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Identification of psychoactive substances of natural origin

Brain

Expert Pharmacologist
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The use of psychoactive substances has been growing rapidly all over the world. There is a huge class of substances of natural origin, consisting of mushrooms and plants containing a large range of alkaloids that cause relaxing, stimulating and hallucinogenic effects. The intake of some of these substances is conditioned by religious beliefs and cultural aspects, which makes the law very uncertain and, sometimes, ambiguous. However, the abuse of these substances can pose a high risk to one’s health, since their metabolism and action have not been fully studied yet. Moreover, psychoactive substances of natural origin are widespread both in dark net and in clearnet, they appear quickly, which requires developing complex analytic models, able to detect these substances and control their use thoroughly. In the present study we discuss their main toxicological aspects, traditional application and therapeutic potential, as well as the development of analytical methods for studying several plant samples in biological matrices: Areca catechu, Argyreia nervosa, Lophophora williamsii, Catha edulis, Ayahuasca, Datura stramonium, Mitragyna speciosa, Piper methystirum. In countries of the European Union about 96 million people admit to having used drugs. The most often used was cannabis (about 27.4%), then cocaine (5.4%), ecstasy (4.1%) and amphetamines (3.7%).

Recently, there has been a high tendency for new psychoactive substances use. The European Monitoring Center for Drugs and Drug Addiction (EMCDDA) defines a new psychoactive substance as «a new narcotic or psychotropic drug, in pure form or in preparation, that is not controlled by the United Nations Drug Conventions, but which may pose a public health threat comparable to that posed by substances listed in these conventions”. These drugs are popular due to the fact that they can be synthesized most quickly, they have low cost, intense psychoactive effects, however, they also have high-risk potential and low control. Constant appearance of new psychoactive substances due to the changes in synthesis ways and variations of molecules is a topic of concern of commercialization control, which forced the United Nations Office on Drugs and Crime (UNODC) to develop and implement an early warning system for detecting these compounds. New psychoactive substances (NPS) can be both of synthetic and natural origin. The most recognized synthetic substances are synthetic cannabinoids, cathinones and opioids, piperazines, phenylethylamines, designated benzodiazepines, indolalkylamines and arylcyclohexylamines. NPS of natural origin mainly consist of alkaloids, as a rule, present in plants and mushrooms. These plants are most often found in South America, Asia, as well as in Africa and, depending on their constituent components, cause corresponding effects. The metabolism of these substances has not been fully studied and therefore, the resulting metabolites and their potential concentrations are unknown. Also, there is a certain importance of studying this issue in terms of identifying toxicity (both acute and chronic), which is unknown for many of these substances. Thus, the development of analytical methods is of a great value for the identification and quantification of potentially hazardous compounds present in natural products.

Areca catechu (Betel Quid).
This plant species is most common in Africa, Europe and America, besides its main origin - Asia (Sri Lanka and Malaysia). Areca nut is the fruit of this plant, which for many centuries has been used as a traditional means for performing rituals. Usually, it was chewed or consumed together with some drinks (ground in a mortar). According to statistics, Areca nut is the fourth most common and used natural drug because of its effects, among other things, it is also used as an aphrodisiac. Arecoline is the main psychoactive compound, present in fruits of A.catechu. This compound is an alkaloid, its pharmacodynamic profile involves gamma-aminobutyric acid (GABA) inhibition and nonselective agonism of nicotinic and muscarinic acids. When entered the body, arecoline quickly passes the blood-brain barrier, affecting the parasympathetic nervous system. This fruit causes rapid addiction and many side effects, for example, from side of the digestive system (nausea or vomiting, functional dyspeptic disorders, constipation with dynamic intestinal obstruction, also, there is a pronounced withdrawal syndrome, manifested by insomnia, mood swings, irritability and anxiety). Other side effects that occur when it is consumed in large quantities, or when it is used in long-term, are rare but dangerous and consist of extrapyramidal syndrome, asthma, myocardial infarction or acute coronary syndrome.

