, MDE, as well as 4-hydroxymethamphetamine showed a cross-reactivity that would allow this procedure to be used as a screening tool.

Cody, J.T. Cross-Reactivity of Amphetamine Analogues with Roche Abuscreen Radioimmunoassay Reagents, J. Anal. Tox. 14 50-53 (1990).

Some 15 variously substituted amphetamine and phenethylamine derivatives, with and without N-substituents, were screened at various concentrations using the Roche Abuscreen Radioimmunoassay for amphetamines. Using amphetamine as a standard, only MDA was found to cross-react. All other compounds were negative, even at the highest concentrations. These included MDMA, MDE, MDOH, N,N-dimethyl-MDA, 2-MA, 4-hydroxyamphetamine, 2,5-DMA, TMA, methamphetamine, DOM, DOET, DOB, 2C-B and mescaline.

Cody, J.T. Detection of D,L-Amphetamine, D,L-Methamphetamine, and Illicit Amphetamine Analogs Using Diagnostic Products Corporation's Amphetamine and Methamphetamine Radioimmunoassay. J. Anal. Tox. 14 321-324 (1990).

The commercial radioimmune assay procedures for amphetamine and methamphetamine were evaluated for a number of illicit drugs with the amphetamine backbone. MDA and MDMA gave substantial cross reactivity with both kits, but most of the others (DOM, mescaline, DOET. 2C-B, DOB, TMA) did not.

Dal Cason, T. The Characterization of Some 3,4-Methylenedioxyphenylisopropylamine (MDA) Analogs. J. Forensic Sci. 34 28-961 (1989).

The synthesis and complete spectroscopic identification of several N-alkylated homologues of MDA are presented. The compounds include MDA (and its acetyl derivative), MDMA, MDE, MDPR, MDIP, MDOH (and its acetyl derivative), MDDM, and the acetyl derivative of the oxime of MDP-2-P. Included are melting points, as well as GCMS, NMR, IR and HPLC details.

DeRuiter, J., Clark, C.R. and Noggle Jr., F.T. Liquid Chromatographic and Mass Spectral Analysis of 1-(3,4-Methylenedioxyphenyl)-1-propanamines: Regioisomers of the 3,4- Methylenedioxyamphetamines. J. Chrom. Sci., 28 129-132 (1990).

The chromatographic and spectroscopic properties, but not the synthetic details, are given for a series of alpha-ethyl benzylamines isomeric with MDA. The N-H, methyl, dimethyl, ethyl, propyl and isopropyl homologues are discussed.

Eichmeier, L.S. and Caplis, M.E. The Forensic Chemist; An "Analytic Detective." Anal. Chem. 47 841A-844A (1975).

An analytical anecdote is presented showing the logical procedure used to distinguish MDMA from closely related drugs such as MDA in a seized sample. MDMA was acknowledged to be similar to MDA but, whereas MDA is a controlled substance, MDMA is exempt (sic) from Federal control.

Fitzgerald, R.L., Blamke, R.V., Glennon, R.A., Yousif, M.Y., Rosecrans, J.A. and Poklis, A. Determination of 3,4-Methylenedioxyamphetamine and 3,4-Methylenedioxymethamphetamine Enantiomers in Whole Blood. J. Chrom. 490 59-69 (1989).

Extracts of whole blood containing added MDA or MDMA were derivatized with N-trifluoroacetyl-L-prolyl chloride. The resulting diastereoisomers were separated by GC, allowing a sensitivity of analysis in the nanogram range.

Gan, B.K., Baugh, D., Liu, R.H. and Walia, A.S. Simultaneous Analysis of Amphetamine, Methamphetamine, and 3,4-Methylenedioxymethamphetamine (MDMA) in Urine Samples by Solid-phase Extraction, Derivatization, and Gas Chromatography/Mass Spectrometry. J. For. Sci. 36 1331 (1991).

A method is described in which the extracts of urine are derivatized with trifluoroacetic anhydride. Deuterated amphetamine and methamphetamine were used as internal standards.

