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Clinal geographic variation in mescaline concentration among Texas populations of Lophophora williamsii (Cactaceae)
Abstract
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.
... Mescaline, the predominant psychoactive compound in L. williamsii, has long been recognized as a sympathomimetic agent, producing vivid changes in sensory perception when ingested (Huxley 1954;Kumla and Szopa 2007;Simpson and Ogorzaly, 2013). Mescaline concentrations in L. williamsii have typically been found to range from a little less than 2% to around 4% of the dry weight of each crown (Bruhn and Holmstedt 1974;Hulsey et al. 2011). ...
... 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. ...
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.
... The various steps within the MESQ procedure are aligned so that the procedure is equally useful for the determination of very low tissue concentrations in seedlings (down to 0.01%) as well as for high concentrations in the quantification of high potency specimens (up to 1% in fresh tissue) [16,30,31,57] and concentrated aqueous extracts. Quantification is therefore possible over the course of 2 orders of magnitude. ...
... This discovery of the uneven distribution of mescaline in the green parenchyma of a single specimen, as with the newly discovered gradient in Echinopsis, calls into question conclusions of previously published research. Studies using the entire Lophophora button for analysis may compare them correctly [31], but the results of studies that took only unspecified biopsies [16,57] should be reinterpreted with caution in light of this new knowledge. ...
Mescaline quantification in cactus tissue. Mescaline distribution in specimens of Lophophora williamsii and Echinopsis pachanoi peruviana lageniformis.
Trichocereus pachanoi peruvianus bridgesii.
Peyote.
... The various steps within the MESQ procedure are aligned so that the procedure is equally useful for the determination of very low tissue concentrations in seedlings (down to 0.01%) as well as for high concentrations in the quantification of high potency specimens (up to 1% in fresh tissue) [16,30,31,57] and concentrated aqueous extracts. Quantification is therefore possible over the course of 2 orders of magnitude. ...
... This discovery of the uneven distribution of mescaline in the green parenchyma of a single specimen, as with the newly discovered gradient in Echinopsis, calls into question conclusions of previously published research. Studies using the entire Lophophora button for analysis may compare them correctly [31], but the results of studies that took only unspecified biopsies [16,57] should be reinterpreted with caution in light of this new knowledge. ...
p>ABSTRACT
Background. Peganum Harmala (Syrian rue, Nitrariaceae) has a long and widespread history of ethnopharmacological use. Due to its rich and diverse alkaloid content, the traditional application of whole plant material or full alkaloid extract is inherently unspecific and therefore susceptible to side effects. Simultaneously, incorrect phytochemical procedures for its use in ayahuasca-analogues cause intoxications in misinformed users.
Aim of the study. Providing harm-reduction by developing easily applicable, safe and effective isolation protocols for harmine, harmaline (dihydroharmine) and tetrahydroharmine (leptaflorine) from Peganum Harmala seed.
Materials and methods. Only commonly available equipment and reagents were used for isolating the alkaloids. Following extraction, harmine and harmaline were separated using 2 low-tech methods (selective precipitation using sodium bicarbonate or pH-metry). Then, zinc-acetic acid reduction of both harmine and harmaline was attempted. The identity and purity of the obtained alkaloids were confirmed using microscopy and melting point determination.
Results. Using pH-metry for the separation of harmine and harmaline proved rapid, effective and recovered 91% of alkaloids. Selective precipitation of the alkaloids with sodium bicarbonate had a yield of 76%. Hydrogenation of harmaline to tetrahydroharmine using zinc-acetic acid had a yield of 83%. Harmine however could not be hydrogenated by zinc-acetic acid. The melting ranges of the obtained alkaloids were narrow and consistent with literature. Based on these results, isolation protocols were developed.
