Jan-Erik Lindgren

“Ayahuasca,” the South American hallucinogenic drink: An ethnobotanical and chemical investigation

The Sharanahua and Culina, small Indian tribes located in the southwestern Amazon basin, use a hallucinogenic drink for medicinal and social purposes. This decoction, called “Ayahuasca” in Peru, is prepared from Banisteriopsis Caapi stems and Psychotria sp. leaves. These plants have been botanically identified on the basis of voucher herbarium specimens and investigated for alkaloid content by means of a gas chromatography-mass spectrometry technique. A list of other occasional plant admixtures is given. Harmine, Harmaline, Tetrahydroharmine, Harmol and 6-Methoxytryptamine have been found in Banisteriopsis Caapi. Dimethyltryptamine, Monomethyltryptamine and 2-methyl-1,2,3,4-tetrahydro-β-carboline have been found in Psychotria viridis and Psychotria carthaginensis. Harmine, Harmaline, Tetrahydroharmine and Dimethyltryptamine have been found in the drink. Quantitative calculations show the amount of each alkaloid administered in the Ayahuasca drink.

Quantitation of Δ1‐tetrahydrocannabinol in plasma from cannabis smokers

A method to identify and accurately measure non‐labelled Δ1‐tetrahydrocannabinol (Δ1‐THC) in blood of cannabis smokers has been developed. It consists of the following steps: To a 5 ml plasma sample is added deuterated Δ1‐THC (Δ1‐THC‐d2) as internal standard. After extraction with light petroleum and evaporation, the Δ1‐THC containing fraction is separated by chromatography on Sephadex LH‐20 (1 times 40 cm) using light petroleum‐chloroform‐ethanol (10:10:1) as eluant. A fraction containing Δ1‐THC is collected and subjected to mass fragmentography (LKB 9000; 3% OV‐17/Gas‐Chrom Q; 230°). The mass spectrometer was adjusted to record the intensities of m/e 299 and 314 of Δ1‐THC and m/e 301 and 316 of Δ1‐THC‐d2. The standard curve was made by plotting peak height m/e 299/m/e 301. Peak levels of 19–26 ng ml−1 were reached within 10 min after smoking a cigarette containing 10 mg Δ1‐THC.

Cocaine in blood of coca chewers.

Coca leaves (Erythroxylum coca Lamarck) and powder (5 - 10 g) were taken orally by human subjects in the same way as South American natives do. The cocaine, as measured by mass fragmentography, was immediately detected in the blood, reached peak concentrations from 10 - 150 ng/ml plasma at 0.38 - 1.95 hours, and persisted in the plasma for more than 7 hours. Half-lives of the elimination of cocaine were calculated and ranged from 1.0 to 1.9 hours. The absorption half-lives ranged from 0.2 to 0.6 hours. The shape of the curves fits with the subjective effects reported. There is no reason to believe that the stimulating effect achieved by the use of either coca leaves or powder is not due to cocaine.

Identification of monohydroxylated metabolites of cannabidiol formed by rat liver.

Cannabidiol (CBD) was metabolized in vitro by rat liver enzymes. Unchanged CBD and eight monohydroxylated metabolites were isolated and positively identified. As previously reported, 7‐hydroxy‐CBD was the major metabolite. The second most abundant metabolite was 6α‐hydroxy‐CBD; whereas only a trace amount of 6β‐hydroxy‐CBD was found. In addition hydroxylation occurred in all positions of the pentyl side chain, 4″‐hydroxy‐CBD being most abundant. 3″‐Hydroxy‐CBD was formed in half of the yield of 4″‐hydroxy‐CBD, while 1″‐, 2″‐, and 5″‐hydroxy‐CBD were each formed in approximately one fourth of the yield of 4″‐hydroxy‐CBD.

Metabolism of 5-methoxy-N,N dimethyltryptamine-14C in the rat

Abstract The metabolism of 5-methoxy-N,N-dimethyltryptamine-14C has been investigated in the rat after i.p. injection (5 mg/kg). About 59–65 per cent of the radioactivity is excreted in the 24 hr urine, 4–9 per cent is eliminated in the faeces and 1 per cent as carbon dioxide during this time. Of the metabolites appearing in the urine 54 per cent is present as 5-methoxyindoleacetic acid, 9 per cent as bufotenine, 23 per cent as bufotenine glucuronide and 14 per cent as 5-hydroxyindoleacetic acid. Considerable differences in the metabolism occurred at high dose levels. 5-Methoxyindoleacetic acid-3H is not demethylated to 5-hydroxyindoleacetic acid.I.p. administered 6-hydroxy-5-methoxy-N,N-dimethyltryptamine-3H is excreted mainly unchanged and to a minor degree as conjugate and as 6-hydroxy-5-methoxyindoleacetic acid. 5-Methoxy-N,N-dimethyltryptamine is not 6-hydroxylated to a detectable degree in vivo and 6-hydroxylation is apparently of no importance for the psychotropic activity of 5-methoxy-N,N-dimethyltryptamine.

