Article

New mescaline concentrations from 14 taxa/cultivars of Echinopsis spp. (Cactaceae) ("San Pedro") and their relevance to shamanic practice

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  • Cactus Conservation Institute
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Abstract

The aim of the present study is to determine in a procedurally uniform manner the mescaline concentrations in stem tissue of 14 taxa/cultivars of the subgenus Trichocereus of the genus Echinopsis (Cactaceae) and to evaluate the relationship (if any) between mescaline concentration and actual shamanic use of these plants. Columnar cacti of the genus Echinopsis, some of which are used for diagnostic and therapeutic purposes by South American shamans in traditional medicine, were selected for analysis because they were vegetative clones of plants of documented geographic origin and/or because they were known to be used by practitioners of shamanism. Mescaline content of the cortical stem chlorenchyma of each cactus was determined by Soxhlet extraction with methanol, followed by acid-base extraction with water and dichloromethane, and high-pressure liquid chromatography (HPLC). By virtue of the consistent analytical procedures used, comparable alkaloid concentrations were obtained that facilitated the ranking of the various selected species and cultivars of Echinopsis, all of which exhibited positive mescaline contents. The range of mescaline concentrations across the 14 taxa/cultivars spanned two orders of magnitude, from 0.053% to 4.7% by dry weight. The mescaline concentrations reported here largely support the hypothesis that plants with the highest mescaline concentrations - particularly E. pachanoi from Peru - are most associated with documented shamanic use.

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... DMT and its diethyl analogue (Figure 1 bottom right) show structural resemblance to the neurotransmitter serotonin and thereby function as agonists at 5-HT 2A and related receptors (Nichols, 2016;Luethi and Liechti, 2020). Another traditional hallucinogen is mescaline, a phenethylamine alkaloid found in cacti (Ogunbodede et al., 2010;Nichols, 2016;Luethi and Liechti, 2020). It is a partial agonist at 5-HT 2A and 5-HT 2B receptors and a full agonist at the 5-HT 2C receptor (Dinis-Oliveira et al., 2019). ...
... Mescaline is an alkaloid biosynthesised from tyrosine in different cacti, where it is found at concentrations of 0.05-4.7% by dry weight (Ogunbodede et al., 2010). Lophophora williamsii (peyote cactus) and several Echinopsis species (e.g., Echinopsis pachanoi and Echinopsis peruvianus, also known as the San Pedro and the Peruvian torch cacti) have a long-standing use in religious ceremonies and traditional medicine of South American indigenous populations. ...
... Lophophora williamsii (peyote cactus) and several Echinopsis species (e.g., Echinopsis pachanoi and Echinopsis peruvianus, also known as the San Pedro and the Peruvian torch cacti) have a long-standing use in religious ceremonies and traditional medicine of South American indigenous populations. The hallucinogenic effects of these cacti were attributed to their relatively high mescaline contents (Ogunbodede et al., 2010;Dinis-Oliveira et al., 2019;da Silveira Agostini-Costa, 2020). Interestingly, OCT1 deficiency or reduced activity is more frequently found in Central and South American populations than in most other parts of the world and the prevalence of inactive alleles generally increases further south on the American continent (Figure 7) (Seitz et al., 2015). ...
Article
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Psychostimulants are used therapeutically and for illegal recreational purposes. Many of these are inhibitors of the presynaptic noradrenaline, dopamine, and serotonin transporters (NET, DAT, and SERT). According to their physicochemical properties, some might also be substrates of polyspecific organic cation transporters (OCTs) that mediate uptake in liver and kidneys for metabolism and excretion. OCT1 is genetically highly polymorphic, with strong effects on transporter activity and expression. To study potential interindividual differences in their pharmacokinetics, 18 psychostimulants and hallucinogens were assessed in vitro for transport by different OCTs as well as by the high-affinity monoamine transporters NET, DAT, and SERT. The hallucinogenic natural compound mescaline was found to be strongly transported by wild-type OCT1 with a K m of 24.3 µM and a vmax of 642 pmol × mg protein-1 × min-1. Transport was modestly reduced in variants *2 and *7, more strongly reduced in *3 and *4, and lowest in *5 and *6, while *8 showed a moderately increased transport capacity. The other phenylethylamine derivatives methamphetamine, para-methoxymethamphetamine, (-)-ephedrine, and cathine ((+)-norpseudoephedrine), as well as dimethyltryptamine, were substrates of OCT2 with K m values in the range of 7.9-46.0 µM and vmax values between 70.7 and 570 pmol × mg protein-1 × min-1. Affinities were similar or modestly reduced and the transport capacities were reduced down to half in the naturally occurring variant A270S. Cathine was found to be a substrate for NET and DAT, with the Km being 21-fold and the vmax 10-fold higher for DAT but still significantly lower compared to OCT2. This study has shown that several psychostimulants and hallucinogens are substrates for OCTs. Given the extensive cellular uptake of mescaline by the genetically highly polymorphic OCT1, strong interindividual variation in the pharmacokinetics of mescaline might be possible, which could be a reason for highly variable adverse reactions. The involvement of the polymorphic OCT2 in the renal excretion of several psychostimulants could be one reason for individual differences in toxicity.
... These can include defatting, lyophilization, extraction, pH adjustment, and recrystallization steps, among others, prior to analysis (11)(12)(13)(14). For example, one sample preparation method for analysis of mescaline in peyote by LC-MS requires Soxhlet extraction with methanol at 40°C for 8 h, followed by rotary evaporation, resuspension in water, acidification, defatting twice with an organic solvent, alkalization, extraction twice with solvent, subsequent evaporation of the solvent, resuspension in methanol, and syringe filtering before analysis can occur (15). Another method reported the need for four extractions with diethyl ether over 24 h, five extractions with methanol-ammonia for 24 h, rotary evaporation, resuspension in methanol, and syringe filtering (16). ...
... Concentrations of mescaline in E. pachanoi, E. peruviana, and E. lageniformis tissues have been previously reported and were found to be within the range of 0-5% by weight (15,16). In agreement with previous studies, the concentrations determined here fell within this range. ...
... While the mescaline content of Echinopsis cacti has been studied before using conventional methods, the application of DART-HRMS to its determination has several key advantages. For example, reports of GC-MS and LC-MS analysis of such samples often involve extensive sample pretreatment steps (including Soxhlet extraction, defatting, pH manipulations and even derivatization) and the analytical run of a single sample can take the better part of an h (15,18). By comparison, DART-HRMS could be used to analyze a whole, unprocessed plant sample as shown in Fig. 1A) to confirm the presence of mescaline in a matter of seconds, while the entire analytical run of blanks, calibrator solutions, quality control samples, and replicates of unknown plant material can be completed in less than 30 min. ...
Article
Unregulated cacti from the genus Echinopsis are used recreationally as mescaline‐containing alternatives to the outlawed peyote. Echinopsis‐derived plant materials appear in a variety of nondescript forms, making rapid assessment of whether they are mescaline‐containing materials or simply innocuous plant‐derived food products, very challenging. Reported here is a DART‐HRMS approach for the rapid detection of mescaline in whole plant material and a validated method for the quantification of mescaline in cactus tissue, using mescaline‐d9 as the internal standard. Calibration curves exhibited R2 values of ≥0.995, and the method exhibited a LLOQ and a linear range of 1 ppm and 1–100 ppm, respectively. Application of the method to commercially available Echinopsis spp. yielded results consistent with previous studies performed by GC‐ and LC‐MS, with mescaline levels of <2% dry weight in all cases. Therefore, DART‐HRMS is a suitable technique for the rapid screening of mescaline and its subsequent quantification within complex plant‐derived matrices.
... The procedure for extraction of alkaloids from the pulverized tissue samples was similar to that of Ogunbodede (2010) and Hulsey et al. (2011): an initial methanol extract was paper-filtered and evaporated to dryness, followed by redissolving the residue in dichloromethane, which underwent washing with acidic (pH 3) and basic (pH 12) aqueous solutions; then finally the dried dichloromethane extract was redissolved in methanol, which was filtered through a 0.2 micron filter and stored at −20°C until it was analyzed by HPLC (Snyder and Kirkland 1974;Ogunbodede 2010;Hulsey et al. 2011). During this part of the procedure, three samples were accidentally spilled so that, of the 13 plants, complete sets of data exist for only 10 plants. ...
