Trimethoxyphenethylamine
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Trimethoxyphenethylamine
Trimethoxyphenethylamines (TMPEA) are a group of positional isomers of the psychedelic cactus alkaloid mescaline. Some of them are described in the book PiHKAL by Alexander Shulgin and Ann Shulgin. * 2,3,4-trimethoxyphenethylamine ( Isomescaline) * 2,3,5-trimethoxyphenethylamine ( 2C-TMA-4) * 2,3,6-trimethoxyphenethylamine ( 2C-TMA-5) * 2,4,5-trimethoxyphenethylamine ( 2C-O) * 2,4,6-trimethoxyphenethylamine ( 2C-TMA-6) * 3,4,5-trimethoxyphenethylamine (Mescaline) * 4-bromo-2,5,beta-trimethoxyphenethylamine (BOB (psychedelic)) * 4-methyl-2,5,β-trimethoxyphenethylamine ( BOD (psychedelic)) * N-(2-methoxybenzyl)-3,4,5-trimethoxyphenethylamine ( NBOMe-mescaline) See also * Substituted methoxyphenethylamine * Methoxyphenethylamine * Dimethoxyphenethylamine * Methoxyamphetamine * Dimethoxyamphetamine * Trimethoxyamphetamine 3,4,5-Trimethoxyamphetamine (TMA, TMA-1, or 3,4,5-TMA), also known as α-methylmescaline or mescalamphetamine, is a psychedelic drug of the phenethylamine and amp ...
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Mescaline
Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a natural product, naturally occurring psychedelic drug, psychedelic alkaloid, protoalkaloid of the substituted phenethylamine class, found in Cactus, cacti like peyote (''Lophophora williamsii'') and San Pedro cactus, San Pedro (certain species of the Echinopsis genus) and known for its Serotonin, serotonergic Hallucinogen, hallucinogenic effects. Mescaline is typically taken orally and used recreationally, spiritually, and medically, with psychedelic effects occurring at doses from 100 to 1,000 mg, including microdosing below 75 mg, and it can be consumed in pure form or via mescaline-containing cacti. Mescaline induces a psychedelic experience characterized by vivid visual patterns, altered perception of time and self, synesthesia, and spiritual effects, with an onset of 0.5–0.9 hours and a duration that increases with dose, ranging from about 6 to 14 hours. Mescaline h ...
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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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Trimethoxyamphetamines
Trimethoxyamphetamines (TMAs) are a family of positional isomer, positionally isomeric psychedelic drug, psychedelic hallucinogenic drug, hallucinogenic psychoactive drug, drugs. There exist six different TMAs that differ only in the positions of the three methoxy Functional group, groups: 3,4,5-trimethoxyamphetamine, TMA (TMA-1), 2,4,5-trimethoxyamphetamine, TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are substituted amphetamines and are structural analog, 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 receptor, 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 chemical synthesis, synthesized by Hey, in 1947. Synt ...
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Dimethoxyamphetamine
Dimethoxyamphetamine (DMA) is a series of six lesser-known psychedelic drugs similar in structure to the three isomers of methoxyamphetamine and six isomers of trimethoxyamphetamine. The isomers are 2,3-DMA, 2,4-DMA, 2,5-DMA, 2,6-DMA, 3,4-DMA, and 3,5-DMA. Three of the isomers were characterized by Alexander Shulgin in his book ''PiHKAL''. Little is known about their dangers or toxicity. Pharmacology 3,4-DMA, 2,4-DMA, 2,5-DMA, and their ''N''-methyl analogues all fail to produce stimulus generalization to dextroamphetamine in rodent drug discrimination tests, suggesting that they lack psychostimulant- or amphetamine-like effects, at least in rodents. This is in contrast to 2-methoxyamphetamine (OMA), 3-methoxyamphetamine (MMA), and 4-methoxyamphetamine (PMA), which all produce substitution for dextroampehtamine, albeit with far lower potency than amphetamine, methamphetamine, and other stimulants. Positional isomers 2,4-DMA * ''Dosage'': 60 mg or greater * ''Du ...
