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Harmaline
Harmaline, also known as 7-methoxyharmalan or as 3,4-dihydro-7-methoxy-1-methyl-β-carboline, is a fluorescent indole alkaloid from the group of harmala alkaloids and β-carbolines. It is the partly hydrogenated form of harmine. It is a reversible monoamine oxidase inhibitor (RIMA). It produces vivid dream-like visual effects and physical discomfort at oral doses of 300 to 400mg, often leading users to seek solitude in a quiet, dark environment. Plants containing harmaline are combined in ayahuasca to inhibit monoamine oxidase, allowing orally ingested DMT to remain active in the brain and produce psychoactive effects. Harmala alkaloids, including harmaline, are psychoactive on their own in humans, with harmaline being particularly hallucinogenic, although other compounds such as harmine and tetrahydroharmine have also been reported to produce hallucinogenic effects as well. Harmaline exhibits weak affinity for 5-HT2A and 5-HT2C receptors, partially substitutes for the ...
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6-methoxyharmalan
6-Methoxyharmalan, or 6-methoxyharmalane, also known as 6-methoxy-1-methyl-3,4-dihydro-β-carboline, is a naturally occurring serotonin receptor modulator, monoamine oxidase inhibitor, and hallucinogen of the β-carboline family related to harmaline (7-methoxyharmalan). It is a cyclized tryptamine and analogue of 5-MeO-DMT and melatonin (''N''-acetyl-5-methoxytryptamine). The compound has been isolated from '' Virola'' species. Use and effects 6-Methoxyharmalan has been reported to be hallucinogenic in humans at a dose of 1.5mg/kg (~100mg) orally, with slightly (1.5-fold) greater potency than harmaline. Its onset of action via oral administration is about 1hour. The drug also produces hallucinogenic effects at a dose of 1mg/kg intravenously and with a near-immediate onset by this route. Its hallucinogenic effects are described as similar to those of harmaline. The hallucinogenic effects of β-carbolines like harmaline and 6-methoxyharmalan have been described as qualitatively ...
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Substituted β-carboline
A substituted β-carboline is a chemical compound featuring a β-carboline moiety (chemistry), moiety with one or more chemical substituent, substitutions. β-Carbolines include more than one hundred alkaloids and synthetic compounds. The effects of these substances depend on their respective substituent. Natural β-carbolines primarily influence brain functions but can also exhibit antioxidant effects. Synthetically designed β-carboline Derivative (chemistry), derivatives have recently been shown to have Neuroprotection, neuroprotective, Neuroenhancement, cognitive enhancing and anti-cancer properties. β-Carbolines are indole alkaloids featuring a fused pyridine and indole ring structure similar to tryptamine, forming a three-ringed system with variable saturation in the third ring. β-Carboline alkaloids naturally occur widely in prokaryotes, plants, animals, certain marine tunicates, and foods like coffee and smoked meats, and are also responsible for the fluorescence of sco ...
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Harmine
Harmine is a β-carboline and a harmala alkaloid. It occurs in a number of different plants, most notably ''Peganum harmala'' and ''Banisteriopsis caapi''. Harmine reversibly inhibits monoamine oxidase A (MAO-A), an enzyme which breaks down monoamines, making it a reversible inhibitor of monoamine oxidase A (RIMA). Harmine does not inhibit MAO-B. Harmine is also known as banisterin, banisterine, telopathin, telepathine, leucoharmine and yagin, yageine. The biosynthesis of harmine likely begins with L-tryptophan, which is decarboxylated to tryptamine—an intermediate also used in serotonin synthesis—before undergoing a series of reactions to form harmine, with feeding experiments supporting tryptamine’s role as an intermediate rather than a primary precursor. It is essential for enabling the oral activity of DMT in ayahuasca and is also used as a fluorescent pH indicator and in PET imaging to study MAO-A-related brain disorders. Pharmaceutical-grade harmine hydrochloride i ...
