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3,4-Ethylidenedioxyamphetamine
3,4-Ethylidenedioxyamphetamine (EIDA) is a substituted derivative of 3,4-methylenedioxyamphetamine (MDA), which was developed by David Nichols and coworkers, in the course of research to determine the bulk tolerance around the benzodioxole portion of the MDA molecule. EIDA was found to produce similar effects to MDA in animals but with less than half the potency, while the isopropylidenedioxy derivative (IPIDA, IDA) did not substitute for MDA and instead had sedative and convulsant effects. This shows limited bulk tolerance at this position and (as with 2C-G-5) makes it likely the activity of EIDA will reside primarily in one enantiomer, although only the racemic mix has been studied as yet. See also * 3,4-Isopropylidenedioxyamphetamine (IDA) * Difluoromethylenedioxyamphetamine (DiFMDA) * F-2 (psychedelic) * 3,4-Ethylenedioxyamphetamine (EIDA) * 3,4-Ethylenedioxymethamphetamine (EDMA) * 3,4-Ethylenedioxymethcathinone 3,4-Ethylenedioxymethcathinone (EDMC), or 3,4-ethyle ...
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3,4-Ethylenedioxyamphetamine
3,4-Ethylenedioxyamphetamine (EDA), also known as EDA-6, is a drug of the substituted amphetamine, amphetamine family related to 3,4-methylenedioxyamphetamine (MDA). It is closely related to structural analog, analogues including 3,4-ethylenedioxymethamphetamine (EDMA), 3,4-ethylidenedioxyamphetamine (EIDA), and 3,4-isopropylidenedioxyamphetamine (IDA). EDMA, the ''N''-methyl group, methylated analogue of EDA, is known to be a serotonin–norepinephrine–dopamine releasing agent (SNDRA). According to Alexander Shulgin however, the drug only produced limited psychoactive drug, psychoactive effects in humans at doses in the range of 150 to 250mg. See also * 3,4-Ethylenedioxymethamphetamine (EDMA) * 3,4-Ethylenedioxymethcathinone (EDMC) * 3,4-Ethylidenedioxyamphetamine (EIDA) * 3,4-Isopropylidenedioxyamphetamine (IDA) * 3,4-Dimethoxyamphetamine (DMA) References

Ethylenedioxyphenethylamines Monoamine releasing agents Substituted amphetamines {{Psychoactive-stub ...
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Difluoromethylenedioxyamphetamine
Difluoromethylenedioxyamphetamine (DFMDA, DiFMDA) is a substituted derivative of 3,4-methylenedioxyamphetamine (MDA), which was developed by Daniel Trachsel and coworkers, along with the corresponding fluorinated derivatives of MDMA, MDEA, BDB and MBDB, with the aim of finding a non-neurotoxic drug able to be used as a less harmful substitute for entactogenic drugs such as MDMA. Since a major route of the normal metabolism of these compounds is scission of the methylenedioxy ring, producing neurotoxic metabolites such as alpha-methyldopamine, it was hoped that the difluoromethylenedioxy bioisostere would show increased metabolic stability and less toxicity. These compounds have not yet been tested in animals to verify whether they show similar pharmacological activity to the non-fluorinated parent compounds, although ''in vitro'' binding studies show DFMDA to have a SERT affinity in between that of MDA and MDMA. It is also now generally accepted that MDMA neurotoxicity results ...
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3,4-Isopropylidenedioxyamphetamine
3,4-Isopropylidenedioxyamphetamine (IDA) is a monoamine releasing agent (MRA) of the amphetamine family related to 3,4-methylenedioxyamphetamine (MDA). It is considerably less potent than MDA as an MRA ''in vitro''. IDA fully substituted for MDMA and LSD in animal drug discrimination tests, albeit with 5- to 7-fold lower potency than MDA. See also * 3,4-Ethylidenedioxyamphetamine (EIDA) * 3,4-Ethylenedioxyamphetamine (EDA) * 3,4-Ethylenedioxymethamphetamine (EDMA) * 3,4-Ethylenedioxymethcathinone 3,4-Ethylenedioxymethcathinone (EDMC), or 3,4-ethylenedioxy-''N''-methylcathinone, is a monoamine releasing agent (MRA) of the cathinone family related to methylone (3,4-methylenedioxymethcathinone; MDMC). It is the β- keto or cathinone analog ... (EDMC) References Entactogens Methylenedioxyphenethylamines Monoamine releasing agents Psychedelic phenethylamines Substituted amphetamines {{Psychoactive-stub ...
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3,4-Ethylenedioxymethamphetamine
3,4-Ethylenedioxy-''N''-methylamphetamine (EDMA) is an entactogen drug of the methamphetamine class. It is an analogue of MDMA where the methylenedioxy ring has been replaced by an ethylenedioxy ring. EDMA was first synthesized by Alexander Shulgin. In his book ''PiHKAL'', the dosage is listed as 150–250 mg, and the duration listed as 3–5 hours. According to Shulgin, EDMA produces only mild psychedelic effects consisting of paresthesia, nystagmus, and hypnogogic imagery, with few to no other symptoms. It has been found that EDMA acts as a non-neurotoxic serotonin releasing agent with moderately diminished potency relative to MDMA, and with negligible effects on dopamine release. However, subsequent research found that EMDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA) with values of 117nM for serotonin release, 325nM for norepinephrine release, and 597nM for dopamine release in rat brain synaptosomes. Compared to MDMA, EDMA was about half as ...
