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5C-D
5C-D, also known as 4-methyl-2,5-dimethoxy-α-propylphenethylamine, is a putatively non-hallucinogenic serotonin 5-HT2 receptor agonist of the phenethylamine and α-propylphenethylamine families related to the 4C drug Ariadne (4C-D). At the serotonin 5-HT2A receptor, 5C-D is a potent and higher-efficacy partial agonist, with an of 291nM and an of 69%. It is about half as potent as Ariadne as a serotonin 5-HT2A receptor agonist and has about 15% lower efficacy in activating the receptor in comparison. 5C-D has also been shown to be a serotonin 5-HT2B receptor agonist. In contrast to Ariadne and serotonergic psychedelics, 5C-D does not produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. 5C-D was first described in the scientific literature by Michael Cunningham and colleagues by 2023. It was synthesized and assessed during structure–activity relationship (SAR) studies of Ariadne. See also * Substituted methoxyphenethylamine * 4C and ...
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Substituted Methoxyphenethylamine
Methoxyphenethylamines (MPEAs), as well as methoxyamphetamines (MAs) in the case of the amphetamine (α-methylphenethylamine) homologues, are substituted phenethylamines with one or more methoxy groups. In some cases, one or more of the methoxy groups may also be extended to form other alkoxy and related groups such as ethoxy or propoxy. Methoxyphenethylamines may have additional substitutions as well. Many methoxyphenethylamines that have multiple methoxy groups in the 2- through 5-positions of the phenyl ring, for instance mescaline, 2C-B, TMA, DOM, and 25I-NBOMe, are serotonin 5-HT2A receptor agonists and serotonergic psychedelics. Other methoxyphenethylamines, particularly monomethoxyamphetamines like ''para''-methoxyamphetamine (PMA), are monoamine releasing agents of serotonin, norepinephrine, and/or dopamine, with stimulant and/or entactogen-related effects. Compounds closely related to methoxyphenethylamines include methylenedioxyphenethylamines (MDxx) like M ...
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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, methoxy groups at the 2 and 5 carbon, positions of the phenyl ring, phenyl ring (chemistry), ring and a 4-position chemical substitution, substituent. These chemical compound, compounds are structural analog, analogues of the 2C (psychedelics), 2Cs and DOx drugs, but the α-alkyl group, alkyl side chain, chain has been further lengthed (0 carbons for 2C, 1 carbon for DOx, and 2 carbons for 4C). The most notable and well-known of the 4C drugs is Ariadne (drug), Ariadne (4C-D). This drug produces only threshold psychedelic effects and has been described as non-hallucinogenic or as having "the alert of a psychedelic, with none of the rest of the package". These unique properties have made Ariadne of interest for potential therapeutic applications. In contrast to Ar ...
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Serotonin
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 vas ...
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5-HT2B Receptor
5-Hydroxytryptamine receptor 2B (5-HT2B) also known as serotonin receptor 2B is a protein that in humans is encoded by the ''HTR2B'' gene. 5-HT2B is a member of the 5-HT2 receptor, 5-HT2 receptor family that binds the neurotransmitter serotonin (5-hydroxytryptamine, 5-HT). Like all 5-HT2 receptors, the 5-HT2B receptor is Gq protein, Gq/G11-protein coupled, leading to downstream activation of phospholipase C. Tissue distribution and function First discovered in the stomach of rats, 5-HT2B was challenging to characterize initially because of its structural similarity to the other 5-HT2 receptors, particularly 5-HT2C. The 5-HT2 receptors (of which the 5-HT2B receptor is a subtype) mediate many of the central and peripheral physiologic functions of serotonin. Cardiovascular effects include contraction of blood vessels and shape changes in platelets; central nervous system (CNS) effects include neuronal sensitization to tactile stimuli and mediation of some of the effects of halluci ...
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Methoxyphenethylamines
Methoxyphenethylamine, or monomethoxyphenethylamine, may refer to: * 2-Methoxyphenethylamine (2-MPEA) * 3-Methoxyphenethylamine (3-MPEA) * 4-Methoxyphenethylamine (4-MPEA) See also * Substituted methoxyphenethylamine * Dimethoxyphenethylamine * Trimethoxyphenethylamine * Methoxyamphetamine * Dimethoxyamphetamine * Trimethoxyamphetamine {{Chemistry index Methoxyphenethylamines ...