... The procedure for extraction of alkaloids from the pulverized tissue samples was similar to that of Ogunbodede (2010) and Hulsey et al. (2011): an initial methanol extract was paper-filtered and evaporated to dryness, followed by redissolving the residue in dichloromethane, which underwent washing with acidic (pH 3) and basic (pH 12) aqueous solutions; then finally the dried dichloromethane extract was redissolved in methanol, which was filtered through a 0.2 micron filter and stored at −20°C until it was analyzed by HPLC (Snyder and Kirkland 1974;Ogunbodede 2010;Hulsey et al. 2011). During this part of the procedure, three samples were accidentally spilled so that, of the 13 plants, complete sets of data exist for only 10 plants. ...
... The identity of mescaline was confirmed by GC-MS (as in Rösner et al. 2007;Ogunbodede, 2010;Hulsey et al., 2011). ...
Article
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We evaluated the pharmacological consequences of tissues other than crown being included with harvested peyote. Mean mescaline concentrations were determined for crown, non-chlorophyllous stem, and root, using mature individuals from the same population in South Texas. Samples of each tissue—crown, non-chlorophyllous stem, and root—were taken from each of 13 individual plants. Samples were dried, triturated, defatted, and extracted with methylene chloride, using an acid-base aqueous wash to recover the alkaloids. The concentration of mescaline in each sample was determined by HPLC. The average mescaline concentration in non-chlorophyllous stem was an order of magnitude lower than that in crown, whereas the mescaline concentration in root was two orders of magnitude lower than that in crown. These results show that non-chlorophyllous stem is a poor source of mescaline, and root is an extremely poor source. These results have important implications for conservation, suggesting that non-traditional harvesting of peyote for religious or medicinal use involving the cutting of non-chlorophyllous tissue are contributing to the death of plants and the subsequent failure to regenerate new crowns. Therefore, this practice should be reevaluated by peyote harvesters and users.
... Stems were cut in ~0.5-kg slices and ground in a blender, mixed with EtOH 96% (580 g tissue in 0.6 L), and then filtered to remove solid material. The extractions were carried out by partitioning the concentrated EtOH with diluted acid as described in Ogunbodede et al. (2010), with minor modifications. ...
... One of them was mescaline (see fragmentation features in Ogunbodede et al., 2010) and the other was described as a novel vegetable base called trichocereine (N-dimethylmescaline; Fig. 5). The latter was reported as a new natural phenylethylamine alkaloid particular to this species (Reti & Castrillón, 1951). ...
Article
The host-plant environment of phytophagous insects directly affects various aspects of an insect's life cycle. Interestingly, relatively few insect groups have specialized in the exploitation of plants in the Cactaceae family, potentially because of the chemical and ecological challenges imposed by these plants. The cactophilic Drosophila buzzatii Patterson & Wheeler, 1942 is a well-studied model in evolutionary ecology, partially because of its ability to exploit toxic cactus hosts. Previous studies have shown a negative effect on performance when flies are reared in an alternative columnar cactus host of the genus Trichocereus, relative to its primary cactus host, Opuntia. These observations were attributed to the presence of alkaloids in Trichocereus tissues, a chemical deterrent to herbivores that indirectly affects Drosophila larvae; however, the putative toxic effect of alkaloids has never been tested directly in D. buzzatii. The present study is the first attempt to relate chemical extracts in Trichocereus terscheckii Britton & Rose, 1920 with detrimental effects on D. buzzatii. We assessed the effects of a crude alkaloid extract, rich in phenylethylamines, and a ‘non-alkaloid fraction’ on viability and adult wing morphology. Our results indicate that rearing larvae on an artificial diet containing different concentrations of the crude alkaloid extract decreased pupal viability and adult size in a concentration-dependent manner. We discuss the role of cactus alkaloids in the evolution of host-plant use in cactophilic flies.
... Some of the references to relative alkaloid levels among Trichocereus species in the cactus literature we have mentioned, were very plausibly based on some biochemical analyses of some individuals, but most such reports appear to be based on popular behaviors or shamanic communications. Although several different scientific publications had reported the content of alkaloids (particularly mescaline, the predominant psychoactive alkaloid) of the "San Pedro", only recently has a paper been published (Ogunbodede et al. 2010) with analyses made on several samples of mostly known origin, in a comparative way (similar sampling, the same techniques and instrumentation, etc.) The results reported in that paper suggest that the content of mescaline is higher in plants actually used by shamans than in other cultivated or wild plants. ...
... On the other hand, as mentioned, it is worth noting that Ritter (1981Ritter ( : 1324 and Madsen (1989: 27−28), the two authors who extensively observed the plants in the field, respectively consider T. pachanoi and T. peruvianus to be conspecific, distinguishable at the form level (Ritter 1981), and indistinguishable and thus synonymous (Madsen 1989). The paper of Ogunbodede et al. (2010) is also based on documented field samples plus cultivated ones; the quantitative phytochemical differences between the samples of E. peruviana and E. pachanoi in our opinion may be attributed to a broad range of phenotypic plasticity within a single species, which is more compatible with the taxonomic recognition of our two varieties, rather than two separate species. (Fig. 5). ...
Article
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This paper clarifies the identity of Cereus macrogonus Salm-Dyck, the type species of the genus Trichocereus (Berger) Riccob., and specifies its synonyms and affinities. It is also intended to contribute toward stabilizing the generic nomenclature. An examination of Salm-Dyck's original description of C. macrogonus leads to an interpretation of the species, very plausibly of Peruvian origin, as a cactus which was later also named Trichocereus peruvianus Britton & Rose. A Neotype is designated that is consistent with the protologue. That interpretation coincides with the use of this name (C. macrogonus) in the botanical literature and in horticulture, which has been adhered to up to now. Trichocereus pachanoi Britton & Rose is here presented as a variety of T. macrogonus (Salm-Dyck) Riccob.: T. macrogonus var. pachanoi (Britton & Rose) S.Albesiano & R.Kiesling, nov. comb., and a lectotype for it is designated.
... Although the most common cactus used for shamanic activities in South America is Trichocereus pachanoi ( " San Pedro " ; Ogunbodede et al., 2010), in Argentina is more frequent to find the similar T. terscheckii, also being called " San Pedro " and probably used indistinctly (Schultes et al., 2001). This species represented the first case where mescaline was found in a different species than Lophophora williamsii ( " Peyote " ; Reti and Castrillon 1951). ...
... This species represented the first case where mescaline was found in a different species than Lophophora williamsii ( " Peyote " ; Reti and Castrillon 1951). However, content of alkaloids is higher in Trichocereus pachanoi (up to 6 % of dry weight) compare to the 0.25-1.5 % found in T. terscheckii, although alkaloids content is highly variable among Trichocereus species (Ogunbodede et al., 2010). Interestingly in this last species it was found a higher proportion of a new natural phenylethylamine alkaloid named trichocereine (N-dimethylmescaline) without any apparent hallucinogenic property (Reti and Castrillon 1951). ...
Article
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Columnar cacti Trichocereus terscheckii is an important source of food and water for insects, birds and wild cattle in dry areas of North West Argentina. Their fruits have been suggested as a plausible source of food, but are not directly included in the human diet yet. Stem chemistry has long been of interest because of its hallucinogenic properties, but little is known about the nutritional value. In this work, basic nutritional composition of a mature stem was analyzed establishing moisture, total fat, ash, fiber, protein, lipidic and sugar profile. The main constituents fatty acid found in T. terscheckii were linolenic, linoleic, palmitic and oleic acids, but also a rare isomer of oleic acid was relatively abundant. This pattern did not agree with the profiles found in other species of columnar cacti. Current exploration of nutritional profiles of T. terscheckii stem provides novel information that contributes to a better understanding of this species whose slow development rate, high water storage capacity and hallucinogenic properties are features that make it especially vulnerable to an increased rate of extraction, habitat fragmentation and extensive cattle ranching.
... terscheckii is rich in the alkaloids mescaline and trichocereine, hallucinogenic compounds derived from phenylethylamine (Reti & Castrillon 1951;Ogunbodede et al. 2010). Besides a preference for oviposition in Opuntia cacti, previous studies have shown that breeding in T. ...