Gough, T.A. and Baker, P.B. Identifiction of Major Drugs of Abuse Using Chromatography. J. Chromatog. Sci. 20 289-329 (1982).

An extensive review of the analytical identification of many abuse drugs is abstracted. MDMA is mentioned as one of these. There is no new experimental information presented.

Gupta, R.C. and Lundberg, G.D. Application of Gas Chromatography to Street Drug Analysis. Clin. Tox. 11 437-442 (1977).

A gas chromatography screening procedure is described, in which the retention times of over 100 drugs are compared to those of methapyriline or codeine. MDMA is amongst them.

Hansson, R.C. Clandestine Laboratories. Production of MDMA 3,4-Methylenedioxymethamphetamine. Analog. 9 1-10 (1987).

A compilation of forensic information pertaining to MDMA is presented, including spectra (UV, MS, IR), synthetic approaches, and observations from clandestine laboratory operations (seen in Australia).

Hearn, W.L., Hime, G. and Andollo, W. Recognizing Ecstasy: Adam and Eve, the MDA Derivatives - Analytical Profiles. Abstracts of the CAT/SOFT Meetings, Oct. 29 - Nov. 1, 1986, Reno/Lake Tahoe, Nevada, USA.

A study is reported comparing MDA, MDMA and MDE in the EMIT immunoanalytical assay system that is designed for amphetamine. Even though they are all of decreased reactivity, there is cross-reactivity and they may be picked up as positives. Using the bottom limit cut-off of 300 nanograms/mL for amphetamine there would be a response from as little as 10-15 mg/mL of MDMA. This is a value that might be encountered in the early stages of MDMA use.

Helmlin, H., and Brenneisen, R. Determination of Psychotropic Phenylalkylamine Derivatives in Biological Matrices by High-Performance Liquid Chromatography with Photodiode-Array Detection. J. Chromatog. 593 87-94 (1992)

An HPCL analysis procedure was described for the analysis of MDMA and MDA in human urine. Six hours following the administration of a 1.7 mg/kg dosage to several patients, urine concentrations ranged from 1.48 to 5.05 ug/ml. The major metabolite, MDA, showed concentrations ranging from 0.07 to 0.90 ug/ml. A separate study of the cactus Trichocereus patchanol showed a mescaline content of from 1.09 to 23.75 ug/ml

Helmlin, H-J. and Brenneisen, R. Determination of Psychotropic Phenylalkylamine Derivatives in Biological Matrices by High-performance Liquid Chromatography with Photodiode-array Detection. J. Chrom. 593 87-94 (1992).

An HPLC analytical scheme has been developed for the characterization and potential quantitative measurement of some fifteen phenethylamine drugs of forensic interest. Of specific clinical interest was the urine analyses of several patients following the administration of 1.7 mg/Kg of MDMA. These values, from samples collected about six hours following drug administration, showed a range of 1.48 - 5.05 ug/mL for MDMA, and 0.07 - 0.90 ug/mL for the metabolite, MDA.

Helmlin, H. -J., Bracher, K., Salamone, S.J. and Brenneisen, R., Analysis of 3,4-Methylenedioxymethamphetamine (MDMA) and its Metabolites in Human Plasma and Urine by HPLC-DAD, GC-MS and Abuscreen-Online. Abstracts from CAT/SOFT Joint Meeting, October 10-16, 1993, Phoenix, Arizona.

Urine and plasma samples were taken from a number of patients being administered 1.5 mg/Kg MDMA for psychotherapy research purposes. Maximum plasma levels (300 ng/mL) were seen at 140 minutes. The main urinary metabolites were 4-hydroxy-3-methoxymethamphetamine and 3,4-dihydroxymethamphetamine, both excreted in conjugated form. The two N-demethylated homologues of these compounds were present as minor metabolites. The cross-reactivity of the Abuscreen immunoassay for both the metabolites (including MDA, another metabolite) and the parent drug were determined.

