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Iboga Alkaloid
Iboga alkaloids are alkaloid constituents of ''Tabernanthe iboga''. Iboga alkaloids include ibogaine, tabernanthine, coronaridine, voacangine, ibogamine, and harmaline, among others. Noribogaine is a major active metabolite of ibogaine, and 18-methoxycoronaridine 18-Methoxycoronaridine (18-MC, or MM-110) is a derivative of ibogaine invented in 1996 by the research team around the pharmacologist Stanley D. Glick from the Albany Medical College and the chemists Upul K. Bandarage and Martin E. Kuehne fro ... is a synthetic derivative of coronaridine. References {{alkaloid-stub ...
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Alkaloid
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and, more rarely, other elements such as chlorine, bromine, and phosphorus.Chemical Encyclopedia: alkaloids
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Alkaloids are produced by a large variety of organisms including , , Medicinal plant, plants, an ...
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Tabernanthe Iboga
''Tabernanthe iboga'' (iboga) is an evergreen rainforest shrub native to Central Africa. A member of the Apocynaceae family indigenous to Gabon, the Democratic Republic of Congo, and the Republic of Congo, it is cultivated across Central Africa for its medicinal and other effects. In African traditional medicine and rituals, the yellowish root or bark is used to produce hallucinations and near-death outcomes, with some fatalities occurring. In high doses, ibogaine is considered to be toxic, and has caused serious comorbidities when used with opioids or prescription drugs. The United States Drug Enforcement Administration (DEA) lists ibogaine as a controlled substance of the Controlled Substances Act. Description Iboga is native to tropical forests, preferring moist soil in partial shade. It bears dark green, narrow leaves and clusters of white tubular flowers on an erect and branching stem, with yellow-orange fruits resembling Chili pepper , Normally growing to a height of ...
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Ibogaine
Ibogaine is a naturally occurring psychoactive substance found in plants in the family Apocynaceae such as ''Tabernanthe iboga'', ''Voacanga africana'', and ''Tabernaemontana undulata''. It is a psychedelic with dissociative properties. Preliminary research indicates that it may help counter drug addiction. Its use has been associated with serious side effects and death. Between the years 1990 and 2008, a total of 19 fatalities temporally associated with the ingestion of ibogaine were reported, from which six subjects died of acute heart failure or cardiopulmonary arrest. The total number of subjects who have used it without major side effects during this period remains unknown. It is used as an alternative medicine treatment for drug addiction in some countries. Its prohibition in other countries has slowed scientific research. Ibogaine is also used to facilitate psychological introspection and spiritual exploration. Various derivatives of ibogaine designed to lack psychedel ...
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Tabernanthine
Tabernanthine is an alkaloid found in ''Tabernanthe iboga''. It has been used in laboratory experiments to study how addiction affects the brain. Tabernanthine persistently reduced the self-administration of cocaine and morphine in rats. Pharmacology It is kappa opioid agonist (Ki = 0.15 μM) and NMDA receptor (Ki = 10.5 μM) antagonist. Compared to ibogaine, it binds weakly to σ1 and σ2 receptor. See also * Coronaridine * Ibogamine * Voacangine Voacangine (12-methoxyibogamine-18-carboxylic acid methyl ester) is an alkaloid found predominantly in the root bark of the ''Voacanga africana'' tree, as well as in other plants such as ''Tabernanthe iboga'', ''Tabernaemontana africana'', ''Trach ... * Tabernaemontanine * Tabernanthalog References Alkaloids found in Iboga NMDA receptor antagonists Azepines Quinuclidine alkaloids Tryptamine alkaloids {{nervous-system-drug-stub ...
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Coronaridine
Coronaridine, also known as 18-carbomethoxyibogamine, is an alkaloid found in ''Tabernanthe iboga'' and related species, including ''Tabernaemontana divaricata'' for which (under the now obsolete synonym ''Ervatamia coronaria'') it was named. Like ibogaine, (''R'')-coronaridine and (''S'')-coronaridine can decrease intake of cocaine and morphine intake in animals and it may have muscle relaxant and hypotensive activity. Chemistry Congeners Coronaridine congers are important in drug discovery and development due to multiple actions on different targets. They have ability to inhibit Cav2.2 channel, modulate and inhibit subunits of nAChr selectively such as α9α10, α3β4 and potentiate GABAA activity. Pharmacology Coronaridine has been reported to bind to an assortment of molecular sites, including: μ-opioid (Ki = 2.0 μM), δ-opioid (Ki = 8.1 μM), and κ-opioid receptors (Ki = 4.3 μM), NMDA receptor (Ki = 6.24 μM) (as an antagonist), and nAChRs (as an antagonist). It h ...
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Voacangine
Voacangine (12-methoxyibogamine-18-carboxylic acid methyl ester) is an alkaloid found predominantly in the root bark of the ''Voacanga africana'' tree, as well as in other plants such as ''Tabernanthe iboga'', ''Tabernaemontana africana'', ''Trachelospermum jasminoides'', ''Tabernaemontana divaricata'' and ''Ervatamia yunnanensis''. It is an iboga alkaloid which commonly serves as a precursor for the semi-synthesis of ibogaine. It has been demonstrated in animals to have similar anti-addictive properties to ibogaine itself. It also potentiates the effects of barbiturates. Under UV-A and UV-B light its crystals fluoresce blue-green, and it is soluble in ethanol. Pharmacology Pharmacodynamics Voacangine exhibits AChE inhibitory activity. Docking simulation reveals that it has inhibitory effect on VEGF2 kinase and reduces angiogenesis. Like ibogaine, its a potent HERG blocker in vitro. It also acts as antagonist to TRPM8 and TRPV1 receptor but agonist of TRPA1. Pharmacokinetics The a ...