... Finally, the organic fraction was dried on a rotary evaporator and weighted. This protocol is based on the methodology described in Reti & Castrillon (1951) and Ogunbodede et al. (2010) and yields an alkaloid fraction enriched in phenylethylamines with mescaline-related compounds (Corio et al. 2013). Estimated alkaloids concentration in T. terscheckii´s was 0.4 mg/g, while O. sulphurea yielded 0.05 mg/g. ...
Article
High-throughput transcriptome studies are breaking new ground to investigate the responses that organisms deploy in alternative environments. Nevertheless much remains to be understood about the genetic basis of host plant adaptation. Here, we investigate genome-wide expression in the fly Drosophila buzzatii raised in different conditions. This species uses decaying tissues of cactus of the genus Opuntia as primary rearing substrate, and secondarily, the necrotic tissues of the columnar cactus Trichocereus terscheckii. The latter constitutes a harmful host, rich in mescaline and other related phenylethylamine alkaloids. We assessed transcriptomic responses of larvae reared in O. sulphurea and T. terscheckii, with and without the addition of alkaloids extracted from the latter. Whole genome expression profiles were massively modulated by the rearing environment, mainly by the presence of T. terscheckii alkaloids. Differentially expressed genes were mainly related to detoxification, oxidation-reduction and stress response, however, we also found genes involved in development and neurobiological processes. In conclusion, our study contributes new data onto the role of transcriptional plasticity in response to alternative rearing environments. This article is protected by copyright. All rights reserved.
... Mescaline occurs naturally in some members of the Cactaceae plant family ( Fig. 1) [28][29][30][31][32][33][34][35]. It is also found in small amounts in certain members of the Fabaceae (bean) family, including Acacia berlandieri [36]. ...
... Peyote contains a large spectrum of phenylethylamine (or phenethylamine or β -phenylethylamine) alkaloids, the principal being mescaline for which the content of Lophophora williamsii is about 0.4% fresh (undried) and 3-6% dried [28,42]. Besides mescaline, dozens of different alkaloids have already been identified in this cactus ( Fig. 3) [43][44][45][46]. ...
Article
Background: Mescaline (3,4,5-trimethoxyphenethylamine), mainly found in the Peyote cactus (Lophophora williamsii), is one of the oldest known hallucinogenic agents that influence human and animal behavior, but its psychoactive mechanisms remain poorly understood. Objectives: This article aims to fully review pharmacokinetics and pharmacodynamics of mescaline, focusing on the in vivo and in vitro metabolic profile of the drug and its implications for the variability of response. Methods: Mescaline pharmacokinetic and pharmacodynamic aspects were searched in books and in PubMed (U.S. National Library of Medicine) without a limiting period. Biological effects of other compounds found in peyote were also reviewed. Results: Although its illicit administration is less common, in comparison with cocaine and Cannabis, it has been extensively described in adolescents and young adults, and licit consumption often occurs in religious and therapeutic rituals practiced by the Native American Church. Its pharmacodynamic mechanisms of action are primarily attributed to the interaction with the serotonergic 5-HT2A-C receptors, and therefore clinical effects are similar to those elicited by other psychoactive substances, such as lysergic acid diethylamide (LSD) and psilocybin, which include euphoria, hallucinations, depersonalization and psychoses. Moreover, as a phenethylamine derivative, signs and symptoms are consistent with a sympathomimetic effect. Mescaline is mainly metabolized into trimethoxyphenylacetic acid by oxidative deamination but several minor metabolites with possible clinical and forensic repercussions have also been reported. Conclusion: Most reports concerning mescaline were described in a complete absence of exposure confirmation, since toxicological analysis is not widely available. Addiction and dependence are practically absent and it is clear that most intoxications appear to be mild and are unlikely to produce life-threatening symptoms, which favors the contemporary interest in the therapeutic potential of the drugs of the class.
... The plant material was collected in the northwest of Argentina, in the Valle Fertil Natural Park (public land of the province of San Juan) and the identification of the cactus was performed by Alejandro Saint-Esteven et al 85 . We isolated alkaloids from plant tissues through the alkaline-CH 2 Cl 2 extraction method 16,40 . The chemical profile of the extracted fraction was accomplished by GC-MS (Thermo Scientific EM/DSQ II-Trace GC Ultra AI3000). ...
Article
Full-text available
Cultural transformations of lifestyles and dietary practices have been key drivers of human evolution. However, while most of the evidence of genomic adaptations is related to the hunter-gatherer transition to agricultural societies, little is known on the infuence of other major cultural manifestations. Shamanism is considered the oldest religion that predominated throughout most of human prehistory and still prevails in many indigenous populations. Several lines of evidence from ethno-archeological studies have demonstrated the continuity and importance of psychoactive plants in South American cultures. However, despite the well-known importance of secondary metabolites in human health, little is known about its role in the evolution of ethnic diferences. Herein, we identifed candidate genes of adaptation to hallucinogenic cactus in Native Andean populations with a long history of shamanic practices. We used genome-wide expression data from the cactophilic fly Drosophila buzzatii exposed to a hallucinogenic columnar cactus, also consumed by humans, to identify ortholog genes exhibiting adaptive footprints of alkaloid tolerance. Genomic analyses in human populations revealed a suite of ortholog genes evolving under recent positive selection in indigenous populations of the Central Andes. Our results provide evidence of selection in genetic variants related to alkaloids toxicity, xenobiotic metabolism, and neuronal plasticity in Aymara and Quechua populations, suggesting a possible process of gene-culture coevolution driven by religious practices.
... If mes- caline is available, it gives a greenish to brown color [35]. Detection of mescaline could be made with GC combined with MS [36,37]. The m/z top peak is 30, m/z 2 nd highest is 182 and m/z 3 rd highest is 166. ...
Article
Full-text available
The classical hallucinogens having an affinity towards 5HT2A receptors are discussed, along with their common behavioral effects, toxicity and psychiatric complications which could have long-term consequences on individuals. A survey has been done on the various analytical methods used for determination and quantification of hallucinogens: colorimetrical reactions (Marquis, Ehrlich tests), gas chromatography with mass spectrometry (when the substances are not thermo labile), tandem mass spectrometry, high-performance liquid chromatography with UV detection, IR spectroscopy. Methods most often used to analyze biological samples like urine, blood or plasma immunological methods for quick detection, which results are confirmed later by the other methods mentioned above have been also discussed.
... The rationale of including treatments varying in the concentration of the alkaloid fraction was to uncover natural variation that flies may encounter in nature. Actually, alkaloid concentration may vary depending on cactus age and other ecological variables as soil properties and elevation [47], [48], [49]. In addition, water evaporation may contribute to increase alkaloids concentration in the rotting pocket during the decaying process [50]. ...
Article
Full-text available
The evolution of cactophily in the genus Drosophila was a major ecological transition involving over a hundred species in the Americas that acquired the capacity to cope with a variety of toxic metabolites evolved as feeding deterrents in Cactaceae. D. buzzatii and D. koepferae are sibling cactophilic species in the D. repleta group. The former is mainly associated with the relatively toxic-free habitat offered by prickly pears (Opuntia sulphurea) and the latter has evolved the ability to use columnar cacti of the genera Trichocereus and Cereus that contain an array of alkaloid secondary compounds. We assessed the effects of cactus alkaloids on fitness-related traits and evaluated the ability of D. buzzatii and D. koepferae to exploit an artificial novel toxic host. Larvae of both species were raised in laboratory culture media to which we added increasing doses of an alkaloid fraction extracted from the columnar cactus T. terschekii. In addition, we evaluated performance on an artificial novel host by rearing larvae in a seminatural medium that combined the nutritional quality of O. sulphurea plus amounts of alkaloids found in fresh T. terschekii. Performance scores in each rearing treatment were calculated using an index that took into account viability, developmental time, and adult body size. Only D. buzzatii suffered the effects of increasing doses of alkaloids and the artificial host impaired viability in D. koepferae, but did not affect performance in D. buzzatii. These results provide the first direct evidence that alkaloids are key determinants of host plant use in these species. However, the results regarding the artificial novel host suggest that the effects of alkaloids on performance are not straightforward as D. koepferae was heavily affected. We discuss these results in the light of patterns of host plan evolution in the Drosophila repleta group.
