Do You Have to Pull the Skin Off Baby Woodrose Seeds
Ergine
Ergine could theoretically exist produced via a procedure analogous to that used to produce peptides with carboxy-concluding amides, such as peptide hormones in mammals and insects and the antibody myxothiazol in myxobacteria.
From: Recent Advances in Phytochemistry , 2006
Integrative Plant Biochemistry
Daniel G. Panaccione , ... Christine Grand. Coyle , in Recent Advances in Phytochemistry, 2006
Acknowledgments
Research in the authors' laboratories was supported by USDA NRI grants 2001-35319-10930 and 2005-35318-16184. We thank Sarah O'Connor (MIT) for helpful suggestions regarding ergine biosynthesis. Preliminary sequence data from the A. fumigatus genome were obtained from The Institute for Genomic Research web site at http://www.tigr.org . Sequencing of the A. fumigatus genome was funded past the National Institute of Allergy and Communicable diseases grant U01 AI 48830 to David Denning and William Nierman, the Wellcome Trust, and Fondo de Investigaciones Sanitarias.
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Alkaloids
West.A. Kukula-Koch , J. Widelski , in Pharmacognosy, 2017
nine.ix.1 Indole Alkaloids
This group of nitrogen-containing compounds is not homogenous. Several subgroups of these compounds were distinguished, amongst them the following types: Strychnos alkaloids (strychnine, brucine, vomicine), yohimbans (yohimbine, reserpine, deserpidine), heteroyohimbans (ajmalicine, reserpiline), Vinca alkaloids (vinblastine, vincristine, vincamine), beta-carbolines (harmine, harmaline), kratom alkaloids (mitragynine), tryptamines (psilocybin, serotonin), ergolines/clavine alkaloids (ergine, ergotamine, lysergic acid), and Tabernanthe iboga alkaloids (ibogaine, voacangine, coronaridine).
Besides monoterpene indole alkaloids contain an indole, dihydroindole, or oxindole skeleton coupled with a monoterpene unit of measurement derived from secologanin. They typically contain ii nitrogen atoms, one indolic, and the 2nd from the N1-position of the indole ring.
Various groups of indole alkaloids take been isolated from more than thirty botanical families including the Apocynaceae, Rubiaceae, Loganiaceae, Passifloraceae, likewise equally several fungi.
Several accept medical applications: vincamine and isovincamine from Vinca modest are used to treat hypertension; vincristine and vinblastine have antiproliferative and cytotoxic activities and are isolated from the leaves of Catharanthus roseus; and harmine from Passiflora incarnata is used every bit a tranquilizer [20] (run across Table nine.7).
Table ix.seven. The Characteristics of the Well-nigh Prominent Indole Alkaloids
| Alkaloid | Pharmacological Action | Adverse Effects |
|---|---|---|
| Ajmaline | Adrenolytic activeness against alpha receptors which results in:
|
|
| Vincamine | – Cognitive vasodilator in cerebral anoxia often used with papaverine or heptaminol |
|
| ||
| Vinblastine |
| Astringent allergic reactions, bone marrow toxicity, blood in urine, infection, astringent bleeding, pain in bones, sudden shortness of breath, constipation, headache, vomiting, stomach pain, loss of appetite, deep ulcers |
| Vincristine |
| Hyponatremia, constipation, hair loss, peripheral neuropathy (dysesthesia, dumb neuromuscular transmission) |
| Reserpine |
| High dosage:
|
| Semisynthetic Derivatives | ||
| Rivastigmine |
| Nausea, vomiting, severe skin redness, irritation, inability to urinate, heavy sweating, seizures, diarrhea |
References Table 7: [13]; Monographs of the European Scientific Cooperative on Phytotherapy (ESCOP); European Pharmacopoeia 8.0.
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Natural Product (Fungal and Herbal) Novel Psychoactive Substances
Simon Gibbons , Warunya Arunotayanun , in Novel Psychoactive Substances, 2013
Argyreia nervosa (Hawaiian Baby Woodrose)
Argyreia nervosa syn. Argyreia speciosa, also known as Hawaiian baby woodrose, elephant creeper and woolly morn celebrity, is a large climber in the Convolvulaceae plant family and is a relative of the forenoon glories and bindweeds [83]. In Ayurvedic medicine, every part of the plant including the seed, leaf, bark and root have usage every bit they possess a wide-range of pharmacological activities such as antimicrobial, antidiarrhoeal, hepatoprotective, anticonvulsant, antioxidant, aphrodisiac, immunomodulatory, analgesic and anti-inflammatory activity [83]. The seeds are the primary NPS materials used equally a hallucinogen, and accept been used traditionally in a number of diseases in India because of their hypotensive, spasmolytic and anti-inflammatory properties while in Hawaii they are used for religious and sacramental purposes [83].
A. nervosa is recognised as a plant containing lysergic acid amide (LSA), also known as ergine (0.04% past weight) ( Fig. 14.10) [84], a precursor to lysergic acrid diethylamide (LSD, LSD-25), a well-known synthetic hallucinogenic substance and controlled drug of corruption.
Figure 14.ten. Lysergic acrid amide (ergine), a component of Hawaiian baby woodrose is structurally similar to LSD.
