3-methoxyamphetamine
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3-Methoxyamphetamine
''meta''-Methoxyamphetamine (MMA), also known as 3-methoxyamphetamine (3-MA), is a stimulant drug from the amphetamine family. It has similar effects in animal drug discrimination tests to the more widely known derivative 4-methoxyamphetamine (PMA), although with a slightly different ratio of monoamine release, being a combined serotonin, dopamine, and norepinephrine releasing agent rather than a fairly selective serotonin releaser like PMA. 3-Methoxyamphetamine has similarly appeared on the illicit market as a designer drug alternative to MDMA, although far more rarely than its infamous positional isomer. It produces gepefrine, a cardiac stimulant, as one of its major metabolites. See also * 2-Methoxyamphetamine (OMA) * 3-Methylamphetamine (3-MA) * 3-Fluoroamphetamine (3-FA) * 3-Trifluoromethylamphetamine (Norfenfluramine) * 3-Methoxy-4-methylamphetamine (MMA) * 3-Methoxymethamphetamine 3-Methoxymethamphetamine (also known as ''meta''-methoxymethamphetamine or MM ...
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3-Methoxy-4-methylamphetamine
3-Methoxy-4-methylamphetamine (MMA) is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes. It was first synthesized in 1970 and was encountered as a street drug in Italy in the same decade.de Zorzi C, Cavalli A, Un nuovo allucinogeno: la MMA (p-metil-m-metossi anfetamina) ''Zacchia''. 1974;49 (1) p.58-68 MMA was largely forgotten until being reassayed by David E. Nichols as a non-neurotoxic MDMA analogue in 1991, and has subsequently been sold as a designer drug on the internet since the late 2000s (decade). In animal studies, MMA fully substitutes for MDMA and MBDB, partially substitutes for LSD, and does not substitute for amphetamine. Additionally, it has been shown to potently inhibit the reuptake of serotonin and does not produce serotonergic neurotoxicity in rodents. These data appear to confer a profile of MMA as a selective serotonin releasing agent (SSRA) and 5-HT2A receptor agonist. At high doses, such as 120 mg, the effects are p ...
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4-methoxyamphetamine
''para''-Methoxyamphetamine (PMA), also known as 4-methoxyamphetamine (4-MA), is a designer drug of the amphetamine class with serotonergic effects. Unlike other similar drugs of this family, PMA does not produce stimulant, euphoriant, or entactogen effects, and behaves more like an antidepressant in comparison, though it does have some psychedelic properties. PMA has been found in tablets touted as MDMA (ecstasy) although its effects are markedly different compared to those of MDMA. The consequences of such deception have often included hospitalization and death for unwitting users. PMA is commonly synthesized from anethole, the flavor compound of anise and fennel, mainly because the starting material for MDMA, safrole, has become less available due to law enforcement action, causing illicit drug manufacturers to use anethole as an alternative. Adverse effects PMA has been associated with numerous adverse reactions including death. Effects of PMA ingestion include ma ...
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3-Fluoroamphetamine
3-Fluoroamphetamine (3-FA; PAL-353) is a stimulant drug from the amphetamine family which acts as a monoamine releaser with similar potency to methamphetamine but more selectivity for dopamine and norepinephrine release over serotonin. It is self-administered by mice to a similar extent to related drugs such as 4-fluoroamphetamine and 3-methylamphetamine. Legal status China As of October 2015 3-FA is a controlled substance in China. See also * 2-Fluoroamphetamine (2-FA) * 3-Fluoroethamphetamine (3-FEA) * 3-Fluoromethamphetamine (3-FMA) * 3-Hydroxyamphetamine (Gepefrine) * 3-Methylamphetamine (3-MA) * 3-Methoxyamphetamine (3-MeOA) * 3-Trifluoromethylamphetamine (Norfenfluramine) * 4-Fluoroamphetamine 4-Fluoroamphetamine (4-FA; 4-FMP; PAL-303; "Flux"), also known as ''para''-fluoroamphetamine (PFA) is a psychoactive research chemical of the phenethylamine and substituted amphetamine chemical classes. It produces stimulant and entactogenic ef ... (4-FA) References ...
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Mouth
In animal anatomy, the mouth, also known as the oral cavity, or in Latin cavum oris, is the opening through which many animals take in food and issue vocal sounds. It is also the cavity lying at the upper end of the alimentary canal, bounded on the outside by the lips and inside by the pharynx. In tetrapods, it contains the tongue and, except for some like birds, teeth. This cavity is also known as the buccal cavity, from the Latin ''bucca'' ("cheek"). Some animal phyla, including arthropods, molluscs and chordates, have a complete digestive system, with a mouth at one end and an anus at the other. Which end forms first in ontogeny is a criterion used to classify bilaterian animals into protostomes and deuterostomes. Development In the first multicellular animals, there was probably no mouth or gut and food particles were engulfed by the cells on the exterior surface by a process known as endocytosis. The particles became enclosed in vacuoles into which enzymes were secr ...
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Gepefrine
3-Hydroxyamphetamine (INN; trade names Pressionorm, Gepefrine, and Wintonin), also known as meta-hydroxyamphetamine, and α-methyl-''meta''-tyramine, is an antihypotensive or sympathomimetic agent of the amphetamine family that is marketed in certain European countries. It is a known metabolite of amphetamine in rats. See also * 3,4-Dihydroxyamphetamine * Norfenfluramine * 4-Hydroxyamphetamine * Metaraminol Metaraminol, previously sold under the brand name Aramine among others and also known as metaradrine, is a stereoisomer of ''meta''-hydroxynorephedrine (3,β-dihydroxyamphetamine), is a potent sympathomimetic amine used in the prevention and tr ... * ''meta''-Tyramine References {{Phenethylamines Substituted amphetamines Phenols Sympathomimetics Norepinephrine-dopamine releasing agents ...
