2,3,5-trimethoxyamphetamine
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2,3,5-trimethoxyamphetamine
Trimethoxyamphetamines (TMAs) are a family of positionally isomeric psychedelic hallucinogenic drugs. There exist six different TMAs that differ only in the positions of the three methoxy groups: TMA (TMA-1), TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are substituted amphetamines and are analogues of the phenethylamine cactus alkaloid mescaline and the DOx drugs. The mechanism of action of the TMAs is different from that of the unsubstituted compound amphetamine, probably involving agonist activity on serotonin receptors such as the 5-HT2A receptors instead of the monoamine releasing agent actions typical of most amphetamines. This action on serotonergic receptors likely underlies the psychedelic effects of these compounds. TMA was first synthesized by Hey, in 1947. Synthesis data as well as human activity data has been published by Alexander Shulgin in his book ''PiHKAL''. The most important TMA compound from a pharmacological standpoint is TMA-2, as this isomer has be ...
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Positional Isomer
In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The term metamer was formerly used for the same concept. For example, butanol , methyl propyl ether , and diethyl ether have the same molecular formula but are three distinct structural isomers. The concept applies also to polyatomic ions with the same total charge. A classical example is the cyanate ion and the fulminate ion . It is also extended to ionic compounds, so that (for example) ammonium cyanate and urea are considered structural isomers,William F. Bynum, E. Janet Browne, Roy Porter (2014)''Dictionary of the History of Science'' page 218. and so are methylammonium formate and ammonium acetate . Structural isomerism is the most radical type of isomerism. It is opposed to stereoisomerism, in which the atoms and bonding s ...
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Amphetamine
Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity; it is also used to treat binge eating disorder in the form of its inactive prodrug lisdexamfetamine. Amphetamine was discovered as a chemical in 1887 by Lazăr Edeleanu, and then as a drug in the late 1920s. It exists as two enantiomers: levoamphetamine and dextroamphetamine. ''Amphetamine'' properly refers to a specific chemical, the Racemic mixture, racemic free base, which is equal parts of the two enantiomers in their pure amine forms. The term is frequently used informally to refer to any combination of the enantiomers, or to either of them alone. Historically, it has been used to treat nasal congestion and depression. Amphetamine is also used as an Performance-enhancing substance, athletic performance enhancer and Nootropic ...
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Japan
Japan is an island country in East Asia. Located in the Pacific Ocean off the northeast coast of the Asia, Asian mainland, it is bordered on the west by the Sea of Japan and extends from the Sea of Okhotsk in the north to the East China Sea in the south. The Japanese archipelago consists of four major islands—Hokkaido, Honshu, Shikoku, and Kyushu—and List of islands of Japan, thousands of smaller islands, covering . Japan has a population of over 123 million as of 2025, making it the List of countries and dependencies by population, eleventh-most populous country. The capital of Japan and List of cities in Japan, its largest city is Tokyo; the Greater Tokyo Area is the List of largest cities, largest metropolitan area in the world, with more than 37 million inhabitants as of 2024. Japan is divided into 47 Prefectures of Japan, administrative prefectures and List of regions of Japan, eight traditional regions. About three-quarters of Geography of Japan, the countr ...
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Netherlands
, Terminology of the Low Countries, informally Holland, is a country in Northwestern Europe, with Caribbean Netherlands, overseas territories in the Caribbean. It is the largest of the four constituent countries of the Kingdom of the Netherlands. The Netherlands consists of Provinces of the Netherlands, twelve provinces; it borders Germany to the east and Belgium to the south, with a North Sea coastline to the north and west. It shares Maritime boundary, maritime borders with the United Kingdom, Germany, and Belgium. The official language is Dutch language, Dutch, with West Frisian language, West Frisian as a secondary official language in the province of Friesland. Dutch, English_language, English, and Papiamento are official in the Caribbean Netherlands, Caribbean territories. The people who are from the Netherlands is often referred to as Dutch people, Dutch Ethnicity, Ethnicity group, not to be confused by the language. ''Netherlands'' literally means "lower countries" i ...