However, neurological effects of LSA are like to those of scopolamine and not to LSD despite the high caste of similarity between both structures (Fig. 14.x). The major components in seeds of A. nervosa are alkaloids (0.5–0.9% by weight) [85], mainly the ergoline-type alkaloids including ergine (d-lysergic acrid amide, LSA) and isoergine (l-lysergic acid amide, the isomer of LSA). These 2 natural products are found in the highest pct at 0.136% and 0.188%, respectively, of total alkaloids along with ergometrine, lysergol, isolysergol and chanoclavine [84,85]. The amount of indole alkaloids present in Hawaiian babe woodrose seeds is the highest among plants in the Convolvulaceae plant family [85] and 10-fold greater than that of Ipomoea violacea (Morning Glory), a related psychoactive plant in the same family unit.
NPS users consume on average five to ten seeds of Hawaiian baby woodrose, which is equivalent to 0.14% LSA by weight [4,86], by swallowing the whole or crushed seeds equally well as drinking an alcoholic extract or an infusion. This cloth is sometimes used together with marijuana [87]. Reports from users say that the seeds generate LSD-like actions affecting all sensations, nausea, vomiting, mydriasis, impaired motor skills, along with tranquillising effects which tin can final for equally long equally half dozen–eight hours [86,88]. Hawaiian babe woodrose seeds can ofttimes be confused with the seeds of I. violacea which are normally dosed at 100–300 seeds (0.02% LSA) [4]. Ingesting more than 12 seeds of A. nervosa tin can cause highly unpleasant furnishings such every bit agitation and tachycardia to fatal doses where the LD50 of seed excerpt is 500 mg/kg of torso weight [4,87,89]. There take been a number of clinical reports of toxicity with reports describing mild to serious adverse effects ranging from nausea, vomiting, tachycardia, hypertension, agitation, disturbances in orientation, visual and auditory hallucination, psychosis and anxiety [86,xc]. In one case an individual experienced hallucinations subsequently ingesting the seeds together with smoking Cannabis and he was found dead subsequently jumping from a fourth floor [91].
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Natural Product Biosynthesis by Microorganisms and Plants, Part A
Daniel G. Panaccione , ... Simona Florea , in Methods in Enzymology, 2012
3.three Quantification
Peak areas are calculated by chromatographic software, and areas are converted to concentration by comparison to a standard curve, which may be derived from internal or external standards. In research with well-characterized Neotyphodium spp., ergotamine is frequently added to extraction solvent to serve every bit an internal standard for fluorescence HPLC (e.thousand., Panaccione et al., 2003; Spiering et al., 2002). Ergotamine is non produced by whatsoever known species of Neotyphodium, is commercially available, and is structurally like to the Neotyphodium ergot alkaloids, including ergovaline and ergine, making it an first-class choice for an internal standard for alkaloids that fluoresce maximally at 310/410 nm. Ergonovine also is commercially available, fluoresces strongly at 310/410 nm, and tin can exist used as an internal or external standard, depending on whether the samples potentially contain that particular ergot alkaloid. For samples containing analytes that fluoresce more strongly at 272/372 nm, agroclavine has been used as an external standard (Coyle, Cheng, O'Connor, & Panaccione, 2010; Coyle et al., 2007; Panaccione & Coyle, 2005). Information technology was used as an external as opposed to an internal standard because initially the molds in the Eurotiales were not as well characterized as the Neotyphodium spp., and the beingness of natural agroclavine producers could non be excluded. Moreover, genetic modification of the ergot alkaloid pathway resulted in production of agroclavine (Coyle et al., 2010). At the time, the nowadays chapter was written, agroclavine was no longer available commercially in the U.s.a.. Dihydroergotamine or dihydroergocristine, which take fluorescence properties like to agroclavine (Panaccione & Coyle, 2005) and are commercially available, may exist substituted as a concentration standard for ergot alkaloids lacking a double bond conjugated to the indole ring (i.e., those having no 9,ten double bail).
The outcome of 8-epimers of lysergyls also needs to be considered with respect to quantification of ergot alkaloids. In protic solvents, lysergyl derivatives readily form stereoisomers effectually carbon 8. The propensity to isomerize is a consequence of their oxidation country at carbon 17 and the 9,x double bond in band D. When such molecules are in protic solvents, the carbonyl grouping at carbon 17 readily forms an enol isomer. Reversion to the carbonyl form may take place in such a style as to yield either of two stereoisomers (Fig. 12.three). The names of most lysergyls (naturally occurring in their eightDue south forms) end with—ine (e.g., ergotamine, ergonovine, ergovaline), and the name of the eightR-epimers ends with an—inine suffix (due east.k., ergotaminine, ergonovinine, ergovalinine). In other cases, an iso-prefix is added to the name of the alkaloid (e.one thousand., isolysergic acid for the viiiR-epimer of lysergic acid). Epimerization occurs spontaneously, and the charge per unit of epimerization varies among ergot alkaloids (Martínková, Křen, Cvak, Ovesná, & Přepechalová, 2000; our unpublished data). Martínková et al. (2000) found that ergine more rapidly isomerized to erginine than did lysergic acrid to isolysergic acid. We take observed that ergonovine is particularly tiresome to isomerize compared to other lysergic acid amides and ergopeptines. Epimers are hands separated past the HPLC approach described above (e.chiliad., Panaccione et al., 2003; Spiering et al., 2002), with 8R-epimers having a greater retentivity fourth dimension than the naturally occurring 8 South forms. Most in vitro bear witness indicates that only the viiiSouthward-isomers are biologically active, but Stutz, Stadler, Vigouret, and Jaton (1978) found certain 8R-epimers to take enhanced dopaminergic activity. Since the viiiR-epimers form readily during extraction, our do has been to measure out both isomers and sum the values for quantitative analysis.