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Tetrahydroharmine
Tetrahydroharmine (THH) is a fluorescent indole alkaloid and β-carboline that occurs in the tropical liana species ''Banisteriopsis caapi''. Effects THH has been reported to produce psychoactive effects similar to those of harmaline in humans. It has been reported to be about one-third as potent as harmaline at a dose of 300mg orally. THH is believed to be one of the constituents of ''Banisteriopsis caapi'' responsible for the hallucinogenic effects of the plant. Pharmacology THH, like other harmala alkaloids in ''B. caapi'', namely harmaline and harmine, is a reversible inhibitor of monoamine oxidase A (RIMA), but it also inhibits the reuptake of serotonin. THH contributes to ''B. caapi'''s psychoactivity as a serotonin reuptake inhibitor. In contrast to other β-carbolines, THH shows minimal affinity for the serotonin 5-HT2A receptor (Ki = >10,000nM for racemic THH and ''R''(+)-THH, Ki = 5,890nM for ''S''(–)-THH). Similarly, THH shows negligible affinity for the ...
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Harmala Alkaloid
Harmala alkaloids are several alkaloids that act as monoamine oxidase inhibitors (MAOIs). These alkaloids are found in the seeds of ''Peganum harmala'' (also known as harmal or Syrian rue), as well as ''Banisteriopsis caapi'' (ayahuasca), leaves of tobacco and coffee beans. The alkaloids include harmine, harmaline, harmalol, and their derivatives, which have similar chemical structures, hence the name "harmala alkaloids". These alkaloids are of interest for their use in Amazonian shamanism, where they are derived from other plants. Harmine, once known as telepathine and banisterine, is a naturally occurring substituted β-carboline, β-carboline alkaloid that is structurally related to harmaline, and also found in the vine ''Banisteriopsis caapi''. Tetrahydroharmine is also found in ''B. caapi'' and ''P. harmala''. Dr. Alexander Shulgin has suggested that harmine may be a breakdown product of harmaline. Harmine and harmaline are reversible inhibitors of monoamine oxidase A (RIMA ...
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Ayahuasca
AyahuascaPronounced as in the UK and in the US. Also occasionally known in English as ''ayaguasca'' (Spanish-derived), ''aioasca'' (Brazilian Portuguese-derived), or as ''yagé'', pronounced or . Etymologically, all forms but ''yagé'' descend from the compound Quechua word ''ayawaska'', from ''aya'' () and ''waska'' (). For more names for ayahuasca, see § Etymology. is a South American psychoactive decoction prepared from '' Banisteriopsis caapi'' vine and a dimethyltryptamine (DMT)-containing plant, used by Indigenous cultures in the Amazon and Orinoco basins as part of traditional medicine and shamanism. The word ayahuasca, originating from Quechuan languages spoken in the Andes, refers both to the ''B. caapi'' vine and the psychoactive brew made from it, with its name meaning “spirit rope” or “liana of the soul.” The specific ritual use of ayahuasca was widespread among Indigenous groups by the 19th century, though its precise origin is uncertain. Ayahuasca ...
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6-methoxytetrahydroharman
6-MeO-THH, also known as 6-methoxy-1,2,3,4-tetrahydroharman, is a β-carboline (or more specifically a pinoline) derivative and a structural isomer of tetrahydroharmine (7-MeO-THH). It is mentioned in Alexander Shulgin's book ''TiHKAL'' (''Tryptamines I Have Known and Loved''), stating that 6-MeO-THH is very similar to the other carbolines. The compound has been isolated from certain plants of the ''Virola'' family. Effects 6-MeO-THH is reported to be hallucinogenic similarly to other β-carbolines like harmaline. Limited testing suggests that it possesses mild psychoactive effects at a dose of 1.5mg/kg orally and is said to be about one-third as potent as 6-methoxyharmalan and three times as potent as harmaline. Pharmacology Very little is known about the psychoactivity of 6-MeO-THH in humans. Studies in rats have shown it to bind to a number of serotonin 5-HT1 receptors and 5-HT2 receptors, dopamine D2 receptors, benzodiazepine receptors, and imidazoline receptors. S ...
