1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole
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1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole
1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole (4,5-DHP-DMT) is a tricyclic tryptamine derivative which acts as a potent and reasonably selective partial agonist for the serotonin receptor 5-HT, with a Ki of 17.0 nM, and moderate selectivity over related serotonin receptors. It has lower 5-HT affinity and efficacy than the related compound AL-37350A, but higher lipophilicity. See also * 4,5-MDO-DMT * 4,5-MDO-DiPT * 5-MeO-DMT * CP-132,484 CP-132,484 is a tryptamine derivative which acts as a potent and selective agonist for the 5-HT2 family of serotonin receptors. It has reasonable selectivity for 5-HT2A and 5-HT2C subtypes over 5-HT2B, but is only slightly selective for 5-HT2A ... * RU-28306 References Serotonin receptor agonists Tryptamines Dihydropyrans Heterocyclic compounds with 3 rings Dimethylamino compounds {{nervous-system-drug-stub ...
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CP-132,484
CP-132,484 is a tryptamine derivative which acts as a potent and selective agonist for the 5-HT2 family of serotonin receptors. It has reasonable selectivity for 5-HT2A and 5-HT2C subtypes over 5-HT2B, but is only slightly selective for 5-HT2A over 5-HT2C. This compound and several related analogues have been shown to have ocular hypotensive activity in animal models, suggesting they may be useful for the treatment of glaucoma. See also * AL-37350A * AL-38022A * 1-Methylpsilocin * 4,5-DHP-DMT 1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole (4,5-DHP-DMT) is a tricyclic tryptamine derivative which acts as a potent and reasonably selective partial agonist for the serotonin receptor 5-HT, with a Ki of 17.0 nM, and moderate selectivit ... References Dihydropyrans Serotonin receptor agonists Tryptamines Heterocyclic compounds with 3 rings {{nervous-system-drug-stub ...
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4,5-MDO-DiPT
4,5-MDO-DiPT, or 4,5-methylenedioxy-N,N-diisopropyltryptamine, is a lesser-known psychedelic drug. It is the 4,5- methylenedioxy analog of DiPT. 4,5-MDO-DiPT was first synthesized by Alexander Shulgin. In his book ''TiHKAL'' (''Tryptamines I Have Known and Loved''), 4,5-MDO-DiPT produces slight LSD-like effects after several hours. Very little data exists about the pharmacological properties, metabolism, and toxicity of 4,5-MDO-DiPT. See also * 4,5-DHP-DMT * 4,5-MDO-DMT * 5,6-MDO-DiPT * Tryptamine * DiPT * Psychedelics, dissociatives and deliriants Hallucinogens are a large, 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. Most hallucinogens can be categorized ... External links 4,5-MDO-DiPT Entry in ''TIHKAL''4,5-MDO-DIPT Entry in TiHKAL • info Psychedelic tryptamines Diisopropylamino compounds {{Psychoactive-stub ...
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AL-37350A
AL-37350A (4,5-DHP-AMT) is a tryptamine derivative which acts as a potent and selective agonist for the serotonin receptor 5-HT2A, with a Ki of 2.0 nM, and moderate selectivity over the related 5-HT2B and 5-HT2C receptors. It has been shown to have ocular hypotensive activity in animal models, suggesting it may be useful for the treatment of glaucoma. See also * AL-38022A * CP-132,484 CP-132,484 is a tryptamine derivative which acts as a potent and selective agonist for the 5-HT2 family of serotonin receptors. It has reasonable selectivity for 5-HT2A and 5-HT2C subtypes over 5-HT2B, but is only slightly selective for 5-HT2A ... * 4,5-DHP-DMT References Dihydropyrans Serotonin receptor agonists Tryptamines {{nervous-system-drug-stub ...
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Tricyclic
Tricyclics are chemical compounds that contain three interconnected rings of atoms. Many compounds have a tricyclic structure, but in pharmacology, the term has traditionally been reserved to describe heterocyclic drugs. Among these are antidepressants, antipsychotics, anticonvulsants, and antihistamines (as antiallergens, anti-motion sickness drugs, antipruritics, and hypnotics/sedatives) of the dibenzazepine, dibenzocycloheptene, dibenzothiazepine, dibenzothiepin, phenothiazine, and thioxanthene chemical classes, and others. History * Promethazine and other first generation antihistamines with a tricyclic structure were discovered in the 1940s. * Chlorpromazine, derived from promethazine originally as a sedative, was found to have neuroleptic properties in the early 1950s, and was the first typical antipsychotic. * Imipramine, originally investigated as an antipsychotic, was discovered in the early 1950s, and was the first tricyclic antidepressant. * Carbamazepine was disco ...