... For the alkaloid extraction, we followed the procedure of Obungodede et al., 2010. A sample of aerial parts consisting of the outermost parenchyma and chlorenchyma, the last being the tissue of higher alkaloid concentration within the plant (Ogunbodede et al., 2010), was grinded and blended with EtOH (1L/1kg) and then filtered. The organic extract was concentrated on a rotatory evaporator to an aqueous suspension and 500 mL of 10% HCl were added. ...
... These results are consistent with the idea that alkaloids are part of antiherbivory defence mechanisms to which insects must adapt to successfully exploit the resource (Wink, 2006). In addition, alkaloids' concentrations are highly variable among Trichocereus species, depending on the environment, individuals, organs and seasons (Reti & Castrillon, 1951;Wink, 2006;Ogunbodede et al., 2010). In fact, T. terscheckii alkaloid concentration can vary from 0.25 to 1.5% of plant dry weight (Reti & Castrillon, 1951), indicating that this host plant may be regarded as an unpredictable and variable (even extreme) stressor, making it a potential marginal habitat for D. buzzatii. ...
Article
Host shifts cause drastic consequences on fitness in cactophilic species of Drosophila. It has been argued that changes in the nutritional values accompanying host shifts may elicited these fitness responses, but they may also reflect the presence of potentially toxic secondary compounds that affect resource quality. Recent studies reported that alkaloids extracted from the columnar cactus Trichocereus terscheckii are toxic for the developing larvae of D. buzzatii. In the present study we tested the effect of artificial diets including increasing doses of host alkaloids on developmental stability and wing morphology in D. buzzatii. We found that alkaloids disrupt normal wing venation patterning and affect viability, wing size and fluctuating asymmetry suggesting the involvement of stress-response mechanisms. Theoretical implications are discussed in the context of developmental stability, stress, fitness and their relationship with robustness, canalization and phenotypic plasticity.This article is protected by copyright. All rights reserved.
... The peyote cactus (Lophophora williamsii), the San Pedro Cactus (Trichocereus pachanoi) and a number of other cacti contain psychoactive quantities of the classic hallucinogen mescaline and other related alkaloids (Gabermann, 1978;Ogunbodede et al., 2010). Peyote buttons have been harvested by Native peoples in North America for at least 5500 years (El-Seedi et al., 2005). ...
... A sample of 2.0 g of the ground dry cactus tissue from each population was then Soxhlet-extracted with 200 ml HPLC-grade methanol for 8 h. The methanol extract was evaporated to dryness, and the residue of the extract was dissolved in 200 ml HPLC-grade water, which underwent acid-base extraction with dichloromethane, as described in Ogunbodede et al. (2010). The dichloromethane was evaporated to dryness, and the residue, containing the mescaline and related alkaloids, was redissolved in 10.0 ml of methanol and stored at −20ºC in a labeled vial. ...
Article
A phytochemical analytical study was conducted to address the question of whether Lophophora williamsii (peyote) plants from Chihuahuan Desert populations in the Trans-Pecos region of West Texas exhibited higher tissue concentrations of mescaline than plants from Tamaulipan Thornscrub populations of South Texas. This question is of cultural significance to the Native American peyote religion, which involves the ingestion of peyote as a psyehopharmacologically active sacrament. Tissue samples were field-collected from 10 individuals in each of four L. williamsii populations, two of which were located in the Chihuahuan Desert, and two of which were located in the Tamaulipan Thornscrub ecoregion. For each of the four populations, the tissue samples from 10 individual plants were pooled, the alkaloids were extracted, and the average mescaline concentration of the population was determined by HPLC. There was limited geographic variation in mescaline concentration; the highest concentration (3.52% of dry tissue) was only 27% greater than the lowest (2.77%), and the difference between the Chihuahuan Desert populations and the Tamaulipan Thornscrub populations was not significant. However, mescaline concentrations increased significantly along a gradient from southeast to northwest, i.e., from the southeasternmost Tamaulipan Thornscrub population to the northwestemmost Chihuahuan Desert population.
... A single T. peruvianus specimen gave 0.24% of mescaline, and the more mescaline-rich of two T. bridgesii samples contained 0.47%, apparently contradicting some popular reports that these cacti are more potent than T. pachanoi. 26 Only the green tissue was analyzed, which is generally used to prepare wachuma extracts and is reasonable in view of analytical results with peyote and is also suggested for the more closely related T. terscheckii, which contains less mescaline than its N,N-dimethyl derivative trichocereine. 27 Nevertheless, more thorough analyses are necessary to better characterize mescaline-rich accessions and determine the distribution of mescaline and mescaline precursors 28 at different distances from the axis and from the tip of this cactus, which grows more than 5 m tall. ...
Article
Archeological studies in the USA, Mexico and Peru suggest that mescaline, as a cactus constituent, has been used for more than 6000 years. Although it is a widespread cactus alkaloid, it is present in high concentrations in few species, notably the North American peyote (Lophophora williamsii) and the South American wachuma (Trichocereus pachanoi, T. peruvianus and T. bridgesii). Spanish 16th century chroniclers considered these cacti “diabolic”, leading to their prohibition, but their use persisted to our days and has been spreading for the last 150 years. In the late 1800s peyote attracted scientific attention, mescaline was isolated, and its role in the psychedelic effects of peyote tops or “mescal buttons” was demonstrated. Its structure was established by synthesis in 1929, and alternative routes were developed providing larger amounts for pharmacological and biosynthetic research. Although its effects are attributed mainly to its action as a 5-HT2A serotonin receptor agonist, mescaline binds in a similar concentration range to 5-HT1A and 2A receptors. It is largely excreted unchanged in human urine, and its metabolic products are apparently unrelated to its psychedelic properties. Its low potency is probably responsible for its relative neglect by recreational substance users, as the successful search for structure-activity relationships in the hallucinogen field focused largely on finding more potent analogs. Renewed interest in the possible therapeutic applications of psychedelic drugs may hopefully lead to novel insights regarding the commonalities and differences between the actions of individual classic hallucinogens.
... To create the selective environments, tissues rich in alkaloids (chlorenchyma) were extracted from the columnar cactus T. terscheckii, dehydrated and sieved to a fine powder. Given that alkaloid concentrations are highly variable in T. terscheckii (0.25-> 1.2% of dry weight), and depending on the season may reach extreme levels (Reti and Castrillón 1951;Meyer and Fogleman 1987;Ogunbodede et al. 2010), in addition to the Control regime (100% standard medium = 0% alkaloids), we considered alternative stress scenarios by including a Soft regime (50/50% standard and chlorenchyma medium = 1.5% alkaloids) and Hard regime (25% standard medium and 75% chlorenchyma powder = 2.25% alkaloids). Population size was kept at a minimum of 200 individuals per replicate population and maintained in discrete generations for 20 cycles. ...
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The rapid diversification of sexual traits is a common phenomenon accompanying the evolution of reproductive isolation, yet the evolutionary mechanisms driving such diversification are often unknown. Based on experimentally evolved strains of two sister species of cactophilic Drosophila, we investigated the correlated evolution of primary and secondary sexual traits to semi-natural environments enriched in secondary metabolites. We compared patterns of morphological evolution in the size and shape of male wing and genitalia of Drosophila buzzatii and Drosophila koepferae selected for different levels of alkaloid intensities for 20 generations. We found similar modes of selection operating among organs but not among species. The evolution of these traits in D. koepferae were compatible with patterns of stabilizing selection, while in D. buzzatii were characterized by directional changes. We also found that allometric variation was an important component of genital shape evolution, whereas changes in the wing morphology were less pronounced and mostly non-allometric. Overall, our data suggest that the diversification of sexual traits in this species pair is related to the evolution of dissimilar genetic architectures and reinforced by divergent ecological responses.
... Entheogens (Ancient Greek: entheos (e G mheoy) -'full of god' and genesthai (gem" rhai) -'to come into being' or 'generate') are naturally occurring hallucinogenic compounds that can induce 'mystical' or 'mysticaltype' experiences (Blinderman, 2016;Griffiths et al., 2006Griffiths et al., , 2008. Whilst arguably only relevant to a minority of the UK general population, Article 18 of the UN Universal Declaration of Human Rights (UN, 1948) and Article 9 of the ECHR (ECHR, 2019) could be interpreted to suggest that the use of naturally occurring entheogens such as mescaline, derived from San Pedro and Peyote cacti (El-Seedi et al., 2005;Ogunbodede et al., 2010), and psilocybin, derived from Psilocybe mushrooms, is an issue of relevance to human rights due to their uses in religious (Richards, 2005), shamanic (Metzner, 1998) and spiritual healing practices . However, the view that using certain drugs is part of freedom of religion is not the generally accepted opinion. ...
