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GC/MS analysis of morning glory seeds freely in commerce: can they be considered “herbal highs”?

Abstract

Background

The so-called “herbal highs” are substances derived from natural plants with effects on the central nervous system. Lisergamide, ergine or LSA is the basis of different types of drugs, which are in seeds of Ipomoea violacea, also known as Morning Glory, and other seeds.

In our study we analysed the presence of lysergic acid amide (LSA) in seeds of Ipomoea violacea seized by the Italian Police, in others purchased through the Internet, and in other varieties of Ipomoea sold for ornamental purposes, to assess whether the actual consumption of ornamental seeds could contain hallucinogenic doses of LSA.

Methods

The analyses were conducted at the Laboratory of Forensic Toxicology of the Section of Legal Medicine of the University of Perugia, using GC/MSD system. For analysis, 300 mg of seeds (

8 seeds) from each specimen were chosen.

Results

Analysis revealed that 300 mg of Ipomoea violacea seeds resulting from police seizures, equivalent to approximately 8 seeds, contained a percentage of LSA equal to 0.062%. This finding is in agreement with what was indicated in literature, as the ingestion of 250 seeds would lead to a dose of approximately 6 mg of LSA, capable of provoking hallucinogenic effects.

The analysis of 300 mg of Ipomoea Rubrocerulea seeds bought on the commercial marketdetected an average concentration of LSA of 0.011%. The Ipomoea mix contained a concentration of LSA about 10 times lower than that of seized Morning Glory seeds.

Conclusion

Seeds bought on the commercial market contained doses of LSA capable of provoking hallucinogenic effects. In the absence of data on the toxicity resulting from the ingestion of seeds for ornamental purposes, we believe that further research on the actual safety of ornamental seeds is necessary.

Background

In recent years, interest in non-conventional drugs has increased. The so-called “herbal highs” are substances derived from natural plants with effects on the central nervous system (Halpern, 2004; Bilgrey, 2016; Zuba et al., 2011).

These drugs are called “legal highs”, underlining the fact that they have easy accessibility, low cost, and are not illegal (Aoun et al., 2014).

Lisergamide (Juszczak & Swiergiel, 2013), ergine or LSA is the basis natural drugs, which are contained in brown seeds of Rivea Corymbosa, of Ipomoea violacea also known as Morning Glory and of Argyreya Nervosa known as Hawaiian Baby Woodrose. These plants are members of Convulacee family and are infected by a kind of clavicipitaceus fungus that is responsible for the biosynthesis of alkaloids. The most important alkaloids are ergine and isoergine, which is ergine enatiomer. In these seeds, other bases especially chanoclavine, elymoclavina, and lysergol can also be found.

Studies on seeds of Morning Glory began in 1955 when a psychiatrist published notes on self-experimentation with Rivea seeds, showing that they provoked hallucinations. This announcement prompted chemists to analyse this plant, but until 1960 they failed to identify the active substance. At that time the chemist Hoffmann Albert (Hofmann, 1963), who discovered LSD, analysed the plant and found several alkaloids closely related to that powerful synthetic hallucinogen.

The discovery of ergot alkaloids in seeds of Rivea Corymbosa, Ipomoea violacea and Argyreia nervosa in the early 60s was rather unexpected and of particular interest from a phytochemical point of view, since the lysergic acid alkaloids, until then, were isolated only in the genus Claviceps fungus, Penicillium or Rhizopus (Steiner et al., 2006).

The ingestion of Ipomoea violacea seeds produces effects comparable to those produced by Argyreia nervosa seeds. These effects, although minor, are similar to those of LSD.

In general, seeds are ingested whole or broken and immersed in water. Data in literature suggest that in order to have the hallucinogenic effects, 10 seeds Argyreia nervosa (Al-Assmar, 1999), and from 150 to 200 seeds of Morning Glory are typically ingested (Schultes, 1960).

Ergine hallucinogenic activity (LSA) is carried out starting from the assumption of 2–5 mg (Schultes & Hofmann, 1980). LSA effects, lasting about 4–8 h, are associated with feelings of tranquility, dysphoria, psychedelic visual effects, color visions. In humans, the lethal dose is 14 mg / kg.

In addition to desired effects, LSA has several side effects (Juszczak & Swiergiel, 2013). In a recent review, different symptoms following the ingestion of these seeds were reported: the most troubling of them was suicidal ideation. In literature, anorexia, nausea, memory loss, dissociative reactions and schizophrenic relapse are the major psychotic adverse effects that may occur as a result of ingestion of the seeds. Furthermore, in the past fatal cases occurred after taking seeds containing LSA have been described (Gertsch & Wood, 2003; Cohen, 1964; Brady, 1968; Ingram, 1964; Flach, 1967; Whelan et al., 1968). The ingestion of seeds was frequently associated with taking drugs such as cannabis and hashish (Hofmann, 1963). Interactions due to ingestion of Argyreia nervosa, Ipomoea violacea or Rivea Corymbosa and other drugs are still unknown. However it has been shown that the metabolism of LSD analogous is inhibited by drugs used in HIV therapy. This suggests the possibility that patients, treated with antiretroviral drugs, taking LSD or Argyreia nervosa, Ipomoea violacea or Rivea Corymbosa, may manifest an increase in the toxicity induced by such hallucinogens (Klinke et al., 2010).