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3,4-Ethylenedioxymethcathinone
3,4-Ethylenedioxymethcathinone (EDMC), or 3,4-ethylenedioxy-''N''-methylcathinone, is a monoamine releasing agent (MRA) of the cathinone family related to methylone (3,4-methylenedioxymethcathinone; MDMC). It is the β- keto or cathinone analogue of 3,4-ethylenedioxymethamphetamine (EDMA). EDMC acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA). Its values for induction of monoamine release are 347nM for serotonin, 327nM for norepinephrine, and 496nM for dopamine in rat brain synaptosomes. These potencies were about 1.4-fold, 2.2-fold, and 3.7-fold lower than those of methylone, respectively. The drug was first described in 2015, whereas EDMA has been described much earlier. See also * 3,4-Ethylenedioxyamphetamine 3,4-Ethylenedioxyamphetamine (EDA), also known as EDA-6, is a drug of the substituted amphetamine, amphetamine family related to 3,4-methylenedioxyamphetamine (MDA). It is closely related to structural analog, analogues including 3,4-eth ...
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Methylenedioxyphenethylamines
The substituted methylenedioxyphenethylamines (abbreviated as MDxx) represent a diverse chemical class of compounds derived from phenethylamines. This category encompasses numerous Psychoactive drug, psychoactive substances with Empathogen, entactogenic, Psychedelic drug, psychedelic, and/or stimulant properties, in addition to entheogens. These compounds find application as research chemicals, designer drugs, and 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 notable MDxx class substances 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- ...
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David E
David (; , "beloved one") was a king of ancient Israel and Judah and the third king of the United Monarchy, according to the Hebrew Bible and Old Testament. The Tel Dan stele, an Aramaic-inscribed stone erected by a king of Aram-Damascus in the late 9th/early 8th centuries BCE to commemorate a victory over two enemy kings, contains the phrase (), which is translated as " House of David" by most scholars. The Mesha Stele, erected by King Mesha of Moab in the 9th century BCE, may also refer to the "House of David", although this is disputed. According to Jewish works such as the '' Seder Olam Rabbah'', '' Seder Olam Zutta'', and '' Sefer ha-Qabbalah'' (all written over a thousand years later), David ascended the throne as the king of Judah in 885 BCE. Apart from this, all that is known of David comes from biblical literature, the historicity of which has been extensively challenged,Writing and Rewriting the Story of Solomon in Ancient Israel; by Isaac Kalimi; pa ...
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1,3-Benzodioxole
1,3-Benzodioxole (1,2-methylenedioxybenzene) is an organic compound with the formula CHOCH. The compound is classified as benzene derivative and a heterocyclic compound containing the methylenedioxy functional group. It is a colorless liquid. Although benzodioxole is not particularly important, many related compounds containing the methylenedioxyphenyl group are bioactive, and thus are found in pesticides and pharmaceuticals. Preparation 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes. See also * 1,4-Benzodioxine * MDMA * Methylenedioxy * Safrole Safrole is an organic compound with the formula CH2O2C6H3CH2CH=CH2. It is a colorless oily liquid, although impure samples can appear yellow. A member of the phenylpropanoid family of natural products, it is found in sassafras plants, among ot ... * Piperonal References {{heterocyclic-stub ...
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2C-G-5
2C-G is a psychedelic phenethylamine of the 2C-series. First synthesized by Alexander Shulgin, it is sometimes used as an entheogen. It has structural and pharmacodynamic properties similar to 2C-D and Ganesha. Like many of the phenethylamines in ''PiHKAL'', 2C-G and its homologs have only been taken by Shulgin and a small test group, making it difficult to ensure completeness when describing effects. Chemistry 2C-G is 3,4-dimethyl-2,5-dimethoxyphenethylamine, with the formula . Dosage and effects In Shulgin's book ''PiHKAL'', the dosage range is listed as 20 to 35 mg. Effects are similar to the related Ganesha, and are extremely long lasting; the duration is 18–30 hours. Visual effects are muted or absent, and it is described in ''PiHKAL'' as an "insight-enhancer". Unlike other members of the 2C-series, 2C-G is nearly as potent as its amphetamine form. Homologs Several homologs of 2C-G were also synthesized by Shulgin. These include 2C-G-3, 2C-G-5, and 2C-G-N. S ...
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Enantiomer
In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities which are mirror images of each other and non-superposable. Enantiomer molecules are like right and left hands: one cannot be superposed onto the other without first being converted to its mirror image. It is solely a relationship of chirality (chemistry), chirality and the permanent three-dimensional relationships among molecules or other chemical structures: no amount of re-orientation of a molecule as a whole or conformational isomerism, conformational change converts one chemical into its enantiomer. Chemical structures with chirality rotate plane-polarized light. A mixture of equal amounts of each enantiomer, a ''racemic mixture'' or a ''racemate'', does not rotate light. Stereoisomers include both enantiomers and diastereomers. Diaste ...
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F-2 (psychedelic)
F-2, also known as 6-(2-aminopropyl)-5-methoxy-2-methyl-2,3-dihydrobenzofuran or as benzofuran-2-methyl-5-methoxy-6-(2-aminopropane), is a lesser-known psychedelic drug. F-2 was first synthesized by Alexander Shulgin. In his book ''PiHKAL'', the minimum dosage is listed as 15 mg, and its duration is unknown. F-2 produces few to no effects at this dose in humans. Animal studies showed it to substitute for the psychedelic drug DOM, but with less than one tenth the potency. F-2 is the derivative of 6-APDB with a methyl group at the carbon atom of the 3,4- methylenedioxy ring and a methoxy group at the 6 position. Legality United Kingdom This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act. See also * F-22 (drug) * Substituted benzofuran The substituted benzofurans are a class of chemical compounds based on the heterocyclic compound, heterocyclic and polycyclic compound, polycyclic compound benzofuran. Many medicines use the benzofuran ...
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