Para-Iodomethamphetamine
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Para-Iodomethamphetamine
''para''-Iodomethamphetamine (PIMA), also known as 4-iodo-''N''-methylamphetamine (4-IMA) or as D-9, is a monoaminergic drug of the amphetamine family related to ''para''-chloroamphetamine (PCA). It is the ''N''-methyl analogue of ''para''-iodoamphetamine (PIA). The drug is active in producing behavioral effects in animals, including hallucinogen-like effects. However, it is unclear whether these effects actually represent hallucinogenic reactions. PIMA does not appear to have been assessed, but other ''para''-halogenated amphetamines, such as PCA, are known to act as monoamine releasing agents and as monoaminergic neurotoxins. They have not proved to be psychedelic in humans. PIMA was studied by Joseph Knoll and colleagues in the 1960s or 1970s. See also * Substituted amphetamine Substituted amphetamines, or simply amphetamines, are a chemical class, class of compounds based upon the amphetamine structure; it includes all derivative (chemistry), derivative compounds w ...
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Monoaminergic
Monoaminergic means "working on monoamine neurotransmitters", which include serotonin, dopamine, norepinephrine, epinephrine, and histamine. A monoaminergic, or monoaminergic drug, is a chemical, which functions to directly modulate the serotonin, dopamine, norepinephrine, epinephrine, and/or histamine neurotransmitter systems in the brain. Monoaminergics include catecholaminergics (which can be further divided into adrenergics and dopaminergics), serotonergics, and histaminergics. Examples of monoaminergic drugs include monoamine precursors, monoamine receptor modulators, monoamine reuptake inhibitors, monoamine releasing agents, and monoamine metabolism modulators such as monoamine oxidase inhibitors. See also * Adenosinergic * Adrenergic * Cannabinoidergic * Cholinergic * Dopaminergic * GABAergic * Glycinergic * Histaminergic * Melatonergic A melatonergic agent (or drug) is a chemical which functions to directly modulate the melatonin system in the body or brain. Exam ...
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Substituted Amphetamine
Substituted amphetamines, or simply amphetamines, are a chemical class, class of compounds based upon the amphetamine structure; it includes all derivative (chemistry), derivative compounds which are formed by replacing, or substitution reaction, 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, Empathogen-entactogen, empathogens, and hallucinogens, among others. Examples of substituted amphetamines are amphetamine (itself), methamphetamine, ephedrine, cathinone, phentermine, mephentermine, tranylcypromine, bupropion, methoxyphenamine, selegiline, amfepramone, amfepramone (diethylpropion), pyrovalerone, MDMA (ecstasy), and 2,5-dimethoxy-4-methylamphetamine, DOM (STP). Some of amphetamine's substituted Derivative (chemistry), derivatives occur in nature, for example in the leaves of ''Ephedra (genus), Ephedra'' and khat plants. Amphetamine w ...
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N-Methyl-DOI
''N''-Methyl-DOI, also known as 2,5-dimethoxy-4-iodo-''N''-methylamphetamine (2,5-IDNA), is a serotonin receptor modulator of the phenethylamine, amphetamine, and DOx families related to the serotonergic psychedelic DOI. It is a potent agonist of the serotonin 5-HT2A receptor similarly to DOI. However, ''N''-methyl-DOI was about 3.8-fold less potent than DOI as a serotonin 5-HT2A receptor agonist in terms of and showed reduced maximal efficacy compared to DOI ( = 64% vs. 83%). On the other hand, it showed similar efficacy in activating the serotonin 5-HT2A receptor to the psychedelic 2C-I ( = 68%). ''N''-Methyl-DOI was first described in the scientific literature, as a potential radiopharmaceutical for medical imaging, by 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 chemist ...
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Para-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 effects. As a recreational drug, 4-FA is sometimes sold along with related compounds such as 2-fluoroamphetamine and 4-fluoromethamphetamine. Usage 4-FA is popular in the Netherlands where it is predominantly used for its specific effects (77% of users) rather than its legal status (18%). 4-FA has become illegal since May 2017. Effects The subjective effects of 4-fluoroamphetamine include euphoria which some find similar to the effects of MDMA and amphetamine, increased energy (stimulation), mood elevation, feelings of warmth and empathy, excessive talking, bruxism, and suppressed appetite (anorexic). The general course of effects involves primarily empathogenic effects for the first few hours, which fades out as increased stimulation d ...
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Para-Chloromethamphetamine
''para''-Chloromethamphetamine (also known as 4-chloromethamphetamine and 4-CMA; code name Ro 4-6861) is a stimulant that is the ''N''-methyl derivative and prodrug of the neurotoxic drug ''para''-chloroamphetamine (4-CA). It has been found to decrease serotonin in rats. Further investigation into the long-term effects of chloroamphetamines discovered that administration of 4-CMA caused a prolonged reduction in the levels of serotonin and the activity of tryptophan hydroxylase in the brain one month after injection of a single dose of the drug. Another study on rats found that 4-chloromethamphetamine was more potent at inducing conditioned taste aversion than methamphetamine. 4-Chloromethamphetamine was further investigated in the 1960s along with 4-CA and it was noted that they differed from their parent amphetamine and methamphetamine substances by exhibiting only a slight central stimulant effect in both animals and humans and that they acted like antidepressants rather t ...