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Background Contemporary research indicates that the legal classifications of cannabis (Schedule 2, Class B), 3,4-methylenedioxymethamphetamine (MDMA) (Schedule 1, Class A) and psilocybin (Schedule 1, Class A) in the United Kingdom are not entirely based on considerations of harm and therapeutic utility. The legal classifications of the substances discussed are typically determined by legislators such as Parliament and, therefore, may be a reflection of the views or perceived views of the general public. Objective The aim of the study was to provide an indication of the underlying psychology regarding the legislated sale of alcohol, tobacco, cannabis, MDMA and psilocybin in pharmacies according to a UK general population sample. Methods A sample of 105 UK nationals was selected for the survey. Participants were asked questions on perceived relative harm of the five substances. After viewing contemporary information on reported relative harm and therapeutic applications, the participants were asked questions related to using the pharmacy retail model for the sale of the substances discussed. Participants who opposed the substances being sold primarily in pharmacies were asked to explain their rationale according to a predetermined list of options for each of the five drugs. Participants were also asked whether they consider it a human right to be legally permitted to consume the substances. Results The participants' perceptions of relative harm (tobacco > MDMA > psilocybin > alcohol > cannabis) were not in agreement with the relative harm reported in the literature (alcohol > tobacco > cannabis > MDMA > psilocybin). Principal objections to the currently illicit substances being legally available in pharmacies include it sending the wrong message; it feels wrong; it is too dangerous; disliking the smell of cannabis; disapproval of the people; and not liking the idea of people using psychoactive drugs for entertainment or to have mystical/religious experiences. Overall, the participants determined that being legally permitted to consume the substances discussed is an issue of relevance to human rights. A majority of the male participants concluded that being legally permitted to consume alcohol, tobacco, cannabis and Psilocybe mushrooms is a human right in contrast to the majority of female participants who solely considered alcohol consumption to be a human right. Conclusions The data suggest that the legal classifications may not simply be based on considerations of harm. Misperceptions of the dangers, biases and non-health-related aversions likely contribute to the continuation of policies that do not reflect the state of scientific research.
... Although the chemical composition in E. lepidosperma is not documented detailedly, this plant has been reported containing two types of alkaloids, ephedrine and pseudoephedrine [19]. Previous studies have shown that breeding in an alkaloid-rich host plant Trichocereus terscheckii [20,21] affects fitness in D. buzzatii, such as decreasing viability, body size and starvation resistance, and extending development [22][23][24][25]. Therefore, adaptation to a new host plant such as E. lepidosperma for S. yangi entails the acquisition of mechanisms aimed to face such chemical challenges. ...
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Background Although the importance of host plant chemistry in plant–insect interactions is widely recognized, our understanding about the genetic basis underlying the relationship between changes in midgut proteins and adaptation of plant-feeding insects to novel host plants and habitats is very limited. To address this knowledge gap, the transcriptional profiles of midguts among three populations of the cicada Subpsaltria yangi Chen were compared. Among which, the Hancheng (HC) and Fengxiang (FX) populations occurring in the Loess Plateau feed on Ziziphus jujuba Mill. var. spinosa (Bunge) Hu ex H. F. Chow, while the population occurring in a much drier habitat in the Helan (HL) Mountains is locally specialized on a chemically divergent plant, Ephedra lepidosperma C. Y. Cheng. Results Based on comparative analysis, 1826 (HL vs HC) differentially expressed genes (DEGs) and 723 DEGs (HL vs FX) were identified between the populations utilizing different host plants, including 20, 36, 2, 5 and 2 genes related to digestion, detoxification, oxidation-reduction, stress response and water-deprivation response, respectively, and 35 genes presumably associated with osmoregulation. However, only 183 DEGs were identified between the HC and FX populations, including two genes related to detoxification, two genes related to stress response, and one gene presumably associated with osmoregulation. These results suggest that the weakest expression differences were between the populations utilizing the same host plant and occurring in the closest habitats, which may help explain the metabolic mechanism of adaptation in S. yangi populations to novel host plants and new niches. Conclusions The observed differences in gene expression among S. yangi populations are consistent with the hypothesis that the host plant shift and habitat adaptation in the HL population was facilitated by differential regulation of genes related to digestion, detoxification, oxidation-reduction, stress response, water-deprivation response and osmoregulation. The results may inform future studies on the molecular mechanisms underlying the relationship between changes in midgut proteins and adaptation of herbivorous insects to novel host plants and new niches. Electronic supplementary material The online version of this article (10.1186/s12864-019-5547-y) contains supplementary material, which is available to authorized users.
... IV.4.1.2. Extrapolation à d'autres espèces végétales utilisées en médecine traditionnelle Au Pérou, le cactus de San Pedro ou Echinopsis pachanoi était utilisé dans les rituels de guérison pour ses propriétés hallucinogènes(Armijos et al., 2014;Ogunbodede, et al., 2010). Il était administré aux PVE durant les rituels(Carod-Artal & Vázquez-Cabrera, 2006) et son utilisation pourrait être mieux explorée puisqu'il agit sur le SNC et qu'il aurait également une propriété antimicrobienne sélective (Aboye et al., 2015). ...
Thesis
Sur près de 70 millions de personnes vivant avec l’épilepsie (PVE) dans le monde, 150 000 vivent au Pérou et 52 000 au Laos, avec un déficit de traitement (proportion de PVE qui ne reçoit pas de médicaments antiépileptiques adaptés), respectivement de 75% et 97%. Notre objectif principal était de caractériser l’utilisation des plantes médicinales dans la prise en charge de l’épilepsie. Les objectifs spécifiques visaient à : (i) faire l’état des lieux des connaissances sur les plantes médicinales utilisées comme antiépileptiques dans les pays d’Asie, d’Amérique Latine et d’Afrique, (ii) déterminer la place de la phytothérapie dans l’itinéraire thérapeutique des PVE (iii) évaluer l’efficacité pharmacologique d’extraits de plantes utilisées pour soigner l’épilepsie dans deux communautés rurales du nord du Pérou. D’abord, nous avons utilisé une approche bibliographique exhaustive de la littérature spécialisée. L’approche de terrain au Pérou et au Laos a combiné des outils épidémiologiques et ethnopharmacologiques. La troisième partie de ce travail était une étude pilote ayant pour objectif d’évaluer la faisabilité et la pertinence de réaliser des tests pharmacologiques de l’efficacité de plantes sur différents modèles d’épilepsie. Nous avons identifié 106 publications portant sur l’utilisation de plantes dans l’épilepsie(études réalisées entre 1982 et 2017). Sur le terrain, le pourcentage de recours aux remèdes à base de plantes était de 66,7% au Pérou et de 71,1% au Laos. Au total, 66 espèces végétales ont été citées par les patients et tradipraticiens au Pérou et 87 au Laos. Un effet antiépileptique potentiel avec les extraits de Valeriana officinalis et Melissa officinalis a été observé. La place de la médecine traditionnelle est telle dans l’itinéraire thérapeutique d’un patient épileptique qu’il serait intéressant qu’elle soit partie intégrante du système de soins.
... Cacti are succulent plants which have been used for their functional properties and industrial utility [4][5][6]. Different cacti species obtained by cultivated or wild-collected methods have been used as food sources and fodder, for ornamental purposes, and for medicinal purposes (due to their antioxidant [7], antimutagenic [8], and bactericidal [9] properties), and have been cataloged as a source of bioactive compounds including alkaloids [10,11] and phenolics [12,13]. ...