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Substituted Amphetamines
Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents. The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. Examples of substituted amphetamines are amphetamine (itself), methamphetamine, ephedrine, cathinone, phentermine, mephentermine, bupropion, methoxyphenamine, selegiline, amfepramone (diethylpropion), pyrovalerone, MDMA (ecstasy), and DOM (STP). Some of amphetamine's substituted derivatives occur in nature, for example in the leaves of ''Ephedra'' and khat plants. Amphetamine was first produced at the end of the 19th century. By the 1930s, amphetamine and some of its derivative compounds found use as decongestants in the symptomatic treatment of colds and also occasionally as psychoac ...
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4-Ethoxyamphetamine
''para''-Ethoxyamphetamine, also known as 4-ethoxyamphetamine (4-ETA), is a psychoactive drug and research chemical of the phenethylamine and amphetamine chemical classes which is closely related to the infamous ''para''-methoxyamphetamine (PMA). ''para''-Ethoxyamphetamine has similar effects to PMA in animal studies, although with slightly weaker stimulant effects. Like PMA, it has prominent MAOI activity, and is likely to have similar dangers associated with its use. See also * ''para''-Methoxyamphetamine (PMA) * 2,5-Dimethoxy-4-ethoxyamphetamine 2,5-Dimethoxy-4-ethoxyamphetamine (MEM) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin. In his book '' PiHKAL'', he lists the active dose range as 20–50 mg, and ... (MEM) * 2,5-Dimethoxy-4-propoxyamphetamine (MPM) References {{DEFAULTSORT:Ethoxyamphetamine, 4- Substituted amphetamines Serotonin releasing agents ...
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3-Methoxymethamphetamine
3-Methoxymethamphetamine (also known as ''meta''-methoxymethamphetamine or MMMA), which is most closely related to 3-methoxyamphetamine and PMMA and shares similar monoamine releasing effects, although its effects have not been studied so extensively as other related drugs. It is an agonist of human TAAR1. See also * PMA * Fenfluramine * 2-Methoxymethamphetamine * 3-Chloromethamphetamine * 3-Methoxy-4-methylamphetamine 3-Methoxy-4-methylamphetamine (MMA) is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes. It was first synthesized in 1970 and was encountered as a street drug in Italy in the same decade.de Zorzi C, Cavalli A, Un ... * 4-Fluoromethamphetamine * 4-Methylmethamphetamine References Methamphetamines Phenol ethers Serotonin-norepinephrine-dopamine releasing agents TAAR1 agonists {{nervous-system-drug-stub ...
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Norfenfluramine
Norfenfluramine, or 3-trifluoromethylamphetamine, is a never-marketed drug of the amphetamine family that behaves as a serotonin and norepinephrine releasing agent and potent 5-HT2A, 5-HT2B, and 5-HT2C agonist. The action of norfenfluramine on 5-HT2B receptors on heart valves leads to a characteristic pattern of heart failure following proliferation of cardiac fibroblasts on the tricuspid valve, known as cardiac fibrosis. This side effect led to the withdrawal of fenfluramine as an anorectic agent worldwide, and to the withdrawal of benfluorex in Europe, as both fenfluramine and benfluorex form norfenfluramine as an active metabolite. It is a human TAAR1 agonist. See also * Fenfluramine * Benfluorex Benfluorex, sold under the brand name Mediator, is an anorectic and hypolipidemic agent that is structurally related to fenfluramine (a substituted amphetamine). It may improve glycemic control and decrease insulin resistance in people with poorly ... * Norfenfluramine is the pre ...
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3-Methylamphetamine
3-Methylamphetamine (3-MeA; PAL-314) is a stimulant drug from the amphetamine family. It is self-administered by mice to a similar extent to 4-fluoroamphetamine and has comparable properties as a monoamine releaser, although with a more balanced release of all three monoamines, as opposed to the more dopamine/noradrenaline selective fluoro analogues. See also * 2-Methylamphetamine * 3-Methylmethamphetamine * 4-Methylamphetamine 4-Methylamphetamine (4-MA; PAL-313; Aptrol; p-TAP) is a stimulant and anorectic drug of the phenethylamine and amphetamine chemical classes. In vitro, it acts as a potent and balanced serotonin, norepinephrine, and dopamine releasing agent with ... * 3,4-Dimethylamphetamine * 3-Trifluoromethylamphetamine References Substituted amphetamines Serotonin-norepinephrine-dopamine releasing agents {{nervous-system-drug-stub ...
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Metabolite
In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, catalytic activity of their own (usually as a cofactor to an enzyme), defense, and interactions with other organisms (e.g. pigments, odorants, and pheromones). A primary metabolite is directly involved in normal "growth", development, and reproduction. Ethylene exemplifies a primary metabolite produced large-scale by industrial microbiology. A secondary metabolite is not directly involved in those processes, but usually has an important ecological function. Examples include antibiotics and pigments such as resins and terpenes etc. Some antibiotics use primary metabolites as precursors, such as actinomycin, which is created from the primary metabolite tryptophan. Some sugars are metabolites, such as fructose or glucose, which are both p ...
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