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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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Methoxyamphetamine
Methoxyamphetamine may refer to: * 2-Methoxyamphetamine (2-MA) or ''ortho''-methoxyamphetamine (OMA) * 3-Methoxyamphetamine (3-MA) or ''meta''-methoxyamphetamine (MMA) * 4-Methoxyamphetamine (4-MA) or ''para''-methoxyamphetamine (PMA) See also * Substituted methoxyphenethylamine * Dimethoxyamphetamine * Trimethoxyamphetamine * Methoxyphenethylamine * Dimethoxyphenethylamine * Trimethoxyphenethylamine Trimethoxyphenethylamines (TMPEA) are a group of positional isomers of the psychedelic cactus alkaloid mescaline. Some of them are described in the book PiHKAL by Alexander Shulgin and Ann Shulgin. * 2,3,4-trimethoxyphenethylamine ( Isomescaline) * ... {{Chemistry index Methoxyphenethylamines Substituted amphetamines ...
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Dimethoxyphenethylamine
Dimethoxyphenethylamine may refer to: * 2,3-Dimethoxyphenethylamine (2,3-DMPEA; DMPEA-2) * 2,4-Dimethoxyphenethylamine (2,4-DMPEA; DMPEA-3) * 2,5-Dimethoxyphenethylamine (2C-H; 2,5-DMPEA; DMPEA-4) * 2,6-Dimethoxyphenethylamine (2,6-DMPEA; DMPEA-5) * 3,4-Dimethoxyphenethylamine (3,4-DMPEA; DMPEA; DMPEA-1) * 3,5-Dimethoxyphenethylamine (3,5-DMPEA; DMPEA-6) See also * Substituted methoxyphenethylamine * Methoxyphenethylamine * Trimethoxyphenethylamine * Methoxyamphetamine * Dimethoxyamphetamine * Trimethoxyamphetamine 3,4,5-Trimethoxyamphetamine (TMA, TMA-1, or 3,4,5-TMA), also known as α-methylmescaline or mescalamphetamine, is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the trimethoxyamphetamine (TMA) series of positiona ... {{Phenethylamines Methoxyphenethylamines ...
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Isomescaline
Isomescaline (2,3,4-trimethoxyphenethylamine) is a lesser-known compound based on a well-known psychedelic drug. It is an isomer of mescaline, as well as an analog of TIM-2, TIM-3, and TIM-4. Isomescaline was first synthesized by Alexander Shulgin. In his book ''PIHKAL'', it is suggested that any potentially active dose would be "greater than 400 mg". Despite its structural similarity to mescaline, isomescaline has produced no effects in humans. Very little data exists about the pharmacological properties, metabolism, and toxicity of isomescaline. See also * Substituted mescaline analogue A substituted mescaline analogue, also known as a scaline and typically but not always a 4-substituted 3,5-dimethoxyphenethylamine, is an analogue of the phenethylamine serotonergic psychedelic mescaline (3,4,5-trimethoxyphenethylamine). Other ... References Phenol ethers Scalines {{Psychoactive-stub ...
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Methoxyphenethylamine
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 3,4,5-Trimethoxyamphetamine (TMA, TMA-1, or 3,4,5-TMA), also known as α-methylmescaline or mescalamphetamine, is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the trimethoxyamphetamine (TMA) series of positiona ... {{Chemistry index Methoxyphenethylamines ...
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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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2C-O
2C-O, also known as 2,4,5-trimethoxyphenethylamine (2,4,5-TMPEA) or TMPEA-2, is a chemical compound of the phenethylamine and 2C families. It is a positional isomer of mescaline (3,4,5-trimethoxyphenethylamine) and is the α-desmethyl analogue of 2,4,5-trimethoxyamphetamine (TMA-2). The drug is the parent compound of the 2C-O series of drugs. 2C-O appears to be inactive in terms of psychoactive effects in humans. It was first described by Jansen in 1931. Chemistry 2C-O is a member of a class of chemical compounds commonly known as phenethylamines. Its full chemical name is 2-(2,4,5-trimethoxyphenyl)ethanamine; it is also known as 2,4,5-trimethoxyphenethylamine and 2,4,5-TMPEA. A variety of derivatives of 2C-O, named 2C-O-2 (4-ethoxy-2,5-dimethoxyphenethylamine) through 2C-O-27, have been developed and studied. One particularly notable derivative is 2C-O-4 (4-isopropoxy-2,5-dimethoxyphenethylamine). Effects 2C-O at a dose of under 300mg was reported to produce similar psych ...
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