Holsten, D.W. and Schieser, D.W. Controls over the Manufacture of MDMA. J. Psychoactive Drugs 18 371-2 (1986).

A strong argument is made for attending to the quality of manufacture, and the basic concepts of ethical principles in the exploring of drugs that have not been evaluated against the usual pharmaceutical standards. Government interference in such studies becomes necessary, to safeguard the public.

Julian, E.A. Microcrystalline Identification of Drugs of Abuse: The Psychedelic Amphetamine. J. Forensic Sciences 35 821-830 (1990).

The diliturate salts (5-nitrobarbituric acid salts) of several psychedelic amphetamines have been made and observed. The amines were PA, MDA MMDA (1, not 2 as implied), DOM, DOB, TMA, Mescaline, MDMA and MDEA. Photographs of the crystals are shown.

Kunsman, G.W., Manno, J.E., Cockerham, K.R. and Manno, B.R. Application of the Syva EMIT and Abbott TDx Amphetamine Immuniassays to the Detection of 3,4-Methylenedioxmethamphetamine (MDMA) and 3,4-Methylenedioxyethamphetamine (MDEA) in Urine. J. Anal. Tox. 14 149-153 (1990).

Two popular immunological drug assays, designed for the determination of amphetamine, have been applied to urines that had been spiked with varying amounts of MDMA and MDE. The EMIT assay was insensitive except at the highest level, but there was considerable cross-reactivity with the fluorescent polarization assay.

Lim, H.K., Su, Z. and Foltz, R.L. Stereoselective Disposition: Enantioselective Quantitation of 3,4-(Methylenedioxy)Methamphetamine and Three of its Metabolites by Gas Chromatography/Electron Capture Negative Ion Chemical Ionization Mass Spectrometry. Biol. Mass Spect. 22 403-11 (1993).

A sensitive assay for MDMA and three of its metabolites has been developed. It recognizes the optical activity of the chiral centers, and has been used to determine the degree of asymmetric metabolism of racemic MDMA in both rats and mice.

Lim, H.K., Zeng, S., Chei, D.M. and Flotz, R.L. Comparitive Investigation of Disposition of 3,4-(Methylenedioxy)methamphetamine (MDMA) in the Rat and the Mouse by a Capillary Gas Chromatography-Mass Spectrometry Assay Based on Perfluorotributylamine-enhanced Ammonia Positive Ion Chemical Ionization . J. Pharmaceut. Biomed. Anal. 10 657-665 (1992). An assay is described that allows a quantitative measure of MDMA and three

of its primary metabolites, methylenedioxamphetamine, 4-hydroxy-3-methoxymethamphetamine and 4-hydroxy-3-methoxyamphetamine. The latter two metabolites were excreted mainly as the glucuronide and sulfate conjugates. The metabolic patterns of the rat and the mouse are compared.

Michel, R.E., Rege, A.B. and George, W.J. High-Pressure Liquid Chromatography / Electrochemical Detection Method for Monitoring MDA and MDMA in Whole Blood and Other Biological Tissues. J. Neurosci. Methods 50 61-66 (1993).

An method is described for the analysis of MDMA and MDA in biological samples. It claims a high sensitivity and a short turn-around time. MDE is used as an internal standard. Spiked blood samples, rather than actual clinical specimens, were used.

Noggle, F.T., Clark, C.R. and DeRuiter, J. Liquid Chromatographic and Spectral Methods for the Differentiation of 3,4-Methylenedioxymethamphetamine (MDMA) from Regioisomeric Phenethylamines. J. Liq. Chromatog. 14 913-1928 (1991).

Three isomers of MDMA, with the changes restricted to the alpha-carbon and the nitrogen substituents, have been synthesized. These are the two phenethylamines N-ethyl and N,N-dimethyl-3,4-methylenedioxyphenethylamine, and 1-(3,4-methylenedioxyphenyl-2-aminobutane (BDB). Although their mass spectra are quite similar, they can be distinguished from one-another by HPLC.