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However, the use of this fruit for medicinal purposes was described in ancient times by Buddhists, so А. Catechu intake is associated with a feeling of satisfaction, a weak psychostimulating effect, stress and anxiety reduction, the gums strengthening and breathing alleviating. In addition, it was previously used in the treatment of malaria, fever, hypertension, urolithiasis, as well as in the treatment of digestive system diseases. There are a number of specific studies that have shown that the use of areca nuts is associated with antimicrobial action, as well as with a positive effect on the cardiovascular system functioning.

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A. catechu is not considered a controlled substance, so the USA and European Union do not have any legislation on their use. This fact is connected with the development of several analytical methods that allow the identification of these substances. Traditional samples, such as blood, are now used to detect the most common substances. For example, for quantitative determination of arecoline by LC-MS/MS, 1 ml of blood is used with a detection limit (LOD) of 0.02 ng/ml and a quantitative determination limit (LOQ) of 0.5 ng/ml. Urine is also another biological matrix used to detect arecoline. Pichini and al. developed an analytical method using HPLC-MC equipment that uses 1 ml of urine in samples of 1 gram of meconium and umbilical cord serum (1 ml). In addition, there are alternative arecoline detection methods using dental nitrate and breast milk.

Argyreia nervosa (Adhoguda).
This class of natural psychoactive substances is native to India, but is widespread both in Europe and in Africa. This plant is also called by other names: Adhoguda, Vidhara, Elephant Creeper, Rivea corymbosa, Hawaiian Baby Woodrose or Morning Glory, Ipomoea violacea. It contains psychoactive alkaloids in its seeds. Isoergine and lysergamide are compounds associated with this plant’s hallucinogenic properties. They cause effects, similar to LSD, but still different according to subjective opinions of users. In A. nervosa seeds, the content of ergoline alkaloids ranges from 0.5 to 0.9%, 0.19% of which is Isoergine and 0.14% is LSA. The former’s action involves binding to dopamine D2 receptors, followed by inhibition of adenylate cyclase and a decrease in cAMP production. Also, this plant has been used for medical purposes as a diuretic and aphrodisiac, and some researchers have described analgesic, anti-inflammatory, immune-modulating and hepatoprotective properties. The roots of A.nervosa are used in treatment of diseases of the central nervous system, rheumatism, gonorrhea and chronic stomach ulcers. On the other hand, antimicrobial activity was associated with plant leaves, that contain other alkaloids besides the ones mentioned above: erginine, ergometrine, lysergol, peniclavine, chanoclavin I, chanoclavin II, ergometrinine, elimoclavin in particular. However, their effects have not been studied yet.

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LSА is a controlled substance in some of European countries, Great Britain and Italy in particular. It is also considered a controlled substance in the USA; however, the plant itself and its seeds are sold without any restrictions. Currently, there are some analytical methods that can be used to identify LSA. Paulke and al. describe a technique using 1 ml of serum and urine to quantify LSA. Analytes are extracted using the SPE method and quantified on HPLC-FLD equipment with detection and quantification limits of 0.05-0.15 ng/ml and 0.17 ng/ml, respectively. The percentage recovery varies from 69.4% to 78.8%.

Ayahuasca (“Hoasca”).
Ayahuasca – the word Quechua is obviously formed by 2 terms, which mean “soul” and “vine”, but the drink is also known as caapi, daime, hoasca, yage, natema. It is a psychoactive drink, used traditionally in South America. However, recently, it has been exported to other countries in Europe and Asia. It consists of a brown, thick and oily liquid obtained as a result of burning chips from the stem of Banisteriopsis caapi and leaves of Psychotria viridis. There are other plants involved in Ayahuasca making, for example, Brugmansia suaveolens, Psychotria carthagenensis, Nicotiana tabacum, Tabernaemontana spp., Brunfelsia spp., Datura suaveolens, Iochroma fuchsioides, Malouetia tamarquina, Juanulloa spp., Peganum harmala, which also have certain action on physical and mental systems, causing the clinical effects of intoxication.