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Tryptamines
Substituted tryptamines, or serotonin analogues, are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring, joined to an amino (NH2) group via an ethyl (−CH2–CH2−) sidechain. In substituted tryptamines, the indole ring, sidechain, and/or amino group are modified by substituting another group for one of the hydrogen (H) atoms. Well-known tryptamines include serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine alkaloids are found in fungi, plants and animals; and sometimes used by humans for the neurological or psychotropic effects of the substance. Prominent examples of tryptamine alkaloids include psilocybin (from "psilocybin mushrooms") and DMT. In South America, dimethyltryptamine is obtained from numerous plant sources, like chacruna, and it is often used in ayahuasca brews. Many synthetic tryptamines ...
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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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RU-28306
RU-28306 is a tricyclic tryptamine derivative which acts as a serotonin receptor agonist, with selectivity for 5-HT1 and 5-HT2 subtypes. It can be regarded either as a conformationally constrained derivative of DMT, or a structurally simplified analogue of LSD, but the binding affinity of racemic RU-28306 is closer to that of DMT, though with relatively higher affinity for 5-HT2 subtypes and lower for 5-HT1. It has been sold as a designer drug and was first reported to the EMCDDA by a forensic laboratory in Slovenia in 2017. See also * 4,5-DHP-DMT * Bay R 1531 Bay R 1531 is a tricyclic tryptamine derivative which acts as a selective serotonin receptor 5-HT1A agonist. It was researched unsuccessfully for the treatment of stroke but remains in use for scientific research. See also * 8-OH-DPAT * RDS- ... * NDTDI * RU-24,969 References {{Tryptamines Serotonin receptor agonists Tryptamines Phenethylamines ...
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5-MeO-DMT
5-MeO-DMT (5-methoxy-''N'',''N''-dimethyltryptamine) or O-methyl-bufotenin is a psychedelic of the tryptamine class. It is found in a wide variety of plant species, and also is secreted by the glands of at least one toad species, the Colorado River toad. Like its close relatives DMT and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include Five-methoxy, The power, and Toad venom. Chemistry 5-MeO-DMT was first synthesized in 1936, and in 1959 it was isolated as one of the psychoactive ingredients of '' Anadenanthera peregrina'' seeds used in preparing Yopo snuff. It was once believed to be a major component of the psychoactive effects of the snuff, although this has recently been shown to be unlikely, due to the limited or sometimes even non-existent quantity contained within the seeds, which instead achieve their psychoactivity from the ''O''-demethylated metabolite of 5-MeO-DMT, bufotenin. It is metabolized mainly by CYP2D6. Effects D ...
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4,5-MDO-DMT
4,5-MDO-DMT, or 4,5-methylenedioxy-''N'',''N''-dimethyltryptamine, is a lesser-known psychedelic drug. It is the 4,5-methylenedioxy analog of DMT. 4,5-MDO-DMT was first synthesized by Alexander Shulgin, though in his book ''TiHKAL'' it was not tested to determine its psychoactive effects. 4,5-MDO-DMT has been the subject of limited subsequent testing; with behavioral disruption studies performed in male rats indicating that its hallucinogenic potency is less than that of 4,5-MDO-DiPT 4,5-MDO-DiPT, or 4,5-methylenedioxy-N,N-diisopropyltryptamine, is a lesser-known psychedelic drug. It is the 4,5- methylenedioxy analog of DiPT. 4,5-MDO-DiPT was first synthesized by Alexander Shulgin. In his book ''TiHKAL'' (''Tryptamines I Hav ... but greater than that of 5,6-MDO-DiPT. References External links 4,5-MDO-DMT Entry in ''TIHKAL''4,5-MDO-DMT Entry in TiHKAL • info Psychedelic tryptamines {{Psychoactive-stub ...
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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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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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