Figure 12.3. Epimerization around carbon 8, via keto-enol tautomerization, in lysergyls.
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Tryptamines
Shaun 50. Greene , in Novel Psychoactive Substances, 2013
Pharmacodynamics
Mechanism of Activeness
The predominant clinical effect produced by tryptamine exposure is hallucinations, mediated by agonism at 5HT1A and 5HT2A receptors [3,35,36]. Tryptamines exhibit less selectivity and affinity for 5HT2A receptors compared to hallucinogenic phenylethylamines [iv]. However, virtually tryptamines exhibit hallucinogenic properties, rather than entactogenic or stimulant properties. The alpha methylated tryptamines possess an alpha carbon methyl grouping, and exhibit relatively greater stimulant activity, like the amphetamines with like structures [17]. Examples include AMT and v-methoxy-alpha-methyltryptamine (5-MeO-AMT). Other receptors implicated in tryptamine fundamental nervous system (CNS) interaction include vesicular monoamine transporter two (VMAT2), sigma-i receptor, trace-amine-associated receptors (TAAR) and serotonin transporter (SERT) [35,37–39].
DMTs pharmacodynamic backdrop have been studied in more than detail than other tryptamines. DMT binds to 5HT1A, 5HT1B, 5-HT1D, 5HT2A, 5HT2B, 5HT2C, 5HT6, and 5HT7 receptors [35,40–42]. Agonist activity has been demonstrated at 5HT1A, 5HT2A and 5HT2C receptors [36,40,42]. DMT also has affinity for sigma-i, alpha1-adrenergic, alpha2-adrenergic, SERT, VMAT2, imidazoline-1 and TAAR receptors [38,39]. Like many hallucinogens the primary receptor responsible for DMTs psychedelic effects appears to be 5HT2A, but there is also indirect evidence of 5HT2C contribution; DMTs ECl for the 5HT2C receptor is lower than the ECl for the 5HT2A receptor [42]. Following administration of typical psychedelic doses of DMT, blood and plasma DMT concentrations are within the range required to produce 50% of the maximal result (EC50) at 5HT2A receptors, suggesting a probable agonist 5HT2C effect following recreational DMT doses [12,13,36,40,43].
Other unsubstituted tryptamines including AMT and AET have hallucinogenic and stimulatory furnishings [24]. AMT is a reuptake inhibitor and releaser of serotonin, noradrenaline and dopamine [4,44]. DPT is unique in producing aural rather than visual hallucinations. Evidence from a rodent report suggests both 5HT1A and 5HT2A receptors mediate DPTs pharmacological furnishings, but the exact mechanism behind its unique psychoactive auditory upshot remains unknown [43].
The pharmacodynamic properties of the elementary 4-substituted tryptamines have non been studied. User reports of exposure to these substances illustrate like clinical effects to psilocin exposure, suggesting a similar mechanism of action. Psilocin is a partial 5HT2A agonist and has stimulatory furnishings at other serotonin receptors, just has little result at dopamine or noradrenergic receptors [4,25,45].
Uncomplicated five-substituted tryptamines inhibit monoamine reuptake, but appear to have minimal effect on monoamine release [44]. An in vitro study demonstrated 5-MeO-DiPTs ability to deed as a selective high affinity inhibitor of SERT, but did non produce serotonin release [27]. Simple 5-substituted tryptamines possess a methoxyl or hydroxyl grouping at position five of the tryptamine ring, increasing the potency of the molecule compared to its unsubstituted relation [46]. 5-MeO-DiPT is seven times more strong than DMT [47].
Although extracts of plants from the Convolvulaceae family containing alkaloids including ergine have been used as psychoactive substances for centuries, little is known virtually their pharmacodynamic properties. Ergines tryptamine ring structure, structural similarity to LSD and reported psychoactive effects suggest that 5-HT receptor agonism is the predominant pharmacodynamic effect [vi,48].
Mitragynine is a μ- and δ-opioid receptor agonist; even so, information technology is structurally similar to the alpha-2 receptor antagonist yohimbine and exhibits yohimbine-like binding to alpha-adrenergic receptors [9,49]. At low doses (ten–30 mg) users report predominantly stimulatory effects consequent with a possible yohimbine-like effect [fifty]. Mitragynine may also activate noradrenergic and serotonergic pathways in the spinal cord, block alpha-2 adrenergic receptors and stimulate 5-HT2A receptors [51,52]. Kratom, the plant containing mitragynine, also contains a number of additional alkaloids including 7-hydroxymitragyine that possess stiff opioid agonism. Recently it has been suggested that 7-hydroxymitragyine may be the predominant agile alkaloid within kratom, rather than mitragynine [53].