Conclusions. Harmine, harmaline and tetrahydroharmine can be isolated with good yields from Peganum Harmala seed following protocols that are applicable in traditional and other low-tech settings. This study showed zinc-acetic acid to be effective in the reductive synthesis of tetrahydroharmine and also proposes a rapid, precise and high yielding method for the bulk separation of harmine and harmaline using basic pH-metry.</p
... Lemaire, 1845) and quantity assays (e.g. Hulsey, Abul Kalam, Daley, Fowler, & Terry, 2011), while more recent research (Ermakova & Terry, 2020) has drawn attention to sustainability (Ermakova, 2019). While land clearing and the resulting loss of habitat is the primary threat faced by Peyote in the wild, the wild harvest of Peyote creates additional pressures (Trout & Friends, 2015). ...
Background and Aims
Both Peyote and San Pedro cacti contain mescaline, a classical psychedelic eliciting mystical and visual effects, but only Peyote is a vulnerable species. We sought to address the questions 1; do people who use Peyote substitute with San Pedro, and vice versa, and; 2. how popular is the use of wild harvested mescaline cactus compared with the use of cultivated plants?
Methods
Data were collected as part of the 2022 Global Drug Survey, a self-report survey distributed internationally in 11 languages. We asked mescaline cacti consumers about consumption practices, preferences and conservation and conducted chi square tests of associations comparing all motivations by preferred mescaline source.
Results
Of participants who reported using mescaline in the last 12 months (N = 284; 73.2% male, 21.8% female, 5.0% other gender; mean age 36.3, SD 12.5), 20.0% reported consuming Peyote collected from native habitats. Of participants specifying Peyote as their preferred source of mescaline, 82.2% had consumed Peyote in the past 12 months. Indigenous cultural traditions (57.8%), availability (40.0%) and environmental sustainability (33.3%) were the most commonly reported motivations for Peyote preference (n = 45), whereas for San Pedro (n = 86), availability (54.7%), potency (45.3%) and indigenous cultural traditions (44.2%) were most the commonly reported San Pedro preference motivations. Price and potency were significantly more likely to be chosen by those preferring San Pedro compared with Peyote. Less than 7% of participants who consumed San Pedro in the past 12 months had consumed San Pedro from native habitats. Of the participants who specified San Pedro as their preferred source of mescaline, 96.5% had consumed San Pedro in past 12 months. San Pedro was the most commonly reported source of mescaline product consumed (56.1%) with Trichocereus bridgesii being the most reported preferred San Pedro species. Mescaline cacti consumed in the last 12 months rarely deviated from mescaline cacti of preference.
Conclusions
Wild Peyote is not the most popular mescaline source, but consumption of related products remains unsustainable. Promoting San Pedro as a Peyote substitute may act as an intervention to reduce Peyote consumption.
... The average concentrations varied within a fairly narrow range (2.77 to 3.52%) and did not differ significantly by location. 25 A study of interindividual variation in T. pachanoi was published in 2010. Identical processing of dried subepidermal green tissue from five different specimens gave results ranging from 0.54 to 4.7% mescaline evidencing the high variability of this species. ...
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.
An overview & summary of the analytical accounts for the family Cactaceae that have reported alkaloids, steroids, triterpenoids, saponins, betalains, polysaccharides, simple sugars, volatile compounds or other organic molecules. Reports of biominerals are also included. The 2014 revision now incorporates a summary overview of the pertinent ethnographic literature, claims for various bioactivities (in vitro and in vivo), medicinal applications (folk and modern) and dispells a number of urban mythologies. Light version is specifically intended for ease of use in research. (It omits hundreds of pages of photographs.) 2014 version with bad link corrections performed January 2018.
Over the last four decades, the size and density of populations of Lophophora williamsii (peyote) have diminished markedly in large areas of South Texas where licensed peyote distributors harvest the cactus for ceremonial use by the Native American Church. Part of the problem lies in the fact that some harvesters are cutting plants too low on the subterranean stem or taproot. That practice precludes the regeneration of new stems and ultimately results in the death of the decapitated plants. To address this problem, we describe the anatomical distinctions between subterranean stem and root in L. williamsii as follows: The stem cortex can be distinguished by the cortical bundles running through the parenchyma, in contrast to the root cortex, which consists of pure parenchyma without cortical bundles. The pith at the center of the stem is pure parenchyma (without xylem) and is readily distinguished from the dilatated metaxylem (with masses of dark-staining metaxylem tracheary elements) occupying the center of the root. With these new anatomical tools, it is now possible to set up titration experiments, first in the greenhouse and then in the field, to generate practical biometric data to determine the maximum depth at which the peyote harvesters can cut the plants without significantly reducing the survival rate of the rootstocks left in the ground after harvest.
