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O-Acetylbufotenine
''O''-Acetylbufotenine (5-AcO-DMT, bufotenine acetate) is a tryptamine derivative which produces psychedelic-appropriate responding in animal studies. It is an acylated derivative of bufotenine with higher lipophilicity that allows it to cross the blood–brain barrier; once inside the brain, it is metabolised to bufotenine. It also acts directly as an agonist at 5-HT1A and 5-HT1D receptors. See also * 4-AcO-DMT * 5-EtO-DMT * 5-HO-AMT * 5-HO-DiPT 5-HO-DiPT (5-hydroxy-''N,N''-di-''iso''-propyltryptamine) is a tryptamine derivative which acts as a serotonin receptor agonist. It is primarily known as a metabolite of the better known psychoactive drug 5-MeO-DiPT, but 5-HO-DiPT has also rarely ... References Designer drugs Psychedelic tryptamines Serotonin receptor agonists Tertiary amines Acetate esters {{nervous-system-drug-stub ...
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5-EtO-DMT
5-Ethoxy-DMT (5-ethoxy-''N'',''N''-dimethyltryptamine, 5-EtO-DMT, ''O''-ethylbufotenine) is a tryptamine derivative which has been previously synthesized as a chemical intermediate, but has not been studied to determine its pharmacology. The widespread recreational use of ''N'',''N''-dialkylated 5-methoxytryptamine derivatives including 5-MeO-DMT, 5-MeO-MiPT and 5-MeO-DiPT has led to concern that the 5-ethoxy homologs of these drugs could emerge as novel designer drugs, and consequently 5-EtO-DMT and other derivatives including 5-EtO-DET, 5-EtO-DPT, 5-EtO-DiPT, 5-EtO-DALT, 5-EtO-MPT, 5-EtO-MiPT, 5-EtO-EiPT, 5-EtO-MET and 5-EtO-EPT have been synthesized as analytical standards in order to facilitate future research into these compounds. See also * 5-Benzyloxytryptamine 5-Benzyloxytryptamine (5-BT), is a tryptamine derivative which acts as an agonist at the 5-HT1D, 5-HT2 and 5-HT6 serotonin receptors, and an antagonist of TRPM8. Legality 5-Benzyloxytryptamine is illegal ...
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Bufotenine
Bufotenin (5-HO-DMT, bufotenine) is a tryptamine derivative - more specifically, a DMT derivative - related to the neurotransmitter serotonin. It is an alkaloid found in some species of toads (especially the skin), mushrooms and plants. The name bufotenin originates from the toad genus ''Bufo'', which includes several species of psychoactive toads, most notably ''Incilius alvarius'', that secrete bufotoxins from their parotoid glands. Bufotenin is similar in chemical structure to the psychedelics psilocin (4-HO-DMT), 5-MeO-DMT, and DMT, chemicals which also occur in some of the same fungus, plant, and animal species as bufotenin. Nomenclature Bufotenin (bufotenine) is also known by the chemical names 5-hydroxy-''N'',''N''-dimethyltryptamine (5-HO-DMT), ''N'',''N''-dimethyl-5-hydroxytryptamine, dimethyl serotonin, and mappine. History Bufotenin was isolated from toad skin, and named by the Austrian chemist Handovsky at the University of Prague during World War I. The structure ...
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Tryptamine
Tryptamine is an indolamine metabolite of the essential amino acid, tryptophan. The chemical structure is defined by an indole ─ a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the first one being the heterocyclic nitrogen). The structure of tryptamine is a shared feature of certain aminergic neuromodulators including melatonin, serotonin, bufotenin and psychedelic derivatives such as dimethyltryptamine (DMT), psilocybin, psilocin and others. Tryptamine has been shown to activate trace amine-associated receptors expressed in the mammalian brain, and regulates the activity of dopaminergic, serotonergic and glutamatergic systems. In the human gut, symbiotic bacteria convert dietary tryptophan to tryptamine, which activates 5-HT4 receptors and regulates gastrointestinal motility. Multiple tryptamine-derived drugs have been developed to treat migraines, while trace amine-associated receptors are being explored as a ...