In summary the hallucinogenic effect of tryptamines appear to exist produced predominantly through agonism at 5HT2A receptors, although numerous other receptors including 5HT1A and 5HT2C are also likely to contribute. A number of 4-substituted tryptamines take greater noradrenergic effect, while potency is increased by substitution at position five on the tryptamine band. Pharmacodynamic properties of most of the designer synthetic recreational tryptamines have not been studied in item.
Positive or Desired Clinical Effects
Published substance-user reports on Cyberspace sites, including Erowid (http://www.erowid.org) and Drugs-Forum (http://www.drugs-forum.com), are the primary source of information regarding the positive furnishings experienced by users following use of these substances. Few published controlled studies exist. Although useful, these sites are subject to reporting bias and inability to accurately confirm exposure.
DMT, the archetypical tryptamine, offers an insight into the psychoactive properties of other tryptamines. In recreational doses DMT produces sudden onset of intense visual hallucinations [xi,14,43]. Sympathomimetic effects such as dilated pupils, tachycardia and hypertension are more prominent at lower doses [14,25]. Some users written report that the experience is more than intense than that post-obit LSD exposure [25].
Unlike DMT, constructed unsubstituted simple tryptamines are orally active. Smoking and nasal insufflation are likewise mutual methods of administration. Positive effects reported past users vary, just visual hallucinations are universal [25,26]. The exception is DiPT, which is unique in producing auditory distortion at lower doses and auditory hallucinations at higher doses [20,26]. AET and AMT have stimulatory furnishings at lower doses [18,19,26]. AET is described by users as having psychoactive properties similar to three,4-methylenedioxymethamphetamine (MDMA) [eighteen,26]. General positive effects reported past users of unsubstituted simple tryptamines include: 'rushing' sensation, both open and closed centre 'pleasant' visual hallucinations, increased mood, energy, libido, concentration and empathogenic qualities [25,26]. Oral doses, duration of activeness and characteristic positive effects of common synthetic simple unsubstituted tryptamines are summarised in Tabular array 15.1.
Constructed 4-substituted simple tryptamines are orally agile. User reports suggest synthetic 4-substituted unproblematic tryptamines produce clinical effects very similar to those mediated by psilocin [25]. Visual hallucinations predominate, with varying reports of other furnishings including euphoria, increased libido, increased energy and enhanced thought processes and appreciation of music [25,26,28–33]. Full general positive effects reported by users of 4-substituted simple tryptamines include: increased laughing, intense visual hallucinations, 'rushing' awareness, euphoria, increased libido, enhanced tactile sensations, increased concentration and a feeling of warmth and inner peace [25,26]. Oral doses, duration of action and characteristic positive effects of the more than mutual synthetic simple iv-substituted tryptamines are summarised in Table 15.2.
Tabular array fifteen.2. Constructed four-Substituted Elementary Tryptamines: Recreational Doses, Duration of Effect, Desired Clinical Effects
| Tryptamine | Oral Dose (mg) | Duration of Activeness (hours) | Desired Clinical Furnishings (Selected Only) |
|---|---|---|---|
| 4-HO-MET | x–0 [29] | 4–half-dozen [29] | Moving ridge-like pattern with distortion of colour/sound/course [26,29] Increased appreciation of music |
| iv-HO-DET | 10–v [30] | 4–6 [xxx] | Hallucinations like to those produced by LSD [26,30] |
| 4-HO-DiPT | xv–0 [31] | 2–iii [31] | Rapid onset, very brusque acting [31] Visual and auditory hallucinations |
| 4-HO-MiPT | 12–5 [32] | four–6 [32] | Increased mood, laughing, creative thinking, appetite, sexual interest, music appreciation. Reduced anxiety [32,54] |
| 4-Acetoxy-DMT | 10–0 [33] | 3–6 [33] | Increased energy, euphoria, colourful visual furnishings Abstruse, associative thought patterns [25,26,33] |
| 4-Acetoxy-DiPT | 15–0 [31] | 2–3 [31] | Gentle, less intense than other tryptamines [31,54] Enhanced sensuality, libido, increased appreciation of music |
4-HO-MET: 4-hydroxy-North-methyl-N-ethyltryptamine; 4-HO_DET: 4-hydroxy-Northward,Northward-diethyltryptamine; 4HO-DiPT: 4-hydroxy-di-isopropyltryptamine; iv-HO-MiPT: 4-hydroxy-N-methyl-North-isopropyltryptamine; 4-Acetoxy-DMT: four-acetoxy-N,N-dimethyltryptamine; 4-Acetoxy-DiPT: 4-acetoxy-N,N-diisopropylryptamine.
Although v-substituted unproblematic tryptamines are more potent than their unsubstituted cousins, clinical effects are similar to the unsubstituted molecule [iv,46]. Visual hallucinations are reported following exposure to all of the synthetic v-substituted simple tryptamines. Other positive reported effects include: intense 'rushing' sensation (when smoked), euphoria, increased libido, increased free energy, sexually 'interesting' interactions, increased concentration and sociability, a reduction in fear and anxiety, enhanced appreciation of music and food, and facilitation of 'life-changing spiritual experiences' [25,26,34,55,56]. Users of 5-MeO MiPT report marked increase in enjoyment obtained from tactile stimulation, and synaesthetic furnishings [25,26]. Oral doses, elapsing of action and positive effects of the synthetic simple 5-substituted tryptamines are summarised in Tabular array fifteen.iii.