Biliary excretion of Δ1-tetrahydrocannabinol and its metabolites in the rat☆

Abstract Δ1-Tetrahydrocannabinol (Δ1-THC) administered i.v. (1 mg/kg) to anaesthetized rats with cannulated bile ducts is rapidly eliminated as metabolites in the bile. 60–70 per cent in 6 hr. In comparison with the slow excretion via faeces an extensive enterohepatic circulation, which may be of toxicological importance, is indicated. Unchanged Δ1-THC and cannabinol are eliminated in low amounts (0.05 0.1 percent) in the bile. A few per cent consists of two or more mono-oxygenated metabolites. neither of which is identical with 7-hydroxy-Δ1-THC or 6-β-hydroxy-Δ1-THC. The main part of the non-conjugated metabolites is present as compounds more polar than 7-hydroxy-Δ1-THC and as carboxylic acids. These acids were more polar than Δ1-THC-7-oic acid which could not be identified in a free or conjugated form. In the rat about 60 per cent of the metabolites are eliminated as water-soluble conjugates. Hydrolysis with glucuronidase liberated aglycones which were mainly neutral whereas hydrolysis with alkali released neutral but also some acidic compounds. 7-Hydroxy-Δ1-THC was identified as an aglycone of glucuronic acid and furthermore, three mono-oxygenated cannabinoids were isolated after hydrolysis and partially characterized.

Plasma kinetics of methaqualone in man after single oral doses

SummaryPlasma concentrations of methaqualone were followed for several days after single oral doses in 5 healthy subjects. The analysis of methaqualone was performed by gas chromatography-mass spectrometry (mass fragmentography). The plasma levels of methaqualone were interpreted according to a two compartment model. The elimination rate of methaqualone was found to be much slower than has been reported previously, half lives in the β-phase ranging from 19.6 to 41.5 h.

Fate and Metabolism of Some Hallucinogenic Indolealkylamines

Publisher Summary Many of the indole bases closely related to 5-HT are studied as hallucinogenic agents. Among them are dimethyltryptamine (DMT), 5- hydroxydimethyltryptamine (5-OH-DMT, bufotenine) and 5-methoxydimethyltryptamine (5-MeO-DMT). The first of these bases to receive pharmacologic attention was bufotenine (5-OH-DMT). Bufotenine injections have an effect on the central nervous system, whereas DMT has psychotomimetic action. 5-methoxydimethyltryptamine in low doses elicits hyperactivity in a conditioned avoidance response situation. This effect is enhanced by pretreatment with SKF 525 A. The metabolic fate of the three substances is studied in rats and metabolites in urine, identified by gas chromatography and mass spectrometry. The main metabolite of administered 5-methoxy-dimethyltryptamine is 5-methoxyindoleacetic acid, which represents a major part of the urinary excretion. Of the other compounds, the corresponding acids seem to represent main excretion products. The metabolism of the indolealkylamines and the theory of B-hydroxylation are discussed in this chapter.

Peyote Alkaloids: Identification in a Prehistoric Specimen of Lophophora from Coahuila, Mexico

Mescaline, anhalonine, lophophorine, pellotine, and anhalonidine have been identified in alkaloid extracts of a prehistoric specimen of Lophophora from a burial cave in west central Coahuila, Mexico. The specimen is associated with radiocarbon dates of A.D. 810 to 1070 and is one of the oldest materials ever submitted to alkaloid analysis.

Computer-controlled mass fragmentography with digital signal processing

Abstract A system for multiple ion detection has been developed in which both the control of the gas chromatograph-mass spectrometer (CG-MS) and signal processing are confined to the computer. The computer focuses on a certain mass by adding to the accelerating voltage of the GC-MS a voltage from a digital to analog converter and booster amplifier. The digital treatment of the signals offers more satisfactory control of the baseline and gain and at the same time allows expansion of the number of channels without hardware modification. The sampled data are continually displayed on the oscilloscope of the computer and all questions and answers are observed on the oscilloscope. The operator. can set a baseline level, sample rate and gain for each channel. The data and calculated results are displayed on the oscilloscope and can be presented as hard copy on the teletype or plotter. The usefulness of the new system is demonstrated with regard to the metabolism of pentachlorophenol.