Noggle, F.T., Clark, C.R. and DeRuiter, J. Liquid Chromatorgraphic and Mass Spectral Analysis of 1-(3,4-Methylenedioxyphenyl)-3-Butanamines, Homologues of 3,4-Methylenedioxyamphetamines. J. Chrom. Sci. 27 240-243 (1989).

The HPLC and GC properties of several homologues of MDA and MDMA are reported employing the homologous ketone 3,4-methylenedioxyphenyl-3-butanone are studied. These include the primary amine, and the N-methyl, ethyl, dimethyl, (n)-propyl and (i)-propyl homologues. The N-hydroxy was made, but its possible thermal instability was not discussed.

Noggle Jr., F.T., Clark, C.R. and DeRuiter, J. Identification of Safrole and Bromosafrole in Samples from the Clandestine Synthesis of MDMA from Sassafras Oil. Microgram 24 7-13 (1991).

An analysis of seized samples from an illicit MDMA laboratory showed one to be sassafras oil that contained safrole by GCMS. The other appeared to be the result of the addition of hydrobromic acid to safrole to produce two "bromosafroles." Addition of methylamine to this material produced some MDMA.

Noggle Jr., F.T., Clark, C.R. and DeRuiter, J. Gas Chromatographic and Mass Spectrometric Analysis of Samples from a Clandestine Laboratory Involved in the Synthesis of Ecstasy from Sassafras Oil. J. Chrom. Sci. 29 168-173 (1991).

Samples from a clandestine laboratory gave, on GC-MS analysis, evidence for the intended synthesis of MDMA from the oil of sassafras. The natural component safrole gave, with the addition of HBr, the 2-bromopropane intermediate which, on treatment with methylamine, gave MDMA.

Noggle Jr., F.T., DeRuiter, J. and Long, M.J. Spectrophotometric and Liquid Chromatographic Identification of 3,4-Methylenedioxyphenylisopropylamine and its N-Methyl and N-Ethyl Homologues are presented. J. A. O. A. C. 69 681-686 (1986).

A synthesis of MDEA (the N-ethyl homolog of MDA) is reported, and the infra-red spectra of the free bases, the hydrochloride salts, and the phenylisothiocyanate adducts are recorded, as is the HPLC retention behaviour for both the bases and these derivatives.

Noggle Jr., F.T., Clark, C.R., Andurkar, S. and DeRuiter, J. Methods for the Analysis of 1-(3,4-Methylenedioxyphenyl)-2-Butanamine and N-Methyl-1-(3,4-Methylenedioxyphenyl)-2- Propanamine (MDMA). J. Chrom. Sci. 29 103-106 (1991).

The infra-red and mass spectra, and the GC and HPLC retention times, of these two known compounds, are given.

Noggle Jr., F.T., Clark, C.R., Bouhadir, K.H. and DeRuiter, J. Liquid Chromatographic and Mass Spectral Analysis of 1-(3,4-Methylenedioxyphenyl)-3-propanamines: Regioisomers of MDMA. J. Chrom. Sci. 29 78-82 (1991).

A series of N-substituted homologues of methylenedioxyphenyl-(n)-propylamine was prepared, and described by chromatographic and spectroscopic means. No melting points or other synthetic analytical detail was given.

Noggle, F.T., Clark, C.R., Pitts-Monk, P. and De Ruiter, J. Liquid Chromatographic and Mass Spectral Analysis of 1-(3,4-Dimethoxyphenyl)-2-propanamines: Analogs of MDMA. J. Chrom. Sci. 29 253-257 (1991).

A number of 3,4-dimethoxy counterparts of MDMA and its homologues have been prepared and analysed by HPLC. Described are 3,4-dimethoxyamphetamine, the N-methyl, the N- ethyl, and the N,N-dimethyl homologues.

Noggle Jr., R.T., Clark, C.R., Valaer, A.K. and DeRuiter, J. Liquid Chromatographic and Mass Spectral Analysis of N-Substituted Analogues of 3,4-Methylenedioxyamphetamine. J. Chromatog. Sci. 26 410 (1988).