In our study we tried to analyse the presence of lysergic acid amide in seeds of Ipomoea violacea seized by Italian Police, in others purchased through the Internet, and in other varieties of Ipomoea sold for ornamental purposes, to assess whether the actual intake of ornamental seeds could contain hallucinogenic doses of LSA. In addition we also evaluated and described the most suitable methods for the extraction and the quantitative determination of LSA (Mussof & Daldrup, 1997).

Methods

The analyses were conducted at the Laboratory of Forensic Toxicology of the Section of Legal Medicine of the University of Perugia during May 2015. The reference standards used were purchased from the company Sigma – Aldrich and / or LGC Standards s.r.l.

Morning glory seeds (Fig. 1) used in the research were seized by the police during an operation for the prevention and suppression of illicit traffic of narcotic drugs and psychotropic substances, and delivered to the Forensic Toxicology Laboratory of the University of Perugia Section for the identification and qualitative and quantitative analysis.

Seized Seeds – Morning Glory

Seeds of Heavenly Blue (Ipomoea Rubrocerulea) were bought on the internet from a site of ornamental plants; seeds of a mix of varieties of Ipomoea, purple and others were instead purchased directly in a shop for ornamental plants.

The chemical-toxicological analysis have been performed using GC / MSD system 6850/5973 Network, Agilent Technologies company, ion source connected to capillary HP5ms, 25 mm ID, column length 30 m.

For analyses, 300 mg of seeds (

8 seeds) from each specimen were chosen. Each sample was washed with 3 ml of distilled water and 2 ml of dichloromethane, and then crushed in a mortar with quartz.

All the finely crushed material was collected in graduated glass tubes. Distilled water and a few drops of 1 N NaOH were added to obtain sharply basic pH. Then the aqueous solution was extracted three times with a chloroform-methanol-NH4OH solution in 9: 90: 1 aspect ratio. The extracts were dried under a stream of nitrogen at a temperature below 40 °C. Finally 100 μl of methanol RPE was added (Witters, 1975).

The LSA dilutions to obtain the calibration curve were prepared from a stock solution in methanol (1 mg / ml). The solution was diluted with methanol to obtain four concentrations of LSA included in a range between 10 and 100 μg / ml (Fig. 2) (Littlewood, 1970; Crawford, 1970).

The sample was introduced using splitless injection; programmed temperature for all analytes started at 150 °C for 2 mins, then, with a thermal gradient of 30 °C per min reached a temperature of 290 °C remaining constant for other 25 mins. Helium was used as carrier gas, setting a flow rate of 1 ml / min and the injector temperature was set at 280 °C. The analytes, eluted from the chromatographic column, arrived via transfer line, whose temperature was set at 300 °C, in the ionization source of the mass spectrometer, characterized by a temperature of 300 °C. Here they were ionized through the ‘application of a potential of 70 eV and an emission of current of 200 uA. The characterization of all analytes was carried out in full-scan mode (range m / z 50–800).

For quantitative analysis of LSA, MS-SIM acquisition mode was chosen; mass spectra were obtained by selecting at least three characteristic ions.

LSA wasidentified through its molecular ion m/z 267 and ion fragments 221 and 207. Analyses were repeated three times.

Method validation

The method linearity for each compound was investigated in the range 10–100 mcg/ml. Calibration curves were established with three replicates at each concentration.

Sensitivity was evaluated by determination of the LOD and the limit of quantitation (LOQ). A series of decreasing concentrations of drug-fortified solutions was analysed to determine LOD and LOQ. The LOD was determined as the concentration with a signal/noise (S/N) ratio of at least 3, while the LOQ was the lowest concentration with a S/N ratio of at least 10. The acceptable value for the regression coefficient (R2) was set at > .98. R2, LOD and LOQ values were respectively of 0.99671, 5 ng/ml, 10 ng/ml.

Results and discussion

All the used extractive methods revealed the presence of LSA in seeds of Ipomoea violacea, but the system with ammonium hydroxide, methanol and chloroform, provided excellent results in terms of yield compared to other systems adopted in preliminary screening tests. During fragmentation, the ion fragment m/z 267 had a value that was double, in terms of abundance ions, so it was used to quantify LSA. Chromatographic analysis revealed the presence of LSA in Ipomoea violacea seeds (Morning Glory), Ipomoea Rubrocerulea and Ipomoea mix (Figs. 3, 4 and 5).

