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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.

Morning Glory Guide: Seeds, Effects, Common Uses, Safety

Table of Contents

Morning Glories are a group of over a thousand flowering plants that are members of the Bindweed (Convolvulaceae) family. Morning Glory species are commonly used as ornamentals around the world, and some of these varieties produce seeds that contain a psychedelic tryptamine called d-lysergic acid amide, or LSA. LSA, also known as ergine, is structurally similar to LSD and produces a trip with similar effects to its chemical cousin. Morning glory seeds have a long history of use as an entheogen in South and Central Mexico and are nowadays consumed in many parts of the world for their psychedelic effects.

What is Morning Glory?

Morning Glories are annual climbing vines that grow between 2 to 4 meters in height and produce heart-shaped leaves. In late summer, they bloom funnel-shaped flowers in a wide range of colors, including white, red, blue, purple, and yellow. When the dead flowers fall off, the plant forms round seed pods that contain four to six small black seeds per pod.

The many species of Morning Glory are native to New World tropical and subtropical regions but are naturalized and cultivated in many other parts of the world. The most well-known varieties that produce psychoactive alkaloids like LSA are Ipomoea violacea (Beach Moonflower), Ipomoea tricolor (Mexican Morning Glory), and Turbina corymbosa (Christmas Vine). I. tricolor is the most well-known variety in the United States, sold commercially with names such as Heavenly Blue, Pearly Gates, Flying Saucers, Blue Star, Summer Skies, and Wedding Bells.

While all of these Morning Glory varieties contain LSA, the highest concentration is found in the seeds of Argyreia nervosa, or Hawaiian Baby Woodrose. Being in the same family (Convolvulaceae), Hawaiian Baby Woodrose is closely related to the above-mentioned species. It is native to the Indian subcontinent but cultivated in many other parts of the world.

Street Names

  • MG seeds
  • Glories
  • Heavenly Blue
  • Pearly Gates
  • Flying Saucers
  • Summer Skies
  • Wedding Bells
  • Blue Stars

Common Ways to Use Morning Glory

Morning glory seeds are ingested orally, most commonly by chewing and swallowing the normal or sprouted seeds and extracting the alkaloids in cold water. Due to the fact that LSA is heat-sensitive, morning glory seeds are generally not smoked. However, according to anecdotal reports, smoking grounded seeds can create psychoactive effects due to the presence of other alkaloids in the seeds.

Some individuals perform advanced extractions (such as non-polar/polar solvent extractions) to reduce nausea, ameliorate vasoconstrictive effects, and eliminate the need to consume a lot of seed matter. In this section, however, we will overview the most common preparation methods that don’t involve intensive extractions.

Chewing Method

In the chewing method, morning glory seeds are chewed to a paste for a few minutes and then swallowed. Alternatively, the LSA can be absorbed sublingually (with 1.5x the oral dose) by chewing and keeping the seed matter under the tongue for thirty minutes and then spitting it out. The chewing method is simple and effective but is generally recognized as the most unpleasant because of the highest chance of nausea, the dirt-like taste, and the large number of seeds required.

Cold Water Extraction Method

Extracting the LSA in cold water is the method used traditionally by Mexican shamans, who grind the seed in a metate, wrap it in a linen cloth, and soak it in cold water to prepare a tea.

The cold water infusion is made by first grinding the seeds with a mortar and pestle or coffee grinder to a fine powder. LSA and the other psychoactive alkaloids are contained within the embryo of the seed, so grinding them finely allows for the most efficient extraction. From there, the powder is steeped in cold water for at least an hour. The infusion is then strained for drinking. Some users then add lemon or other citrus juice to mask the taste of the seeds.

Germination Method

Eating the sprouted seeds is a recommended method to reduce nausea, which is typically brought on by certain compounds in the seed husks. In this method, the seeds are germinated by first filing them down with a nail file and then soaking them overnight in warm water (purified or boiled). From here, the seed husks are easily removed the next morning, leaving the sprouts or little “brains” that are then eaten. Some users report this method may lead to a less intense trip compared to the other methods.