Tabular array fifteen.3. Synthetic 5-Substituted Simple Tryptamines: Recreational Doses, Elapsing of Effect, Desired Clinical Effects
| Tryptamine | Oral Dose (mg) | Duration Activeness (hours) | Desired Clinical Effects (Selected Only) |
|---|---|---|---|
| 5-MeO-DMT | Smoked 6–20 [57] Insufflated 2–xv [57] | ane–2 [57] one–2 [57] |
|
| 5-MeO-AMT | ii.5–four.5 [58] | 12–18 [58] | Increased mood, energy, sociability, artistic thinking, sexual interest, laughing [45] |
| 5-MeO-DiPT | 6–12 [59] | iv–8 [59] | Emotionally opening, increased mood, libido, euphoria, improved self-conviction, reduced fearfulness/anxiety, enhancement of and appreciation for music [25,26] |
| 5-MeO-MiPT | 4–six [lx] | 4–6 [lx] | Increased tactile stimulation, synaesthetic effects, libido Increased appreciation of food, sound [26,43] |
| 5-MeO-DALT | 12–20 [61] | 2–4 [61] | Reduced visual hallucinations, just reported changes in perception of space and time [26] |
5-MeO-DMT: v-methoxy-dimethyltrptamine; five-MeO-AMT: v-methoxy-alpha-methyltrptamine; five-MeO-DiPT: 5-methoxy-diisopropyltrptamine; 5-MeO-MiPT: 5-methoxy-Due north-methyl-Due north-isopropyltrptamine; 5-MeO-DALT: N,Due north-diallyl-v-methoxytrptamine.
Leaves of the Mitragyna species (also known equally kratom) containing alkaloids including mitragynine and 7-hydroxymitragynine have been used as an opioid substitute, stimulant and antidiarrhoeal agent in Thailand and other areas of Southeast Asia for centuries [62]. Kratom has been advocated equally an offshoot to chronic pain therapy, and facilitator of reducing opioid dependence. Kratom users report mild caffeine similar stimulation at low does (2–4 g), with subtle calming opioid-like effects at higher doses (>5 thou). Others report simultaneous sedation and stimulation. Some users report very mild open and closed eye visual furnishings. Effects are dose dependent and begin 10–20 minutes after chewing the leaves and last 2–three hours. Kratom can likewise be smoked and brewed as a tea [62,63].
Argyreia nervosa is a climbing vine more commonly known as Hawaiian baby woodrose, which belongs to the morning glory family (Convolvulaceae). Seeds of Hawaiian babe woodrose contain psychoactive alkaloids including ergine [half-dozen]. Other members of the morning glory family also contain ergine within their seeds. Seeds are ingested with a typical dose being between 25 and 400 seeds depending on the species used and desired effect level. Onset of effect occurs in 20–xl minutes and full elapsing is 5–8 hours. Positive effects reported by users include: euphoria, increased mood, feeling of insight and date, closed and open eye visual hallucinations, increased sensual and aesthetic appreciation, and increased laughter [54].
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General Toxicologic Pathology
Wanda 1000. Haschek , ... Val R. Beasley , in Handbook of Toxicologic Pathology (2nd Edition), 2002
B. TOXICOLOGY
1. Toxins
Ergot alkaloids can be divided into ii structural groups: amino acrid alkaloids (e.g., ergotamine) and amine alkaloids and congeners (eastward.m., lysergic acid and ergonovine) (Fig. 17). Amino acrid alkaloids and amine alkaloids are derived from lysergic acid. Amino acrid alkaloids are the virtually physiologically active with ergotamine and ergocristine of greatest importance. Of amine alkaloids, ergonovine is amid the nearly potent. Amino acid alkaloids are potent vasoconstrictors and are highly oxytocic (stimulate uterine smoothen muscle) if given intravenously, but not orally. Amino acid alkaloids also inhibit nerves stimulated by sympathomimetic amines. Amine alkaloids are rapid acting, powerful oxytocics and weak vasoconstrictors. Lysergic acid diethylamide (LSD) causes depersonalization or hallucinations and may produce toxic psychosis.
Figure 17. Chemical structures of selected ergot alkaloids and dopamine. The structural similarity of ergot alkaloids to dopamine influences activeness at the dopamine receptor.
The toxic effects of Claviceps spp.-infected grains and grasses are due to numerous ergot alkaloids, such as ergotamine, ergocristine, and ergonovine, that are present in the sclerotia. Nigh or all of the toxicological problems associated with tall fescue are believed to be caused by endophyte-produced alkaloids, with amino acid alkaloids being primarily responsible. Ergovaline accounts for about 90% of the amino acid alkaloids in endophyte-infected fescue. Nonetheless, some questions regarding the identity of the toxin(s) causing endophyte-infected fescue toxicity still remain.
Ergovaline is believed to business relationship for the decrease in prolactin and other major effects of endophyte-infected fescue, most of which are compatible with the effect of ergot alkaloids (vasoconstrictive and dopamine agonist properties). Other ergot alkaloids include ergosine, ergonine, and lysergic acrid amide (ergine). Lysergic acid has sedative properties as well as effects on the autonomic nervous organisation, such as hypersalivation, emesis, dizziness, and diarrhea. Loline alkaloids are another course of alkaloids that originate from the endophyte in tall fescue. These are saturated pyrrolizidine alkaloids. Their part, if any, in fescue toxicoses is considered minor.
