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Voacamine
Voacamine, also known under the older names voacanginine and vocamine, is a naturally occurring dimeric indole alkaloid of the secologanin type, found in a number of plants, including ''Voacanga africana'' and ''Tabernaemontana divaricata''. It is approved for use as an antimalarial drug in several African countries. Voacamine exhibits cannabinoid CB1 receptor antagonistic activity. Chemistry Structure There is considerable confusion about the absolute stereochemical configuration of voacamine and the originally published absolute structure had to be later revised. It has an ibogaine unit joined with vobasine unit. Adverse Effect Voacamine can cause hypertension in high dose. See also * Vincamine * 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'', '' Tra ... * Vobtusine R ...
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Indole Alkaloid
Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids. History The action of some indole alkaloids has been known for ages. Aztecs used the psilocybin mushrooms which contain alkaloids psilocybin and psilocin. The flowering plant ''Rauvolfia serpentina'' which contains reserpine was a common medicine in India around 1000 BC. Africans used the roots of the perennial rainforest shrub Iboga, which contain ibogaine, as a stimulant. An infusion of Calabar bean seeds was given to people accused of crime in Nigeria: its rejection by stomach was regarded as a sign of ...
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Indole Alkaloids
Indole alkaloids are a class of alkaloids containing a Moiety (chemistry), structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids. History The action of some indole alkaloids has been known for ages. Aztecs used the psilocybin mushrooms which contain alkaloids psilocybin and psilocin. The flowering plant ''Rauvolfia serpentina'' which contains reserpine was a common medicine in India around 1000 BC. Africans used the roots of the perennial rainforest shrub Tabernanthe iboga, Iboga, which contain ibogaine, as a stimulant. An infusion of Calabar bean seeds was given to people accused of crime in Nigeria: its rejection by s ...
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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 ...
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Vobtusine
Vobtusine is an alkaloid found in several different plants in the genus ''Voacanga''. See also *Apparicine * Affinisine *Voacamine *Lochnericine Lochnericine is an indole alkaloid present in the roots of ''Catharanthus roseus''. It is also present in ''Tabernaemontana divaricata''. Chemistry Synthesis Lochnericine is formed from stereoselective epoxidation of carbons 6 and 7 of tabers ... References {{Reflist Indole alkaloids Alkaloids found in Apocynaceae ...
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Dimer (chemistry)
In chemistry, dimerization is the process of joining two identical or similar Molecular entity, molecular entities by Chemical bond, bonds. The resulting bonds can be either strong or weak. Many symmetrical chemical species are described as dimers, even when the monomer is unknown or highly unstable. The term ''homodimer'' is used when the two subunits are identical (e.g. A–A) and ''heterodimer'' when they are not (e.g. A–B). The reverse of dimerization is often called Dissociation (chemistry), dissociation. When two oppositely-charged ions associate into dimers, they are referred to as ''Bjerrum pairs'', after Danish chemist Niels Bjerrum. Noncovalent dimers Anhydrous carboxylic acids form dimers by hydrogen bonding of the acidic hydrogen and the carbonyl oxygen. For example, acetic acid forms a dimer in the gas phase, where the monomer units are held together by hydrogen bonds. Many OH-containing molecules form dimers, e.g. the water dimer. Dimers that form based on w ...
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Secologanin
Secologanin is a secoiridoid monoterpene synthesized from geranyl pyrophosphate in the mevalonate pathway. Secologanin then proceeds with dopamine or tryptamine to form ipecac and terpene indole alkaloids, respectively. Biosynthesis Secologanin biosynthesis begins from geranyl pyrophosphate (GPP) taken from the mevalonate pathway used to make terpenoid The terpenoids, also known as isoprenoids, are a class of naturally occurring organic compound, organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeabl ...s. Recent efforts have characterized the entire secologanin biosynthetic pathway. Secologanin is formed from loganin through the action of the enzyme secologanin synthase. Secologanin is then able to proceed onto produce ipecac and terpene indole alkaloids. References {{Reflist Glucosides Methyl esters Aldehydes Vinyl compounds ...
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Voacanga Africana
''Voacanga'' is a genus of plants in the family Apocynaceae found in Africa, Southeast Asia, New Guinea, and Australia. the World Checklist of Selected Plant Families recognises 13 species:Search for "Voacanga", ;Species # ''Voacanga africana'' Otto Stapf (botanist), Stapf ex George Francis Scott-Elliot, Scott-Elliot - tropical W + C + E + S Africa # ''Voacanga bracteata'' Stapf - tropical W + C Africa # ''Voacanga caudiflora'' Stapf - tropical W Africa # ''Voacanga chalotiana'' Jean Baptiste Louis Pierre, Pierre ex Stapf - tropical C Africa # ''Voacanga foetida'' (Carl Ludwig Blume, Blume) Robert Allen Rolfe, Rolfe -Java, Borneo, Sumatra, Philippines # ''Voacanga globosa'' (Francisco Manuel Blanco, Blanco) Elmer Drew Merrill, Merr. - Philippines # ''Voacanga gracilipes'' (Friedrich Anton Wilhelm Miquel, Miq.) Friedrich Markgraf, Markgr. - Maluku # ''Voacanga grandifolia'' (Miq.) Rolfe - Indonesia, Philippines, New Guinea, Queensland # ''Voacanga havilandii'' Henry Nicholas Rid ...