History & Traditional Uses

Morning glory seeds have been used since ancient times for their entheogenic and medicinal properties, particularly among the indigenous peoples of Mexico. Similar to the ritualistic use of peyote cactus and psilocybin mushrooms, the Aztecs would consume morning glory seeds in religious ceremonies to commune with their gods and in shamanic healing practices to diagnose and heal various afflictions. The Aztecs referred to the seeds of Ipomoea tricolor as tlitliltzin, the Nahuatl word for “black”, and the seeds of Turbina corymbosa as ololiuqui, a Nahuatl word meaning “round thing.”

In Oaxaca, Mexico, the ethnobotanist Richard Evan Schultes documented the ritualistic use of morning glory seeds by Zapotec shamans in 1941. The Zapotecs refer to the seeds of T. corymbosa as badoh and the black seeds of I. tricolor as badoh negro. Still today, morning glory seeds play an ongoing role as a sacrament and divinatory psychedelic in Southern and Central Mexico, particularly among the Mazatec, Zapotec, Chinantec, and Mixtec cultures.

Modern Day Discovery

In 1959, Schultes sent samples of the Mexican morning glory species Turbina corymbosa to Albert Hofmann, the swiss Chemist who discovered LSD. Hofmann elucidated its chemical constituents and, much to his astonishment, found the seeds contain alkaloids similar to the ones derived from ergot fungus that he had been investigating for decades.

Specifically, Hofmann identified the main psychoactive constituent to be lysergic acid amide (LSA), which he incidentally dosed in a self-experiment in 1947 before knowing it was a natural compound. In addition, he found the seeds contain lysergic acid hydroxyethylamide, ergonovine, and other chemically-related alkaloids, all of which are structurally similar to LSD.

Once knowledge of the entheogenic use of morning glory seeds by Mexican Native Americans became widespread and the psychoactive compounds present in the seeds were identified, they began to be used around the world for their psychedelic effects due to their high availability and relative legality.

Commonly Reported Effects of Morning Glory

Similar to other classic psychedelics, the LSA in morning glory seeds produces its effects by binding to 5-HT2A receptors. LSA is also present in the leaves and stems of morning glories, but in a much lesser concentration than the seeds.

The high from morning glory seeds has been likened to a more gentle and sedating LSD trip, given that LSD is at least an order of magnitude more potent and produces more stimulatory effects. When taken orally, the effects come up typically 30 minutes to 2 hours later and last from 5 to 12 hours. In addition, after-effects may be present for 2-48 hours following ingestion.

It may be difficult to control the dosage because the quantity of LSA can vary from batch to batch among the different varieties. With that said, as a general rule of thumb:

  • A light dose is produced from 50-100 seeds
  • A common dose is 100-250 seeds
  • And a strong dose is 250-400+ seeds

Psychological effects

Depending on the set and setting, and the number of seeds consumed, the psychological effects may consist of:

  • Sedation
  • Euphoria
  • Increased introspection and self-reflection
  • Thought acceleration
  • Dream-like state of consciousness
  • Changes in sensory perception
  • Visual and auditory hallucinations
  • Enhancement of sensory sensitivity
  • Depersonalization
  • Sense of unity and interconnectedness
  • Spiritual enhancement

Physiological effects

According to trip reports, nausea is one of the most common physiological effects of morning glory seeds. This can be alleviated by fasting and taking motion sickness pills like Dramamine.

Other physiological effects may include:

  • Spontaneous bodily sensations (tingling)
  • Stomach cramps
  • Vomiting
  • Bodily discomfort
  • Chills
  • Pupil dilation
  • Vasoconstriction (tightening of blood vessels)
  • Increased blood pressure
  • Increased heart rate
  • Muscle tremors
  • Decrease in motor ability (at high doses)

Adverse effects

Morning glory seeds commonly produce side effects that are mostly gastrointestinal and vasoconstrictive in nature. The gastrointestinal side effects are mostly due to other compounds (such as glycosides) present in the seeds, rather than LSA itself. In general, adverse effects may include:

  • Stomach pain
  • Nausea
  • Leg cramps
  • Anxiety
  • Dizziness
  • Confusion
  • Paranoia
  • Apathy
  • Temporary psychosis (in individuals predisposed)

In addition to these side effects, some users may experience an LSA hangover that can last a day or so that may be characterized by headache, exhaustion, blurred vision, vertigo, and physical inertia.

Safety Precautions

Research is scarce to non-existent on the long-term safety and toxicity of LSA. Similar to other psychedelics, LSA is not considered to be addictive, and there are known no cases of fatal toxicity due to LSA ingestion alone.