2. Biodistribution, Metabolism, and Excretion
Although ergot alkaloids disappear rapidly from blood and tissue, their physiologic effects persist for a long time. For example, ergotamine produces vasoconstriction that lasts for at least 24 hr despite a plasma half-life of near 2 hr. Ergotamine is absorbed poorly and erratically from the upper gastrointestinal tract with a high start-laissez passer clearance past the liver. Ergotamine is metabolized (detoxified) in the liver by cytochrome P450 enzymes with metabolites excreted primarily in the bile. Ergot alkaloids are not transferred in the milk of cows consuming ergot. Meat and milk residues have non been detected in whatsoever field outbreaks.
In humans, bioavailability depends on the route of administration, only tin besides vary widely when given repeatedly to the aforementioned patient. Bioavailability is <v% with oral formulations with peak plasma levels occurring at 1 to 3hr. Assimilation is considerably higher with rectal administration (as suppositories). LSD is absorbed rapidly after oral administration and is distributed widely. LSD crosses the claret—barrier easily and enters the brain, its target site of action.
iii. Mechanism of Activity
The wide spectrum of pharmacological activity of ergot alkaloids is, in general, attributed to their action as partial agonists and antagonists at adrenergic, dopaminergic, and tryptaminergic [besides chosen serotonin or serotonergic, e.m., 5-hydroxytryptamine (v-HT)] receptors. For instance, the marked effects of ergotamine on the cardiovascular organization are due to simultaneous peripheral vasoconstriction, depression of vasomotor centers, and peripheral adrenergic blockade. The spectrum of effects depends on the agent, species, tissue, and experimental or physiologic weather condition.
The principal effects of ergot alkaloids are due to deportment on the central nervous arrangement (cardinal/neurohormonal) and direct stimulation of polish muscle (peripheral). Primal neurohormonal effects are due to the structural similarity of ergot alkaloids to biogenic amines. Dopaminergic activity, through activation of D2-dopamine receptors in pituitary lactotrophs, can result in a reduction of prolactin secretion past the pituitary, which can reduce milk production. Other neuroendocrine compounds whose secretion is affected include epinephrine and norepinephrine, melatonin (secreted by the pineal gland), and serotonin. The resulting neurotransmitter imbalance affects growth, reproduction, and the ability to respond to seasonal changes in photoperiod and environmental temperature.
Peripheral effects include vasoconstriction, elevated blood pressure level, and damage to the capillary endothelium. Wrinkle of all smooth muscle, vascular and nonvascular, occurs independent of innervation or chemic mediators. Blood vessels in all vascular beds are constricted past the ergot alkaloids, but the larger arteries are most sensitive. Occlusion may be demonstrated by arteriograms. The overall result is ischemia of tissues perfused by the artery. It is possible for blood menstruation to exist reestablished without permanent damage or the tissue may go gangrenous. The limbs, toes, ears, and tail are often affected, just usually not all in the same creature. Occasionally, scattered areas of the skin may likewise become gangrenous.
During the third trimester of pregnancy, ergot alkaloids accept an oxytocin-like effect on the uterus and can induce labor, every bit uterine muscle is more sensitive to ergot at this fourth dimension than other smooth muscle. In early pregnancy, these alkaloids are more stimulatory to the cervix than to the uterus.
Various ergot alkaloids, including LSD, produce hallucinogenic effects. The toxic mechanism of LSD is likely related to perturbations of serotonergic neurotransmission, resulting in profound alterations in perception, mood, and judgement, as well every bit hallucinogenic effects in humans. This effect appears to be mediated by the activation of 5-HT1c receptors. Catecholaminergic stimulation also occurs, resulting in mydriasis, increased blood pressure, tachycardia, elevated trunk temperature, tremors, and hyperreflexia.
four. Species Susceptibility
Individual responses vary with the total corporeality and mixture of individual alkaloids in the feed, frequency of ingestion, climatic weather (cool, wet weather is associated with apparent increases in the risk of gangrenous lesions), and species. The gangrenous form tin can affect all domestic animals, birds, and humans. The extremities (nose, ears, tail, and limbs) are affected due to the vasoconstriction of arterioles and harm to capillary endothelium. The convulsive form can occur in cattle, horses, sheep, and humans, is manifested by convulsions and incoordination, and may be accompanied by lameness, difficulty in breathing, excessive salivation, and diarrhea. Reproductive effects are characterized by ballgame, loftier neonatal bloodshed, and reduced lactation or agalactia.
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Hallucinogenic drugs in pre-Columbian Mesoamerican cultures
F.J. Carod-Artal , in Neurología (English language Edition), 2015
Ololiuhqui
The convolvulaceae are a family of herbaceous ornamental plants with infundibular (bell-shaped) flowers. Unlike species have seeds containing different alkaloids of the LSD family, such as d -lysergic acid amide (ergine) and isoergine, which act as partial serotonergic agonists.
