4C-B Structure
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4C-B Structure
4C-B, also known as 4C-DOB or DOB-B, as well as 4-bromo-2,5-dimethoxy-α-ethylphenethylamine, is a lesser-known psychedelic drug of the phenethylamine, phenylisobutylamine, and 4C families related to 2C-B and DOB. It is a reasonably potent 5-HT2A receptor partial agonist with a Ki of 7.6nM, but has relatively low efficacy (15% relative to 5-HT). It is briefly mentioned in Alexander Shulgin's book PiHKAL (Phenethylamines i Have Known And Loved) but was never tested by him, however it has subsequently been tested by Daniel Trachsel and colleagues and was found to be active in a dose range of 50 to 80mg with a duration of around 8hours, producing pronounced psychedelic effects, though with generally milder effects than 2C-B or DOB. See also * 4C (psychedelics) 4C (4C-''x''), also known as 4-substituted 2,5-dimethoxy-α-ethylphenethylamines, is a general name for the family of psychedelic drug, psychedelic and related phenylisobutylamines (α-ethylphenethylamines) having methoxy ...
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Oral Administration
Oral administration is a route of administration whereby a substance is taken through the Human mouth, mouth, swallowed, and then processed via the digestive system. This is a common route of administration for many medications. Oral administration can be easier and less painful than other routes of administration, such as Injection (medicine), injection. However, the onset of action is relatively low, and the effectiveness is reduced if it is not absorbed properly in the digestive system, or if it is broken down by digestive enzymes before it can reach the bloodstream. Some medications may cause gastrointestinal side effects, such as nausea or vomiting, when taken orally. Oral administration can also only be applied to conscious patients, and patients able to swallow. Terminology ''Per os'' (; ''P.O.'') is an adverbial phrase meaning literally from Latin "through the mouth" or "by mouth". The expression is used in medicine to describe a treatment that is taken orally (but not ...
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5-HT2A Receptor
The 5-HT2A receptor is a subtype of the 5-HT2 receptor, 5-HT2 receptor that belongs to the serotonin receptor family and functions as a GPCR, G protein-coupled receptor (GPCR). It is a cell surface receptor that activates multiple intracellular signalling cascades. Like all 5-HT2 receptors, the 5-HT2A receptor is coupled to the Gq protein, Gq/G11 signaling pathway. It is the primary excitatory receptor subtype among the serotonin-responsive GPCRs. The 5-HT2A receptor was initially noted for its central role as the primary target of serotonergic psychedelic drugs such as LSD and psilocybin mushrooms. It later regained research prominence when found to mediate, at least in part, the effects of many antipsychotic drugs, particularly atypical antipsychotic, atypical antipsychotics. Downregulation of post-synaptic 5-HT2A receptors is an adaptive response triggered by chronic administration of selective serotonin reuptake inhibitors (SSRIs) and atypical antipsychotics. Elevated 5-HT2A ...
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Bromoarenes
In organic chemistry, an aryl halide (also known as a haloarene) is an aromatic compound in which one or more hydrogen atoms directly bonded to an aromatic ring are replaced by a halide ion (such as fluorine F''−'', chlorine Cl−1,−3,−5, bromine Br−1, or iodine I−). Aryl halides are distinct from haloalkanes (alkyl halides) due to significant differences in their methods of preparation, chemical reactivity, and physical properties. The most common and important members of this class are aryl chlorides, but the group encompasses a wide range of derivatives with diverse applications in organic synthesis, pharmaceuticals, and materials science. Classification according to halide Aryl fluorides Aryl fluorides are used as synthetic intermediates, e.g. for the preparation of pharmaceuticals, pesticides, and liquid crystals. The conversion of diazonium salts is a well established route to aryl fluorides. Thus, anilines are precursors to aryl fluorides. In the classic Schiemann ...
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5-HT2A Agonists
Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, memory, and physiological processes such as vomiting and vasoconstriction. In the CNS, serotonin regulates mood, appetite, and sleep. Most of the body's serotonin—about 90%—is synthesized in the gastrointestinal tract by enterochromaffin cells, where it regulates intestinal movements. It is also produced in smaller amounts in the brainstem's raphe nuclei, the skin's Merkel cells, pulmonary neuroendocrine cells, and taste receptor cells of the tongue. Once secreted, serotonin is taken up by platelets in the blood, which release it during clotting to promote vasoconstriction and platelet aggregation. Around 8% of the body's serotonin is stored in platelets, and 1–2% is found in the CNS. Serotonin acts as both a vasoconstrictor and v ...
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ZC-B
ZC-B (3-(4-bromo-2,5-dimethoxyphenyl)azetidine) is a phenethylamine derivative which acts as a serotonin receptor agonist selective for the 5-HT2 subtypes, with an EC50 of 1.6nM at 5-HT2A, vs 5.8nM at 5-HT2C. It is structurally related to the psychedelic phenethylamines 2C-B and DOB, but with the amine side chain conformationally restricted as an azetidine ring. See also * DOB * β-Methyl-2C-B * 4C-B * TCB-2 TCB-2 is a hallucinogen discovered in 2006 by Thomas McLean working in the lab of David Nichols at Purdue University. It is a conformationally-restricted derivative of the phenethylamine 2C-B, also a hallucinogen, and acts as a potent agonis ... * LPH-5 * LSZ References {{Phenethylamines 2,5-Dimethoxyphenethylamines Designer drugs Serotonin receptor agonists Azetidines Bromoarenes ...