Effects of this psychoactive substance are caused by synergic potential of N, N-dimethyltryptamine (DMT), hallucinogenic compounds of P. Viridis and of C. edulis, which are mainly located in some countries of West Africa, and also garmine, garmaline and tetrahydroharmine (THH), located in Yemen, Ethiopia and the Arabian Peninsula. This plant is often used as a medicinal product, its β-carbolinic alkaloids are present in B. Caapi. DMT is a tryptamine, which is often abused because it is able to simulate the effects of synthetic cathinones, but with a lower risk of acting as an agonist of serotonin receptors (5-HT1A/2A/2C). In case of intoxication with this compound, no deaths have been reported yet. C. edulis is also used recreationally. When ingested, it is metabolized by peripheral monoamine oxidase A and is usually consumed in an inactive state. DMT enters the body together with β-carbolinic alkaloids, through chewing the leaves. Moreover, THH also inhibits serotonin reuptake, enhancing the effects of phenylpropanolamine.

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Effects can be variable, including visual hallucinations, hyperthermia, mydriasis, various changes in the endocrine, cardiovascular and immune systems. Side effects such as vomiting, agitation, hypertension, paranoia, anxiety and depression have also been described. However, several studies have reported on the therapeutic potential of this plant: antimicrobial and antioxidant action, as well as a positive effect on the cells of dopaminergic neurons. After single use of Ayahuasca, symptoms of depression are significantly reduced. Other studies show that the use of this decoction significantly reduces anxiety and panic, as well as the addictive negative potential associated with the use of alcohol and other drugs, reduces physical pain, problems with attention and concentration, fatigue, insomnia, irritability and obsessive thoughts.

Ayahuasca has been used as a part of religious rituals in the Amazon for many centuries, and recently, it has been used by such religious organizations as the União do Vegetal (UDV) and the Santo Daime. DMT-containing substances are under control in the USA and some European countries. However, viridis and B. Caapi use is not controlled in any way, and Ayahuasca use is legal in the USA and Brasil. Currently, there are several analytical techniques that allow the detection and quantification of Ayahuasca compounds and its metabolites. For example, Yritia and oliveira and al. have developed analytical methods using SPE and LLE.Pichini conducted a study were using only 25 mg of hair, hydrolyzing by means of a M3 reagent, he quantitatively identified DMT, with LOD values of 0.01-0.02 ng/mg, and LOQ from 0.03-0.05 ng/mg, with recovery from 76.6% to 97.4%.
Datura stramonium (Jimson Weed).
D. stramonium is mainly located in the USA and is a seasonal grass, growing in natural conditions. This plant species is known as Jimson Weed and was traditionally used by the Pueblo Indians due to its analgesic properties. In Western medicine, raspberry grass was also used in the treatment of asthma. This plant is usually used by eating seeds or flowers in their pure form without pretreatment. However, tinctures are also made. Leaves, flowers and seeds are consumed after a small high-temperature treatment, or in the form of an "Asthmador" powder by inhalation. Clinical effects involve hallucinations, caused by alkaloids scopolamine and atropine. They are considered tertiary amines, so they easily pass through the blood-brain barrier. Considering the main actions of scopolamine (antimuscarinic action), typical side effects are frequently registered: tachypnea, delirium, psychomotor agitation, mydriasis, blurred vision and photophobia, as well as peripheral vasodilation, thermoregulation disorder, vomiting, constipation and urination disorders. In case of high doses, acute coronary syndrome, convulsions and pronounced indirect respiratory depression may occur.