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Para-Chloroamphetamine
''para''-Chloroamphetamine (PCA), also known as 4-chloroamphetamine (4-CA), is a serotonin–norepinephrine–dopamine releasing agent (SNDRA) and serotonergic neurotoxin of the amphetamine family. It is used in scientific research in the study of the serotonin system, as a serotonin releasing agent (SRA) at lower doses to produce serotonergic effects, and as a serotonergic neurotoxin at higher doses to produce long-lasting depletions of serotonin. PCA has also been clinically studied as an appetite suppressant and antidepressant, but findings of neurotoxicity in animals discouraged further evaluation. It has also been encountered as a designer drug, although it never achieved popularity, again perhaps due to its neurotoxicity. Effects PCA was studied clinically as an appetite suppressant and antidepressant and its effects in these studies were described. It has been said to have only slight stimulant effects and to behave more like an antidepressant than a stimulant. At doses ...
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Para-Bromomethamphetamine
''para''-Bromomethamphetamine (PBMA; developmental code name V-111), also known as 4-bromomethamphetamine (4-BMA), is a monoaminergic drug of the amphetamine family related to ''para''-chloroamphetamine (PCA; 4-chloroamphetamine). It was studied by József Knoll and colleagues in the 1970s and 1980s. Pharmacology Originally thought to selectively act on serotonin, PBMA was subsequently found to act not only on serotonin but also on norepinephrine and dopamine similarly to PCA. It has been reported to produce pharmacological effects that have been said to be "somewhat similar" or "indistinguishable" to those of lysergic acid diethylamide (LSD) and various other hallucinogens in various animal species. However, when the drug was subsequently tested in humans, it showed no hallucinogenic effects whatsoever. This is analogous to the case of PCA, which can produce the head-twitch response in rodents but is not hallucinogenic in humans. The hallucinogen-like effects of PBMA in animal ...
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Para-Bromoamphetamine
''para''-Bromoamphetamine (PBA), also known as 4-bromoamphetamine (4-BA), is an amphetamine derivative which acts as a serotonin-norepinephrine-dopamine releasing agent (SNDRA) and produces stimulant effects. Another related compound is ''para''-bromomethamphetamine (PBMA) known by the codename V-111. Pharmacology PBA has been found to be a monoamine oxidase A (MAO-A) inhibitor, with an of 1,500nM. Neurotoxicity Like most other ''para''-substituted amphetamines, PBA can be neurotoxic and may deplete the brain of 5-hydroxyindoles for at least a week. See also * Substituted amphetamines * 4-Bromomethcathinone (4-BMC) * 4-Fluoroamphetamine 4-Fluoroamphetamine (4-FA; 4-FMP; PAL-303; "Flux"), also known as ''para''-fluoroamphetamine (PFA) is a psychoactive drug, psychoactive research chemical of the phenethylamine and substituted amphetamine chemical classes. It produces stimulant a ... (4-FA) * ''para''-Chloroamphetamine (PCA) * ''para''-Iodoamphetamine (PIA) * ''para'' ...
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Para-Iodoamphetamine
''para''-Iodoamphetamine (PIA), also known as 4-iodoamphetamine (4-IA), is a monoamine releasing agent (MRA) and serotonergic neurotoxin of the amphetamine family related to ''para''-chloroamphetamine (PCA). Pharmacology Pharmacodynamics PIA acts as a serotonin releasing agent (SRA). In animal drug discrimination tests, PIA fully substitutes for MDMA and (+)-MBDB. It also has very low affinity for certain serotonin receptors, including the serotonin 5-HT1 receptor (Ki = 7,660nM) and the serotonin 5-HT2 receptor (Ki = 43,000nM). PIA has been described as having either similar serotonergic neurotoxicity as PCA or as having much weaker serotonergic neurotoxicity than PCA. Chemistry PIA, also known as 4-iodoamphetamine, is a phenethylamine and amphetamine derivative and a ''para''-halogenated amphetamine. Analogues PIA is closely related to other ''para''-halogenated amphetamines such as PCA, ''para''-bromoamphetamine (PBA), and ''para''-fluoroamphetamine (PFA). Iofetamin ...
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Joseph Knoll
Joseph is a common male name, derived from the Hebrew (). "Joseph" is used, along with " Josef", mostly in English, French and partially German languages. This spelling is also found as a variant in the languages of the modern-day Nordic countries. In Portuguese and Spanish, the name is "José". In Arabic, including in the Quran, the name is spelled , . In Kurdish (''Kurdî''), the name is , Persian, the name is , and in Turkish it is . In Pashto the name is spelled ''Esaf'' (ايسپ) and in Malayalam it is spelled ''Ousep'' (ഔസേപ്പ്). In Tamil, it is spelled as ''Yosepu'' (யோசேப்பு). The name has enjoyed significant popularity in its many forms in numerous countries, and ''Joseph'' was one of the two names, along with ''Robert'', to have remained in the top 10 boys' names list in the US from 1925 to 1972. It is especially common in contemporary Israel, as either "Yossi" or "Yossef", and in Italy, where the name "Giuseppe" was the most common ma ...
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