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Psychedelic
Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression, and Transcendence'' Sometimes, they are called classic hallucinogens, serotonergic hallucinogens, or serotonergic psychedelics, and the term ''psychedelics'' is used more broadly to include all hallucinogens; this article uses the narrower definition of ''psychedelics''. Psychedelics cause specific psychological, visual, and auditory changes, and often a substantially altered state of consciousness.Leary, Timothy; Metzner, Ralph (1964). ''The Psychedelic Experience: A Manual Based on The Tibetan Book of the Dead'' Psychedelic states are often compared to meditative, psychodynamic or transcendental types of alterations of mind. The "classical" psychedelics, the psyc ...
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Lipophilicity
Lipophilicity (from Greek λίπος "fat" and φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar solvents are themselves lipophilic (translated as "fat-loving" or "fat-liking"), and the axiom that "like dissolves like" generally holds true. Thus lipophilic substances tend to dissolve in other lipophilic substances, but hydrophilic ("water-loving") substances tend to dissolve in water and other hydrophilic substances. Lipophilicity, hydrophobicity, and non-polarity may describe the same tendency towards participation in the London dispersion force, as the terms are often used interchangeably. However, the terms "lipophilic" and "hydrophobic" are not synonymous, as can be seen with silicones and fluorocarbons, which are hydrophobic but not lipophilic. __TOC__ Surfactants Hydrocarbon-based surfactants are compounds that are amphiphilic (or amphipathic), having a hy ...
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Blood–brain Barrier
The blood–brain barrier (BBB) is a highly selective semipermeable membrane, semipermeable border of endothelium, endothelial cells that prevents solutes in the circulating blood from ''non-selectively'' crossing into the extracellular fluid of the central nervous system where neurons reside. The blood–brain barrier is formed by endothelial cells of the Capillary, capillary wall, astrocyte end-feet ensheathing the capillary, and pericytes embedded in the capillary basement membrane. This system allows the passage of some small molecules by passive transport, passive diffusion, as well as the selective and active transport of various nutrients, ions, organic anions, and macromolecules such as glucose and amino acids that are crucial to neural function. The blood–brain barrier restricts the passage of pathogens, the diffusion of solutes in the blood, and Molecular mass, large or Hydrophile, hydrophilic molecules into the cerebrospinal fluid, while allowing the diffusion of Hydr ...
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4-AcO-DMT
''O''-Acetylpsilocin (also known as psilacetin, 4-acetoxy-DMT, 4-AcO-DMT, or synthetic shrooms) is a semi-synthetic psychoactive drug that has been suggested by David Nichols to be a potentially useful alternative to psilocybin for pharmacological studies, as they are both believed to be prodrugs of psilocin. However, some users report that ''O''-acetylpsilocin's subjective effects differ from those of psilocybin and psilocin. Additionally, some users prefer 4-AcO-DMT to natural psilocybin mushrooms due to feeling fewer adverse side effects such as nausea and heavy body load, which are more frequently reported in experiences involving natural mushrooms. It is the acetylated form of the psilocybin mushroom alkaloid psilocin and is a lower homolog of 4-AcO-MET, 4-AcO-DET, 4-AcO-MiPT and 4-AcO-DiPT. History ''O''-Acetylpsilocin (psilacetin) and several other esters of psilocin were patented on January 16, 1963 by Sandoz Ltd via Albert Hofmann & Franz Troxler. Despite this, p ...