Several spectral properties, and the HPLC separation characteristics of MDMA and several of its homologues and analogues (MDE, MDPR, DMMA and MDOH) are described.

Noggle Jr., F.T., DeRuiter, J., McMillian, C.L. and Clark, C.R. Liquid Chromatographic Analysis of some N-Alkyl-3,4-Methylenedioxyamphetamines. J. Liq. Chromatog. 10 2497-2504 (1987).

The HPLC separation characteristics of MDA, MDMA, MDE and MDDM (N,N-dimethyl-MDA) are reported on a reversed phase column.

Noggle Jr., F.T., Clark, C. R. and DeRuiter, J. Gas Chromatographic and Mass Spectrometric Analysis of N-Methyl-1-aryl-2-propanamines Synthesized from the Substituted Allylbenzenes Present in Sassafras Oil. J. Chrom. Sci. 20 267-271 (1991).

The several allylaromatic essential oils in Sassafras have been studied in the regeospecific addition of HBr to form the beta-bromopropane. The bromine atom was subsequently displace with methylamine to form the corresponding methamphetamine. Safrole gives rise to MDMA.

O'Brian, B.A., Bonicamp, J.M. and Jones, D.W., Differentiation of Amphetamine and its Major Hallucinogen Derivatives using Thinlayer Chromatography. J. Anal. Tox. 6 143-147 (1982).

Two thin-layer chromatographic systems, and several procedures for detection, are described for MDMA and 18 analogues. The retention times and the visualization colour changes are compared and described. Detection limits in urine were determined from artificially spiked samples. The reference sample of MDMA was synthesized from MDA by methylation with methyl iodide, and separation from the co-generated dimethyl and trimethylammonium homologues by liquid- liquid extraction and preparative TLC.

Poklis, A., Fitzgerald, R.L., Hall, K.V. and Saady, J.J. Emit-d.a.u. Monoclonal Amphetamine / Methamphetamine Assay. II. Detection of Methylenedioxyamphetamine (MDA) and Methylenedioxymethamphetamine (MDMA). For. Sci. Intern. 59 63-70 (1993)

MDA and MDMA have been found to be cross-reactive in both the monoclonal and the polyclonal immunological EMIT assay. The former was much more sensitive, presumably sufficiently so for the detection of these drugs in urine following clinical intoxication.

Ramos, J.M., Johnson, S. and Poklis, A. MDMA and MDA Cross Reactivity Observed with Abbott TDx Amphetamine/Methamphetamine Reagents. Clin. Chem. 34 991 (1988).

A study of the cross-reactivity of MDMA and MDA with the Abbott TDx fluorescent polarization immuno assay showed that these two drugs gave positive tests for amphetamine and methamphetamine at levels that were clinically relevant. This expands the utility of this screening procedure, but also demands additional care in the interpretation of positive results that are obtained clinically.

Renton, R.J., Cowie, J.S. and Oon, M.C. A Study of the Precursors, Intermediates and Reaction By-Products on the Synthesis of 3,4-Methylenedioxymethylamphetamine and its Application to Forensic Drug Analysis. Foren. Sci. Intern. 60 189-202 (1993).

MDMA was prepared by three separate synthetic routes, and the trace byproducts and impurities were identified and presented in a way that probable synthetic method could be deduced for legal purposes.

Ruangyuttikarn, W. and Moody, D.E. Comparison of Three Commercial Amphetamine Immunoassays for Detection of Methamphetamine, Methylenedioxyamphetamine, Methylenedioxymethamphetmaine, and Methylenedioxyethylamphetamine. J. Anal. Toxicol. 12 229-233 (1988).

Three commercial immunoassays for the detection of amphetamine in urine (Abuscreen, a radioimmune assay, RIA; EMIT, a homogeneous enzyme immuno assay procedure; and TDx, a fluorescent polarization immuno assay, FPIA) have been assayed for their responses to methamphetamine, MDA, MDMA, and MDE. Some cross-reactivity to amphetamine is seen with all compounds, but the response is extremely variable depending upon the assay employed.