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Research Chemical
Research chemicals are chemical substances which scientists use for medical and scientific research purposes. One characteristic of a research chemical is that it is for laboratory research use only; a research chemical is not intended for human or veterinary use. In the United States, this distinction is required on the labels of research chemicals and exempts them from regulation under parts 100-740 in Title 21 of the Code of Federal Regulations ( 21CFR). Background Agricultural research chemicals Research agrochemicals are created and evaluated to select effective substances for commercial off-the-shelf end-user products. Many research agrochemicals are never publicly marketed. Agricultural research chemicals often use sequential code name A code name, codename, call sign, or cryptonym is a code word or name used, sometimes clandestinely, to refer to another name, word, project, or person. Code names are often used for military purposes, or in espionage. They may also be ...
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Grey Market
A grey market or dark market (sometimes confused with the similar term "parallel import, parallel market") is the trade of a commodity through distribution channels that are not authorised by the original manufacturer or trademark proprietor. Grey market products (grey goods) are products traded outside the authorised manufacturer's channel. Etymology Manufacturers of computers, telecom, and technology equipment often sell these products through distributors. Most distribution agreements require the distributor to resell the products strictly to end users. However, some distributors choose to resell products to other resellers. In the late 1980s, manufacturers labelled the resold products as the "grey market". Description Grey market goods are goods sold outside the authorized distribution channels by entities which may have no relationship with the producer of the goods. This form of parallel import frequently occurs when the price of an item is significantly higher in one ...
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Recreational Drug
Recreational drug use is the use of one or more psychoactive drugs to induce an altered state of consciousness, either for pleasure or for some other casual purpose or pastime. When a psychoactive drug enters the user's body, it induces an Substance intoxication, intoxicating effect. Recreational drugs are commonly divided into three categories: depressants (drugs that induce a feeling of relaxation and calmness), stimulants (drugs that induce a sense of energy and alertness), and hallucinogens (drugs that induce perceptual distortions such as hallucination). In popular practice, recreational drug use is generally tolerated as a social behaviour, rather than perceived as the medical condition of self-medication. However, drug use and drug addiction are Social stigma, severely stigmatized everywhere in the world. Many people also use prescribed and controlled depressants such as opioids, opiates, and benzodiazepines. What controlled substances are considered generally unlawful t ...
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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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Human
Humans (''Homo sapiens'') or modern humans are the most common and widespread species of primate, and the last surviving species of the genus ''Homo''. They are Hominidae, great apes characterized by their Prehistory of nakedness and clothing#Evolution of hairlessness, hairlessness, bipedality, bipedalism, and high Human intelligence, intelligence. Humans have large Human brain, brains, enabling more advanced cognitive skills that facilitate successful adaptation to varied environments, development of sophisticated tools, and formation of complex social structures and civilizations. Humans are Sociality, highly social, with individual humans tending to belong to a Level of analysis, multi-layered network of distinct social groups — from families and peer groups to corporations and State (polity), political states. As such, social interactions between humans have established a wide variety of Value theory, values, norm (sociology), social norms, languages, and traditions (co ...
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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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Monoamine Releasing Agent
A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the release of one or more monoamine neurotransmitters from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrations of the neurotransmitters and hence enhanced signaling by those neurotransmitters. The monoamine neurotransmitters include serotonin, norepinephrine, and dopamine; MRAs can induce the release of one or more of these neurotransmitters. MRAs work by reversing the direction of the monoamine transporters (MATs), including the serotonin transporter (SERT), norepinephrine transporter (NET), and/or dopamine transporter (DAT), causing them to promote efflux of non-vesicular cytoplasmic monoamine neurotransmitter rather than reuptake of synaptic monoamine neurotransmitter. Many, but not all MRAs, also reverse the direction of the vesicular monoamine transporter 2 (VMAT2), thereby additionally resulting in efflux of vesicular monoamine neuro ...
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