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Ibogamine
Ibogamine is an anti-convulsant, anti-addictive, CNS stimulant alkaloid found in ''Tabernanthe iboga'' and Crepe Jasmine (''Tabernaemontana divaricata''). Basic research related to how addiction affects the brain has used this chemical. Ibogamine persistently reduced the self-administration of cocaine and morphine in rats. The same study found that ibogamine (40 mg/kg) and coronaridine (40 mg/kg) did not produce "any tremor effects in rats that differ significantly from saline control". While the related alkaloids ibogaine (20–40 mg/kg), harmaline (10–40 mg/kg) and desethylcoronaridine (10–40 mg/kg) were "obviously tremorgenic". Chemistry Synthesis Ibogamine can be prepared from one-step demethoxycarbonylation process through coronaridine. Pharmacology Like ibogaine, it has seems to have similar pharmacology. It has effects on KOR, NMDAR, nAChR and serotonin sites. It also inhibits acetylcholinesterase and butyrylcholinesterase See also ...
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Harmaline
Harmaline is a fluorescent indole alkaloid from the group of harmala alkaloids and beta-carbolines. It is the partly hydrogenated form of harmine. Occurrence in nature Various plants contain harmaline including ''Peganum harmala'' (Syrian rue) as well as the hallucinogenic beverage ayahuasca, which is traditionally brewed using ''Banisteriopsis caapi''. Present at 3% by dry weight, the harmala alkaloids may be extracted from the Syrian rue seeds. Effects Harmaline is a central nervous system stimulant and a "reversible inhibitor of MAO-A (RIMA)". This means that the risk of a hypertensive crisis, a dangerous high blood pressure crisis from eating tyramine-rich foods such as cheese, is likely lower with harmaline than with irreversible MAOIs such as phenelzine. The harmala alkaloids are psychoactive in humans. Harmaline is shown to act as an acetylcholinesterase inhibitor. Harmaline also stimulates striatal dopamine release in rats at very high dose levels. Since harmal ...
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Noribogaine
Noribogaine (actually O-desmethylibogaine), or 12-hydroxyibogamine, is the principal psychoactive metabolite of the oneirogen ibogaine. It is thought to be involved in the antiaddictive effects of ibogaine-containing plant extracts, such as ''Tabernanthe iboga''. Pharmacology Noribogaine is a potent serotonin reuptake inhibitor, but does not affect the reuptake of dopamine. Unlike ibogaine, noribogaine does not bind to the sigma-2 receptor. Similarly to ibogaine, noribogaine acts as a weak NMDA receptor antagonist and binds to opioid receptors. It has greater affinity for each of the opioid receptors than does ibogaine. Noribogaine is a hERG inhibitor and appears at least as potent as ibogaine. The inhibition of the hERG potassium channel delays the repolarization of cardiac action potentials, resulting in QT interval prolongation and, subsequently, in arrhythmias and sudden cardiac arrest. κ-Opioid receptor Noribogaine has been determined to act as a biased agonist of th ...
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Active Metabolite
An active metabolite is an active form of a drug after it has been processed by the body. Metabolites of drugs An active metabolite results when a drug is metabolized by the body into a modified form which continues to produce effects in the body. Usually these effects are similar to those of the parent drug but weaker, although they can still be significant (see e.g. 11-hydroxy-THC, morphine-6-glucuronide). Certain drugs such as codeine and tramadol have metabolites (morphine and ''O''-desmethyltramadol respectively) that are stronger than the parent drug and in these cases the metabolite may be responsible for much of the therapeutic action of the parent drug. Sometimes, however, metabolites may produce toxic effects and patients must be monitored carefully to ensure they do not build up in the body. This is an issue with some well-known drugs, such as pethidine (meperidine) and dextropropoxyphene. Prodrugs Sometimes drugs are formulated in an inactive form that is designe ...
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18-methoxycoronaridine
18-Methoxycoronaridine (18-MC, or MM-110) is a derivative of ibogaine invented in 1996 by the research team around the pharmacologist Stanley D. Glick from the Albany Medical College and the chemists Upul K. Bandarage and Martin E. Kuehne from the University of Vermont. In animal studies it has proved to be effective at reducing self-administration of morphine, cocaine, methamphetamine, nicotine and sucrose. It has also been shown to produce anorectic effects in obese rats, most likely due to the same actions on the reward system which underlie its anti-addictive effects against drug addiction. 18-MC was in the early stages of human testing by the California-based drug development company Savant HWP before being acquired by MindMed, a Canadian pharmaceutical company newly listed on the NASDAQ in April 2021.
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Iboga Alkaloids
Iboga alkaloids are alkaloid constituents of ''Tabernanthe iboga''. Iboga alkaloids include ibogaine, tabernanthine, coronaridine, voacangine, ibogamine, and harmaline, among others. Noribogaine is a major active metabolite of ibogaine, and 18-methoxycoronaridine 18-Methoxycoronaridine (18-MC, or MM-110) is a derivative of ibogaine invented in 1996 by the research team around the pharmacologist Stanley D. Glick from the Albany Medical College and the chemists Upul K. Bandarage and Martin E. Kuehne fro ... is a synthetic derivative of coronaridine. References {{alkaloid-stub ...
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