The so-called “herbal highs” are substances derived from natural plants with effects on the central nervous system. Lisergamide, ergine or LSA is the basis of different types of drugs, which are in seeds of Ipomoea violacea, also known as Morning Glory, and other seeds. In our study we analysed the presence of lysergic acid amide (LSA) in seeds of Ipomoea violacea seized by the Italian Police, in others purchased through the Internet, and in other varieties of Ipomoea sold for ornamental purposes, to assess whether the actual consumption of ornamental seeds could contain hallucinogenic doses of LSA. The analyses were conducted at the Laboratory of Forensic Toxicology of the Section of Legal Medicine of the University of Perugia, using GC/MSD system. For analysis, 300 mg of seeds (~8 seeds) from each specimen were chosen. Analysis revealed that 300 mg of Ipomoea violacea seeds resulting from police seizures, equivalent to approximately 8 seeds, contained a percentage of LSA equal to 0.062%. This finding is in agreement with what was indicated in literature, as the ingestion of 250 seeds would lead to a dose of approximately 6 mg of LSA, capable of provoking hallucinogenic effects. The analysis of 300 mg of Ipomoea Rubrocerulea seeds bought on the commercial marketdetected an average concentration of LSA of 0.011%. The Ipomoea mix contained a concentration of LSA about 10 times lower than that of seized Morning Glory seeds. Seeds bought on the commercial market contained doses of LSA capable of provoking hallucinogenic effects. In the absence of data on the toxicity resulting from the ingestion of seeds for ornamental purposes, we believe that further research on the actual safety of ornamental seeds is necessary.

Lsa: Everything You Need To Know

Contents:

What Is Lsa?

LSA, d-lysergic acid amide or ergine, is a product during the creation of LSD, and psychoactive in itself. It was later discovered to be natural, and is known as a chemical in Morning Glory seeds, as well as Ololiuhqui (Rivea corymbosa) & Hawaiian Baby Woodrose (Argyreia nervosa) seeds, some Convolvulaceae vines, and fungi such as Sleepy Grass. Chemically it is known as LA-111, and is an ergoline alkoid.

As a precursor to LSD, the chemical structure of LSA and LSD is similar. Although active in microgram doses, LSA is not as potent as synthesised LSD, and shows a distinct character in its effects.

In the black market, LSA has often been sold as LSD, since it is much easier to obtain. Morning glory is the best known source of LSA, and its effects have been known to the native tribes since ancient times.

While both Hawaiian Baby Woodrose Vine and Morning Glory contain abundant LSA, garden center type seeds of the Morning Glory can be covered in fungicide to prevent mold.

Lsa Chemistry

Upon analysis, Albert Hoffman found LSA to be very similar to LSD in structure. The main difference being that LSA has NH2, whereas LSD has N(C2H5)2. LSA is largely insoluble in water, but can be dissolved in ethyl alcohol and methyl alcohol.

Jonathan Ott reported large, over ten-fold variations of alkaloid concentration from batch to batch of various LSA seeds. Some other ergoline alkaloids discovered in the seeds were: ergonovine, elymoclavine and lysergol.

“TiHKAL: The Continuation” is a book published by Alexander Shulgin. The work paints a broad picture of tryptamines, and delves into the mental and physiological effects of LSA. Shulgin says that a half milligram dosage (a tiny amount, but large compared to LSD doses) of LSA led to “a tired, dreamy state,” lingering off after around 5 hours. He dismisses its epimer as a major active psychoactive in Morning Glory seeds, citing Albert Hofmann’s self-trial of the substance, in which Hofmann said he got little effect but a feeling of “tiredness and emptiness.”

He writes that the LSA epimer is C-8 inverted, identifying it as either isoergine or d –isolysergamide. Pointing to the fact that lysergic acid and ergine are scheduled in the US, he proposes that it is simply a governing tactic to better enforce the laws surrounding LSD, since they are involved in its synthesis. Shulgin’s book sheds much needed light on the chemistry of LSA & LSD, describing their drug relatives and other tryptamines. However, debates on the similarity between an LSA and LSD trip still continue.

Lsa Effects

Whilst not as powerful as LSD, LSA can induce light to medium strength psychedelic effects that are reminiscent of LSD, although distinctly more sedative and with more physical side effects. LSA produces most of the common effects known from the class of psychedelic substances. Indigenous Mexican tribes used LSA in sacred ceremonies, providing further evidence for their entheogenic value. Effects vary largely from person to person.

History Of Lsa

The Spanish conquistadors considered the rituals a diabolic blasphemy and attempted to stop its use as well as prevent knowledge from spreading. LSA seeds were rediscovered in 1941, when enthobotanist Richard Schultes reported of their usage dating back to Aztec times. Later, it was reported to be used in ceremonies of the Zapotec Indians.

Samples of Ololiuqui (Turbina corymbosa) seeds have been sent to Albert Hofmann, the creator of LSD, for analysis – he was surprised to find the active compounds to be remarkably similar to LSD. First self-experiments are reported to have made him feel tired and put him in a dream like state.

Legality

Seeds containing LSA, such as Morning Glory, are not illegal. However, the production, extraction and consumption of LSA is illegal in many countries around the world. For example, LSA is considered a controlled substance in the Netherlands, a Class A drug in the UK and a schedule III drug in the USA.

Countries that do not currently have a classification for LSA or enforce any law include Canada and Hungary.

Drug Testing

LSA is not looked for specifically in most standard and extended drug tests. However, due to its chemical structure and nature, it has the potential to possibly trigger an alert on tests looking for LSD.

LSA, or D-lysergic acid amide, is a psychoactive chemical that shares many similarities with LSD. Find out all there is to know about this natural psychedelic.