The known fatalities have resulted from improper set and setting as well as adverse drug interactions. Morning Glory seeds should be consumed in a safe area with a trip sitter present. They should not be ingested with MAOI antidepressants and lithium, as these are potentially dangerous combinations. Selective serotonin reuptake inhibitors (SSRIs) are known to diminish LSA’s effects greatly, which may require the consumption of many more seeds, potentially resulting in more adverse effects.

Sometimes, commercial suppliers will coat morning glory seeds with toxic chemicals, including pesticides and an antifungal called methylmercury. These coatings can cause nausea, vomiting, severe stomach cramps, and potential neurotoxicity. For this reason, users should wash the seeds thoroughly and choose untreated, pesticide-free seeds to minimize the risk of toxicity and side effects associated with these chemicals.

The consumption of morning glory seeds should be avoided in people with liver disorders and a history of psychosis. Additionally, due to its uterotonic effects, morning glory seeds should not be used by pregnant women.

Is Morning Glory Legal?

Seeds containing LSA, such as Morning Glory and Hawaiian Baby Woodrose, are not illegal to grow, possess, and distribute. The seeds are widely found in nurseries, gardening stores, and online botanical suppliers. One exception is in Arizona, where Ipomoea species are prohibited to cultivate as they are labeled as “noxious weeds.”

In many countries, extracting, producing, and consuming LSA is illegal. Pure LSA is federally scheduled in the US as a Schedule III drug, the same class as ketamine, codeine, and anabolic steroids. In the United Kingdom, LSA is seen as a precursor to LSD and therefore classified as a Class A substance, a classification shared with heroin, LSD, MDMA, and cocaine. Extracted LSA is illegal to consume, sell, and possess in the Netherlands, Australia, Germany, Turkey, Sweden, and New Zealand.

Do Morning Glories Come Back Every Year?

Yes, Morning Glories are annuals. They will reseed and come back each year.

How Fast Does Morning Glory Grow?

Morning Glories are known for their rapid growth rate, growing up to 12 feet or more in a single season (a few months after seeds sprout).

How Often Do You Water Morning Glories?

As seedlings, Morning Glories should be watered several times a week. They do best in the early stages when the top inch of the soil is kept moist. Once they’re established, they require less water. If they’re growing outdoors, outdoor rainfall will be plenty. During dry spells, they may need to be watered weekly. Being deep-rooting plants, over-frequent watering will stress them and cause them to root close to the surface, depriving them of nutrients.

Should You Fertilize Morning Glories?

While Morning Glories are known to bloom in poor soil, they do well when fertilized with low nitrogen, high phosphorus fertilizers every 4 to 5 weeks. Nitrogen-rich fertilizers will result in dense foliage and no flowers.

How Long Do Morning Glory Seeds Last?

When stored properly in a sealed container in a cool, dark place, Morning Glory seeds can last up to five years.

How Long Does a Morning Glory Bloom Last?

Morning Glory flowers last a single day, opening up in the morning and fading away by late afternoon. The plant will continually produce new flowers until frost. Morning Glories will commonly bloom in August or early September.

Are Morning Glories Bad for Dogs?

Yes, the ergot alkaloids present in Morning Glory (Ipomoea sp.) flowers and seeds are toxic to dogs. They can potentially cause severe gastrointestinal symptoms such as nausea, vomiting, diarrhea, and loss of appetite, as well as other adverse effects such as tremors, ataxia, agitation, and disorientation.

Disclaimer: Morning Glory is a potentially categorized as an illegal drug. Reality Sandwich is not encouraging the use of this drug where it is prohibited. However, we believe that providing information is imperative for the safety of those who choose to explore this substance. This guide is intended to give educational content and should in no way be viewed as medical recommendations.

RS Contributing Author: Dylan Beard

Dylan Beard is a freelance science writer and editor based in the beautiful Pacific Northwest. After finishing his physics degree and dabbling in neuroscience research at UC Santa Barbara in 2017, he returned to his first love: writing. As a long-term fan of the human brain, he loves exploring the latest research on psychedelics, nootropics, psychology, consciousness, meditation, and more. When not writing, you can probably find him on hiking trails around Oregon and Washington or listening to podcasts. Feel free to follow him on Insta @dylancb88.

This guide covers what you need to know about Morning Glory, including common effects and uses, legality, safety precautions and top trends today.