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Peganum Harmala
''Peganum harmala'', commonly called wild rue, Syrian rue, African rue, esfand or espand,Mahmoud OmidsalaEsfand: a common weed found in Persia, Central Asia, and the adjacent areasEncyclopædia Iranica Vol. VIII, Fasc. 6, pp. 583–584. Originally published: 15 December 1998. Online version last updated 19 January 2012 or harmel (among other similar pronunciations and spellings), is a perennial, herbaceous plant, with a woody underground rootstock, of the family (biology), family Nitrariaceae, usually growing in saline soils in Desert#Classification, temperate desert and Mediterranean climate, Mediterranean regions. Its common English-language name came about because of a resemblance to rue (to which it is not related). Its seeds contain a high concentration (at least 5.9% by weight) of diverse beta-carboline alkaloids. It has deep roots and a strong smell, finely divided leaves, white flowers rich in alkaloids, and small Capsule (fruit), seed capsules containing numerous dark, ...
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Dimethyltryptamine
Dimethyltryptamine (DMT), also known as ''N'',''N''-dimethyltryptamine (''N'',''N''-DMT), is a Psychedelic drug, serotonergic hallucinogen and Investigational New Drug, investigational drug of the substituted tryptamine, tryptamine family that natural product, occurs naturally in many plants and animals, including humans. DMT is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen. DMT has a rapid onset of action, onset, intense effects, and a relatively short duration of action. For those reasons, DMT was known as the "businessman's trip" during the 1960s in the United States, as a user could access the full depth of a psychedelic experience in considerably less time than with other substances such as Lysergic acid diethylamide, LSD or psilocybin mushrooms. DMT can be inhaled or injected and its effects depend on the dose, as well as the mode of administration. When inhaled or injected, the effects last about five to fifteen minutes ...
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N,N-Dimethyltryptamine
Dimethyltryptamine (DMT), also known as ''N'',''N''-dimethyltryptamine (''N'',''N''-DMT), is a serotonergic hallucinogen and investigational drug of the tryptamine family that occurs naturally in many plants and animals, including humans. DMT is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen. DMT has a rapid onset, intense effects, and a relatively short duration of action. For those reasons, DMT was known as the "businessman's trip" during the 1960s in the United States, as a user could access the full depth of a psychedelic experience in considerably less time than with other substances such as LSD or psilocybin mushrooms. DMT can be inhaled or injected and its effects depend on the dose, as well as the mode of administration. When inhaled or injected, the effects last about five to fifteen minutes. Effects can last three hours or more when orally ingested along with a monoamine oxidase inhibitor (MAOI), such as the ...
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Alkaloid
Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large variety of organisms including bacteria, fungus, fungi, Medicinal plant, plants, and animals. They can be purified from crude extracts of these organisms by acid-base extraction, or solvent extractions followed by silica-gel column chromatography. Alkaloids have a wide range of pharmacology, pharmacological activities including antimalarial medication, antimalarial (e.g. quinine), asthma, antiasthma (e.g. ephedrine), chemotherapy, anticancer (e.g. omacetaxine mepesuccinate, homoharringtonine), cholinomimetic (e.g. galantamine), vasodilation, vasodilatory (e.g. vincamine), Antiarrhythmic agent, antiarrhythmic (e.g. quinidine), analgesic (e.g. morphine), antibacterial (e.g. chelerythrine), and anti-diabetic, antihyperglycemic activities (e.g. berb ...
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Hallucinogen
Hallucinogens, also known as psychedelics, entheogens, or historically as psychotomimetics, are a large and diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, mood, and perception as well as other changes. Hallucinogens are often categorized as either being psychedelics, dissociatives, or deliriants, but not all hallucinogens fall into these three classes. Examples of hallucinogens include psychedelics or serotonin 5-HT2A receptor agonists like LSD, psilocybin, mescaline, and DMT; dissociatives or NMDA receptor antagonists like ketamine, PCP, DXM, and nitrous oxide; deliriants or antimuscarinics like scopolamine and diphenhydramine; cannabinoids or cannabinoid CB1 receptor agonists like THC, nabilone, and JWH-018; κ-opioid receptor agonists like salvinorin A and pentazocine; GABAA receptor agonists like muscimol and gaboxadol; and oneirogens like ibogaine and harmaline, a ...
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