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5-HT2B 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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Structure–activity Relationship
The structure–activity relationship (SAR) is the relationship between the chemical structure of a molecule and its biological activity. This idea was first presented by Alexander Crum Brown and Thomas Richard Fraser at least as early as 1868. The analysis of SAR enables the determination of the chemical group responsible for evoking a target biological effect in the organism. This allows modification of the effect or the Potency (pharmacology), potency of a bioactive compound (typically a drug) by changing its chemical structure. Medicinal chemistry, Medicinal chemists use the techniques of chemical synthesis to insert new chemical groups into the biomedical compound and test the modifications for their biological effects. This method was refined to build mathematical relationships between the chemical structure and the biological activity, known as quantitative structure–activity relationships (QSAR). A related term is structure affinity relationship (SAFIR). Structure-biodeg ...
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Chemical Synthesis
Chemical synthesis (chemical combination) is the artificial execution of chemical reactions to obtain one or several products. This occurs by physical and chemical manipulations usually involving one or more reactions. In modern laboratory uses, the process is reproducible and reliable. A chemical synthesis involves one or more compounds (known as '' reagents'' or ''reactants'') that will experience a transformation under certain conditions. Various reaction types can be applied to formulate a desired product. This requires mixing the compounds in a reaction vessel, such as a chemical reactor or a simple round-bottom flask. Many reactions require some form of processing (" work-up") or purification procedure to isolate the final product. The amount produced by chemical synthesis is known as the '' reaction yield''. Typically, yields are expressed as a mass in grams (in a laboratory setting) or as a percentage of the total theoretical quantity that could be produced based ...
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Scientific Literature
Scientific literature encompasses a vast body of academic papers that spans various disciplines within the natural and social sciences. It primarily consists of academic papers that present original empirical research and theoretical contributions. These papers serve as essential sources of knowledge and are commonly referred to simply as "the literature" within specific research fields. The process of academic publishing involves disseminating research findings to a wider audience. Researchers submit their work to reputable journals or conferences, where it undergoes rigorous evaluation by experts in the field. This evaluation, known as peer review, ensures the quality, validity, and reliability of the research before it becomes part of the scientific literature. Peer-reviewed publications contribute significantly to advancing our understanding of the world and shaping future research endeavors. Original scientific research first published in scientific journals co ...
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Head-twitch Response
The head-twitch response (HTR), also sometimes known as wet dog shakes (WDS) in rats, is a rapid side-to-side head movement that occurs in mice and rats in association with serotonin 5-HT2A receptor activation. Serotonergic psychedelics like lysergic acid diethylamide (LSD) and psilocybin consistently induce the HTR in rodents. Because of this, the HTR is widely employed in scientific research as an animal behavioral model of hallucinogen effects and in the discovery of new psychedelic drugs. The HTR is one of the only behavioral paradigms for assessment of psychedelic-like effects in animals, with the other most notable test being drug discrimination. However, the HTR is far less costly and time-consuming than drug discrimination and hence has become much more popular in recent years. Limitations of the HTR include the fact that various other drugs besides serotonin 5-HT2A receptor agonists, such as NMDA receptor antagonists and muscarinic acetylcholine receptor antagonists, ...
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Serotonergic Psychedelic
Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic hallucinogens or serotonergic hallucinogens, the term ''psychedelic'' is sometimes used more broadly to include various other types of hallucinogens as well, such as those which are atypical or adjacent to psychedelia like salvia and MDMA, respectively. Classic psychedelics generally cause specific psychological, visual, and auditory changes, and oftentimes a substantially altered state of consciousness. They have had the largest influence on science and culture, and include mescaline, LSD, psilocybin, and DMT. There are a large number of both naturally occurring and synthetic serotonergic psychedelics. Most psychedelic drugs fall into one of the three families of chemical compounds: tryptamines, phenethylamines, or lysergamides. They pro ...
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