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Tabernaemontana Divaricata
''Tabernaemontana divaricata'', commonly called pinwheel flower, crape jasmine, East India rosebay, and Nero's crown, is an evergreen shrub or small tree native to South Asia, Southeast Asia and China. In zones where it is not hardy it is grown as a house/glasshouse plant for its attractive flowers and foliage. The stem exudes a milky latex when broken, whence comes the name milk flower Description The plant generally grows to a height of and is dichotomously branched. The large shiny leaves are deep green and about in length and in width. The waxy blossoms are found in small clusters on the stem tips. The (single) flowers have the characteristic 'pinwheel' shape also seen in other genera in the family Apocynaceae such as '' Vinca'' and '' Nerium''. Both single and double-flowered forms are cultivated, the flowers of both forms being white. The plant blooms in spring but flowers appear sporadically all year. The flowers have a pleasing fragrance. More than 66 alkaloids are ...
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Antimalarial Drug
Antimalarial medications or simply antimalarials are a type of antiparasitic chemical agent, often naturally derived, that can be used to treat or to prevent malaria, in the latter case, most often aiming at two susceptible target groups, young children and pregnant women. As of 2018, modern treatments, including for severe malaria, continued to depend on therapies deriving historically from quinine and artesunate, both parenteral (injectable) drugs, expanding from there into the many classes of available modern drugs. Incidence and distribution of the disease ("malaria burden") is expected to remain high, globally, for many years to come; moreover, known antimalarial drugs have repeatedly been observed to elicit resistance in the malaria parasite—including for combination therapies featuring artemisinin, a drug of last resort, where resistance has now been observed in Southeast Asia. As such, the needs for new antimalarial agents and new strategies of treatment (e.g., new com ...
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Cannabinoid
Cannabinoids () are several structural classes of compounds found primarily in the ''Cannabis'' plant or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tetrahydrocannabinol (THC) (delta-9-THC), the primary psychoactive compound in Cannabis (drug), cannabis. Cannabidiol (CBD) is also a major constituent of temperate cannabis plants and a minor constituent in tropical varieties. At least 100 distinct phytocannabinoids have been isolated from cannabis, although only four (i.e., THCA, CBDA, CBCA and their common precursor CBGA) have been demonstrated to have a biogenetic origin. It was reported in 2020 that phytocannabinoids can be found in other plants such as rhododendron, licorice and liverwort, and earlier in Echinacea. Phytocannabinoids are multi-ring phenolic compounds structurally related to THC, but endocannabinoids are fatty acid derivatives. Nonclassical synthetic cannabinoids (cannabimimetics) include aminoalkylindoles, 1,5-diarylpyrazoles, qu ...
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Cannabinoid Receptor Type 1
Cannabinoid receptor 1 (CB1), is a G protein-coupled cannabinoid receptor that in humans is encoded by the ''CNR1'' gene. And discovered, by determination and characterization in 1988, and cloned in 1990 for the first time. The human CB1 receptor is expressed in the peripheral nervous system and central nervous system. It is activated by endogenous cannabinoids called endocannabinoids, a group of retrograde neurotransmitters that include lipids, such as anandamide and 2-arachidonoylglycerol; plant phytocannabinoids, such as docosatetraenoylethanolamide found in wild dagga, the compound tetrahydrocannabinol which is an active constituent of the psychoactive drug cannabis; and synthetic analogs of tetrahydrocannabinol. CB1 is antagonized by the phytocannabinoid tetrahydrocannabivarin at low doses and at higher doses, it activates the CB1 receptor as an agonist, but with less potency than tetrahydrocannabinol. The primary endogenous agonist of the human CB1 receptor ...
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Cannabinoid Receptor Antagonist
A cannabinoid receptor antagonist, also known simply as a cannabinoid antagonist or as an anticannabinoid, is a type of cannabinoidergic drug that binds to cannabinoid receptors (CBR) and prevents their activation by endocannabinoids. They include antagonists, inverse agonists, and antibodies of CBRs. The discovery of the endocannabinoid system led to the development of CB1 receptor antagonists. The first CBR inverse agonist, rimonabant, was described in 1994. Rimonabant blocks the CB1 receptor selectively and has been shown to decrease food intake and regulate body-weight gain. The prevalence of obesity worldwide is increasing dramatically and has a great impact on public health. The lack of efficient and well-tolerated drugs to cure obesity has led to an increased interest in research and development of CBR antagonists. Cannabidiol (CBD), a naturally occurring cannabinoid and a non-competitive CB1/CB2 receptor antagonist, as well as Δ9-tetrahydrocannabivarin (THCV), a naturally ...
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