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Substituted Methylenedioxyphenethylamine
Substitution reaction, Substituted methylenedioxy- phenethylamines (MDxx) are a large chemical class of derivative (chemistry), derivatives of the phenethylamines, which includes many psychoactive drugs that act as entactogens, psychedelic drug, psychedelics, and/or stimulants, as well as entheogens. These agents are used as research chemicals, designer drugs and as recreational substances. The base chemical compound, compound of the MDxx class is methylenedioxyphenethylamine, 3,4-methylenedioxyphenethylamine (MDPEA), and the prototypical agent of this class is MDMA, 3,4-methylenedioxy-''N''-methylamphetamine (MDMA; "ecstasy"). Other mentionables include 3,4-methylenedioxyamphetamine (MDA), methylenedioxyethylamphetamine, 3,4-methylenedioxy-''N''-ethylamphetamine (MDEA; "Eve"), methylbenzodioxolylbutanamine, ''N''-methyl-1,3-benzodioxolylbutanamine (MBDB; "Eden"), and methylenedioxymethcathinone, 3,4-methylenedioxy-''N''-methylcathinone (βk-MDMA; "Methylone"). List of substitu ...
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Methylenedioxyphenethylamine
3,4-Methylenedioxyphenethylamine, also known as 3,4-MDPEA, MDPEA, and homopiperonylamine, is a substituted phenethylamine formed by adding a methylenedioxy group to phenethylamine. It is structurally similar to MDA, but without the methyl group at the alpha position. According to Alexander Shulgin in his book '' PiHKAL'', MDPEA appears to be biologically inactive. This is likely because of extensive first-pass metabolism by the enzyme monoamine oxidase. However, if MDPEA were either used in high enough of doses (e.g., 1-2 grams), or in combination with a monoamine oxidase inhibitor (MAOI), it is probable that it would become sufficiently active, though it would likely have a relatively short duration of action. This idea is similar in concept to the use of selective MAOA inhibitors and selective MAOB inhibitors in augmentation of dimethyltryptamine (DMT) and phenethylamine (PEA), respectively. See also * Substituted methylenedioxyphenethylamine Substitution ...
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Methylenedioxyethylamphetamine
3,4-Methylenedioxy-''N''-ethylamphetamine (MDEA; also called MDE and colloquially, Eve) is an empathogenic psychoactive drug. MDEA is a substituted amphetamine and a substituted methylenedioxyphenethylamine. MDEA acts as a serotonin, norepinephrine, and dopamine releasing agent and reuptake inhibitor. Possession of MDEA is illegal in most countries. Some limited exceptions exist for scientific and medical research. Uses Medical MDEA currently has no accepted medical uses. Recreational MDEA is used recreationally in a similar manner to MDMA (also called ecstasy), however the subjective effects of MDEA are milder and shorter lasting. Alexander Shulgin reported it to be stoning in high doses. Most frequently consumed orally, recreational doses of MDEA are in the range 100 to 200 mg. Infrequently, MDEA is an adulterant of ecstasy pills. Studies conducted in the 1990s found MDEA present in approximately four percent of ecstasy tablets. Adverse effects Reported adverse ...
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MDMA (simple)
3,4-Methylenedioxymethamphetamine (MDMA), commonly seen in tablet form (ecstasy) and crystal form (molly or mandy), is a potent empathogen–entactogen with stimulant properties primarily used for recreational purposes. The desired effects include altered sensations, increased energy, empathy, and pleasure. When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours. MDMA was first developed in 1912 by Merck. It was used to enhance psychotherapy beginning in the 1970s and became popular as a street drug in the 1980s. MDMA is commonly associated with dance parties, raves, and electronic dance music. It may be mixed with other substances such as ephedrine, amphetamine, and methamphetamine. In 2016, about 21 million people between the ages of 15 and 64 used ecstasy (0.3% of the world population). This was broadly similar to the percentage of people who use cocaine or amphetamines, but lower than for cannabis or opioids. In the United S ...
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2,3-Methylenedioxyamphetamine
2,3-Methylenedioxyamphetamine (2,3-MDA) or ORTHO-MDA is an amphetamine derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. ... which is mentioned in PIHKAL as a fairly potent and long-lasting stimulant drug, but with little or none of the entactogenic effects associated with its better-known structural isomer MDA. References External links MDA entry in PiHKALMDA entry in PiHKAL • info {{DEFAULTSORT:Methylenedioxyamphetamine, 2,3- Substituted amphetamines Benzodioxoles ...
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2,3-MDA
2,3-Methylenedioxyamphetamine (2,3-MDA) or ORTHO-MDA is an amphetamine derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. ... which is mentioned in PIHKAL as a fairly potent and long-lasting stimulant drug, but with little or none of the entactogenic effects associated with its better-known structural isomer MDA. References External links MDA entry in PiHKALMDA entry in PiHKAL • info {{DEFAULTSORT:Methylenedioxyamphetamine, 2,3- Substituted amphetamines Benzodioxoles ...
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3,4-Methylenedioxyamphetamine
3,4-Methylenedioxyamphetamine (also known as MDA and sass) is an empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In terms of pharmacology, MDA acts most importantly as a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal. MDA is rarely sought after as a recreational drug compared to other drugs in the amphetamine family; however, it remains an important and widely used drug due to it being a primary metabolite, the product of hepatic N-dealkylation, of MDMA (ecstasy). In addition, it is common to find MDA as an adulterant of illicitly produced MDMA. Uses Medical MDA currently has no accepted medical use. Recreational MDA is bought, sold, and used as a recreational 'love drug', due to its enhancement of mood and empathy. A recreational dose of MDA is sometimes cited as being ...
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Methoxymethylenedioxyphenethylamine
Lophophine (MMDPEA or 3-methoxy-4,5-methylenedioxyphenethylamine) is a putative psychedelic and entactogen drug of the methylenedioxyphenethylamine class. It is the α-demethylated homologue of MMDA, and is also closely related to mescaline. Alexander Shulgin originally suggested that lophophine may be a natural constituent of peyote (''Lophophora williamsii'') due to it being the only logical chemical intermediate for the biosynthesis of several tetrahydroisoquinolines known to be present in this cactus species. Subsequently, lophophine was indeed shown to be a minor component of both peyote and San Pedro cactus. Shulgin reports that lophophine is active in the dosage range of 150–250 mg. He states that at these doses, lophophine has some similarity to mescaline in action, in producing a peaceful elevation of mood, euphoria, and mild enhancement of visual perception, but without the generation of closed-eye mental imagery. Shulgin also notes that (in cont ...
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Lophophine
Lophophine (MMDPEA or 3-methoxy-4,5-methylenedioxyphenethylamine) is a putative psychedelic and entactogen drug of the methylenedioxyphenethylamine class. It is the α- demethylated homologue of MMDA, and is also closely related to mescaline. Alexander Shulgin originally suggested that lophophine may be a natural constituent of peyote (''Lophophora williamsii'') due to it being the only logical chemical intermediate for the biosynthesis of several tetrahydroisoquinolines known to be present in this cactus species. Subsequently, lophophine was indeed shown to be a minor component of both peyote and San Pedro cactus. Shulgin reports that lophophine is active in the dosage range of 150–250 mg. He states that at these doses, lophophine has some similarity to mescaline in action, in producing a peaceful elevation of mood, euphoria, and mild enhancement of visual perception, but without the generation of closed-eye mental imagery. Shulgin also notes that (in contrast ...
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