A study of the precursors, intermediates and reaction by-products in the synthesis of 3,4-methylenedioxymethylamphetamine and its application to forensic drug analysis.

3,4-Methylenedioxymethylamphetamine (MDMA) was prepared by three synthetic routes. Analytical data from thin-layer chromatography, gas chromatography and gas chromatography-mass spectrometry of the precursors (safrole and isosafrole), intermediates (isosafrole glycol, piperonylmethylketone, N-formyl-3,4-methylenedioxymethylamphetamine, N-formyl-3,4-methylenedioxyamphetamine and 1-(3,4-methylenedioxyphenyl)-2-bromopropane), reaction by-products and the product MDMA were obtained. Further analyses of MDMA using other techniques including 1H- and 13C-nuclear magnetic resonance spectroscopy, X-ray diffraction, infrared spectroscopy, ultraviolet spectroscopy and high performance liquid chromatography were also carried out. The results were then used as reference data for the identification of MDMA in case samples and also to establish the route of synthesis of illicitly prepared MDMA by the study of trace impurities.

Gas chromatographic-mass spectrometric confirmation of radioimmunoassay results for cannabinoids in blood and urine.

A simple gas chromatographic-mass spectrometric (GC-MS) method is described for the detection of 11-nor-9-carboxy-delta 9-tetrahydrocannabinol (delta 9-THC-COOH) in blood and urine samples found to be positive by two in-house cannabinoid radioimmunoassays (RIAs). The delta 9-THC-COOH in the samples, which is partly present as its glucuronide conjugate, is isolated by solvent extraction after hydrolysis of the glucuronide. It is converted to its trimethylsilyl derivative and analysed by capillary GC-MS in the electron impact mode with selected ion recording. All samples that were positive by both RIAs were also positive by GC-MS apart from four blood and two urine samples in which the GC-MS results were inconclusive owing to the presence of coextractives. No sample that was positive by both RIAs was found to be negative by GC-MS.

A fatal poisoning with LSD.

Radioimmunoassay, high-performance liquid chromatography and capillary gas chromatography-mass spectrometry were used to detect and measure LSD in the first reported case of fatal poisoning by LSD. The levels found in ante-mortem serum and plasma and in post-mortem blood, liver blood and stomach contents are given.

A longitudinal study of urinary excretion of N,N,-dimethyltryptamine in psychotic patients.

The excretion of N,N,-dimethyltryptamine (DMT) has been measured in longitudinal studies of five patients with schizophrenic illnesses and in four patients with rapidly or slowly cycling manic-depressive illness. The excretion of DMT was frequently raised in patients when they were psychotic but was usually normal when they had recovered. However, rapid changes in the severity of illness or sudden switches from one mood state to another were not accompanied by changes in the excretion of DMT. These findings contrast with the immediate hallucinogenic effects of an injection of DMT, and suggest that the extracerebral production of DMT (as measured by its urinary excretion) does not provoke the experience of hallucinations in psychotic patients.

Increased excretion of dimethyltryptamine and certain features of psychosis: a possible association.

The excretion of the hallucinogen dimethyltryptamine (DMT) and its precursor N-methyltryptamine (NMT) was studied among 74 recently admitted psychiatric patients and 19 normal persons. Both compounds were detected in 24-hour urine samples from all subjects. Dimethyltryptamine excretion was greatest in schizophrenia, mania, and "other psychosis" and tended to decline as clinical state improved. Psychotic depressives excreted smaller amounts of DMT more akin to those excreted by neurotic and normal subjects. Urinary NMT excretion was unrelated to psychiatric diagnosis. Ratings on the Present State Examination (PSE) also indicated that increased excretion of DMT was associated with psychotic rather than neurotic psychopathology. Forty-three percent of the variance in urinary DMT levels could be explained in terms of six of the 38 PSE syndromes. Syndromes suggesting elation, perceptual abnormalities, and difficulty in thinking and communicating were most correlated with raised urinary DMT excretion.

Urinary excretion of dimethyltryptamine in liver disease.

The urinary excretion of N,N-dimethyltryptamine (DMT) was higher in patients with severe liver disease than in normal subjects. This difference remained significant when patients with all grades of hepatic encephalopathy were excluded. Patients with liver disease whose mental states were normal excreted amounts of DMT similar to those of patients with a hospital diagnosis of schizophrenia.

Factors affecting the urinary excretion of endogenously formed dimethyltryptamine in normal human subjects.

The hallucinogenic substance N',N'-dimethyltryptamine and its precursor N-methyltryptamine were found in 24-h specimens of urine from 19 normal human subjects; the mean excretion rates were 386 ng 24 h(-1) and 856 ng 24 h(-1) respectively. The urinary excretion of both compounds was unrelated to age, sex, urinary volume, or creatinine, nor was any consistent diurnal pattern observed. Rates for the mono and dimethylated compounds were not correlated. Diet and the intestinal flora were excluded as a source of urinary dimethyltryptamine. Administration to 4 subjects of sufficient ammonium chloride to increase the H ion concentration of the urine caused a transient increase in dimethyltryptamine excretion but no consistent increase in the rate for N-methyltryptamine. Acidification of the urine did not appear to be the determining factor in this result since in one subject the same drop in urinary pH was achieved by feeding methionine without any increase in dimethyltryptamine excretion.

Urinary dimethyltryptamine and psychiatric symptomatology and classification.

The excretion of dimethyltryptamine (DMT) was studied amongst 122 recently admitted psychiatric patients and 20 normal subjects. DMT was detected in the urine of 47% of those diagnosed by their psychiatrists as schizophrenic, 38% of those with other non-affective psychoses, 13% of those with affective psychoses, 19% of those with neurotic and personality disorders and 5% of normal subjects. Ninety-nine patients were interviewed in a semi-standardized fashion, and also categorized according to a variety of operational definitions of the psychoses. The operational definitions failed to reveal any group significantly more correlated with urinary DMT than a hospital diagnosis of schizophrenia, but a discriminant function analysis of symptomatology could be used to define a group of 21 patients of whom 15 (71%) excreted detectable DMT. There was a general relationship between psychotic symptoms and urinary DMT, but specifically schizophrenic symptoms did not appear to be major determinants of DMT excretion.