Psilomethoxin
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Psilomethoxin
Psilomethoxin, also known as 5-methoxypsilocin or as 4-hydroxy-5-methoxy-''N'',''N''-dimethyltryptamine (4-HO-5-MeO-DMT), is a chemical compound, compound of the substituted tryptamine, tryptamine family which has been speculated may have psychedelic effects. It is related to psilocin (4-HO-DMT) and 5-MeO-DMT and in terms of chemical structure can be thought of as a combination of the structural features of the two compounds. Scientific research Very little is known about psilomethoxin. The only report of it in the chemical literature was a paper published by Marc Julia's group at the Pasteur Institute in 1965. This paper reports a 10-step chemical synthesis, synthesis of psilomethoxin from ortho-vanillin , ''ortho''-vanillin. Alexander Shulgin hypothesized that psilomethoxin could be biosynthesis, biosynthesized by feeding ''Psilocybe'' cultures with 5-MeO-DMT, referencing a 1988 study by Jochen Gartz where transformation of diethyltryptamine, DET into 4-HO-DET and Ethocybin, 4- ...
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Psymposia
Psymposia is a small not-for-profit organization, media organization, and self-described "watchdog group" reporting on the psychedelic community and focusing on harm reduction. The group was founded in 2014 and became a nonprofit in 2020. Psymposia is leftist and anti-capitalist. They do work within a discipline that they have referred to as "critical psychedelic studies" (as in critical theory). The group's work has been both praised and criticized. They have become increasingly controversial over time due to claims against them of false accusations, aggressive tactics, and politically motivated campaigning against approval of MDMA-assisted psychotherapy. The group is said to have been excluded from the mainstream psychedelic community and banned from conferences. Members Psymposia's members have included co-founders Brian Normand and Brett Greene, journalist Russell Hausfeld, academics Neşe Devenot and Brian Pace, self-described "underground researcher" and anarchist David Ni ...
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Psilocybin
Psilocybin, also known as 4-phosphoryloxy-''N'',''N''-dimethyltryptamine (4-PO-DMT), is a natural product, naturally occurring tryptamine alkaloid and Investigational New Drug, investigational drug found in more than List of psilocybin mushroom species, 200 species of mushrooms, with Hallucinogen, hallucinogenic and Serotonin, serotonergic effects. Effects include euphoria, changes in perception, a distorted sense of time (via brain desynchronization), and perceived spiritual experiences. It can also cause adverse reactions such as nausea and panic attacks. Its effects depend on set and setting and one's subject-expectancy effect, expectations. Psilocybin is a prodrug of psilocin. That is, the compound itself is biologically inactive but quickly converted by the body to psilocin. Psilocybin is transformed into psilocin by dephosphorylation mediated via phosphatase enzymes. Psilocin is structural analog, chemically related to the neurotransmitter serotonin and acts as a binding ...
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Chemical Compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element is therefore not a compound. A compound can be transformed into a different substance by a chemical reaction, which may involve interactions with other substances. In this process, bonds between atoms may be broken or new bonds formed or both. There are four major types of compounds, distinguished by how the constituent atoms are bonded together. Molecular compounds are held together by covalent bonds; ionic compounds are held together by ionic bonds; intermetallic compounds are held together by metallic bonds; coordination complexes are held together by coordinate covalent bonds. Non-stoichiometric compounds form a disputed marginal case. A chemical formula specifies the number of atoms of each element in a compound molecule, usin ...
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Structural Analog
A structural analog, also known as a chemical analog or simply an analog, is a chemical compound, compound having a chemical structure, structure similar to that of another compound, but differing from it in respect to a certain component. It can differ in one or more atoms, functional groups, or substructures, which are replaced with other atoms, groups, or substructures. A structural analog can be imagined to be formed, at least theoretically, from the other compound. Structural analogs are often isoelectronicity, isoelectronic. Despite a high chemical similarity, structural analogs are not necessarily functional analog (chemistry), functional analogs and can have very different physical, chemical, biochemical, or pharmacological properties. In drug discovery, either a large series of structural analogs of an initial lead compound are created and tested as part of a structure–activity relationship study or a database is virtual screening, screened for structural analogs of a ...
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Dimethylamino Compounds
Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005. Structure and synthesis The molecule consists of a nitrogen atom with two methyl substituents and one hydrogen. Dimethylamine is a base (chemistry), weak base and the pKa of the ammonium CH3--CH3 is 10.73, a value above methylamine (10.64) and trimethylamine (9.79). Dimethylamine reacts with acids to form salts, such as dimethylamine hydrochloride, an odorless white solid with a melting point of 171.5 °C. Dimethylamine is produced by catalytic reaction of methanol and ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammoni ...