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Chromatographic separation combined with mass spectrometry is a powerful tool for the characterization of plant metabolites because of its high sensitivity and selectivity. In this work, the phytochemical profile of aerial and radicular parts of Coryphantha macromeris (Engelm.) Britton & Rose growing under greenhouse conditions was qualitatively investigated for the first time by means of modern ultra-high-performance liquid chromatography–tandem mass spectrometry (UHPLC-PDA-HESI-Orbitrap-MS/MS). The UHPLC-PDA-HESI-Orbitrap-MS/MS analysis indicated a high complexity in phenolic metabolites. In our investigation, 69 compounds were detected and 60 of them were identified. Among detected compounds, several phenolic acids, phenolic glycosides, and organic acids were found. Within this diversity, 26 metabolites were exclusively detected in the aerial part, and 19 in the roots. Twenty-four metabolites occurred in both plant parts. According to the relative abundance of peaks in the chromatogram, ferulic and piscidic acids and their derivatives may correspond to one of the main phenolic compounds of C. macromeris. Our results contribute to the phytochemical knowledge regarding C. macromeris and its potential applications in the pharmaceutical and cosmetic industries. Besides, some metabolites and their fragmentation patterns are reported here for the first time for cacti species.
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Natural product novel psychoactive substances ('legal highs') are psychoactive plants or fungi that can be easily acquired from the Internet or retail outlets known as head shops without legal restriction. These materials are either stimulant-, hallucinogenic- or analgesic-like in their effects (or a combination) and many contain phenylethylamine- and tryptamine-derived natural products that are responsible for their pharmacological action. Unfortunately in many cases the chemistry of these materials was studied some time ago and up-to-date chemical and pharmacological analysis of these complex materials is absent, with little understanding of their effects singularly or in combination with other recreational drugs.This chapter covers the chemistry of fungal and herbal novel psychoactive substances and gives an overview of what is currently known of their pharmacology and toxicology. The legality of these materials will vary from country to country and over a period of time as their popularity varies and their adverse effects become better understood.
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The Cactaceae family is native from the American continent but is distributed in the arid and semiarid regions worldwide. Cacti exhibit different morphological (succulent body, extended root system, presence of spines, thick waterproof epidermis) and physiological adaptations (crassulacean acid metabolism) that allow growth in adverse conditions intolerable for most C3 and C4 crops. In addition, these plants produce a wide range of secondary metabolites involved in defense mechanism against biotic and abiotic stresses. The present review focused on the content of alkaloids, phenolic compounds, and terpenes present in cacti plants. Data were limited to those compounds clearly characterized by chromatographic and/or spectrometric techniques in both globular and columnar cacti. Additional information about their pharmacological or biological activities, validated by in vitro or in vivo assays, is also presented. Data revealed that the level of some chemical constituents could give value added to these species from a nutritional, pharmacological, and biological point of view.
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Diferencias en la melanización y el patrón de pigmentación alar en Drosophila buzzatii (Diptera: Drosophilidae) bajo estrés químico  RESUMEN. Recientemente, hemos avanzado en nuestra comprensión de las bases genéticas y los mecanismos subyacentes al proceso de melanización durante el desarrollo, lo que permite el estudio de los procesos evolutivos que gobiernan la variabilidad de pigmentación presente en la naturaleza. Sin embargo, los factores ambientales que contribuyen a dicha variabilidad han recibido poca atención, aún cuando pueden conllevar profundas consecuencias a nivel ecológico. En este trabajo, presentamos un método para analizar los patrones de melanización alar de drosofílidos, de forma cualitativa y cuantitativa. Ponemos a prueba esta metodología comparando las alas de Drosophila buzzatii Patterson & Wheeler, criadas en medio control y con el agregado de alcaloides. Los alcaloides fueron extraídos del huésped secundario de estas moscas, Echinopsis terscheckii (Parm. ex Pfeiff.) Friedrich & Rowley, los cuales, se sabe, presentan efectos negativos en el desarrollo de D. buzzatii. Las moscas criadas en un medio enriquecido con alcaloides mostraron una mayor melanización alar, junto con diferencias en la distribución espacial del pigmento. Planteamos modificaciones a nivel metabólico y de expresión génica para explicar los cambios que las condiciones de estrés inducen sobre el carácter. Proponemos la utilización de este procedimiento para el estudio de la dependencia ambiental de la melanización.
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Mescaline, a natural alkaloid found in the peyote cactus (Lophophora williamsii) in the Americas, has gradually become a drug of abuse in China because of its psychedelic properties. Its intake may lead to hallucinations and confusion or even be life-threatening. Mescaline is classified as a class Ⅰ psychotropic drug in China, which means its use in medicine or scientific research is under strict control of the government. However, studies on surveillance of mescaline abuse in the Chinese population are lacking. A rapid and sensitive liquid chromatography–tandem mass spectrometry (LC-MS/MS) method was developed and validated for the determination and quantification of mescaline in hair. The method had good linearity in the range from 10 to 1000 pg/mg, with the limit of detection (LOD) of 3 pg/mg and the limit of quantitation (LOQ) of 10 pg/mg. The total runtime was 5 min. Acceptable intraday and interday precision (RSD < 15%) and accuracy (bias, -11.2% ∼ 6.8%) were achieved. The recovery was 85.0–101.0%, and the matrix effect was 92.0–105.0%. The validated method was successfully applied to 19 real forensic cases. The concentrations of mescaline in hair ranged from 10 to 784 pg/mg. The method has the benefits of simple sample preparation, high sensitivity, and short running time, making it suitable for large-scale quantitative surveillance analysis of mescaline in forensic toxicology.
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Alkaloids are biologically active compounds widely used as pharmaceuticals and synthesised as secondary methabolites in plants. Many of these compounds are strongly toxic. Therefore, they are often subject of scientific interests and analysis. Since alkaloids — basic compounds appear in aqueous solutions as ionized and unionized forms, they are difficult for chromatographic separation for peak tailing, poor systems efficiency, poor separation and poor column-to-column reproducibility. For this reason it is necessity searching of more suitable chromatographic systems for analysis of the compounds. In this article we present an overview on the separation of selected alkaloids from different chemical groups by liquid chromatography thus indicating the range of useful methods now available for alkaloid analysis. Different selectivity, system efficiency and peaks shape may be achieved in different LC methods separations by use of alternative stationary phases: silica, alumina, chemically bonded stationary phases, cation exchange phases, or by varying nonaqueous or aqueous mobile phase (containing different modifier, different buffers at different pH, ion-pairing or silanol blocker reagents). Developments in TLC (NP and RP systems), HPLC (NP, RP, HILIC, ion-exchange) are presented and the advantages of each method for alkaloids analysis are discussed.
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This chapter reviews what is known about the therapeutic uses of the serotonergic or classic hallucinogens, i.e., psychoactive drugs such as LSD and psilocybin that exert their effects primarily through agonist activity at serotonin 2A (5HT2A) receptors. Following a review of the history of human use and scientific study of these drugs, the data from clinical research are summarized, including extensive work on the use of classic hallucinogens in the treatment of alcoholism and other addictions, studies of the use of LSD and psilocybin to relieve distress concerning death, particularly in patients with advanced or terminal cancer, and more limited data concerning the use of classic hallucinogens to treat mood and anxiety disorders. A survey of possible mechanisms of clinically relevant effects is provided. The well-established safety of classic hallucinogens is reviewed. To provide a clinical perspective, case summaries are provided of two individuals who received treatment in recent controlled trials of psilocybin: one being treated for alcoholism, the other suffering from anxiety and depression related to fear of death due to a cancer diagnosis. Although promising early phase research conducted from the 1950s through the early 1970s was discontinued before firm conclusions could be reached concerning the efficacy of any of the classic hallucinogens for any clinical condition, the research that was conducted in that era strongly suggests that classic hallucinogens have clinically relevant effects, particularly in the case of LSD treatment of alcoholism. In the past decade, clinical trials have resumed investigating the effects of classic hallucinogens in the treatment of existential distress in the face of cancer, and in the treatment of addictions including alcoholism and nicotine addiction. The studies that have been completed to date are not sufficient to establish efficacy, but the outcomes have been very encouraging, and larger trials, up to and including phase 3, are now underway or being planned. Although research has elucidated many of the acute neurobiological and psychological effects of classic hallucinogens on humans, animals, and in vitro systems, the mechanisms of clinically relevant persisting effects remain poorly understood.