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Ariadne (psychedelic)
Ariadne, also known chemically as 4C-D or 4C-DOM, by its developmental code name BL-3912, and by its former tentative brand name Dimoxamine, is a little-known psychoactive drug of the phenethylamine, phenylisobutylamine, and 4C families. It is a homologue of the psychedelics 2C-D and DOM. The drug is a serotonin receptor agonist, including of the serotonin 5-HT2A receptor. However, it is non-hallucinogenic in animals and humans, although it still has some psychoactive effects. It may be non-hallucinogenic due to lower-efficacy partial agonism of the serotonin 5-HT2A receptor. Ariadne was developed by Alexander Shulgin. It was studied at Bristol Laboratories as an antidepressant and for various other uses but was never marketed. There has been renewed interest in Ariadne in the 2020s owing to increased interest in psychedelics for treatment of psychiatric disorders. Effects In his 1991 book ''PiHKAL'', Alexander Shulgin reported testing Ariadne on himself up to a dose ...
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4C-T-2
4C-T-2, also known as 2,5-dimethoxy-4-ethylthio-α-ethylphenethylamine, is a synthetic drug of the phenethylamine, phenylisobutylamine, and 4C families. It is the α- ethylated analogue of 2C-T-2. Pharmacology 4C-T-2 acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. History 4C-T-2 was first described in the scientific literature by at least 2005. It was more fully characterized in 2010 and then in 2023. See also * 2C-T-2 * 4C-B * Aleph-7 * Ariadne In Greek mythology, Ariadne (; ; ) was a Cretan princess, the daughter of King Minos of Crete. There are variations of Ariadne's myth, but she is known for helping Theseus escape from the Minotaur and being abandoned by him on the island of N ... References External links 4C-T-2 - Isomer Design {{Phenethylamines 5-HT2A agonists 5-HT2B agonists 5-HT2C agonists 4C (psychedelics) Phenylisobutylamines Thioethers ...
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Daniel Trachsel
Daniel Trachsel is a Swiss people, Swiss chemist who studies psychedelic drug, psychedelics and entactogens. He has developed and published on a large number of novel psychedelic and entactogen chemical compound, compounds, including their psychoactive drug, psychoactive effects. This has been in a manner similar to that of the psychedelic chemist Alexander Shulgin, which has caused Trachsel to sometimes be referred to as the "German Shulgin". However, unlike Shulgin, Trachsel has distanced himself from any personal self-experimentation, self-experiments. According to Hamilton Morris and Nick Cozzi in mid-2023, Trachel's book ''Phenethylamine: von der Struktur zur Funktion'' (''Phenethylamines: From Structure to Function'') is in the process of being translated into English. It is being independently translated by the Alexander Shulgin Research Institute (ASRI), with tentative publication by Transform Press, and also by chemist David Carlson. Compounds Compounds that were first k ...
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PiHKAL
''PiHKAL: A Chemical Love Story'' is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is Psychoactive drug, psychoactive phenethylamine Derivative (chemistry), chemical derivatives, notably those that act as psychedelic drug, psychedelics and/or empathogen-entactogens. The main title, PiHKAL, is an acronym that stands for "Phenethylamines I Have Known and Loved". The book is arranged into two parts, the first part being a fictionalized autobiography of the couple and the second part describing 179 different psychedelic compounds (most of which Shulgin discovered himself), including detailed synthesis instructions, bioassays, dosages, and other commentary. The second part was made freely available by Shulgin on Erowid while the first part is available only in the printed text. While the reactions described are beyond the ability of people with a basic chemistry education, some tend to emphasize techniques that do not require difficult-to-ob ...
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Alexander Shulgin
Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and pharmacology of such agents—in his mid-life and later, many through preparation in his home laboratory, and testing on himself. He is acknowledged to have introduced to broader use, in the late 1970s, the previously-synthesized compound MDMA ("ecstasy"), in research psychopharmacology and in combination with conventional therapy, the latter through presentations and academic publications, including to psychologists; and for the rediscovery, occasional discovery, and regular synthesis and personal use and distribution, of possibly hundreds of Psychoactive drug, psychoactive compounds (for their Psychedelic drug, psychedelic and MDMA-like empathogenic bioactivity, bioactivities). As such, Shulgin is seen both as a pioneering and a controversi ...
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Partial Agonist
In pharmacology, partial agonists are drugs that bind to and activate a given Receptor (biochemistry), receptor, but have only partial Intrinsic activity, efficacy at the receptor relative to a full agonist. They may also be considered Ligand (biochemistry), ligands which display both agonistic and Receptor antagonist, antagonistic effects—when both a full agonist and partial agonist are present, the partial agonist actually acts as a competitive antagonist, competing with the full agonist for receptor occupancy and producing a net decrease in the receptor activation observed with the full agonist alone. Clinically, partial agonists can be used to activate receptors to give a desired submaximal response when inadequate amounts of the endogenous ligand are present, or they can reduce the overstimulation of receptors when excess amounts of the endogenous ligand are present. Some currently common drugs that have been classed as partial agonists at particular receptors include buspi ...
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2,5-Dimethoxy-4-bromoamphetamine
Dimethoxybromoamphetamine (DOB), also known as brolamfetamine () and bromo-DMA, is a psychedelic drug and substituted amphetamine of the phenethylamine class of compounds. DOB was first synthesized by Alexander Shulgin in 1967. Its synthesis and effects are documented in Shulgin's book '' PiHKAL: A Chemical Love Story''. The drug acts as a serotonin 5-HT2 receptor agonist. Side effects Excessively high doses of DOB may cause diffuse arterial spasm. The vasospasm responded readily to intra-arterial and intravenous vasodilators, such as tolazoline. Interactions Pharmacology Pharmacodynamics DOB is a serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptor agonist. Its psychedelic effects are mediated by its agonistic properties at the 5-HT2A receptor. Due to its selectivity, DOB is often used in scientific research when studying the 5-HT2 receptor subfamily. It is a very weak agonist of the human trace amine-associated receptor 1 (TAAR1) and a weak agonist of the rhesus ...
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