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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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2,5-DMA
2,5-Dimethoxyamphetamine (2,5-DMA), also known as DMA-4 or as DOH, is a drug of the substituted phenethylamine, phenethylamine and substituted amphetamine, amphetamine families. It is one of the dimethoxyamphetamine (DMA) series of positional isomers. The drug is notable in being the parent compound of the DOx (4-substituted-2,5-dimethoxyamphetamine) series of drugs. Use and effects 2,5-DMA is said to be inactive as a serotonergic psychedelic, psychedelic, at least at the doses that have been assessed. However, it has been reported to produce some stimulant-like effects, as well as sympathomimetic effects and mydriasis. The dose range is said to be 80 to 160mg oral administration, orally and its duration of action, duration is 6 to 8hours. Pharmacology 2,5-DMA is a low-potency (pharmacology), potency serotonin 5-HT2A receptor, 5-HT2A receptor partial agonist, with an affinity (pharmacology), affinity (Ki) of 2,502nM, an of 160 to 3,548nM (depending on the signaling cascade and ...
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3,4-DMA
3,4-Dimethoxyamphetamine (3,4-DMA), or simply dimethoxyamphetamine (DMA), is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the dimethoxyamphetamine (DMA) series of positional isomers. The drug has been assessed in various biochemical and preclinical studies. It has been tried in humans at doses of up to 700mg intravenously, with mescaline-like effects reported. 3,4-DMA is also orally active and has produced sympathomimetic effects at a dose of 160mg. Its duration of action is unknown. Its affinity (Ki) for the rat serotonin 5-HT2A receptor has been assessed and was found to be 43,300nM. For comparison, the affinity of ''para''-methoxyamphetamine (PMA) was 33,600nM, of 2,5-dimethoxyamphetamine (2,5-DMA) was 5,200nM, and of 2,5-dimethoxy-4-methylamphetamine (DOM) was 100nM in the same study. 3,4-DMA also showed affinity for the 5-HT1 receptor (Ki = 64,600nM). The drug has additionally been found to be a monoamine oxidase inhibitor (MAOI), wit ...
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3,5-DMA
3,5-Dimethoxyamphetamine (3,5-DMA), also known as DMA-6, is a drug of the amphetamine family and a positional isomer of dimethoxyamphetamine (DMA). It is the parent structure of the 3C (4-substituted 3,5-dimethoxyamphetamine) family of compounds (also known as 3C- scalines). In an early study, it showed similar affinity for serotonin receptors as mescaline (3,4,5-trimethoxyphenethylamine) but had more than an order of magnitude lower affinity than DOx (4-substituted 2,5-dimethoxyamphetamine) drugs like DOM, DOET, and DOB. However, in a later study, it showed no or very low affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = >10,000nM), whereas DOB showed high affinity for these receptors (Ki = 32nM and 64nM, respectively). 3,5-DMA's effects on monoamine reuptake and efflux have also been studied. It appeared to be weak or inactive as a norepinephrine reuptake inhibitor and norepinephrine releasing agent. Likewise, it was a very weak serotonin reuptake inhibitor ( = 1 ...
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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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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 positional isomers. The drug is notable in being the amphetamine (i.e., α-methylated) analogue of mescaline (3,4,5-trimethoxyphenethylamine). Use and effects TMA is a serotonergic psychedelic and produces hallucinogenic effects. It is said to be active at doses of 100 to 250mg and to have a duration of 6 to 8hours. For comparison, mescaline is typically used at doses of 200 to 500mg and is said to have a duration of 10 to 12hours or longer. TMA's positional isomer 2,4,5-trimethoxyamphetamine (2,4,5-TMA or TMA-2) is much more potent than TMA, with a dosage of 20 to 40mg and a duration of 8 to 12hours. Interactions Pharmacology TMA is a low-potency serotonin 5-HT2A receptor partial agonist, with an affinity (Ki) of >12,000nM, an of 1,7 ...
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2,4-DMA
2,4-Dimethoxyamphetamine (2,4-DMA), also known as DMA-3, is a drug of the phenethylamine and amphetamine families. It is one of the dimethoxyamphetamine (DMA) series of positional isomers. It was reported by Alexander Shulgin to be active at a dose of 60mg orally and to produce threshold amphetamine-like stimulant and euphoric effects. However, there was also a "diffusion of association" and Shulgin stated that it was more than just a stimulant. The duration was described as short and effects subsiding at 3hours. Per Shulgin, the drug could be a full stimulant and/or a full psychedelic at sufficiently high doses, but higher doses were not pursued. 2,4-DMA has been found to act as a low-potency full agonist of the serotonin 5-HT2A receptor, with an of 2,950nM and an of 117%. It fully substitutes for DOM in rodent drug discrimination tests. The drug is less potent in this regard than 2,4,5-trimethoxyamphetamine (2,4,5-TMA or TMA-2), but is more potent than 3,4,5-trimethoxy ...