Lophophora williamsii (peyote) is a cactus whose crowns are commercially harvested for religious use as an ingested psychoactive sacrament by members of the Native American Church. Over the past quarter century peyote has become progressively less available, due in part to improper harvesting techniques and excessive harvesting. Since anatomical aspects of the regrowth of peyote and best harvesting practices were explicated in a previous study (Terry & Mauseth 2006), the principal focus in the present study was to determine the effects of harvesting where only best practices were employed. We assessed the effects of (1) harvesting per se (a single harvesting event evaluated after two years), (2) repeated harvesting (two harvesting events two years apart), and (3) not harvesting at alt. After two years, the once-harvested group had a 90% survival rate and the unharvested control group had a 98% survival rate, a difference that was not statistically significant. The above-ground volume of the unharvested plants was significantly larger than that of the regrown harvested plants. While the regrown harvested plants had on average more crowns, their crowns were significantly smaller, in comparison to those of the unharvested plants. After two years, the surviving plants in the harvested group were divided into two subgroups, one of which was harvested for a second time. The other subgroup consisted of plants that had been harvested only once (at the start of the study) and were not reharvested. The weights of the crowns obtained in the second harvest were significantly lower than the weights of the crowns obtained in the first harvest from the same plants two years earlier. The net effect of a single harvesting was a reduction of plant above-ground volume by almost 80% after two years of regrowth. These data reflect what is occurring on a massive scale in habitat where peyote is commercially harvested. The annual numbers of crowns being harvested have not yet decreased drastically, due to the increased number of crowns produced as regrowth in response to harvesting. But the average size of the crowns in the regulated peyote market has decreased markedly due to too-early harvesting of immature regrowth crowns. These results-with emphasis on the conspicuous reduction in mean size of individuals-are typical of overharvested populations of wild-collected species, such as ginseng. The conclusion for conservation management is that reducing the frequency of harvesting of wild peyote would allow regrowth crowns to mature in size-thus reducing the number of crowns per dose required for sacramental consumption. It would also allow regrowth crowns to mature sexually, which would effectively de-suppress the production of seed for the next generation.
We argue that phenotypic plasticity should be broadly construed to encompass a diversity of phenomena spanning several hierarchical levels of organization. Despite seemingly disparate outcomes among different groups of organisms (e.g., the opening/closing of stomata in leaves, adjustments of allocation to growth/reproduction, or the production of different castes in social insects), there are underlying shared processes that initiate these responses. At the most fundamental level, all plastic responses originate at the level of individual cells, which receive and process signals from their environment. The broad variations in physiology, morphology, behavior, etc., that can be produced by a single genotype, can be accounted for by processes regulating gene expression in response to environmental variation. Although evolution of adaptive plasticity may not be possible for some types of environmental signals, in many cases selection has molded responses to environmental variation that generate precise and repeatable patterns of gene expression. We highlight the example of responses of plants to variation in light quality and quantity, mediated via the phytochrome genes. Responses to changes in light at particular stages of plants'' life cycles (e.g., seed germination, competition, reproduction) are controlled by different members of this gene family. The mechanistic details of the cell and molecular biology of phytochrome gene action (e.g., their effects on expression of other genes) is outlined. Plasticity of cells and organisms to internal and external environmental signals is pervasive, and represents not just an outcome of evolutionary processes, but also a potentially important molder of them. Phenotypes originally initiated via a plastic response, can be fixed through genetic assimilation as alternate regulatory pathways are shut off. Evolution of mechanisms of plasticity and canalization can both reduce genetic variation, as well as shield it. When the organism encounters novel environmental conditions, this shielded variation may be expressed, revealing hidden reaction norms that represent the raw material for subsequent evolution.
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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