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David E
David (; , "beloved one") was a king of ancient Israel and Judah and the third king of the United Monarchy, according to the Hebrew Bible and Old Testament. The Tel Dan stele, an Aramaic-inscribed stone erected by a king of Aram-Damascus in the late 9th/early 8th centuries BCE to commemorate a victory over two enemy kings, contains the phrase (), which is translated as " House of David" by most scholars. The Mesha Stele, erected by King Mesha of Moab in the 9th century BCE, may also refer to the "House of David", although this is disputed. According to Jewish works such as the '' Seder Olam Rabbah'', '' Seder Olam Zutta'', and '' Sefer ha-Qabbalah'' (all written over a thousand years later), David ascended the throne as the king of Judah in 885 BCE. Apart from this, all that is known of David comes from biblical literature, the historicity of which has been extensively challenged,Writing and Rewriting the Story of Solomon in Ancient Israel; by Isaac Kalimi; pa ...
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Baeocystin
Baeocystin, also known as norpsilocybin or 4-phosphoryloxy-''N''-methyltryptamine (4-PO-NMT), is a zwitterionic alkaloid and analogue of psilocybin. It is found as a minor compound in most psilocybin mushrooms together with psilocybin, norbaeocystin, aeruginascin, and psilocin. Baeocystin is the ''N''-demethylated derivative of psilocybin and the 4-phosphorylated derivative of 4-HO-NMT (4-hydroxy- ''N''-methyltryptamine). The structures at right illustrate baeocystin in its zwitterionic form. History Baeocystin was first isolated from the mushroom '' Psilocybe baeocystis'', and later from '' P. semilanceata'', '' Panaeolus renenosus'', '' Panaeolus subbalteatus'', and ''Copelandia chlorocystis''. It was first synthesized by Troxler ''et al''. in 1959. Pharmacology Baeocystin is thought to be a prodrug of norpsilocin, analogously to how psilocybin is a prodrug of psilocin. Norpsilocin is a potent and centrally penetrant agonist of the serotonin 5-HT2A receptor and a ...
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Prodrug
A prodrug is a pharmacologically inactive medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug is absorbed, distributed, metabolized, and excreted (ADME). Prodrugs are often designed to improve bioavailability when a drug itself is poorly absorbed from the gastrointestinal tract. A prodrug may be used to improve how selectively the drug interacts with cells or processes that are not its intended target. This reduces adverse or unintended effects of a drug, especially important in treatments like chemotherapy, which can have severe unintended and undesirable side effects. History Many herbal extracts historically used in medicine contain glycosides (sugar derivatives) of the active agent, which are hydrolyzed in the intestines to release the active and more bioavailable aglycone. For example, sal ...
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Usona Institute
The Usona Institute is a 501(c)(3) non-profit medical research organization (MRO) which is developing psychedelic drugs for potential medical use. It was launched by scientist and entrepreneur Bill Linton, who is the founder of the biotechnology company Promega Corporation, and by physician Malynn Utzinger in 2014. The organization is developing psilocybin (4-HO-DMT) for treatment of depression. It started a phase 2 clinical trial of psilocybin for major depressive disorder in 2019. The same year, this candidate received Food and Drug Administration (FDA) "breakthrough therapy" designation. This clinical trial has since been completed and its psilocybin candidate is now in phase 3 clinical studies. In July 2024, it was said that the Usona Institute was leading the largest clinical trial of ongoing psilocybin treatment for depression, a phase 3 trial with 240participants treated with 5 or 25mg psilocybin or placebo. Other candidates of the institute include mebufotenin (5-MeO- ...
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Psilocybin Mushroom
Psilocybin mushrooms, or psilocybin-containing mushrooms, commonly known as magic mushrooms or as shrooms, are a type of hallucinogenic mushroom and a polyphyletic informal group of fungi that contain the prodrug psilocybin, which turns into the psychedelic psilocin upon ingestion. The most potent species are members of genus ''Psilocybe'', such as '' P. azurescens'', '' P. semilanceata'', and '' P. cyanescens'', but psilocybin has also been isolated from approximately a dozen other genera, including '' Panaeolus'' (including '' Copelandia''), '' Inocybe'', '' Pluteus'', ''Gymnopilus'', and '' Pholiotina''. Amongst other cultural applications, psilocybin mushrooms are used as recreational drugs. They may be depicted in Stone Age rock art in Africa and Europe, but are more certainly represented in sculptures and glyphs seen throughout the Americas. Indoor cultivation '' Psilocybe cubensis'' grows naturally in tropical and subtropical conditions, often near ca ...
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