Ruybal, R. Microcrystalline Test for MDMA. Microgram 19 79-80 (1986).

MDMA gives a sensitive microcrystalline test with gold chloride. The crystal form is similar to that of methamphetamine.

Shaw, M.A. and Peel, H.W. Thin-layer Chromatography of 3,4-methylenedioxyamphetamine, 3,4-Methylenedioxymethamphetamine and other Phenethylamine Derivatives. J. Chromatog. 104 201-204 (1975).

A broad study is presented on the TLC analyses of many phenethylamines. The compound specifically named in the title, 3,4-methylenedioxymethamphetamine (MDMA), was a misprint that was subsequently corrected to the intended compound, MMDA. MDMA was not a part of this study.

Simpson, B.J., Simpson, T.P. and Lui, R.H. Microcrystalline Differentiation of 3,4-Methylenedioxyamphetamine and Related Compounds. J. Forensic Sciences 36 908 (1991).

Crystal gold salts can distinguish between MDA, mescaline, and DOET, whereas MDMA and MDE form crystals similar to one another and are not easily distinguished. DOM and N-hydroxy-MDA compounds were soluble in the gold chloride reagents and formed no crystals.

Sutherland, G.J. 3,4-Methylenedioxymethamphetamine (MDMA) A Basis for Quantitation by UV Spectrophotometry. Analog 10 1-3 (1988).

Due to the absence of reference samples of MDMA (in Australia) a seized sample has been evaluated and provides a basis for quantitation employing UV.

Tedeschi, L., Frison, G., Castagna, F., Giorgetti, R. and Ferrara, S.D. Simultaneous Identification of Amphetamine and its Derivatives in Urine Using HPLC-UV. Intern. J. Legal Med. 105 265-9 (1993).

Four compounds are rapidly extracted from urine, derivatized with sodium 1,2-naphthaquinone-4-sulfonate, and separated from one-another by HPLC on an ion-pair reversed phase system, using a detector at 480 nm. The compounds were amphetamine, methamphetamine, 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxymethamphetamine (MDMA).

Verweij, A. Clandestine Manufacture of 3,4-Methylenedioxymethylamphetamine (MDMA) by low pressure Reductive Amination. A Mass Sectrometric Study of some Reaction Mixtures. Forensic Science International, 45 91-96 (1990)

An analysis by GCMD has been made of the contaminants present in illicitly synthesized MDMA. Most of them are ascribed to impurities in the starting piperonyl acetone (piperonal, safrole, isosafrole) or in the starting methylamine (ammonia, dimethylamine, methylethylamine).

Verweij, A.M. Contamination of Illegal Amphetamine. Hydrastatinine as a Contaminant in 3,4-(Methylenedioxy)methylamphetamine. Arch. Krim. 188 54-7 (1991). The presence of hydrastatinine has been reported in the analysis of

illicitly prepared MDMA. This extraordinary chemistry might involve the generation of a phenylacetaldehyde as an intermediate in the oxidation processes involving the conversion of the starting material, safrole. Structural identification depended on the comparisons of mass spectra.

Verweij, A.M.A. and Sprong, A.G.A. A Note About some Impurities in Commercially Available Piperonylmethylketone. Microgram 26 209-213 (1993).

An extensive collection of compounds, structures and IR spectra of impurities in commercial piperonylmethylketone (a precursor to MDMA) is carefully reproduced, to allow a determination to be made of the method of synthesis. The actual source of the precursor ketone that was studied here, however, was apparently not known, so no immediate application of this origin fingerprinting is obvious.

Yamauchi, T. The Analysis of Stimulant-analogue Compounds (3,4-Methylenedioxymethamphetamine Hydrochloride). Kagaku Keisatsu Kenkyusho Hokoku, Hokagaku Hen. 39 23 (1986).

People from abroad have provided samples of drugs that had been heretofore unidentified in Japan. An analytical profile of one such drug, MDMA, is provided employing most modern spectroscopic tools.