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3-methoxyamphetamine
3-Methoxyamphetamine (3-MA), also known as ''meta''-methoxyamphetamine (MMA), is a monoamine releasing agent (MRA) of the amphetamine family. It is a positional isomer of ''para''-methoxyamphetamine (PMA; 4-methoxyamphetamine). Effects According to Alexander Shulgin, 3-MA showed no central or psychedelic effects in humans at a total dose of 50mg (25mg orally twice separated by 3hours). However, sympathomimetic effects have occurred with the drug at an oral dose of 25mg in humans.Schelling, J.L., Dufour, R.J., Jequier, E. (1974) Vasopressor effect of 3-methoxyamphetamine in man. Vortr. Symp. Meeting Date 1970, pp 175-183. "Like other amphetamines, 3-methoxyamphetamine (I) 7862-85-0had a transient pressor effect on man. The minimal effective dose on oral administration was 25 mg. Differences between that dose and a placebo were significant in young normotensive subjects. The acute response of older patients with chronic hypotension to the same dose was unpredictable. Unlike o ...
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2C-H
2C-H, also known as 2,5-dimethoxyphenethylamine (2,5-DMPEA), is a lesser-known drug of the phenethylamine and 2C (4-substituted 2,5-dimethoxyphenethylamine) families. It is the parent compound of the 2C drugs. Use and effects There is no record of 2C-H trials in humans, as it would likely be destroyed by monoamine oxidase enzymes before causing any significant psychoactive effects. In the book ''PiHKAL'', Alexander Shulgin lists both the dosage and duration of 2C-H effects as unknown. Very little data exists about the pharmacological properties, metabolism, and toxicity of 2C-H. Pharmacology 2C-H acts as a partial agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors, albeit with far lower potency than other 2C drugs. It also shows affinity for the serotonin 5-HT1A receptor, higher than that of any other 2C drug. The drug exhibits agonist activity ''in vitro'' at the human trace amine associated receptor 1 (TAAR1). 2C-H produces visual and auditory cha ...
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5-HT2A Receptor
The 5-HT2A receptor is a subtype of the 5-HT2 receptor, 5-HT2 receptor that belongs to the serotonin receptor family and functions as a GPCR, G protein-coupled receptor (GPCR). It is a cell surface receptor that activates multiple intracellular signalling cascades. Like all 5-HT2 receptors, the 5-HT2A receptor is coupled to the Gq protein, Gq/G11 signaling pathway. It is the primary excitatory receptor subtype among the serotonin-responsive GPCRs. The 5-HT2A receptor was initially noted for its central role as the primary target of serotonergic psychedelic drugs such as LSD and psilocybin mushrooms. It later regained research prominence when found to mediate, at least in part, the effects of many antipsychotic drugs, particularly atypical antipsychotic, atypical antipsychotics. Downregulation of post-synaptic 5-HT2A receptors is an adaptive response triggered by chronic administration of selective serotonin reuptake inhibitors (SSRIs) and atypical antipsychotics. Elevated 5-HT2A ...
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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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Psychedelics, Dissociatives And Deliriants
Hallucinogens, also known as psychedelics, entheogens, or historically as psychotomimetics, are a large and diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, mood, and perception as well as other changes. Hallucinogens are often categorized as either being psychedelics, dissociatives, or deliriants, but not all hallucinogens fall into these three classes. Examples of hallucinogens include psychedelics or serotonin 5-HT2A receptor agonists like LSD, psilocybin, mescaline, and DMT; dissociatives or NMDA receptor antagonists like ketamine, PCP, DXM, and nitrous oxide; deliriants or antimuscarinics like scopolamine and diphenhydramine; cannabinoids or cannabinoid CB1 receptor agonists like THC, nabilone, and JWH-018; κ-opioid receptor agonists like salvinorin A and pentazocine; GABAA receptor agonists like muscimol and gaboxadol; and oneirogens like ibogaine and harmaline, among ...
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Mydriasis
Mydriasis is the Pupillary dilation, dilation of the pupil, usually having a non-physiological cause, or sometimes a physiological pupillary response. Non-physiological causes of mydriasis include disease, Physical trauma, trauma, or the use of certain types of drug, drugs. It may also be of unknown cause. Normally, as part of the pupillary light reflex, the pupil dilates in the dark and miosis, constricts in the light to respectively improve vividity at night and to protect the retina from sunlight damage during the day. A ''mydriatic'' pupil will remain excessively large even in a bright environment. The excitation of the radial fibres of the iris which increases the pupillary aperture is referred to as a mydriasis. More generally, mydriasis also refers to the natural dilation of pupils, for instance in low light conditions or under sympathetic stimulation. Mydriasis is frequently induced by drugs for certain Ophthalmology, ophthalmic examinations and procedures, particularly th ...
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