The seeds of Turbina corymbosa (ololiuhqui) and Ipomea violacea (tlilitzin) were consumed by the Maya and Aztec for their psychotropic effects on perception and emotions and to induce trance states. They were commonly used by Mixtec and Zapotec peoples in the state of Oaxaca, and they are used to this day past the local healers who conduct curative and divination ceremonies. Ololiuhqui is very common in Mexico, and it is a type of morning celebrity so named because its flowers close during the night to reopen in the morning. In Spanish, information technology is also known as quiebracajete blanco, or flor de la virgen, since information technology had religious connotations in the 16th century.
T. corymbosa has round coffee-coloured seeds, whereas those of Ipomea violacea are black and called badoh negro. These seeds are footing into pulverization and taken in water, and they induce sensory/perception alterations that include visual illusions, synaesthesia, euphoria, retentiveness changes, and detached somnolence. In its cultural context, in contrast with the practices associated with peyote or hallucinogenic mushroom use, ololiuhqui is well-nigh often taken alone with the healer. The first phase is marked by a psychic void, which is at times accompanied by vasovagal response and vertigo; some hours later on, this is followed by a catamenia of intense repose and sedation.
Ethnohistorical accounts of use of this institute date to the 16th century. During his journey through Oaxaca, court physician Francisco Hernández described how these seeds were used. He reported that a fully hallucinogenic dose contained 100-150 footing seeds dissolved in cold water. 16 In the chapter titled 'Some herbs with intoxicating effects', Fray Bernardino de Sahagún presented the following account of the psychoactive effects of ololiuhqui: xiv
"In that location is an herb named coatl xoxouhquij (light-green snake), and it grows a seed they call ololiuquj. This seed produces inebriation and madness. People mix information technology in potions to give to those they wish to impairment; those who eat information technology announced to come across visions and terrifying things. Sorcerers mix information technology with food and beverage, then exercise those who hate others and wish to do them ill. This herb is medicinal and its seed is used to treat gout; ground seeds are applied to the gout-stricken surface area."
The conquistadors before long associated these trance states and the hallucinogenic effect of the seeds with witchcraft and charlatanism, and they refused to recognise the religious and mystical significance of these ceremonies. In 1591, Juan de Cárdenas described the following in his chronicles of the Indies 17 :
"In sooth they tell usa that peyote, and ololiuhque, when taken by mouth, will cause the wretch who takes them to lose his wits then severely that he sees the devil among other terrible and fearsome apparitions; and he volition be warned (so they say) of things to come, and all this must be tricks and lies of Satanas, whose nature is to deceive, with divine permission, the wretch who on such occasions seeks him".
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Therapeutic potential of indole alkaloids in respiratory diseases: A comprehensive review
Saikat Mitra , ... Jesus Simal-Gandara , in Phytomedicine, 2021
Indole alkaloids
Alkaloids are the most significant secondary metabolites and accept been used for over 4000 years and due to their enormous therapeutic potential (Amirkia and Heinrich, 2014). In 1818, alkaloids were first described by Meissner, who employ the term to describe all organic molecules derive from establish sources that could be distinguished every bit presenting basic characteristics (Preininger, 1975 ). Alkaloids can be classified into many subgroups depending on their structures, including indoles, quinolines, isoquinolines, pyridines, pyrrolidines, pyrrolizidines, tropanes, steroids, and terpenoids. Among these various types of alkaloids, indole alkaloids represent a heterogeneous drove of nitrogen-containing molecules and many varieties of this form of alkaloid exist. Due to the myriad varieties that have been identified, many subsequent subgroups have since been differentiated, including yohimbans (reserpine, yohimbine, and deserpidine), strychnos alkaloids (strychnine, brucine, and vomicine), heteroyohimbans (ajmalicine and reserpine), vinca alkaloids (vinblastine, vincristine, and vinflunine), kratom alkaloids (mitragynine), ergolines/clavinet alkaloids (ergine, ergotamine, and lysergic acid), beta-carbolines (harmine and harmaline), tryptamines (psilocybin and serotonin), and Tabernanthe iboga alkaloids (ibogaine, coronaridine, and voacangine). These indole alkaloids tin can be constitute in species from over 30 botanical families, such every bit Apocynaceae, Passifloraceae, Loganiaceae, and Rubiaceae, in addition to fungi (Kukula-Koch and Widelski, 2017). Alstonia scholaris is a plant in the Apocynaceae family that is used in traditional medicine and is used to care for many respiratory diseases in China (Akbar, 2020). According to the natural products report, viii monoterpenoid indoles derived from Alstonia scholaris have been designated as "hot off the press" compounds (Cao et al., 2016). Moreover, after publishing the structures or bioactivities of potentially agile molecules, scientists have successfully synthesized 16 alkaloids. The metabolites and chemical profiles associated with Alstonia scholaris extracts were determined to include vallesamine, scholaricine, picrinine, and 19-epischolaricine, which were recognized as the primary indole alkaloids found in the constitute leaves (Zhao et al., 2020c). In addition to Alstonia scholaris, Catharanthus roseus is a well-recognized plant with meaning medicinal value that contains a variety of indole alkaloids, many of which are pharmaceutically relevant compounds. Vincristine