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A novel, selective acylation of primary phenylalkyl amines (PPAAs) using hexamethyldisilazane (HMDS) & perfluorocarboxylic acids (PFCAs) is noted. Couples, like HMDS & trifluoroacetic acid (TFA), or HMDS & pentafluoropropionic acid (PFPA), or HMDS & heptafluorobutyric acid (HFBA) trigger PPAAs' quantitative acylation. Processes' selectivity was characterized by applying all couples to derivatize benzyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl amines and their relevant substituted versions. Aliphatic amines were unreactive. Identification, quantification, proportionality and stoichiometry in derivatization processes were determined by gas chromatography-mass spectrometry. Reaction conditions were optimized depending on reagents' molar ratios, solvents and temperatures applied. The new acylation method, in comparison to the traditional ones - obtained with trifluoroacetic anhydride (TFAA), heptafluorobutyric anhydride (HFBAA) and N-methyl-bis(trifluoroacetamide) (MBTFA) - offers numerous advantages. Derivatives, provided by couples, can be directly injected onto the column, avoiding loss of species, saving time, work and cost in preparation process. Due to traditional reagents' excess evaporation by nitrogen drying, the loss of trifluoroacylated species proved to be 65% or less. Regarding heptafluorobutyryl species, their losses varied between 25% and 5%. Unified huge responses, obtained with the HMDS & PFCA couples are attributable to their direct injection onto the column and to fragments sourced from the molecular ions and from their self chemical ionization ([M] , [M+147]+ i.e. [M+(CH3)2-Si=O-Si-(CH3)3]+). The reaction mechanism - due to HMDS symmetrical structure, acting HMDS as acylation generator for PFCAs - was confirmed by Density Functional Theory (DFT) computation.
Chapter
IntroductionToxins Responsible for Plant Poisoning and Poisoning with Herbal SupplementsRole of the Clinical Laboratory in Treating Patients with Plant Poisoning and Toxicity from Using Herbal RemediesDigoxin Immunoassay in Detecting Plant Poisoning and Herbal ToxicityAbnormal Liver Function Tests as an Indication for Plant Poisoning and Herbal ToxicityOther Abnormal Laboratory Tests as Indications for Plant Poisoning and Herbal ToxicityChromatographic Methods for the Diagnosis of Plant Poisoning and Herbal ToxicityMiscellaneous Plant and Herbal Medicine PoisoningsConclusions References
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Naturally occurring cystine knot peptides show a wide range of biological activity, and as they have inherent stability they represent potential scaffolds for peptide-based drug design and biomolecular engineering. Here we report the discovery, sequencing, chemical synthesis, three-dimensional solution structure determination and bioactivity of the first cystine knot peptide from Cactaceae (cactus) family: Ep-AMP1 from Echinopsis pachanoi. The structure of Ep-AMP1 (35 amino acids) conforms to that of the inhibitor cystine knot (or knottin) family but represents a novel diverse sequence; its activity was more than 500 times higher against bacterial than against eukaryotic cells. Rapid bactericidal action and liposome leakage implicate membrane permeabilisation as the mechanism of action. Sequence homology places Ec-AMP1 in the plant C6-type of antimicrobial peptides, but the three dimensional structure is highly similar to that of a spider neurotoxin. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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Contemporary wildlife trade is massively facilitated by the Internet. By design, the dark web is one layer of the Internet that is difficult to monitor and lacks thorough investigation. Here, we accessed a comprehensive database of dark web marketplaces to search across c. 2 million dark web advertisements over 5 years using c. 7k wildlife trade-related search terms. We found 153 species traded in 3,332 advertisements (c. 600 advertisements per year). We characterized a highly specialized wildlife trade market, where c. 90% of dark-web wildlife advertisements were for recreational drugs. We verified that 68 species contained chemicals with drug properties. Species advertised as drugs mostly comprised of plant species, however, fungi and animals were also traded as drugs. Most species with drug properties were psychedelics (45 species), including one genera of fungi, Psilocybe, with 19 species traded on the dark web. The native distribution of plants with drug properties were clustered in Central and South America. A smaller proportion of trade was for purported medicinal properties of wildlife, clothing, decoration, and as pets. Our results greatly expand on what species are currently traded on the dark web and provide a baseline to track future changes. Given the low number of advertisements, we assume current conservation and biosecurity risks of the dark web are low. While wildlife trade is rampant on other layers of the Internet, particularly on e-commerce and social media sites, trade on the dark web may increase if these popular platforms are rendered less accessible to traders (e.g., via an increase in enforcement). We recommend focussing on surveillance of e-commerce and social media sites, but we encourage continued monitoring of the dark web periodically, to evaluate potential shifts in wildlife trade across this more occluded layer of the Internet.
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Alkaloids - Secrets of Life: Alkaloid Chemistry, Biological Significance, Applications and Ecological Role, Second Edition provides knowledge on structural typology, biosynthesis and metabolism in relation to recent research work on alkaloids, considering an organic chemistry approach to alkaloids using biological and ecological explanation. The book approaches several questions and unresearched areas that persist in this field of research. It provides a beneficial text for academics, professionals or anyone who is interested in the fascinating subject of alkaloids. Each chapter features an abstract. Appendices, a listing of alkaloids, and plants containing alkaloids are all included, as are basic protocols of alkaloid analysis.
Chapter
History Identifying Characteristics Exposure Dose Effect Toxicokinetics Histopathology and Pathophysiology Clinical Response Diagnostic Testing Treatment References
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Covering: up to the end of 2011The last five years have seen a dramatic increase in the global popularity of 'Legal Highs', often referred to as Novel Psychoactive Substances (NPS). These materials are single chemicals, plant or fungal materials or their extracts, which may be purchased and possessed without legal restriction in certain countries. The single chemical entity drugs are often closely structurally related to existing controlled drugs of abuse from, for example, the amphetamine (phenethylamine), cannabinoid-mimetic or tryptamine classes, whereas the natural products are from plant or fungal materials that have a long history of pharmacognosy. These natural product legal highs are by their very nature highly chemically complex, and in the clear majority of cases, chemical studies were conducted some considerable time ago. Their pharmacology and toxicology generally focuses on the major active principles with few studies detailing the potentially highly complicated and multiple effects of their extracts. This complexity, coupled with the inherent natural product variability of plant and fungal species, adds a further dimension to the potential harms associated with natural product legal high use. This review encompasses the most popular current legal highs and describes their basic chemistry, usage and preparation, pharmacology, toxicology and discusses the issues surrounding the complexity of these materials, and how this can impact on the evaluation of their harms.
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The alkaloids of 14 species of Trichocereus are reported. Eight different previously known phenethylamines viz. tyramine, N-methyltyramine, hordenine, 3-methoxytyramine, 3,4-dimethoxyphenethylamine, N-methyl-3-methoxytyramine, 3-hydroxy-4,5-dimethoxyphenethylamine, and mescaline were identified in these species. Mescaline was found to occur in T. cuzcoensis, T. fulvilanus, T. taquimbalensis and T. validus. Mescaline was also present in small amounts in Stetsonia coryne together with traces of anhalidine and anhalonidine. 3-Hydroxy-4-methoxyphenethylamine is identified in a plant, Pachycereus pecten-aboriginum, apparently for the first time. The commonly occurring isomer 3-methoxytyramine was found to be the major alkaloid of Trichocereus cuzcoensis. A tetrahydroisoquinoline alkaloid, anhalidine, was isolated from Pelecyphora aselliformis.
Article
An ion-interaction HPLC method is developed for the determination of mescaline in some Cactaceae species, namely Gymnocactus beguinii, Echinocactus polycephalus, Coriphanta radians, Coriphanta scolymoides, Coriphanta palmeri, Lophophora williamsii and Trichocereus pachanoi.Mescaline is characterized by hallucinogenic properties and can be prescribed as a psychodrug.The method makes use of a C18-reversed-phase as the stationary phase and of a 5.0 mM aqueous solution of octylamine o-phosphate as the mobile phase, with spectrophotometric detection at 230 nm.The method is sensitive (detection limit of 35 μg/L) and matrix interference-free.The pretreatment of the sample is performed by grinding the fresh cactus and extracting the jelly pulp obtained either with a methanolic-ammonial solution or an aqueous solution buffered at pH 4.0 (phosphate buffer).The average amounts of mescaline found in Lophophora williamsii and in Trichocereus pachanoi were respectively 2.55 mg and 3.10 mg/g of fresh cactus.
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The chemical examination of nine cacti from Mexico, Costa Rica and. Peru is described. In addition to the known triterpenes oleanolic acid (I) and betulinic acid (III), two new triterpenes were encountered. From L. stellatus and M. eruca there was isolated a new dihydroxy lactone, stellatogenin, which was shown to possess one secondary and one tertiary hydroxyl function by direct correlation with the cactus triterpene thurberogenin. The isolation of a second new triterpene, machaeric acid (21-keto-oleanolic acid) (II), from M. gummosus is recorded.