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5-HO-AMT
α-Methylserotonin (αMS), also known as α-methyl-5-hydroxytryptamine (α-methyl-5-HT) or 5-hydroxy-α-methyltryptamine (5-HO-αMT), is a tryptamine derivative closely related to the neurotransmitter serotonin (5-HT). It acts as a non- selective serotonin receptor agonist and has been used extensively in scientific research to study the function of the serotonin system. Unlike serotonin, αMS is not metabolized by monoamine oxidase on account of the α-methyl substituent blocking the enzyme's access to the amine. As a result, it has a much longer half-life in comparison. Similarly to serotonin however, αMS poorly crosses the blood-brain-barrier due to its free hydroxyl group, and thus has only weak or no central effects when administered peripherally. α-Methyltryptophan (αMTP) is a prodrug to αMS which does cross the blood-brain-barrier and thus efficiently delivers αMS into the central nervous system. As a result, αMTP acts as an orally bioavailable false o ...
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5-HO-DiPT
5-HO-DiPT (5-hydroxy-''N,N''-di-''iso''-propyltryptamine) is a tryptamine derivative which acts as a serotonin receptor agonist. It is primarily known as a metabolite of the better known psychoactive drug 5-MeO-DiPT, but 5-HO-DiPT has also rarely been encountered as a designer drug in its own right. Tests ''in vitro'' show 5-HO-DiPT to have high 5-HT2A affinity and good selectivity over 5-HT1A, while being more lipophilic than the related drug bufotenine (5-HO-DMT), which produces mainly peripheral effects. See also * alpha-Methylserotonin * 4-HO-DiPT 4-Hydroxy-N,N-diisopropyltryptamine (4-HO-DiPT or Iprocin) is a synthetic psychedelic drug. It is a higher homologue of psilocin, 4-HO-DET, and is a positional isomer of 4-HO-DPT and has a tryptamine molecular sub-structure. Dosage 4-HO-DiPT i ... * 4-HO-DSBT * 5-AcO-DMT References Tryptamines Diisopropylamino compounds {{psychoactive-stub ...
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Designer Drugs
A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. Designer drugs include psychoactive substances that have been designated by the European Union as new psychoactive substances (NPS) as well as analogs of performance-enhancing drugs such as designer steroids. Some of these were originally synthesized by academic or industrial researchers in an effort to discover more potent derivatives with fewer side effects, and shorter duration (and possibly also because it is easier to apply for patents for new molecules) and were later co-opted for recreational use. Other designer drugs were prepared for the first time in clandestine laboratories. Because the efficacy and safety of these substances have not been thoroughly evaluated in animal and human trials, the use of some of these drugs may result i ...
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Psychedelic Tryptamines
Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression, and Transcendence'' Sometimes, they are called classic hallucinogens, serotonergic hallucinogens, or serotonergic psychedelics, and the term ''psychedelics'' is used more broadly to include all hallucinogens; this article uses the narrower definition of ''psychedelics''. Psychedelics cause specific psychological, visual, and auditory changes, and often a substantially altered state of consciousness.Leary, Timothy; Metzner, Ralph (1964). ''The Psychedelic Experience: A Manual Based on The Tibetan Book of the Dead'' Psychedelic states are often compared to meditative, psychodynamic or transcendental types of alterations of mind. The "classical" psychedelics, the psyc ...
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Serotonin Receptor Agonists
Serotonin () or 5-hydroxytryptamine (5-HT) is a monoamine neurotransmitter. Its biological function is complex and multifaceted, modulating mood, cognition, reward, learning, memory, and numerous physiological processes such as vomiting and vasoconstriction. Approximately 90% of the serotonin that the body produces is in the intestinal tract. Biochemically, the indoleamine molecule derives from the amino acid tryptophan, via the (rate-limiting) hydroxylation of the 5 position on the ring (forming the intermediate 5-hydroxytryptophan), and then decarboxylation to produce serotonin. Serotonin is primarily found in the enteric nervous system located in the gastrointestinal tract (GI tract). However, it is also produced in the central nervous system (CNS), specifically in the raphe nuclei located in the brainstem, Merkel cells located in the skin, pulmonary neuroendocrine cells and taste receptor cells in the tongue. Additionally, serotonin is stored in blood platelets and is rel ...
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