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Lophophora williamsii (Peyote).
L. williamsii, known as Peyote, is a cactus native to Northern Mexico and the USA. This plant was traditionally eaten during religious rituals by indigenous people. It is usually the pulp of fresh cactus that is used as food, but it can also be consumed in dried form (brewing tea or other drinks from it). L. Williamsii contains a compound named mescaline [2-(3,4,5-trimethylphenyl) ethanamine], which is the reason of its hallucinogenic properties. Also, it is sold as powder. After intake, mescaline enters the central nervous system, acting on serotonergic receptors 5-HT2A, 5-HT2B and 5-HT2C. Effects include compulsion, paranoia, paresthesia, color perception changes, headache, mydriasis, and psychomotor agitation. Also, there are other mild effects on the digestive, urinary and cardiovascular systems: hypertension, tachycardia, vomiting and a decrease in the filtration rate in the glomerular apparatus of the kidneys. However, positive effects are also described: researchers associate the use of this type of plant with positive effects in the complex treatment of rheumatism, infected wounds, burns and snake bites. Another study shows that this plant has antimicrobial properties against Staphylococcus aureus. Nowadays, all substances containing mescaline, are included in Annex I of the 1967 United Nations Convention on Drugs. By UHPLC-MS/MS method using 25 mg of hair, it is possible to perform quantitative identification of this compound with LOD 0.01-0.02 ng/ml, LOQ 0.03-0.05 ng/mg and recovery of 79.6%-97.4%.

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Mitragyna speciosa (Kratom).
M. speciosa, also known as Kratom, emerged on the Asian continent (Biak, Malaysia and Thailand), but at the moment it is already widespread in many parts of the world. For several years, it has been used by rural Asian workers to reduce fatigue and increase labor productivity, as well as for various pain syndromes, diarrhea, hypertension and diabetes mellitus. It has begun to be used for recreational purpose quite recently. Kratom leaves were used as opium replacement in treatment of morphine withdrawal syndrome. The preferred method of Kratom use is chewing fresh leaves; however, some people dry the leaves and smoke them, or brew them and drink them in the form of tea and tinctures. At the moment there are capsules, powders and drinks containing Kratom available. Its psychoactive effects are caused by about 40 different alkaloids. These compounds make up only 0.5-1.5% of the total volume of molecules, and their concentration depends on the harvest season, the age of the plant and geographical location.

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The most common psychoactive substance is mitragynine, which makes up 66.2% of alkaloid content. However, in Malasian plants, its share does not exceed 10%. There are also other alkaloids with pharmacological activity: 7-hydroxmitraginine, corinantheidine, corinantheidine, specioginine: and paynantheine. Alkaloids, present in M. Speciosa, have high lipophilicity and easily pass the blood-brain barrier. They act as inhibitors of k- and μ -opioid receptors. In addition to that, mitragynine binds to δ-opioid receptors, providing an analgesic effect. Also, binding to Ca channels causes their incomplete blocking, affecting the release of neurotransmitters. Carlier and al. use the method of identification by UHPLC-MS with enzymatic hydrolysis via SPE and determine the metabolite in urine using LC-Q/TOF-MS, where LOD = 0.25-1 ng/ml and LOQ = 0.5-1 ng/ml.

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Piper methysticum Forst (Kava).
Roots and stems of P. Methtysticum are used for making Kava – a psychotropic drink from the Pacific region. It was used due to its therapeutic properties: reducing fatigue and anxiety, relieving pain and stabilizing sleep. However, the use of this substance is associated with a hepatotoxic effect. The pharmacological effect is due to kavalactones: kavain and iangonin, also desmethoxy-iangonin, 7,8-dihydrokavain, methysticin and 7,8- dihydromethysticin, to the derivatives of cinnamic acid, flavanones and chalcones. These compounds act as monoamine oxidase B inhibitors, causing norepinephrine and dopamine reduction by interacting with gamma-aminobutyric acid. Sale of P. Methysticum is controlled in the Netherlands, Switzerland and France, it is banned in the UK and in Poland as well, but in most countries it is not processed by legislation and is legal overall. Kavaina can be identified by GC-MS in hair, where LOD is 30 ng/l, and LOQ is about 100 ng/g.​

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