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The dried branches of Trichocereus terscheckii (Parmentier) Britton & Rose contain 0.25 to 1.2% alkaloids. From this source trichocereine, a new vegetable base, and the already known mezcaline have been isolated and characterized. The ratio of trichocereine to mezcaline is 5:1. The chemical structure of trichocereine has been shown to be N-dimethylmezcaline by degradation, and its synthesis has been achieved by allowing 3,4,5-trimethoxy-β-phenylethyl chloride to react with dimethylamine.
Article
This article has attempted to reinterpret a now extinct prehistoric people, the Mochica of Peru, in light of our knowledge of contemporary regional hallucinogenic use. An analysis of Mochica pottery motifs suggests the use of a variety of plant hallucinogens which may have permitted access to supernatural realms. I have argued that studies such as this of prehistoric peoples show the central role that hallucinogenic plants have had throughout time and present a new path to the understanding of prehistoric religions.
Article
Agurell has previously detected (tlc, glc-ms) tyramine, 3-methoxytyramine, and two unknown alkaloids in the Peruvian cactus, Trichocereus peruvianus Br. and R. The presence of mescaline in other similar Trichocereus species prompted us to reinvestigate this species, which is commercially available in the United States. The nonphenolic alkaloid extracts yielded an abundance of crystalline mescaline hydrochloride (0.82% yield) and a trace of 3,4-dimethoxyphenethylamine (tlc-ms). Crystalline tyramine hydrochloride, 3-methoxytyramine hydrochloride, and 3,5 dimethoxy-4-hydroxphenethylamine hydrochloride were isolated from the phenolic alkaloid extracts; the last compound has not been previously crystallized from nature, although it is the immediate biosynthetic precursor of mescaline. Crystalline 2-chloromescaline hydrochloride was isolated drom the nonphenolic extracts; but, as determined by mass-analyzed ion kinetic energy spectrometry, this new compound is an extraction artifact. Both 2-chloromescaline and 2.6-dichloromescaline hydrochlorides were prepared synthetically from mescaline. This cactus species has a mescaline content equal or superior to peyote and should be legally controlled as an item of drug abuse.
Article
Several procedures using high-performance liquid chromatography with photodiode-array detection have been developed to create phytochemical and toxicological profiles of phenylalkylamine derivatives in biological samples (e.g. plant materials and urine). Mescaline-containing cactus samples were extracted with basic methanol, using methoxamine as internal standard; the extraction and clean-up of urine samples were performed on cation-exchange solid-phase extraction columns. The extracts were separated on a 3-micron ODS column with acetonitrile-water-phosphoric acid-hexylamine as the mobile phase. Peak detection was performed at 198 or 205 nm; peak identity and homogeneity were ascertained by on-line scanning of the UV spectra from 190 to 300 nm. The detection limit of phenylalkylamine derivatives in urine and cactus material was 0.026-0.056 micrograms/ml and 0.04 micrograms/mg, respectively. Following a single oral dose of 1.7 mg/kg methylenedioxymethylamphetamine (MDMA) the concentrations found in urine ranged from 1.48 to 5.05 micrograms/ml MDMA and 0.07-0.90 micrograms/ml methylenedioxyamphetamine (a metabolite of MDMA). The mescaline content of the cactus Trichocereus pachanoi varied between 1.09 and 23.75 micrograms/mg.
Article
A detailed investigation of Trichocereus werdermannianus Backbg. revealed the presence of tyramine, 3-methoxytyramine, 3,4-dimethoxyphenylethylamine, 3,5-dimethoxy-4-hydroxyphenylethylamine and mescaline. Trichocereus pachanoi Br. & R., previously known to produce mescaline (16) contained the same compounds and in addition anhalonidine. Two new simple plant alkaloids, 3-methoxytyramine (3) and 3,5-dimethoxy-4-hydroxyphenylethylamine (5a), both hypothetical mescaline precursors were identified by comparison with synthetic material. The investigation was carried out to find intermediates on the path from tyramine to mescaline using gas chromatography-mass spectrometry. The results indicate that this technique may be the method of choice to identify minute amounts of potential alkaloid intermediates.
Article
A rapid and sensitive technique has been developed for the detection and identification of cactus alkaloid. The method is based on TLC, GLC and mass spectrometry. Of 120 cactus species tested about 40% contained alkaloids. The alkaloids in 21 species of cacti, mainly belonging to the genera Cereus, Helianthocereus, Echinopsis and Trichocereus are reported. Mescaline was isolated from T. bridgesii and T. macrogonus. N-methyl-3,4-dimethoxyphenylethylamine is reported to occur in nature for the first time (from Lepidocoryphantha runyonii). In the introduction a short review is given over the basic cactus alkaloids so far isolated from nature.
El género Trichocereus, ecología y contenido mescalínico
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Cjuno, M., Choquenaira, J., Quispe, P., Serrano, C., Tomaylla, C., 2009. El género Trichocereus, ecología y contenido mescalínico. Quepo 23, 38-45.
Essai de localization des alcaloïdes dans le peyotl
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Trout, K., 2005. Trout's Notes on San Pedro & Related Trichocereus Species, Sacred Cacti, third ed., Part B. Better Days Publishing, Austin, 310 pp.
A student's experiment in pharmacognosy: biosynthesis of mescaline in the cactus Trichocereus pachanoi
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Bruhn, J.G., Lundström, J., 1976. A student's experiment in pharmacognosy: biosynthesis of mescaline in the cactus Trichocereus pachanoi. American Journal of Pharmaceutical Education 40, 159-160.
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Schultes, R.E., Hofmann, A., 1980. Botany and Chemistry of Hallucinogens. Charles C. Thomas, Springfield, IL, 462 pp. Serrano, C.A., 2008. Avances en la fitogeografía química del género Trichocereus en el sur del Perú. Quepo 22, 29–34.
Cactaceae of Bolivia: additional department records. Cactaceae Systematics Initiatives
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Taylor, N., 2007. Cactaceae of Bolivia: additional department records. Cactaceae Systematics Initiatives. Bulletin of the International Cactaceae Systematics Group 22, 10-11.
Oral statement on current indigenous use of Peruvian E. pachanoi in shamanic practice, by indigenous plant dealer who requested anonymity
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Anon., 2007. Oral statement on current indigenous use of Peruvian E. pachanoi in shamanic practice, by indigenous plant dealer who requested anonymity.
El uso del “San Pedro” (Echinopsis pachanoi) en medicina tradicional peruana
  • Reyna Pinedo
Reyna Pinedo, V., Flores Garcés, J., 2001. El uso del "San Pedro" (Echinopsis pachanoi) en medicina tradicional peruana. Quepo 15, 28-37.
Estudio farmacológico de la Opuntia cylindrica
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Cruz Sánchez, G., 1948. Estudio farmacológico de la Opuntia cylindrica. Thesis. Instituto de Farmacología y Terapéutica, Universidad Nacional Mayor de San Marcos, Lima, Peru, 27 pp.
Shamanism & the Sacred Cactus
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Sharon, D., 2000. Shamanism & the Sacred Cactus. San Diego Museum Papers 37, San Diego Museum of Man, San Diego, 76 pp.
Avances en la fitogeografía química del género Trichocereus en el sur del Perú
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Serrano, C.A., 2008. Avances en la fitogeografía química del género Trichocereus en el sur del Perú. Quepo 22, 29-34.
Mass Spectra of Designer Drugs, Including Drugs
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Rösner, P., Junge, T., Westphal, F., Fritschi, F., 2007. Mass Spectra of Designer Drugs, Including Drugs, Chemical Warfare Agents, and Precursors, vol. 2. Wiley-VCH Verlag/GmbH & Co./KGaA, Weinheim, 2067 pp.
Présence de mescaline dans une Cactacée péruvienne
  • Poisson
Poisson, J., 1960. Présence de mescaline dans une Cactacée péruvienne. Annales Pharmaceutiques Franç aises 18, 764-765.
Determination of mescaline in hallucinogenic Cactaceae
  • Marini-Bettòlo
El género Trichocereus, ecología y contenido mescalínico
  • Cjuno
Cactaceae of Bolivia: additional department records
  • Taylor