and vinblastine, which were isolated from Catharanthus roseus, are normally used as anticancer chemotherapeutics. Another alkaloid, ajmalicine, has been shown to have anti-arrhythmia and antihypertensive activities, whereas catharanthine and vindoline displayed antibacterial activities, diuretic actions, and antidiabetic properties (Zhu et al., 2015). In improver, Rauwolfia (Rauwolfia serpentina), which belongs to the Apocynaceae family, is an evergreen shrub associated with over 100 species. These plants are native to subtropical and tropical areas of the world, including Asia, Europe, Australia, Africa, South and Primal America. All parts of this establish, including the leaves and stems, incorporate indole alkaloids, only the highest concentration of indole alkaloids has been found in the root bark. Established indole alkaloids found in this species of establish include ajmaline, aricine, coryanthine, canescine, deserpidine, isoserine, neoajmaline, papaverine, rauwolfinine, recanescine, reserpiline, reserpine, sarpagine, serpentine, yohimbine, and yohimbinine (Panwar and Guru, 2011). For decades, bioactive compounds derived from R. serpentina have been used in the practice of Indian traditional medicine to cure a multifariousness of ailments, including intestinal pain, insect and snake bites, dysentery, fever, and malaria. These compounds have likewise been used as a treatment option for fever, insanity, and as a uterine stimulant (Verma and Verma, 2010). Some other medicinal plant, Anthocephalus cadamba, belongs to the Rubiaceae family and is broadly distributed throughout Bangladesh, Republic of india, Thailand, Nepal, People's republic of china, Sri Lanka, Burma, Malaysia, and New Republic of guinea. Anthocephalus cadamba contains a substantial quantity of monoterpene indole compounds, including isodihydroamino cadambine, vallesiachotamine, iso-vallesiachotamine, vincosamide, cadambine, and dihydrocadambine (Dwevedi et al., 2015; Mishra et al., 2018). Anthocephalus cadamba has been used every bit traditional medicine since ancient times to care for several diseases, including fever, blood diseases, uterine complaints, anemia, diabetes mellitus, skin disorders, leprosy, diarrhea, inflammation, coughing, vomiting, hemoptysis, debility, and malaria, and contributes to improved wound-healing (Dubey et al., 2011). Anthrocphalus cadamba has been associated with numerous physiological activities, including antimicrobial, antidiarrheal, antidiabetic, antibacterial, antihepatotoxic, anticancer, and antioxidant activities. Among all known indole alkaloids, vincristine and vinblastine (antitumor leads) from Catharanthus roseus (El-Sayed and Verpoorte, 2007) and reserpine (an antihypertensive agent) from Rauvolfia serpentine (Lobay, 2015; Sagi et al., 2016b) had been the most clinically relevant compounds thus far. Other compounds besides possess essential and potential bioactivities, such as antimicrobial, antiviral, fundamental nervous system stimulation, and antifungal properties. Interestingly, marine-derived indole alkaloids have been very promising and announced to confer significant pharmacological activities. These compounds act as antiparasitic, antiviral, anti-inflammatory, cytotoxic, and serotonergic agents, and antagonistic realms (Gul and Hamann, 2005). The indole-containing alkaloid dragmacidin D inhibits the growth of some gram-negative and gram-positive microbes, including Bacillus subtilis and Escherichia coli. Dragmacidin D can likewise inhibit the growth of various opportunistic yeasts, including Candida albicans, Candida aeruginosa, and Candida neoformans (Dey et al., 2020). Makaluvamine G has moderate inhibitory activity confronting topoisomerase I and can inhibit the activity of Dna and protein (Dey et al., 2020).
To date, most experimental studies on indole alkaloids have aimed to appraise their potential to treat diseases related to respiratory organs. Vinorelbine (Simoens et al., 2008), vinflunine (Simoens et al., 2008), vobtusine, jerantinine (Abubakar and Loh, 2019), and vincristine are among the well-nigh prominent indole alkaloidal compounds that have demonstrated promising cytotoxic activities confronting the A549 lung cancer cell line. Generally, these compounds accumulate intracellularly, following active transporter-mediated uptake, and prevent progression from varying phases of the cell bicycle, leading to cellular apoptosis. In addition to this anticancer activity, other indole alkaloids, such every bit evodiamine (Chen et al., 2018) and olivacine (Schmidt et al., 2018), take revealed noteworthy antimicrobial backdrop confronting Mycobacterium tuberculosis and Staphylococcus aureus, whereas arvelexin (Shin et al., 2011) and eudistomins C and E (Zhang et al., 2015) displayed antiviral potential confronting RNA viruses, including coxsackievirus A-21, equine rhinovirus, and influenza virus A. Arvelexin can inhibit nuclear factor (NF)-κB-induced inflammatory responses past modulating a series of intracellular events associated with the IκB kinase (IKK)–inhibitor κBα (IκBα)–NF-κB signaling pathway. Arvelexin can also inhibit IKKβ-elicited NF-κB activation, in addition to inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX-two) expression (Shin et al., 2011). Thus, the indole alkaloid compounds are used as remedies for respiratory diseases, including tuberculosis, pneumonia, influenza, and the common common cold. Picrinine, scholaricine, 19-epischolaricine, and vallesamine have shown significant potency in the handling of respiratory diseases, including lung emphysema (Zhao et al., 2020c), asthma (Pandey et al., 2020), and acute respiratory infections (ARIs) (Zhao et al., 2021a).
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https://www.sciencedirect.com/science/article/pii/S0944711321001926
Source: https://www.sciencedirect.com/topics/medicine-and-dentistry/ergine
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